# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_1B_380K
_database_code_depnum_ccdc_archive 'CCDC 1428204'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Fe N10 S2'
_chemical_formula_weight         432.33

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'
N N 0.0061 0.0033 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   8.496(8)
_cell_length_b                   9.275(8)
_cell_length_c                   25.99(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.228(14)
_cell_angle_gamma                90
_cell_volume                     2032(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    380(2)

_cell_measurement_reflns_used    3894

_cell_measurement_theta_min      3.1607

_cell_measurement_theta_max      27.4807


_exptl_crystal_description       block

_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.967
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.7140

_exptl_absorpt_correction_T_max  0.8533

_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      380(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'

_diffrn_measurement_method       dtprofit.ref

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            13061
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.161
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             4456
_reflns_number_gt                1938
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1110P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     247
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2474
_refine_ls_wR_factor_gt          0.2093
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.073
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.41111(7) 0.32482(9) 0.12540(3) 0.0933(3) Uani 1 1 d . . . . .
S2 S 0.1338(2) 0.7514(3) 0.06151(11) 0.1797(10) Uani 1 1 d . . . . .
S1 S 0.75413(18) -0.0699(2) 0.13111(8) 0.1381(7) Uani 1 1 d . . . . .
N10 N 0.2898(5) 0.5156(6) 0.1023(2) 0.1163(14) Uani 1 1 d . . . . .
N9 N 0.5443(6) 0.1413(6) 0.1499(2) 0.1177(14) Uani 1 1 d . . . . .
N3 N 0.6322(4) 0.4466(5) 0.14791(17) 0.0981(12) Uani 1 1 d . . . . .
N7 N 0.2473(5) 0.3328(6) 0.2356(2) 0.1134(14) Uani 1 1 d . . . . .
N4 N 0.5253(6) 0.3243(5) 0.05573(17) 0.1101(13) Uani 1 1 d . . . . .
N6 N 0.2566(4) 0.2943(5) 0.18659(19) 0.1007(12) Uani 1 1 d . . . . .
N8 N 0.1184(6) 0.2641(6) 0.2474(2) 0.1213(16) Uani 1 1 d . . . . .
C13 C 0.2252(6) 0.6120(7) 0.0846(2) 0.1042(15) Uani 1 1 d . . . . .
N5 N 0.2218(6) 0.1918(5) 0.08836(19) 0.1085(13) Uani 1 1 d . . . . .
N2 N 0.7068(5) 0.5151(6) 0.18774(17) 0.1110(13) Uani 1 1 d . . . . .
C12 C 0.6306(5) 0.0535(6) 0.14255(18) 0.0943(14) Uani 1 1 d . . . . .
N1 N 0.8442(5) 0.5551(6) 0.1734(2) 0.1214(16) Uani 1 1 d . . . . .
C3 C 0.7213(6) 0.4498(7) 0.1095(2) 0.1114(16) Uani 1 1 d . . . . .
C9 C 0.1350(6) 0.2036(6) 0.1691(3) 0.1099(17) Uani 1 1 d . . . . .
C10 C 0.0513(7) 0.1847(8) 0.2093(3) 0.128(2) Uani 1 1 d . . . . .
H13 H -0.0373 0.1262 0.2098 0.154 Uiso 1 1 calc R U . . .
C4 C 0.6579(8) 0.3797(8) 0.0603(3) 0.134(2) Uani 1 1 d . . . . .
H5 H 0.7179 0.3774 0.0327 0.161 Uiso 1 1 calc R U . . .
C8 C 0.1258(7) 0.1525(7) 0.1163(3) 0.1207(19) Uani 1 1 d . . . . .
H12 H 0.0457 0.0888 0.1036 0.145 Uiso 1 1 calc R U . . .
C2 C 0.8536(7) 0.5181(8) 0.1248(3) 0.136(2) Uani 1 1 d . . . . .
H4 H 0.9366 0.5367 0.1056 0.163 Uiso 1 1 calc R U . . .
C7 C 0.2094(11) 0.1409(8) 0.0352(3) 0.147(2) Uani 1 1 d . U . . .
H10A H 0.1484 0.0522 0.0325 0.176 Uiso 0.51(2) 1 calc R U P A 1
H11A H 0.1507 0.2116 0.0129 0.176 Uiso 0.51(2) 1 calc R U P A 1
H10B H 0.0986 0.1342 0.0208 0.176 Uiso 0.49(2) 1 calc R U P A 2
H11B H 0.2560 0.0456 0.0343 0.176 Uiso 0.49(2) 1 calc R U P A 2
C11 C 0.0763(10) 0.2871(10) 0.3006(3) 0.179(3) Uani 1 1 d . . . . .
H16 H 0.1627 0.3342 0.3214 0.268 Uiso 1 1 calc R U . . .
H14 H 0.0560 0.1957 0.3158 0.268 Uiso 1 1 calc R U . . .
H15 H -0.0169 0.3462 0.2989 0.268 Uiso 1 1 calc R U . . .
C5 C 0.4605(11) 0.2527(10) 0.0067(3) 0.153(3) Uani 1 1 d . U . . .
H6A H 0.5475 0.2246 -0.0120 0.230 Uiso 0.51(2) 1 calc R U P A 1
H7A H 0.3949 0.3208 -0.0148 0.230 Uiso 0.51(2) 1 calc R U P A 1
H6B H 0.4970 0.3031 -0.0223 0.230 Uiso 0.49(2) 1 calc R U P A 2
H7B H 0.4995 0.1544 0.0067 0.230 Uiso 0.49(2) 1 calc R U P A 2
C1 C 0.9582(8) 0.6429(9) 0.2092(3) 0.166(3) Uani 1 1 d . . . . .
H2 H 0.9008 0.7136 0.2264 0.249 Uiso 1 1 calc R U . . .
H3 H 1.0315 0.6906 0.1896 0.249 Uiso 1 1 calc R U . . .
H1 H 1.0155 0.5809 0.2346 0.249 Uiso 1 1 calc R U . . .
C6B C 0.301(3) 0.252(3) 0.0008(4) 0.155(10) Uani 0.49(2) 1 d . . P A 2
H9B H 0.2651 0.2318 -0.0354 0.186 Uiso 0.49(2) 1 calc R U P A 2
H8B H 0.2659 0.3483 0.0079 0.186 Uiso 0.49(2) 1 calc R U P A 2
C6A C 0.358(2) 0.115(2) 0.0160(6) 0.141(7) Uani 0.51(2) 1 d . . P A 1
H9A H 0.3371 0.0626 -0.0165 0.169 Uiso 0.51(2) 1 calc R U P A 1
H8A H 0.4212 0.0522 0.0405 0.169 Uiso 0.51(2) 1 calc R U P A 1


