# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2012


data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)

_journal_coden_Cambridge         1326
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Gabor Molnar'
_publ_contact_author_email       molnar@lcc-toulouse.fr

_publ_section_title              
;
High-Pressure Spin-Crossover in a Dinuclear Fe(II) Complex
;
loop_
_publ_author_name
G.Molnar
P.Guionneau
H.Shepherd
P.Rosa
N.Casati
L.Vendier
;
J.-F.Letard
;
A.Bousseksou

# Attachment '- new_cif_all.cif'

#TrackingRef '- new_cif_all.cif'

#======================================================================
data_ambient
_database_code_depnum_ccdc_archive 'CCDC 857565'
#TrackingRef '- new_cif_all.cif'

#======================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Fe2 N16 S4, 2(C H4 O)'
_chemical_formula_sum            'C38 H34 Fe2 N16 S4 O2'
_chemical_formula_weight         984.78

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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'

_cell_length_a                   15.670(7)
_cell_length_b                   8.175(10)
_cell_length_c                   18.648(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.21(5)
_cell_angle_gamma                90.00
_cell_volume                     2242(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)

_cell_measurement_reflns_used    996

_cell_measurement_theta_max      28.0406
_cell_measurement_theta_min      2.0900
_exptl_absorpt_correction_mu     0.000
_exptl_absorpt_correction_T_max  0.386
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
Gaussian integration over a grid
of 16 x 16 x 16 points = 4096 total grid points
Based upon method of Burnham (1966)

Data corrected for diamond-anvil cell absorption
Note that exptl_absorpt_correction_tmin and _tmax
the total correction factors applied to the intensities
The individual factors are:
range of dac transmission factors (min-max) 0.490 0.563
range of gasket transmission (min-max) 0.788 0.981
range of P media transmission (min-max) 1.000 1.000

thickness of diamond anvil 1: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1

thickness of diamond anvil 2: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1

Gasket shadowing corrections were made based upon
Gasket thickness = 220.0 microns, radius = 375.0 microns
Gasket absorption coeff = 27.90 mm-1
REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF
FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.20

Non-absorbing pressure medium
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'crystal fills hole of diamond-cell gasket'
_exptl_crystal_F_000             1012
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
The sample was placed inside a small screw-driven diamond anvil
cell (DAC) equipped with conical cut diamonds with 800 micron culets; the
diamonds were mounted on tungsten carbide backing seats giving an x-ray
aperture of approximately 80 degrees. A stainless steel gasket was
pre-indented to a thickness of 180-200 microns and a hole of 400 micron
was mechanically drilled through the centre of the indentation, which
served as a sample chamber. The chamber was filled with a single
crystal of 1, two small ruby chips and silicone oil, which
served as a pressure transmitting medium.

No pressure was applied to the sample during the measurement.
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5537
_diffrn_reflns_av_R_equivalents  0.1415
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         17.22
_reflns_number_total             902
_reflns_number_gt                621
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'see _refine_special_details'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Basic models derived from the ambient pressure phases were used as a
starting point for refinement of structural parameters against high
pressure data (to a maximum resolution of 1.2 Angstroms) on F^2^.

Anisotropic temperature factors were refined for iron and sulphur atoms
only due to the relatively low resolution of the experiment. The low
(2/m) symmetry of this sample results in substantially incomplete data
(<65 % to 50 degrees 2theta), as reflected in the refinement statistics.
Low completeness, while not unusual for high pressure single crystal data
sets from small molecule (low symmetry) systems, means that a somewhat
high number of constraints and restraints were used in the refinement of
structural parameters, including AFIX 56 and AFIX 66 commands to model the
aromatic rings and restraints on the Uiso of carbon atoms as follows:

SIMU 0.02 0.04 3 O1 C8 C7 C6 C5 C4 C18 C3 C17 C9 C2 C10 C1 C11 C19 C12 C13 =
C14 C15 C16

The standard deviations used in this restraint and the maximum distance over
which the restraint applies are higher than normal, justified in light of the
acknowledged limitations of the data, as described above.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1509P)^2^+11.1374P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         902
_refine_ls_number_parameters     99
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0966
_refine_ls_wR_factor_ref         0.2896
_refine_ls_wR_factor_gt          0.2391
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.56786(19) 0.3920(6) 0.81788(14) 0.058(2) Uani 1 1 d . . .
S2 S 0.2877(4) 0.1103(13) 0.8010(3) 0.091(5) Uani 1 1 d . . .
S1 S 0.8860(4) 0.5419(15) 0.9081(4) 0.112(5) Uani 1 1 d . . .
N1 N 0.6253(7) 0.342(2) 0.9376(5) 0.058(6) Uiso 1 1 d G . .
C8 C 0.6688(9) 0.195(2) 0.9636(7) 0.060(6) Uiso 1 1 d GU . .
C7 C 0.7086(9) 0.1660(18) 1.0416(8) 0.067(6) Uiso 1 1 d GU . .
H7 H 0.7378 0.0670 1.0590 0.081 Uiso 1 1 calc R . .
C6 C 0.7049(8) 0.285(2) 1.0936(5) 0.066(6) Uiso 1 1 d GU . .
H6 H 0.7316 0.2660 1.1458 0.079 Uiso 1 1 calc R . .
C5 C 0.6614(9) 0.433(2) 1.0676(7) 0.059(6) Uiso 1 1 d GU . .
H5 H 0.6589 0.5127 1.1024 0.071 Uiso 1 1 calc R . .
C4 C 0.6216(8) 0.4616(18) 0.9896(8) 0.051(5) Uiso 1 1 d GU . .
N2 N 0.5378(8) 0.611(2) 0.8737(7) 0.054(6) Uiso 1 1 d G . .
C3 C 0.5754(9) 0.599(2) 0.9546(7) 0.059(6) Uiso 1 1 d GU . .
C2 C 0.5596(9) 0.749(2) 0.9860(6) 0.061(6) Uiso 1 1 d GU . .
H2 H 0.5772 0.7746 1.0377 0.073 Uiso 1 1 calc R . .
C1 C 0.5123(10) 0.8547(19) 0.9245(9) 0.072(7) Uiso 1 1 d GU . .
H1 H 0.4935 0.9609 0.9289 0.086 Uiso 1 1 calc R . .
N7 N 0.4988(8) 0.769(2) 0.8551(6) 0.072(6) Uiso 1 1 d G . .
H7A H 0.4718 0.8067 0.8098 0.087 Uiso 1 1 calc R . .
C18 C 0.3762(15) 0.211(4) 0.8014(10) 0.057(7) Uiso 1 1 d . . .
C17 C 0.7768(16) 0.504(4) 0.8643(11) 0.063(7) Uiso 1 1 d . . .
N3 N 0.6324(8) 0.1484(18) 0.8308(8) 0.064(6) Uiso 1 1 d G . .
C9 C 0.6768(10) 0.093(2) 0.9068(6) 0.067(6) Uiso 1 1 d GU . .
C10 C 0.7206(9) -0.057(2) 0.9035(7) 0.082(7) Uiso 1 1 d GU . .
H10 H 0.7547 -0.1199 0.9452 0.099 Uiso 1 1 calc R . .
C11 C 0.7034(10) -0.0949(18) 0.8254(9) 0.076(7) Uiso 1 1 d GU . .
H11 H 0.7242 -0.1867 0.8070 0.091 Uiso 1 1 calc R . .
N8 N 0.6489(8) 0.032(2) 0.7805(5) 0.070(6) Uiso 1 1 d G . .
H8 H 0.6292 0.0377 0.7314 0.084 Uiso 1 1 calc R . .
N6 N 0.4376(12) 0.299(3) 0.8011(9) 0.070(6) Uiso 1 1 d . . .
N5 N 0.7012(12) 0.480(3) 0.8352(8) 0.057(6) Uiso 1 1 d . . .
O1 O 0.3989(11) -0.170(3) 0.7062(11) 0.120(7) Uiso 1 1 d U . .
C19 C 0.391(2) -0.143(6) 0.6337(17) 0.155(13) Uiso 1 1 d U . .
H19A H 0.3411 -0.2042 0.6003 0.232 Uiso 1 1 calc R . .
H19B H 0.4463 -0.1756 0.6260 0.232 Uiso 1 1 calc R . .
H19C H 0.3811 -0.0281 0.6225 0.232 Uiso 1 1 calc R . .
N4 N 0.5299(9) 0.448(2) 0.6966(5) 0.061(6) Uiso 1 1 d G . .
C12 C 0.4719(10) 0.3451(18) 0.6418(8) 0.078(7) Uiso 1 1 d GU . .
H12 H 0.4410 0.2618 0.6565 0.094 Uiso 1 1 calc R . .
C13 C 0.4602(9) 0.367(2) 0.5650(7) 0.074(7) Uiso 1 1 d GU . .
H13 H 0.4214 0.2982 0.5283 0.089 Uiso 1 1 calc R . .
C14 C 0.5063(9) 0.491(2) 0.5430(5) 0.069(6) Uiso 1 1 d GU . .
C15 C 0.5643(10) 0.5941(19) 0.5978(8) 0.081(7) Uiso 1 1 d GU . .
H15 H 0.5952 0.6774 0.5831 0.097 Uiso 1 1 calc R . .
C16 C 0.5761(9) 0.5723(18) 0.6746(7) 0.082(7) Uiso 1 1 d GU . .
H16 H 0.6149 0.6409 0.7113 0.098 Uiso 1 1 calc R . .