_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 N10 2.097(5) . ?
Fe1 N9 2.098(5) . ?
Fe1 N5 2.156(5) . ?
Fe1 N4 2.159(5) . ?
Fe1 N6 2.204(5) . ?
Fe1 N3 2.207(4) . ?
S2 C13 1.586(6) . ?
S1 C12 1.606(6) . ?
N10 C13 1.118(7) . ?
N9 C12 1.127(6) . ?
N3 N2 1.309(5) . ?
N3 C3 1.326(6) . ?
N7 N8 1.335(6) . ?
N7 N6 1.335(6) . ?
N4 C4 1.230(7) . ?
N4 C5 1.481(8) . ?
N6 C9 1.365(7) . ?
N8 C10 1.305(8) . ?
N8 C11 1.487(9) . ?
N5 C8 1.214(7) . ?
N5 C7 1.452(8) . ?
N2 N1 1.322(6) . ?
N1 C2 1.320(8) . ?
N1 C1 1.497(8) . ?
C3 C2 1.308(8) . ?
C3 C4 1.476(9) . ?
C9 C10 1.348(8) . ?
C9 C8 1.443(9) . ?
C10 H13 0.9300 . ?
C4 H5 0.9300 . ?
C8 H12 0.9300 . ?
C2 H4 0.9300 . ?
C7 C6A 1.435(18) . ?
C7 C6B 1.622(19) . ?
C7 H10A 0.9700 . ?
C7 H11A 0.9700 . ?
C7 H10B 0.9700 . ?
C7 H11B 0.9700 . ?
C11 H16 0.9600 . ?
C11 H14 0.9600 . ?
C11 H15 0.9600 . ?
C5 C6B 1.344(19) . ?
C5 C6A 1.584(18) . ?
C5 H6A 0.9700 . ?
C5 H7A 0.9700 . ?
C5 H6B 0.9700 . ?
C5 H7B 0.9700 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
C1 H1 0.9600 . ?
C6B H9B 0.9700 . ?
C6B H8B 0.9700 . ?
C6A H9A 0.9700 . ?
C6A H8A 0.9700 . ?

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
N10 Fe1 N9 176.63(19) . . ?
N10 Fe1 N5 92.48(19) . . ?
N9 Fe1 N5 90.8(2) . . ?
N10 Fe1 N4 91.06(19) . . ?
N9 Fe1 N4 88.30(19) . . ?
N5 Fe1 N4 90.8(2) . . ?
N10 Fe1 N6 89.94(17) . . ?
N9 Fe1 N6 91.40(18) . . ?
N5 Fe1 N6 76.69(19) . . ?
N4 Fe1 N6 167.44(18) . . ?
N10 Fe1 N3 90.87(17) . . ?
N9 Fe1 N3 85.77(18) . . ?
N5 Fe1 N3 166.85(18) . . ?
N4 Fe1 N3 76.46(18) . . ?
N6 Fe1 N3 116.04(17) . . ?
C13 N10 Fe1 172.3(5) . . ?
C12 N9 Fe1 150.7(5) . . ?
N2 N3 C3 108.6(4) . . ?
N2 N3 Fe1 140.3(3) . . ?
C3 N3 Fe1 111.1(4) . . ?
N8 N7 N6 103.8(5) . . ?
C4 N4 C5 120.5(6) . . ?
C4 N4 Fe1 114.9(4) . . ?
C5 N4 Fe1 124.4(5) . . ?
N7 N6 C9 110.5(5) . . ?
N7 N6 Fe1 140.0(4) . . ?
C9 N6 Fe1 109.4(4) . . ?
C10 N8 N7 112.9(5) . . ?
C10 N8 C11 130.7(6) . . ?
N7 N8 C11 116.4(7) . . ?
N10 C13 S2 177.8(6) . . ?
C8 N5 C7 119.9(6) . . ?
C8 N5 Fe1 115.1(4) . . ?
C7 N5 Fe1 124.9(5) . . ?
N3 N2 N1 105.7(5) . . ?
N9 C12 S1 178.9(5) . . ?
C2 N1 N2 111.0(5) . . ?
C2 N1 C1 128.6(6) . . ?
N2 N1 C1 120.2(6) . . ?
C2 C3 N3 109.4(6) . . ?
C2 C3 C4 133.1(6) . . ?
N3 C3 C4 117.5(5) . . ?
C10 C9 N6 105.8(6) . . ?
C10 C9 C8 136.3(6) . . ?
N6 C9 C8 117.9(5) . . ?
N8 C10 C9 107.0(6) . . ?
N8 C10 H13 126.5 . . ?
C9 C10 H13 126.5 . . ?
N4 C4 C3 119.8(6) . . ?
N4 C4 H5 120.1 . . ?
C3 C4 H5 120.1 . . ?
N5 C8 C9 120.6(5) . . ?
N5 C8 H12 119.7 . . ?
C9 C8 H12 119.7 . . ?
C3 C2 N1 105.3(6) . . ?
C3 C2 H4 127.4 . . ?
N1 C2 H4 127.4 . . ?
C6A C7 N5 115.0(8) . . ?
N5 C7 C6B 109.6(7) . . ?
C6A C7 H10A 108.5 . . ?
N5 C7 H10A 108.5 . . ?
C6A C7 H11A 108.5 . . ?
N5 C7 H11A 108.5 . . ?
H10A C7 H11A 107.5 . . ?
N5 C7 H10B 109.7 . . ?
C6B C7 H10B 109.7 . . ?
N5 C7 H11B 109.7 . . ?
C6B C7 H11B 109.7 . . ?
H10B C7 H11B 108.2 . . ?
N8 C11 H16 109.5 . . ?
N8 C11 H14 109.5 . . ?
H16 C11 H14 109.5 . . ?
N8 C11 H15 109.5 . . ?
H16 C11 H15 109.5 . . ?
H14 C11 H15 109.5 . . ?
C6B C5 N4 111.2(8) . . ?
N4 C5 C6A 112.5(7) . . ?
N4 C5 H6A 109.1 . . ?
C6A C5 H6A 109.1 . . ?
N4 C5 H7A 109.1 . . ?
C6A C5 H7A 109.1 . . ?
H6A C5 H7A 107.8 . . ?