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
Fe1 0.063(3) 0.072(7) 0.037(2) 0.002(2) 0.0154(16) 0.001(2)
S2 0.090(5) 0.103(16) 0.080(5) 0.020(6) 0.031(4) -0.015(5)
S1 0.069(5) 0.153(17) 0.101(5) -0.014(7) 0.014(4) -0.015(5)

_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
Fe1 N6 2.10(2) . ?
Fe1 N5 2.126(19) . ?
Fe1 N1 2.138(10) . ?
Fe1 N4 2.180(9) . ?
Fe1 N2 2.204(15) . ?
Fe1 N3 2.209(14) . ?
S2 C18 1.61(3) . ?
S1 C17 1.65(2) . ?
N1 C8 1.3900 . ?
N1 C4 1.3900 . ?
C8 C9 1.383(16) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.373(17) . ?
N2 N7 1.4200 . ?
N2 C3 1.4200 . ?
C3 C2 1.4200 . ?
C2 C1 1.4200 . ?
C1 N7 1.4200 . ?
C18 N6 1.20(3) . ?
C17 N5 1.14(2) . ?
N3 N8 1.4200 . ?
N3 C9 1.4200 . ?
C9 C10 1.4200 . ?
C10 C11 1.4200 . ?
C11 N8 1.4200 . ?
O1 C19 1.33(3) . ?
N4 C12 1.3900 . ?
N4 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C14 1.554(17) 3_666 ?
C15 C16 1.3900 . ?

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
N6 Fe1 N5 178.5(9) . . ?
N6 Fe1 N1 97.1(6) . . ?
N5 Fe1 N1 82.4(5) . . ?
N6 Fe1 N4 91.1(6) . . ?
N5 Fe1 N4 89.4(6) . . ?
N1 Fe1 N4 171.6(5) . . ?
N6 Fe1 N2 90.6(8) . . ?
N5 Fe1 N2 90.7(7) . . ?
N1 Fe1 N2 75.1(6) . . ?
N4 Fe1 N2 107.1(6) . . ?
N6 Fe1 N3 94.3(8) . . ?
N5 Fe1 N3 84.2(7) . . ?
N1 Fe1 N3 72.8(6) . . ?
N4 Fe1 N3 104.6(5) . . ?
N2 Fe1 N3 147.8(5) . . ?
C8 N1 C4 120.0 . . ?
C8 N1 Fe1 120.5(9) . . ?
C4 N1 Fe1 119.5(9) . . ?
C9 C8 N1 114.7(13) . . ?
C9 C8 C7 125.0(13) . . ?
N1 C8 C7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C6 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C3 C4 C5 127.5(12) . . ?
C3 C4 N1 112.5(12) . . ?
C5 C4 N1 120.0 . . ?
N7 N2 C3 108.0 . . ?
N7 N2 Fe1 140.3(9) . . ?
C3 N2 Fe1 111.5(9) . . ?
C4 C3 C2 130.6(13) . . ?
C4 C3 N2 121.4(13) . . ?
C2 C3 N2 108.0 . . ?
C1 C2 C3 108.0 . . ?
C2 C1 N7 108.0 . . ?
N2 N7 C1 108.0 . . ?
N6 C18 S2 174(3) . . ?
N5 C17 S1 179(2) . . ?
N8 N3 C9 108.0 . . ?
N8 N3 Fe1 135.4(9) . . ?
C9 N3 Fe1 116.3(9) . . ?
C8 C9 C10 136.4(13) . . ?
C8 C9 N3 115.6(13) . . ?
C10 C9 N3 108.0 . . ?
C11 C10 C9 108.0 . . ?
C10 C11 N8 108.0 . . ?
N3 N8 C11 108.0 . . ?
C18 N6 Fe1 163(2) . . ?
C17 N5 Fe1 159.9(17) . . ?
C12 N4 C16 120.0 . . ?
C12 N4 Fe1 120.8(8) . . ?
C16 N4 Fe1 118.4(8) . . ?
C13 C12 N4 120.0 . . ?
C12 C13 C14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 C14 122(2) . 3_666 ?
C13 C14 C14 118(2) . 3_666 ?
C14 C15 C16 120.0 . . ?
C15 C16 N4 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.665
_diffrn_reflns_theta_full        17.22
_diffrn_measured_fraction_theta_full 0.665
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.092

#======================================================================
data_2.5-kbar
_database_code_depnum_ccdc_archive 'CCDC 857566'
#TrackingRef '- new_cif_all.cif'

#======================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Fe2 N16 S4, 2(C H4 O)'
_chemical_formula_sum            'C38 H34 Fe2 N16 S4 O2'
_chemical_formula_weight         984.78

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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'

_cell_length_a                   15.409(11)
_cell_length_b                   8.078(7)
_cell_length_c                   18.56(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.54(13)
_cell_angle_gamma                90.00
_cell_volume                     2163(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    758
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.1160
_cell_measurement_theta_min      2.5164

_exptl_absorpt_correction_mu     0.000
_exptl_absorpt_correction_T_max  0.386
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
Gaussian integration over a grid
of 16 x 16 x 16 points = 4096 total grid points
Based upon method of Burnham (1966)

Data corrected for diamond-anvil cell absorption
Note that exptl_absorpt_correction_tmin and _tmax
the total correction factors applied to the intensities
The individual factors are:
range of dac transmission factors (min-max) 0.490 0.564
range of gasket transmission (min-max) 0.787 0.985
range of P media transmission (min-max) 1.000 1.000

thickness of diamond anvil 1: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1

thickness of diamond anvil 2: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1

Gasket shadowing corrections were made based upon
Gasket thickness = 220.0 microns, radius = 375.0 microns
Gasket absorption coeff = 27.90 mm-1
REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF
FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.20

Non-absorbing pressure medium
;
_exptl_crystal_colour            .
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'crystal fills hole of diamond-cell gasket'
_exptl_crystal_F_000             1012
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
Hydrostatic pressure was generated using a small screw-driven diamond anvil
cell (DAC) equipped with conical cut diamonds with 800 micron culets; the
diamonds were mounted on tungsten carbide backing seats giving an x-ray
aperture of approximately 80deg. A stainless steel gasket was pre-indented
to a thickness of 180-200 microns and a hole of 400 micron was mechanically
drilled through the centre of the indentation, which served as a sample
chamber. The chamber was filled with a single crystal of 1, two small
ruby chips and silicone oil, which served as a pressure
transmitting medium.

The pressure was determined to be 2.5 kbar using the ruby fluorescence
technique
;

_diffrn_ambient_temperature      295(2)
_diffrn_ambient_pressure         250000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5247
_diffrn_reflns_av_R_equivalents  0.1324
_diffrn_reflns_av_sigmaI/netI    0.1175
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         17.22
_reflns_number_total             927
_reflns_number_gt                611
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'see _refine_special_details'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Basic models derived from the ambient pressure phases were used as a
starting point for refinement of structural parameters against high
pressure data (to a maximum resolution of 1.2 Angstroms) on F^2^.

Anisotropic temperature factors were refined for iron and sulphur atoms
only due to the relatively low resolution of the experiment. The low
(2/m) symmetry of this sample results in substantially incomplete data
(<65 % to 50 degrees 2theta), as reflected in the refinement statistics.
Low completeness, while not unusual for high pressure single crystal data
sets from small molecule (low symmetry) systems, means that a somewhat
high number of restraints are necessary in the refinement of structural
parameters, including AFIX 56 and AFIX 66 commands to model the
aromatic rings and restraints on the Uiso of carbon atoms as follows:

SIMU 0.02 0.04 3 O1 C8 C7 C6 C5 C4 C18 C3 C17 C9 C2 C10 C1 C11 C19 C12 C13 =
C14 C15 C16

The standard deviations used in this restraint and the maximum distance over
which the restraint applies are higher than normal, justified in light of the
acknowledged limitations of the data, as described above.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1351P)^2^+9.2586P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         927
_refine_ls_number_parameters     99
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0966
_refine_ls_wR_factor_ref         0.2682
_refine_ls_wR_factor_gt          0.2305
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.56500(18) 0.3927(3) 0.8179(2) 0.0567(18) Uani 1 1 d . . .
S2 S 0.2790(4) 0.1065(7) 0.7982(5) 0.086(3) Uani 1 1 d . . .
S1 S 0.8893(4) 0.5474(8) 0.9135(5) 0.101(3) Uani 1 1 d . . .
N1 N 0.6252(7) 0.3423(16) 0.9373(7) 0.051(5) Uiso 1 1 d G . .
C8 C 0.6702(8) 0.1929(13) 0.9628(8) 0.057(4) Uiso 1 1 d GU . .
C7 C 0.7105(7) 0.1617(11) 1.0412(9) 0.062(4) Uiso 1 1 d GU . .
H7 H 0.7406 0.0618 1.0583 0.075 Uiso 1 1 calc R . .
C6 C 0.7057(7) 0.2800(17) 1.0941(7) 0.060(5) Uiso 1 1 d GU . .
H6 H 0.7327 0.2591 1.1466 0.072 Uiso 1 1 calc R . .
C5 C 0.6607(8) 0.4294(14) 1.0686(8) 0.059(4) Uiso 1 1 d GU . .
H5 H 0.6575 0.5085 1.1040 0.071 Uiso 1 1 calc R . .
C4 C 0.6204(7) 0.4606(11) 0.9902(9) 0.052(4) Uiso 1 1 d GU . .
N2 N 0.5396(8) 0.6100(13) 0.8781(9) 0.060(5) Uiso 1 1 d G . .
C3 C 0.5776(7) 0.6060(13) 0.9597(9) 0.058(5) Uiso 1 1 d GU . .
C2 C 0.5597(8) 0.7611(16) 0.9876(7) 0.056(5) Uiso 1 1 d GU . .
H2 H 0.5771 0.7919 1.0391 0.067 Uiso 1 1 calc R . .
C1 C 0.5105(7) 0.8610(11) 0.9233(9) 0.064(5) Uiso 1 1 d GU . .
H1 H 0.4900 0.9687 0.9252 0.077 Uiso 1 1 calc R . .
N7 N 0.4981(7) 0.7676(15) 0.8556(7) 0.065(6) Uiso 1 1 d G . .
H7A H 0.4703 0.8007 0.8091 0.078 Uiso 1 1 calc R . .
C18 C 0.3701(16) 0.210(3) 0.7987(16) 0.081(8) Uiso 1 1 d . . .
C17 C 0.7767(14) 0.503(2) 0.8675(13) 0.052(6) Uiso 1 1 d . . .
N3 N 0.6288(7) 0.1436(11) 0.8291(9) 0.061(5) Uiso 1 1 d G . .
C9 C 0.6764(10) 0.0892(18) 0.9055(8) 0.062(5) Uiso 1 1 d GU . .
C10 C 0.7254(8) -0.0577(17) 0.9020(8) 0.071(5) Uiso 1 1 d GU . .
H10 H 0.7624 -0.1193 0.9439 0.085 Uiso 1 1 calc R . .
C11 C 0.7081(8) -0.0940(12) 0.8233(9) 0.071(6) Uiso 1 1 d GU . .
H11 H 0.7317 -0.1835 0.8046 0.085 Uiso 1 1 calc R . .
N8 N 0.6484(7) 0.0304(15) 0.7782(7) 0.070(5) Uiso 1 1 d G . .
H8 H 0.6277 0.0362 0.7288 0.085 Uiso 1 1 calc R . .
N6 N 0.4348(11) 0.290(2) 0.8003(12) 0.073(6) Uiso 1 1 d . . .
N5 N 0.7019(12) 0.4827(19) 0.8355(12) 0.073(6) Uiso 1 1 d . . .
O1 O 0.4000(14) -0.143(2) 0.7077(17) 0.161(8) Uiso 1 1 d U . .
C19 C 0.3915(17) -0.132(3) 0.634(2) 0.126(10) Uiso 1 1 d U . .
H19A H 0.3594 -0.2271 0.6063 0.188 Uiso 1 1 calc R . .
H19B H 0.4519 -0.1256 0.6297 0.188 Uiso 1 1 calc R . .
H19C H 0.3571 -0.0335 0.6117 0.188 Uiso 1 1 calc R . .
N4 N 0.5250(8) 0.4482(15) 0.6959(6) 0.056(5) Uiso 1 1 d G . .
C12 C 0.4650(8) 0.3465(13) 0.6400(9) 0.080(5) Uiso 1 1 d GU . .
H12 H 0.4320 0.2639 0.6541 0.096 Uiso 1 1 calc R . .
C13 C 0.4544(8) 0.3680(16) 0.5631(8) 0.083(5) Uiso 1 1 d GU . .
H13 H 0.4143 0.2999 0.5257 0.099 Uiso 1 1 calc R . .
C14 C 0.5038(10) 0.4913(18) 0.5421(7) 0.075(5) Uiso 1 1 d GU . .
C15 C 0.5637(9) 0.5931(14) 0.5979(10) 0.078(5) Uiso 1 1 d GU . .
H15 H 0.5968 0.6756 0.5838 0.094 Uiso 1 1 calc R . .
C16 C 0.5743(7) 0.5715(13) 0.6748(8) 0.087(5) Uiso 1 1 d GU . .
H16 H 0.6144 0.6396 0.7122 0.105 Uiso 1 1 calc R . .