C6B C5 H6B 109.4 . . ?
N4 C5 H6B 109.4 . . ?
C6B C5 H7B 109.4 . . ?
N4 C5 H7B 109.4 . . ?
H6B C5 H7B 108.0 . . ?
N1 C1 H2 109.5 . . ?
N1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
N1 C1 H1 109.5 . . ?
H2 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
C5 C6B C7 119.3(17) . . ?
C5 C6B H9B 107.5 . . ?
C7 C6B H9B 107.5 . . ?
C5 C6B H8B 107.5 . . ?
C7 C6B H8B 107.5 . . ?
H9B C6B H8B 107.0 . . ?
C7 C6A C5 116.1(14) . . ?
C7 C6A H9A 108.3 . . ?
C5 C6A H9A 108.3 . . ?
C7 C6A H8A 108.3 . . ?
C5 C6A H8A 108.3 . . ?
H9A C6A H8A 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 N7 N6 C9 0.0(6) . . . . ?
N8 N7 N6 Fe1 -177.3(4) . . . . ?
N6 N7 N8 C10 1.3(7) . . . . ?
N6 N7 N8 C11 -179.8(5) . . . . ?
C3 N3 N2 N1 -2.1(6) . . . . ?
Fe1 N3 N2 N1 175.9(4) . . . . ?
N3 N2 N1 C2 2.6(7) . . . . ?
N3 N2 N1 C1 177.3(5) . . . . ?
N2 N3 C3 C2 1.0(7) . . . . ?
Fe1 N3 C3 C2 -177.7(4) . . . . ?
N2 N3 C3 C4 -179.2(5) . . . . ?
Fe1 N3 C3 C4 2.1(7) . . . . ?
N7 N6 C9 C10 -1.2(6) . . . . ?
Fe1 N6 C9 C10 176.9(4) . . . . ?
N7 N6 C9 C8 179.3(5) . . . . ?
Fe1 N6 C9 C8 -2.6(6) . . . . ?
N7 N8 C10 C9 -2.1(8) . . . . ?
C11 N8 C10 C9 179.2(6) . . . . ?
N6 C9 C10 N8 1.9(7) . . . . ?
C8 C9 C10 N8 -178.7(7) . . . . ?
C5 N4 C4 C3 -179.6(6) . . . . ?
Fe1 N4 C4 C3 -4.7(9) . . . . ?
C2 C3 C4 N4 -178.5(7) . . . . ?
N3 C3 C4 N4 1.7(10) . . . . ?
C7 N5 C8 C9 -179.1(6) . . . . ?
Fe1 N5 C8 C9 4.9(8) . . . . ?
C10 C9 C8 N5 179.2(7) . . . . ?
N6 C9 C8 N5 -1.5(9) . . . . ?
N3 C3 C2 N1 0.6(8) . . . . ?
C4 C3 C2 N1 -179.1(7) . . . . ?
N2 N1 C2 C3 -2.0(8) . . . . ?
C1 N1 C2 C3 -176.1(6) . . . . ?
C8 N5 C7 C6A -143.6(11) . . . . ?
Fe1 N5 C7 C6A 32.0(13) . . . . ?
C8 N5 C7 C6B 157.9(11) . . . . ?
Fe1 N5 C7 C6B -26.5(13) . . . . ?
C4 N4 C5 C6B -155.0(13) . . . . ?
Fe1 N4 C5 C6B 30.6(15) . . . . ?
C4 N4 C5 C6A 143.9(11) . . . . ?
Fe1 N4 C5 C6A -30.5(12) . . . . ?
N4 C5 C6B C7 -74.7(17) . . . . ?
N5 C7 C6B C5 74.0(17) . . . . ?
N5 C7 C6A C5 -70.0(14) . . . . ?
N4 C5 C6A C7 69.2(14) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6