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
Fe1 0.066(2) 0.052(3) 0.053(5) 0.0006(16) 0.022(2) 0.0004(15)
S2 0.088(5) 0.095(6) 0.076(11) 0.024(4) 0.032(5) -0.009(4)
S1 0.082(5) 0.096(7) 0.113(12) -0.005(4) 0.020(5) -0.002(4)

_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
Fe1 N6 2.086(17) . ?
Fe1 N1 2.120(12) . ?
Fe1 N5 2.145(18) . ?
Fe1 N4 2.175(12) . ?
Fe1 N2 2.188(11) . ?
Fe1 N3 2.217(9) . ?
S2 C18 1.63(2) . ?
S1 C17 1.68(2) . ?
N1 C8 1.3900 . ?
N1 C4 1.3900 . ?
C8 C9 1.383(14) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.368(12) . ?
N2 C3 1.4200 . ?
N2 N7 1.4200 . ?
C3 C2 1.4200 . ?
C2 C1 1.4200 . ?
C1 N7 1.4200 . ?
C18 N6 1.18(2) . ?
C17 N5 1.109(19) . ?
N3 C9 1.4200 . ?
N3 N8 1.4200 . ?
C9 C10 1.4200 . ?
C10 C11 1.4200 . ?
C11 N8 1.4200 . ?
O1 C19 1.34(4) . ?
N4 C12 1.3900 . ?
N4 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C14 1.53(2) 3_666 ?
C15 C16 1.3900 . ?

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
N6 Fe1 N1 97.6(6) . . ?
N6 Fe1 N5 176.4(6) . . ?
N1 Fe1 N5 82.0(6) . . ?
N6 Fe1 N4 90.7(7) . . ?
N1 Fe1 N4 171.2(4) . . ?
N5 Fe1 N4 89.6(7) . . ?
N6 Fe1 N2 93.6(6) . . ?
N1 Fe1 N2 73.2(6) . . ?
N5 Fe1 N2 89.6(5) . . ?
N4 Fe1 N2 109.3(5) . . ?
N6 Fe1 N3 91.5(5) . . ?
N1 Fe1 N3 73.2(5) . . ?
N5 Fe1 N3 85.0(5) . . ?
N4 Fe1 N3 103.8(5) . . ?
N2 Fe1 N3 146.4(6) . . ?
C8 N1 C4 120.0 . . ?
C8 N1 Fe1 120.4(8) . . ?
C4 N1 Fe1 119.6(8) . . ?
C9 C8 C7 124.7(13) . . ?
C9 C8 N1 115.2(13) . . ?
C7 C8 N1 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C6 C5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C3 C4 C5 124.2(12) . . ?
C3 C4 N1 115.8(12) . . ?
C5 C4 N1 120.0 . . ?
C3 N2 N7 108.0 . . ?
C3 N2 Fe1 116.4(8) . . ?
N7 N2 Fe1 135.4(8) . . ?
C4 C3 C2 137.2(12) . . ?
C4 C3 N2 114.8(12) . . ?
C2 C3 N2 108.0 . . ?
C3 C2 C1 108.0 . . ?
C2 C1 N7 108.0 . . ?
C1 N7 N2 108.0 . . ?
N6 C18 S2 177(2) . . ?
N5 C17 S1 176(2) . . ?
C9 N3 N8 108.0 . . ?
C9 N3 Fe1 115.5(9) . . ?
N8 N3 Fe1 135.5(9) . . ?
C8 C9 N3 115.5(14) . . ?
C8 C9 C10 136.3(14) . . ?
N3 C9 C10 108.0 . . ?
C9 C10 C11 108.0 . . ?
N8 C11 C10 108.0 . . ?
N3 N8 C11 108.0 . . ?
C18 N6 Fe1 168.0(18) . . ?
C17 N5 Fe1 156(2) . . ?
C12 N4 C16 120.0 . . ?
C12 N4 Fe1 121.8(8) . . ?
C16 N4 Fe1 117.2(8) . . ?
N4 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 C14 120(2) . 3_666 ?
C15 C14 C14 120(2) . 3_666 ?
C16 C15 C14 120.0 . . ?
C15 C16 N4 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.706
_diffrn_reflns_theta_full        17.22
_diffrn_measured_fraction_theta_full 0.706
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.087

#======================================================================
data_6-kbar
_database_code_depnum_ccdc_archive 'CCDC 857567'
#TrackingRef '- new_cif_all.cif'

#======================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Fe2 N16 S4, 2(C H4 O)'
_chemical_formula_sum            'C38 H34 Fe2 N16 S4 O2'
_chemical_formula_weight         984.78

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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'

_cell_length_a                   15.186(19)
_cell_length_b                   7.967(3)
_cell_length_c                   18.57(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.53(18)
_cell_angle_gamma                90.00
_cell_volume                     2090(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_diffrn_ambient_pressure         600000
_cell_measurement_reflns_used    652
_cell_measurement_theta_min      1.4386
_cell_measurement_theta_max      27.9016
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
Gaussian integration over a grid
of 16 x 16 x 16 points = 4096 total grid points
Based upon method of Burnham (1966)

Data corrected for diamond-anvil cell absorption
Note that exptl_absorpt_correction_tmin and _tmax
the total correction factors applied to the intensities
The individual factors are:
range of dac transmission factors (min-max) 0.490 0.564
range of gasket transmission (min-max) 0.787 0.985
range of P media transmission (min-max) 1.000 1.000

thickness of diamond anvil 1: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1

thickness of diamond anvil 2: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1

Gasket shadowing corrections were made based upon
Gasket thickness = 220.0 microns, radius = 375.0 microns
Gasket absorption coeff = 27.90 mm-1
REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF
FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.20

Non-absorbing pressure medium
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
Hydrostatic pressure was generated using a small screw-driven diamond anvil
cell (DAC) equipped with conical cut diamonds with 800 micron culets; the
diamonds were mounted on tungsten carbide backing seats giving an x-ray
aperture of approximately 80deg. A stainless steel gasket was pre-indented
to a thickness of 180-200 microns and a hole of 400 micron was mechanically
drilled through the centre of the indentation, which served as a sample
chamber. The chamber was filled with a single crystal of 1, two small
ruby chips and silicone oil, which served as a pressure
transmitting medium.

The pressure was determined to be 6 kbar using the ruby fluorescence
technique
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2768
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.1121
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         17.22
_reflns_number_total             654
_reflns_number_gt                435
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'see _refine_special_details'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Basic models derived from the ambient pressure phases were used as a
starting point for refinement of structural parameters against high
pressure data (to a maximum resolution of 1.2 Angstroms) on F^2^.

Anisotropic temperature factors were refined for iron and sulphur atoms
only due to the relatively low resolution of the experiment. The low
(2/m) symmetry of this sample results in substantially incomplete data
(<65 % to 50 degrees 2theta), as reflected in the refinement statistics.
Low completeness, while not unusual for high pressure single crystal data
sets from small molecule (low symmetry) systems, means that a somewhat
high number of restraints are necessary in the refinement of structural
parameters, including AFIX 56 and AFIX 66 commands to model the
aromatic rings and restraints on the Uiso of carbon atoms as follows:

SIMU 0.02 0.04 3 O1 C8 C7 C6 C5 C4 C18 C3 C17 C9 C2 C10 C1 C11 C19 C12 C13 =
C14 C15 C16

ISOR 0.01 0.02 S1 S2 Fe1

The standard deviations used in this restraint (and the maximum distance over
which the restraint applies in the SIMU instructuction) are higher than
normal, justified in light of the acknowledged limitations of the data,
as described above.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1061P)^2^+22.3275P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         654
_refine_ls_number_parameters     99
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2592
_refine_ls_wR_factor_gt          0.2014
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5622(4) 0.3919(4) 0.8175(3) 0.067(4) Uani 1 1 d U . .
S2 S 0.2730(8) 0.1040(8) 0.7947(6) 0.092(8) Uani 1 1 d U . .
S1 S 0.8907(7) 0.5518(9) 0.9168(6) 0.089(8) Uani 1 1 d U . .
N1 N 0.6236(13) 0.3420(17) 0.9373(9) 0.045(6) Uiso 1 1 d G . .
C8 C 0.6703(14) 0.1904(16) 0.9619(10) 0.045(6) Uiso 1 1 d GU . .
C7 C 0.7123(14) 0.1558(14) 1.0406(11) 0.045(6) Uiso 1 1 d GU . .
H7 H 0.7435 0.0544 1.0571 0.054 Uiso 1 1 calc R . .
C6 C 0.7076(14) 0.2727(18) 1.0946(9) 0.055(7) Uiso 1 1 d GU . .
H6 H 0.7356 0.2496 1.1472 0.065 Uiso 1 1 calc R . .
C5 C 0.6609(14) 0.4243(16) 1.0700(10) 0.050(6) Uiso 1 1 d GU . .
H5 H 0.6577 0.5026 1.1061 0.060 Uiso 1 1 calc R . .
C4 C 0.6189(13) 0.4589(14) 0.9913(10) 0.045(6) Uiso 1 1 d GU . .
N2 N 0.5395(13) 0.6139(14) 0.8748(10) 0.038(5) Uiso 1 1 d G . .
C3 C 0.5770(16) 0.6057(15) 0.9570(10) 0.047(6) Uiso 1 1 d GU . .
C2 C 0.5592(16) 0.762(2) 0.9859(9) 0.055(7) Uiso 1 1 d GU . .
H2 H 0.5763 0.7905 1.0378 0.067 Uiso 1 1 calc R . .
C1 C 0.5106(15) 0.8665(16) 0.9217(11) 0.064(8) Uiso 1 1 d GU . .
H1 H 0.4904 0.9757 0.9241 0.076 Uiso 1 1 calc R . .
N7 N 0.4984(14) 0.7750(15) 0.8530(9) 0.056(6) Uiso 1 1 d G . .
H7A H 0.4710 0.8110 0.8064 0.068 Uiso 1 1 calc R . .
C18 C 0.362(3) 0.208(3) 0.8001(19) 0.045(8) Uiso 1 1 d . . .
C17 C 0.781(3) 0.508(3) 0.8728(19) 0.055(8) Uiso 1 1 d . . .
N3 N 0.6273(12) 0.1440(15) 0.8251(11) 0.063(7) Uiso 1 1 d G . .
C9 C 0.6732(16) 0.0873(19) 0.9024(10) 0.044(6) Uiso 1 1 d GU . .
C10 C 0.7250(16) -0.0600(18) 0.9005(10) 0.058(7) Uiso 1 1 d GU . .
H10 H 0.7616 -0.1229 0.9432 0.070 Uiso 1 1 calc R . .
C11 C 0.7111(13) -0.0943(17) 0.8220(12) 0.060(8) Uiso 1 1 d GU . .
H11 H 0.7370 -0.1836 0.8043 0.072 Uiso 1 1 calc R . .
N8 N 0.6507(13) 0.0317(19) 0.7754(9) 0.062(7) Uiso 1 1 d G . .
H8 H 0.6316 0.0389 0.7258 0.075 Uiso 1 1 calc R . .
N6 N 0.428(2) 0.288(2) 0.8014(17) 0.061(7) Uiso 1 1 d . . .
N5 N 0.700(2) 0.481(2) 0.8364(16) 0.061(7) Uiso 1 1 d . . .
O1 O 0.398(3) -0.124(3) 0.698(2) 0.147(10) Uiso 1 1 d U . .
C19 C 0.398(4) -0.134(4) 0.624(3) 0.157(17) Uiso 1 1 d U . .
H19A H 0.4072 -0.2487 0.6125 0.235 Uiso 1 1 calc R . .
H19B H 0.4490 -0.0668 0.6206 0.235 Uiso 1 1 calc R . .
H19C H 0.3391 -0.0937 0.5879 0.235 Uiso 1 1 calc R . .
N4 N 0.5230(12) 0.4528(18) 0.6956(9) 0.050(6) Uiso 1 1 d G . .
C12 C 0.4621(12) 0.3481(16) 0.6394(12) 0.073(8) Uiso 1 1 d GU . .
H12 H 0.4287 0.2647 0.6535 0.088 Uiso 1 1 calc R . .
C13 C 0.4513(14) 0.3680(19) 0.5623(10) 0.072(8) Uiso 1 1 d GU . .
H13 H 0.4106 0.2979 0.5246 0.086 Uiso 1 1 calc R . .
C14 C 0.5014(14) 0.493(2) 0.5413(9) 0.055(7) Uiso 1 1 d GU . .
C15 C 0.5622(12) 0.5974(18) 0.5975(11) 0.062(7) Uiso 1 1 d GU . .
H15 H 0.5957 0.6808 0.5835 0.075 Uiso 1 1 calc R . .
C16 C 0.5731(11) 0.5775(17) 0.6747(10) 0.068(8) Uiso 1 1 d GU . .
H16 H 0.6138 0.6476 0.7123 0.082 Uiso 1 1 calc R . .

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
Fe1 0.072(5) 0.047(2) 0.053(5) -0.004(2) -0.010(4) 0.002(2)
S2 0.089(10) 0.073(5) 0.087(11) 0.021(5) 0.001(9) -0.011(5)
S1 0.055(9) 0.087(5) 0.095(11) -0.008(5) -0.008(9) -0.002(5)

_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
Fe1 N1 2.109(15) . ?
Fe1 N6 2.11(4) . ?
Fe1 N5 2.12(3) . ?
Fe1 N2 2.156(16) . ?
Fe1 N4 2.173(18) . ?
Fe1 N3 2.190(13) . ?
S2 C18 1.56(4) . ?
S1 C17 1.61(3) . ?
N1 C8 1.3900 . ?
N1 C4 1.3900 . ?
C8 C7 1.3900 . ?
C8 C9 1.39(2) . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.371(13) . ?
N2 C3 1.4200 . ?
N2 N7 1.4200 . ?
C3 C2 1.4200 . ?
C2 C1 1.4200 . ?
C1 N7 1.4200 . ?
C18 N6 1.18(5) . ?
C17 N5 1.18(3) . ?
N3 C9 1.4200 . ?
N3 N8 1.4200 . ?
C9 C10 1.4200 . ?
C10 C11 1.4200 . ?
C11 N8 1.4200 . ?
O1 C19 1.38(8) . ?
N4 C12 1.3900 . ?
N4 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C14 1.52(4) 3_666 ?
C15 C16 1.3900 . ?

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
N1 Fe1 N6 96.1(10) . . ?
N1 Fe1 N5 82.0(10) . . ?
N6 Fe1 N5 176.5(7) . . ?
N1 Fe1 N2 73.9(6) . . ?
N6 Fe1 N2 94.0(10) . . ?
N5 Fe1 N2 88.3(9) . . ?
N1 Fe1 N4 170.4(9) . . ?
N6 Fe1 N4 93.4(10) . . ?
N5 Fe1 N4 88.5(10) . . ?
N2 Fe1 N4 107.3(6) . . ?
N1 Fe1 N3 75.4(7) . . ?
N6 Fe1 N3 92.6(8) . . ?
N5 Fe1 N3 84.1(8) . . ?
N2 Fe1 N3 149.1(7) . . ?
N4 Fe1 N3 102.3(7) . . ?
C8 N1 C4 120.0 . . ?
C8 N1 Fe1 119.0(8) . . ?
C4 N1 Fe1 121.0(8) . . ?
N1 C8 C7 120.0 . . ?
N1 C8 C9 114.4(13) . . ?
C7 C8 C9 125.5(13) . . ?
C8 C7 C6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C6 C5 C4 120.0 . . ?
C3 C4 C5 127.8(13) . . ?
C3 C4 N1 111.9(14) . . ?
C5 C4 N1 120.0 . . ?
C3 N2 N7 108.0 . . ?
C3 N2 Fe1 114.7(8) . . ?
N7 N2 Fe1 137.2(8) . . ?
C4 C3 N2 118.3(14) . . ?
C4 C3 C2 133.7(14) . . ?
N2 C3 C2 108.0 . . ?
C1 C2 C3 108.0 . . ?
C2 C1 N7 108.0 . . ?
C1 N7 N2 108.0 . . ?
N6 C18 S2 178(3) . . ?
N5 C17 S1 176(4) . . ?
C9 N3 N8 108.0 . . ?
C9 N3 Fe1 113.2(10) . . ?
N8 N3 Fe1 137.8(11) . . ?
C8 C9 C10 133.4(14) . . ?
C8 C9 N3 117.9(14) . . ?
C10 C9 N3 108.0 . . ?
C9 C10 C11 108.0 . . ?
C10 C11 N8 108.0 . . ?
C11 N8 N3 108.0 . . ?
C18 N6 Fe1 168.7(18) . . ?
C17 N5 Fe1 156(3) . . ?
C12 N4 C16 120.0 . . ?
C12 N4 Fe1 120.0(9) . . ?
C16 N4 Fe1 118.8(9) . . ?
C13 C12 N4 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 C14 121(2) . 3_666 ?
C15 C14 C14 118(2) . 3_666 ?
C16 C15 C14 120.0 . . ?
C15 C16 N4 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.515
_diffrn_reflns_theta_full        17.00
_diffrn_measured_fraction_theta_full 0.520
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.087

#======================================================================
data_9-kbar
_database_code_depnum_ccdc_archive 'CCDC 857568'
#TrackingRef '- new_cif_all.cif'

#======================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Fe2 N16 S4, 2(C H4 O)'
_chemical_formula_sum            'C38 H34 Fe2 N16 S4 O2'
_chemical_formula_weight         984.78

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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'

_cell_length_a                   14.925(9)
_cell_length_b                   7.861(5)
_cell_length_c                   18.28(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.02(10)
_cell_angle_gamma                90.00
_cell_volume                     2002(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    941
_cell_measurement_theta_max      27.9470
_cell_measurement_theta_min      2.7277

_exptl_absorpt_correction_mu     0.000
_exptl_absorpt_correction_T_max  0.379
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
Gaussian integration over a grid
of 16 x 16 x 16 points = 4096 total grid points
Based upon method of Burnham (1966)

Data corrected for diamond-anvil cell absorption
Note that exptl_absorpt_correction_tmin and _tmax
the total correction factors applied to the intensities
The individual factors are:
range of dac transmission factors (min-max) 0.486 0.563
range of gasket transmission (min-max) 0.779 0.985
range of P media transmission (min-max) 1.000 1.000

thickness of diamond anvil 1: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1

thickness of diamond anvil 2: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1

Gasket shadowing corrections were made based upon
Gasket thickness = 220.0 microns, radius = 375.0 microns
Gasket absorption coeff = 27.90 mm-1
REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF
FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.20

Non-absorbing pressure medium
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'crystal fills hole of diamond-cell gasket'
_exptl_crystal_F_000             1012
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
The sample was placed inside a small screw-driven diamond anvil
cell (DAC) equipped with conical cut diamonds with 800 micron culets; the
diamonds were mounted on tungsten carbide backing seats giving an x-ray
aperture of approximately 80 deg. A stainless steel gasket was pre-indented
to a thickness of 180-200 microns and a hole of 400 micron was mechanically
drilled through the centre of the indentation, which served as a sample
chamber. The chamber was filled with a single crystal of 1, two small
ruby chips and silicone oil, which served as a pressure
transmitting medium.

The pressure was determined to be 9 kbar using the ruby fluorescence
technique
;

_diffrn_ambient_temperature      295(2)
_diffrn_ambient_pressure         900000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4115
_diffrn_reflns_av_R_equivalents  0.1466
_diffrn_reflns_av_sigmaI/netI    0.1229
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         17.23
_reflns_number_total             843
_reflns_number_gt                559
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_solution    'see _refine_special_details'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Basic models derived from the ambient pressure phases were used as a
starting point for refinement of structural parameters against high
pressure data (to a maximum resolution of 1.2 Angstroms) on F^2^.

Anisotropic temperature factors were refined for iron and sulphur atoms
only due to the relatively low resolution of the experiment. The low
(2/m) symmetry of this sample results in substantially incomplete data
(<65 % to 50 degrees 2theta), as reflected in the refinement statistics.
Low completeness, while not unusual for high pressure single crystal data
sets from small molecule (low symmetry) systems, means that a somewhat
high number of restraints are necessary in the refinement of structural
parameters, including AFIX 56 and AFIX 66 commands to model the
aromatic rings and restraints on the Uiso of carbon atoms as follows:

SIMU 0.02 0.04 3 O1 C8 C7 C6 C5 C4 C18 C3 C17 C9 C2 C10 C1 C11 C19 C12 C13 =
C14 C15 C16

The standard deviations used in this restraint and the maximum distance over
which the restraint applies are higher than normal, justified in light of the
acknowledged limitations of the data, as described above.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1180P)^2^+6.4121P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         843
_refine_ls_number_parameters     99
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.1016
_refine_ls_wR_factor_ref         0.2583
_refine_ls_wR_factor_gt          0.2263
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5630(2) 0.3898(4) 0.8192(2) 0.0536(19) Uani 1 1 d . . .
S2 S 0.2687(4) 0.1120(8) 0.7967(5) 0.076(3) Uani 1 1 d . . .
S1 S 0.8913(4) 0.5536(8) 0.9205(5) 0.076(3) Uani 1 1 d . . .
N1 N 0.6222(7) 0.3364(17) 0.9363(7) 0.039(5) Uiso 1 1 d G . .
C8 C 0.6692(8) 0.1833(14) 0.9629(9) 0.056(4) Uiso 1 1 d GU . .
C7 C 0.7124(8) 0.1533(12) 1.0429(10) 0.059(4) Uiso 1 1 d GU . .
H7 H 0.7439 0.0508 1.0606 0.070 Uiso 1 1 calc R . .
C6 C 0.7087(8) 0.2764(18) 1.0963(7) 0.055(5) Uiso 1 1 d GU . .
H6 H 0.7376 0.2563 1.1498 0.066 Uiso 1 1 calc R . .
C5 C 0.6617(9) 0.4295(15) 1.0697(9) 0.056(5) Uiso 1 1 d GU . .
H5 H 0.6592 0.5118 1.1055 0.067 Uiso 1 1 calc R . .
C4 C 0.6185(7) 0.4595(11) 0.9898(10) 0.056(4) Uiso 1 1 d GU . .
N2 N 0.5403(8) 0.6111(14) 0.8736(10) 0.052(5) Uiso 1 1 d G . .
C3 C 0.5765(8) 0.6047(14) 0.9568(10) 0.058(5) Uiso 1 1 d GU . .
C2 C 0.5570(9) 0.7635(18) 0.9850(7) 0.053(5) Uiso 1 1 d GU . .
H2 H 0.5730 0.7937 1.0374 0.063 Uiso 1 1 calc R . .
C1 C 0.5087(8) 0.8680(12) 0.9193(9) 0.054(5) Uiso 1 1 d GU . .
H1 H 0.4876 0.9787 0.9210 0.065 Uiso 1 1 calc R . .
N7 N 0.4984(7) 0.7738(17) 0.8505(7) 0.067(6) Uiso 1 1 d G . .
H7A H 0.4715 0.8091 0.8030 0.081 Uiso 1 1 calc R . .
C18 C 0.3660(14) 0.217(2) 0.8007(14) 0.049(7) Uiso 1 1 d . . .
C17 C 0.7793(15) 0.510(2) 0.8713(14) 0.048(6) Uiso 1 1 d . . .
N3 N 0.6256(8) 0.1438(12) 0.8260(9) 0.060(6) Uiso 1 1 d G . .
C9 C 0.6766(10) 0.0821(18) 0.9028(8) 0.055(5) Uiso 1 1 d GU . .
C10 C 0.7288(9) -0.0645(17) 0.8961(8) 0.059(5) Uiso 1 1 d GU . .
H10 H 0.7683 -0.1301 0.9375 0.071 Uiso 1 1 calc R . .
C11 C 0.7101(9) -0.0933(13) 0.8153(9) 0.060(6) Uiso 1 1 d GU . .
H11 H 0.7352 -0.1810 0.7944 0.072 Uiso 1 1 calc R . .
N8 N 0.6464(8) 0.0355(15) 0.7720(7) 0.055(5) Uiso 1 1 d G . .
H8 H 0.6242 0.0460 0.7218 0.065 Uiso 1 1 calc R . .
N6 N 0.4332(12) 0.287(2) 0.8047(12) 0.064(6) Uiso 1 1 d . . .
N5 N 0.7005(12) 0.479(2) 0.8380(12) 0.061(6) Uiso 1 1 d . . .
O1 O 0.3996(11) -0.1139(19) 0.6995(14) 0.104(6) Uiso 1 1 d U . .
C19 C 0.3896(15) -0.130(3) 0.6191(18) 0.086(9) Uiso 1 1 d U . .
H19A H 0.3640 -0.2406 0.6002 0.129 Uiso 1 1 calc R . .
H19B H 0.4513 -0.1175 0.6144 0.129 Uiso 1 1 calc R . .
H19C H 0.3469 -0.0441 0.5887 0.129 Uiso 1 1 calc R . .
N4 N 0.5231(9) 0.4536(17) 0.6997(7) 0.056(5) Uiso 1 1 d G . .
C12 C 0.4639(9) 0.3427(14) 0.6439(10) 0.074(5) Uiso 1 1 d GU . .
H12 H 0.4315 0.2567 0.6590 0.089 Uiso 1 1 calc R . .
C13 C 0.4533(9) 0.3604(17) 0.5656(9) 0.077(6) Uiso 1 1 d GU . .
H13 H 0.4137 0.2863 0.5283 0.093 Uiso 1 1 calc R . .
C14 C 0.5018(10) 0.489(2) 0.5429(7) 0.073(5) Uiso 1 1 d GU . .
C15 C 0.5610(9) 0.5998(15) 0.5987(10) 0.072(5) Uiso 1 1 d GU . .
H15 H 0.5935 0.6859 0.5835 0.086 Uiso 1 1 calc R . .
C16 C 0.5717(8) 0.5821(14) 0.6770(9) 0.077(5) Uiso 1 1 d GU . .
H16 H 0.6113 0.6563 0.7143 0.092 Uiso 1 1 calc R . .

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
Fe1 0.056(2) 0.056(3) 0.040(6) 0.0007(18) 0.007(3) 0.0032(16)
S2 0.078(5) 0.077(6) 0.063(11) 0.023(4) 0.013(5) 0.000(3)
S1 0.051(4) 0.076(6) 0.081(12) -0.009(4) 0.000(5) -0.009(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
Fe1 N6 2.029(17) . ?
Fe1 N1 2.045(13) . ?
Fe1 N5 2.076(17) . ?
Fe1 N2 2.091(11) . ?
Fe1 N4 2.109(12) . ?
Fe1 N3 2.131(9) . ?
S2 C18 1.65(2) . ?
S1 C17 1.63(2) . ?
N1 C8 1.3900 . ?
N1 C4 1.3900 . ?
C8 C7 1.3900 . ?
C8 C9 1.392(15) . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.337(12) . ?
N2 N7 1.4200 . ?
N2 C3 1.4200 . ?
C3 C2 1.4200 . ?
C2 C1 1.4200 . ?
C1 N7 1.4200 . ?
C18 N6 1.121(19) . ?
C17 N5 1.141(19) . ?
N3 N8 1.4200 . ?
N3 C9 1.4200 . ?
C9 C10 1.4200 . ?
C10 C11 1.4200 . ?
C11 N8 1.4200 . ?
O1 C19 1.43(3) . ?
N4 C12 1.3900 . ?
N4 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C14 1.56(2) 3_666 ?
C15 C16 1.3900 . ?

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
N6 Fe1 N1 95.1(7) . . ?
N6 Fe1 N5 175.8(7) . . ?
N1 Fe1 N5 82.3(6) . . ?
N6 Fe1 N2 94.8(6) . . ?
N1 Fe1 N2 75.9(6) . . ?
N5 Fe1 N2 87.7(5) . . ?
N6 Fe1 N4 93.3(7) . . ?
N1 Fe1 N4 171.4(5) . . ?
N5 Fe1 N4 89.2(7) . . ?
N2 Fe1 N4 105.1(6) . . ?
N6 Fe1 N3 91.3(5) . . ?
N1 Fe1 N3 74.8(6) . . ?
N5 Fe1 N3 84.8(5) . . ?
N2 Fe1 N3 150.4(7) . . ?
N4 Fe1 N3 103.4(5) . . ?
C8 N1 C4 120.0 . . ?
C8 N1 Fe1 121.2(8) . . ?
C4 N1 Fe1 118.8(8) . . ?
C7 C8 N1 120.0 . . ?
C7 C8 C9 126.5(13) . . ?
N1 C8 C9 113.1(13) . . ?
C8 C7 C6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C6 C5 C4 120.0 . . ?
C3 C4 C5 125.8(13) . . ?
C3 C4 N1 114.1(13) . . ?
C5 C4 N1 120.0 . . ?
N7 N2 C3 108.0 . . ?
N7 N2 Fe1 137.4(9) . . ?
C3 N2 Fe1 114.5(9) . . ?
C4 C3 C2 135.3(14) . . ?
C4 C3 N2 116.7(14) . . ?
C2 C3 N2 108.0 . . ?
C3 C2 C1 108.0 . . ?
N7 C1 C2 108.0 . . ?
C1 N7 N2 108.0 . . ?
N6 C18 S2 179(2) . . ?
N5 C17 S1 179(2) . . ?
N8 N3 C9 108.0 . . ?
N8 N3 Fe1 134.7(9) . . ?
C9 N3 Fe1 115.9(9) . . ?
C8 C9 C10 137.0(14) . . ?
C8 C9 N3 114.7(14) . . ?
C10 C9 N3 108.0 . . ?
C9 C10 C11 108.0 . . ?
C10 C11 N8 108.0 . . ?
N3 N8 C11 108.0 . . ?
C18 N6 Fe1 173.5(18) . . ?
C17 N5 Fe1 158(2) . . ?
C12 N4 C16 120.0 . . ?
C12 N4 Fe1 118.6(9) . . ?
C16 N4 Fe1 119.8(9) . . ?
C13 C12 N4 120.0 . . ?
C14 C13 C12 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 C14 117(2) . 3_666 ?
C13 C14 C14 123(2) . 3_666 ?
C14 C15 C16 120.0 . . ?
C15 C16 N4 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.693
_diffrn_reflns_theta_full        17.23
_diffrn_measured_fraction_theta_full 0.693
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.094

#======================================================================
data_13-kbar
_database_code_depnum_ccdc_archive 'CCDC 857569'
#TrackingRef '- new_cif_all.cif'

#======================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Fe2 N16 S4, 2(C H4 O)'
_chemical_formula_sum            'C38 H34 Fe2 N16 S4 O2'
_chemical_formula_weight         984.78

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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'

_cell_length_a                   14.849(6)
_cell_length_b                   7.823(4)
_cell_length_c                   18.233(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.47(7)
_cell_angle_gamma                90.00
_cell_volume                     1971(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.1714
_cell_measurement_theta_min      2.7406
_exptl_absorpt_correction_mu     0.000
_exptl_absorpt_correction_T_max  0.392
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
Gaussian integration over a grid
of 16 x 16 x 16 points = 4096 total grid points
Based upon method of Burnham (1966)

Data corrected for diamond-anvil cell absorption
Note that exptl_absorpt_correction_tmin and _tmax
the total correction factors applied to the intensities
The individual factors are:
range of dac transmission factors (min-max) 0.493 0.563
range of gasket transmission (min-max) 0.792 0.985
range of P media transmission (min-max) 1.000 1.000

thickness of diamond anvil 1: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1

thickness of diamond anvil 2: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1

Gasket shadowing corrections were made based upon
Gasket thickness = 220.0 microns, radius = 375.0 microns
Gasket absorption coeff = 27.90 mm-1
REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF
FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.20

Non-absorbing pressure medium
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'crystal fills hole of diamond-cell gasket'
_exptl_crystal_F_000             1012
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
The sample was placed inside a small screw-driven diamond anvil
cell (DAC) equipped with conical cut diamonds with 800 micron culets; the
diamonds were mounted on tungsten carbide backing seats giving an x-ray
aperture of approximately 80 deg. A stainless steel gasket was pre-indented
to a thickness of 180-200 microns and a hole of 400 micron was mechanically
drilled through the centre of the indentation, which served as a sample
chamber. The chamber was filled with a single crystal of 1, two small
ruby chips and silicone oil, which served as a pressure
transmitting medium.

The pressure was determined to be 13 kbar using the ruby fluorescence
technique
;

_diffrn_ambient_temperature      295(2)
_diffrn_ambient_pressure         1300000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2364
_diffrn_reflns_av_R_equivalents  0.1558
_diffrn_reflns_av_sigmaI/netI    0.2233
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         17.22
_reflns_number_total             828
_reflns_number_gt                402
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'see _refine_special_details'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Basic models derived from the ambient pressure phases were used as a
starting point for refinement of structural parameters against high
pressure data (to a maximum resolution of 1.2 angstroms) on F^2^.

Anisotropic temperature factors were refined for iron and sulphur atoms
only due to the relatively low resolution of the experiment. The low
(2/m) symmetry of this sample results in substantially incomplete data
(<65 % to 50 degrees 2theta), as reflected in the refinement statistics.
Low completeness, while not unusual for high pressure single crystal data
sets from small molecule (low symmetry) systems, means that a somewhat
high number of restraints are necessary in the refinement of structural
parameters, including AFIX 56 and AFIX 66 commands to model the
aromatic rings and restraints on the Uiso of carbon atoms as follows:

SIMU 0.02 0.04 3 O1 C8 C7 C6 C5 C4 C18 C3 C17 C9 C2 C10 C1 C11 C19 C12 C13 =
C14 C15 C16

The standard deviations used in this restraint and the maximum distance over
which the restraint applies are higher than normal, justified in light of the
acknowledged limitations of the data, as described above.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         828
_refine_ls_number_parameters     99
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1959
_refine_ls_R_factor_gt           0.1092
_refine_ls_wR_factor_ref         0.2694
_refine_ls_wR_factor_gt          0.2122
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5641(3) 0.3903(5) 0.8217(3) 0.053(2) Uani 1 1 d . . .
S2 S 0.2675(5) 0.1179(10) 0.7971(5) 0.064(4) Uani 1 1 d . . .
S1 S 0.8923(5) 0.5600(10) 0.9219(5) 0.066(4) Uani 1 1 d . . .
N1 N 0.6240(9) 0.337(3) 0.9381(9) 0.056(4) Uiso 1 1 d GU . .
C8 C 0.6699(11) 0.182(2) 0.9634(11) 0.056(4) Uiso 1 1 d GU . .
C7 C 0.7122(9) 0.1465(17) 1.0435(13) 0.054(5) Uiso 1 1 d GU . .
H7 H 0.7429 0.0423 1.0604 0.065 Uiso 1 1 calc R . .
C6 C 0.7086(9) 0.267(3) 1.0983(8) 0.057(5) Uiso 1 1 d GU . .
H6 H 0.7369 0.2436 1.1519 0.068 Uiso 1 1 calc R . .
C5 C 0.6627(12) 0.423(2) 1.0731(13) 0.059(5) Uiso 1 1 d GU . .
H5 H 0.6603 0.5036 1.1098 0.071 Uiso 1 1 calc R . .
C4 C 0.6204(10) 0.4581(17) 0.9930(15) 0.057(4) Uiso 1 1 d GU . .
N2 N 0.5376(11) 0.611(2) 0.8720(13) 0.056(4) Uiso 1 1 d GU . .
C3 C 0.5751(10) 0.607(2) 0.9556(13) 0.060(5) Uiso 1 1 d GU . .
C2 C 0.5578(10) 0.769(3) 0.9833(8) 0.058(5) Uiso 1 1 d GU . .
H2 H 0.5750 0.8009 1.0357 0.070 Uiso 1 1 calc R . .
C1 C 0.5095(10) 0.8731(17) 0.9167(11) 0.059(5) Uiso 1 1 d GU . .
H1 H 0.4895 0.9854 0.9179 0.071 Uiso 1 1 calc R . .
N7 N 0.4970(9) 0.776(2) 0.8479(8) 0.062(5) Uiso 1 1 d GU . .
H7A H 0.4697 0.8104 0.8000 0.074 Uiso 1 1 calc R . .
C18 C 0.3652(17) 0.219(3) 0.8015(16) 0.040(7) Uiso 1 1 d U . .
C17 C 0.784(2) 0.511(3) 0.8721(18) 0.053(7) Uiso 1 1 d U . .
N3 N 0.6250(10) 0.1500(16) 0.8252(13) 0.058(4) Uiso 1 1 d GU . .
C9 C 0.6727(13) 0.081(3) 0.9018(10) 0.055(4) Uiso 1 1 d GU . .
C10 C 0.7241(11) -0.067(2) 0.8945(11) 0.060(5) Uiso 1 1 d GU . .
H10 H 0.7616 -0.1365 0.9357 0.072 Uiso 1 1 calc R . .
C11 C 0.7081(11) -0.0898(16) 0.8135(13) 0.057(5) Uiso 1 1 d GU . .
H11 H 0.7332 -0.1773 0.7922 0.068 Uiso 1 1 calc R . .
N8 N 0.6468(10) 0.044(2) 0.7706(9) 0.056(5) Uiso 1 1 d GU . .
H8 H 0.6265 0.0586 0.7204 0.067 Uiso 1 1 calc R . .
N6 N 0.4341(14) 0.289(3) 0.8026(13) 0.059(5) Uiso 1 1 d U . .
N5 N 0.6998(16) 0.479(3) 0.8418(14) 0.061(4) Uiso 1 1 d U . .
O1 O 0.3940(12) -0.100(2) 0.6974(14) 0.077(7) Uiso 1 1 d U . .
C19 C 0.3867(18) -0.137(3) 0.6192(19) 0.084(11) Uiso 1 1 d U . .
H19A H 0.3990 -0.2563 0.6149 0.126 Uiso 1 1 calc R . .
H19B H 0.4334 -0.0703 0.6066 0.126 Uiso 1 1 calc R . .
H19C H 0.3229 -0.1091 0.5832 0.126 Uiso 1 1 calc R . .
N4 N 0.5232(12) 0.455(2) 0.7025(8) 0.063(5) Uiso 1 1 d GU . .
C12 C 0.4633(11) 0.3430(17) 0.6466(14) 0.068(5) Uiso 1 1 d GU . .
H12 H 0.4312 0.2561 0.6620 0.082 Uiso 1 1 calc R . .
C13 C 0.4514(10) 0.361(2) 0.5678(12) 0.067(6) Uiso 1 1 d GU . .
H13 H 0.4113 0.2861 0.5304 0.080 Uiso 1 1 calc R . .
C14 C 0.4994(14) 0.491(3) 0.5448(8) 0.068(6) Uiso 1 1 d GU . .
C15 C 0.5592(12) 0.6026(19) 0.6008(14) 0.066(5) Uiso 1 1 d GU . .
H15 H 0.5914 0.6894 0.5854 0.079 Uiso 1 1 calc R . .
C16 C 0.5712(10) 0.585(2) 0.6796(12) 0.067(5) Uiso 1 1 d GU . .
H16 H 0.6112 0.6594 0.7170 0.080 Uiso 1 1 calc R . .

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
Fe1 0.054(3) 0.058(5) 0.047(7) 0.001(3) 0.018(3) 0.008(3)
S2 0.073(6) 0.063(9) 0.053(14) 0.021(5) 0.020(7) 0.003(5)
S1 0.038(5) 0.064(9) 0.080(13) -0.014(5) 0.005(6) 0.002(4)

_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
Fe1 N6 2.00(2) . ?
Fe1 N1 2.022(14) . ?
Fe1 N5 2.03(2) . ?
Fe1 N2 2.062(14) . ?
Fe1 N3 2.077(12) . ?
Fe1 N4 2.091(13) . ?
S2 C18 1.63(3) . ?
S1 C17 1.58(3) . ?
N1 C8 1.3900 . ?
N1 C4 1.3900 . ?
C8 C9 1.383(18) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.393(16) . ?
N2 N7 1.4200 . ?
N2 C3 1.4200 . ?
C3 C2 1.4200 . ?
C2 C1 1.4200 . ?
C1 N7 1.4200 . ?
C18 N6 1.15(2) . ?
C17 N5 1.19(2) . ?
N3 C9 1.4200 . ?
N3 N8 1.4200 . ?
C9 C10 1.4200 . ?
C10 C11 1.4200 . ?
C11 N8 1.4200 . ?
O1 C19 1.42(3) . ?
N4 C12 1.3900 . ?
N4 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C14 1.65(3) 3_666 ?
C15 C16 1.3900 . ?

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
N6 Fe1 N1 97.3(8) . . ?
N6 Fe1 N5 176.6(8) . . ?
N1 Fe1 N5 81.6(8) . . ?
N6 Fe1 N2 94.6(7) . . ?
N1 Fe1 N2 77.7(9) . . ?
N5 Fe1 N2 88.3(7) . . ?
N6 Fe1 N3 91.6(7) . . ?
N1 Fe1 N3 76.3(8) . . ?
N5 Fe1 N3 85.0(7) . . ?
N2 Fe1 N3 153.8(9) . . ?
N6 Fe1 N4 91.1(9) . . ?
N1 Fe1 N4 171.4(7) . . ?
N5 Fe1 N4 89.9(8) . . ?
N2 Fe1 N4 103.3(8) . . ?
N3 Fe1 N4 102.0(7) . . ?
C8 N1 C4 120.0 . . ?
C8 N1 Fe1 120.1(14) . . ?
C4 N1 Fe1 119.9(14) . . ?
C9 C8 C7 127(2) . . ?
C9 C8 N1 113(2) . . ?
C7 C8 N1 120.0 . . ?
C8 C7 C6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C6 C5 C4 120.0 . . ?
C5 C4 N1 120.0 . . ?
C5 C4 C3 129(2) . . ?
N1 C4 C3 111(2) . . ?
N7 N2 C3 108.0 . . ?
N7 N2 Fe1 138.6(13) . . ?
C3 N2 Fe1 113.2(13) . . ?
C4 C3 C2 133.7(19) . . ?
C4 C3 N2 118.3(19) . . ?
C2 C3 N2 108.0 . . ?
C3 C2 C1 108.0 . . ?
N7 C1 C2 108.0 . . ?
N2 N7 C1 108.0 . . ?
N6 C18 S2 178(3) . . ?
N5 C17 S1 173(3) . . ?
C9 N3 N8 108.0 . . ?
C9 N3 Fe1 115.3(13) . . ?
N8 N3 Fe1 135.6(13) . . ?
C8 C9 N3 116(2) . . ?
C8 C9 C10 136(2) . . ?
N3 C9 C10 108.0 . . ?
C9 C10 C11 108.0 . . ?
N8 C11 C10 108.0 . . ?
C11 N8 N3 108.0 . . ?
C18 N6 Fe1 170(2) . . ?
C17 N5 Fe1 163(2) . . ?
C12 N4 C16 120.0 . . ?
C12 N4 Fe1 118.3(14) . . ?
C16 N4 Fe1 120.2(14) . . ?
N4 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 C14 124(3) . 3_666 ?
C15 C14 C14 116(3) . 3_666 ?
C16 C15 C14 120.0 . . ?
C15 C16 N4 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.696
_diffrn_reflns_theta_full        17.22
_diffrn_measured_fraction_theta_full 0.696
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.096

#======================================================================
data_16-kbar
_database_code_depnum_ccdc_archive 'CCDC 857570'
#TrackingRef '- new_cif_all.cif'

#======================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Fe2 N16 S4, 2(C H4 O)'
_chemical_formula_sum            'C38 H34 Fe2 N16 S4 O2'
_chemical_formula_weight         984.78

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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'

_cell_length_a                   14.80(2)
_cell_length_b                   7.69(2)
_cell_length_c                   18.15(11)
_cell_angle_alpha                91.0(5)
_cell_angle_beta                 112.0(4)
_cell_angle_gamma                89.4(2)
_cell_volume                     1915(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.1440
_cell_measurement_theta_min      2.7486
_exptl_absorpt_correction_mu     0.000
_exptl_absorpt_correction_T_max  0.397
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
Gaussian integration over a grid
of 16 x 16 x 16 points = 4096 total grid points
Based upon method of Burnham (1966)

Data corrected for diamond-anvil cell absorption
Note that exptl_absorpt_correction_tmin and _tmax
the total correction factors applied to the intensities
The individual factors are:
range of dac transmission factors (min-max) 0.497 0.564
range of gasket transmission (min-max) 0.799 0.984
range of P media transmission (min-max) 1.000 1.000

thickness of diamond anvil 1: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1

thickness of diamond anvil 2: 1.430 mm, mu = 0.2000 mm-1
thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1

Gasket shadowing corrections were made based upon
Gasket thickness = 220.0 microns, radius = 375.0 microns
Gasket absorption coeff = 27.90 mm-1
REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF
FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.20

Non-absorbing pressure medium
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'crystal fills hole of diamond-cell gasket'
_exptl_crystal_F_000             1012
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
The sample was placed inside a small screw-driven diamond anvil
cell (DAC) equipped with conical cut diamonds with 800 micron culets; the
diamonds were mounted on tungsten carbide backing seats giving an x-ray
aperture of approximately 80 deg. A stainless steel gasket was pre-indented
to a thickness of 180-200 microns and a hole of 400 micron was mechanically
drilled through the centre of the indentation, which served as a sample
chamber. The chamber was filled with a single crystal of 1, two small
ruby chips and silicone oil, which served as a pressure
transmitting medium.

The pressure was determined to be 16 kbar using the ruby fluorescence
technique
;

_diffrn_ambient_temperature      295(2)
_diffrn_ambient_pressure         1600000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3749
_diffrn_reflns_av_R_equivalents  0.3196
_diffrn_reflns_av_sigmaI/netI    0.1983
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         15.85
_reflns_number_total             625
_reflns_number_gt                408
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'see _refine_special_details'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Basic models derived from the ambient pressure phases were used as a
starting point for refinement of structural parameters against high
pressure data (to a maximum resolution of 1.2 Angstroms) on F^2^.

Anisotropic temperature factors were refined for iron and sulphur atoms
only due to the relatively low resolution of the experiment. The low
(2/m) symmetry of this sample results in substantially incomplete data
(<65 % to 50 degrees 2theta), as reflected in the refinement statistics.
Low completeness, while not unusual for high pressure single crystal data
sets from small molecule (low symmetry) systems, means that a somewhat
high number of restraints are necessary in the refinement of structural
parameters, including AFIX 56 and AFIX 66 commands to model the
aromatic rings and restraints on the Uiso of carbon atoms as follows:

SIMU 0.02 0.04 3 O1 C8 C7 C6 C5 C4 C18 C3 C17 C9 C2 C10 C1 C11 C19 C12 C13 =
C14 C15 C16

The standard deviations used in this restraint and the maximum distance over
which the restraint applies are higher than normal, justified in light of the
acknowledged limitations of the data, as described above.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1991P)^2^+15.8207P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         625
_refine_ls_number_parameters     99
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.1180
_refine_ls_wR_factor_ref         0.3419
_refine_ls_wR_factor_gt          0.2964
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5645(3) 0.3932(7) 0.8231(4) 0.064(3) Uani 1 1 d . . .
S2 S 0.2643(7) 0.1289(12) 0.8000(7) 0.075(5) Uani 1 1 d . . .
S1 S 0.8920(6) 0.5663(12) 0.9235(7) 0.068(5) Uani 1 1 d . . .
N1 N 0.6170(11) 0.338(3) 0.9349(11) 0.048(8) Uiso 1 1 d G . .
C8 C 0.6631(14) 0.179(2) 0.9599(13) 0.057(6) Uiso 1 1 d GU . .
C7 C 0.7071(12) 0.145(2) 1.0405(15) 0.058(6) Uiso 1 1 d GU . .
H7 H 0.7379 0.0391 1.0572 0.069 Uiso 1 1 calc R . .
C6 C 0.7050(12) 0.270(3) 1.0962(11) 0.056(6) Uiso 1 1 d GU . .
H6 H 0.7345 0.2476 1.1502 0.067 Uiso 1 1 calc R . .
C5 C 0.6590(14) 0.429(3) 1.0712(14) 0.059(6) Uiso 1 1 d GU . .
H5 H 0.6576 0.5127 1.1085 0.071 Uiso 1 1 calc R . .
C4 C 0.6150(12) 0.4631(19) 0.9906(16) 0.059(6) Uiso 1 1 d GU . .
N2 N 0.5434(14) 0.607(2) 0.8700(16) 0.063(10) Uiso 1 1 d G . .
C3 C 0.5768(12) 0.613(3) 0.9542(16) 0.061(7) Uiso 1 1 d GU . .
C2 C 0.5513(13) 0.778(3) 0.9774(11) 0.059(7) Uiso 1 1 d GU . .
H2 H 0.5645 0.8160 1.0293 0.071 Uiso 1 1 calc R . .
C1 C 0.5021(13) 0.874(2) 0.9075(14) 0.062(8) Uiso 1 1 d GU . .
H1 H 0.4775 0.9862 0.9056 0.075 Uiso 1 1 calc R . .
N7 N 0.4972(12) 0.768(3) 0.8411(11) 0.062(9) Uiso 1 1 d G . .
H7A H 0.4710 0.7971 0.7921 0.074 Uiso 1 1 calc R . .
C18 C 0.370(2) 0.229(4) 0.8070(19) 0.039(10) Uiso 1 1 d . . .
C17 C 0.777(2) 0.516(3) 0.8758(19) 0.033(10) Uiso 1 1 d . . .
N3 N 0.6226(12) 0.154(2) 0.8224(15) 0.065(10) Uiso 1 1 d G . .
C9 C 0.6717(16) 0.084(3) 0.8990(12) 0.057(6) Uiso 1 1 d GU . .
C10 C 0.7268(14) -0.062(3) 0.8909(13) 0.059(7) Uiso 1 1 d GU . .
H10 H 0.7658 -0.1327 0.9318 0.071 Uiso 1 1 calc R . .
C11 C 0.7116(14) -0.083(2) 0.8092(15) 0.061(8) Uiso 1 1 d GU . .
H11 H 0.7391 -0.1686 0.7873 0.074 Uiso 1 1 calc R . .
N8 N 0.6472(12) 0.051(2) 0.7669(11) 0.064(9) Uiso 1 1 d G . .
H8 H 0.6268 0.0670 0.7165 0.077 Uiso 1 1 calc R . .
N6 N 0.4398(17) 0.296(3) 0.8080(16) 0.054(9) Uiso 1 1 d . . .
N5 N 0.697(2) 0.485(3) 0.8424(19) 0.074(10) Uiso 1 1 d . . .
O1 O 0.3947(15) -0.092(3) 0.6958(17) 0.083(8) Uiso 1 1 d U . .
C19 C 0.385(2) -0.115(4) 0.616(2) 0.086(12) Uiso 1 1 d U . .
H19A H 0.3445 -0.2140 0.5932 0.129 Uiso 1 1 calc R . .
H19B H 0.4481 -0.1339 0.6135 0.129 Uiso 1 1 calc R . .
H19C H 0.3558 -0.0130 0.5865 0.129 Uiso 1 1 calc R . .
N4 N 0.5196(14) 0.458(3) 0.7037(11) 0.059(9) Uiso 1 1 d G . .
C12 C 0.4614(13) 0.344(2) 0.6453(16) 0.078(8) Uiso 1 1 d GU . .
H12 H 0.4282 0.2557 0.6587 0.093 Uiso 1 1 calc R . .
C13 C 0.4530(14) 0.362(3) 0.5670(14) 0.079(8) Uiso 1 1 d GU . .
H13 H 0.4141 0.2857 0.5279 0.095 Uiso 1 1 calc R . .
C14 C 0.5028(16) 0.494(3) 0.5470(11) 0.080(8) Uiso 1 1 d GU . .
C15 C 0.5609(14) 0.608(2) 0.6053(16) 0.075(8) Uiso 1 1 d GU . .
H15 H 0.5942 0.6962 0.5919 0.090 Uiso 1 1 calc R . .
C16 C 0.5694(12) 0.590(2) 0.6837(14) 0.075(8) Uiso 1 1 d GU . .
H16 H 0.6083 0.6662 0.7227 0.091 Uiso 1 1 calc R . .

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
Fe1 0.072(4) 0.057(6) 0.061(9) 0.002(3) 0.024(4) 0.003(3)
S2 0.084(7) 0.051(10) 0.077(16) 0.020(5) 0.014(7) 0.008(6)
S1 0.058(7) 0.066(10) 0.068(16) -0.006(5) 0.012(7) 0.008(5)

_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
Fe1 N2 1.912(19) . ?
Fe1 N6 1.92(3) . ?
Fe1 N1 1.94(2) . ?
Fe1 N5 2.00(3) . ?
Fe1 N3 2.022(16) . ?
Fe1 N4 2.08(2) . ?
S2 C18 1.71(3) . ?
S1 C17 1.64(3) . ?
N1 C8 1.3900 . ?
N1 C4 1.3900 . ?
C8 C9 1.36(2) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.35(2) . ?
N2 N7 1.4200 . ?
N2 C3 1.4200 . ?
C3 C2 1.4200 . ?
C2 C1 1.4200 . ?
C1 N7 1.4200 . ?
C18 N6 1.15(3) . ?
C17 N5 1.13(3) . ?
N3 C9 1.4200 . ?
N3 N8 1.4200 . ?
C9 C10 1.4200 . ?
C10 C11 1.4200 . ?
C11 N8 1.4200 . ?
O1 C19 1.41(4) . ?
N4 C12 1.3900 . ?
N4 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C14 1.68(4) 3_666 ?
C15 C16 1.3900 . ?

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
N2 Fe1 N6 95.3(10) . . ?
N2 Fe1 N1 78.5(12) . . ?
N6 Fe1 N1 92.6(11) . . ?
N2 Fe1 N5 86.0(10) . . ?
N6 Fe1 N5 177.2(11) . . ?
N1 Fe1 N5 85.2(11) . . ?
N2 Fe1 N3 155.6(12) . . ?
N6 Fe1 N3 91.7(9) . . ?
N1 Fe1 N3 77.9(11) . . ?
N5 Fe1 N3 86.1(9) . . ?
N2 Fe1 N4 101.9(11) . . ?
N6 Fe1 N4 92.1(11) . . ?
N1 Fe1 N4 175.2(8) . . ?
N5 Fe1 N4 90.0(12) . . ?
N3 Fe1 N4 101.2(10) . . ?
C8 N1 C4 120.0 . . ?
C8 N1 Fe1 120.2(15) . . ?
C4 N1 Fe1 119.7(15) . . ?
C9 C8 N1 112(2) . . ?
C9 C8 C7 127(2) . . ?
N1 C8 C7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C5 C6 C7 120.0 . . ?
C4 C5 C6 120.0 . . ?
C3 C4 C5 129(2) . . ?
C3 C4 N1 110(2) . . ?
C5 C4 N1 120.0 . . ?
N7 N2 C3 108.0 . . ?
N7 N2 Fe1 135.6(17) . . ?
C3 N2 Fe1 116.3(17) . . ?
C4 C3 C2 136(2) . . ?
C4 C3 N2 115(2) . . ?
C2 C3 N2 108.0 . . ?
C3 C2 C1 108.0 . . ?
C2 C1 N7 108.0 . . ?
N2 N7 C1 108.0 . . ?
N6 C18 S2 177(3) . . ?
N5 C17 S1 179(3) . . ?
C9 N3 N8 108.0 . . ?
C9 N3 Fe1 114.3(16) . . ?
N8 N3 Fe1 135.8(15) . . ?
C8 C9 N3 115(2) . . ?
C8 C9 C10 137(2) . . ?
N3 C9 C10 108.0 . . ?
C11 C10 C9 108.0 . . ?
C10 C11 N8 108.0 . . ?
C11 N8 N3 108.0 . . ?
C18 N6 Fe1 172(3) . . ?
C17 N5 Fe1 159(3) . . ?
C12 N4 C16 120.0 . . ?
C12 N4 Fe1 120.0(15) . . ?
C16 N4 Fe1 117.8(15) . . ?
C13 C12 N4 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 C14 119(4) . 3_666 ?
C15 C14 C14 121(4) . 3_666 ?
C16 C15 C14 120.0 . . ?
C15 C16 N4 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.695
_diffrn_reflns_theta_full        15.85
_diffrn_measured_fraction_theta_full 0.683
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.116