_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/n
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1B_296K
_database_code_depnum_ccdc_archive 'CCDC 1428205'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Fe N10 S2'
_chemical_formula_weight         432.33

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'
N N 0.0061 0.0033 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   8.1325(5)
_cell_length_b                   8.9739(6)
_cell_length_c                   26.230(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.858(2)
_cell_angle_gamma                90
_cell_volume                     1909.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    6821

_cell_measurement_theta_min      3.2567

_cell_measurement_theta_max      27.4833


_exptl_crystal_description       block

_exptl_crystal_colour            'dark red-purple'

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.028
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.7174

_exptl_absorpt_correction_T_max  0.8467

_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'

_diffrn_measurement_method       dtprofit.ref

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            17255
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.257
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4313
_reflns_number_gt                3764
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+1.5543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4313
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9009(5) 0.5698(5) 0.22343(18) 0.0962(14) Uani 1 1 d . . . . .
H3 H 1.0151 0.5673 0.2162 0.144 Uiso 1 1 calc R U . . .
H1 H 0.8858 0.5146 0.2541 0.144 Uiso 1 1 calc R U . . .
H2 H 0.8672 0.6712 0.2279 0.144 Uiso 1 1 calc R U . . .
C2 C 0.8372(4) 0.4835(4) 0.13306(17) 0.0793(11) Uani 1 1 d . . . . .
H4 H 0.9352 0.5083 0.1188 0.095 Uiso 1 1 calc R U . . .
C3 C 0.7016(4) 0.4196(4) 0.10860(13) 0.0633(8) Uani 1 1 d . . . . .
C4 C 0.6485(5) 0.3653(4) 0.05882(14) 0.0769(11) Uani 1 1 d . . . . .
H5 H 0.7140 0.3730 0.0312 0.092 Uiso 1 1 calc R U . . .
C5 C 0.4282(8) 0.2524(5) 0.00487(13) 0.1083(18) Uani 1 1 d . . . . .
H6 H 0.5142 0.2292 -0.0178 0.130 Uiso 1 1 calc R U . . .
H7 H 0.3608 0.3313 -0.0108 0.130 Uiso 1 1 calc R U . . .
C6 C 0.3198(8) 0.1118(6) 0.01123(17) 0.1122(18) Uani 1 1 d . . . . .
H9 H 0.2903 0.0706 -0.0223 0.135 Uiso 1 1 calc R U . . .
H8 H 0.3848 0.0376 0.0304 0.135 Uiso 1 1 calc R U . . .
C7 C 0.1737(7) 0.1378(5) 0.03617(15) 0.0925(14) Uani 1 1 d . . . . .
H10 H 0.1045 0.0498 0.0329 0.111 Uiso 1 1 calc R U . . .
H11 H 0.1140 0.2196 0.0194 0.111 Uiso 1 1 calc R U . . .
C8 C 0.1068(4) 0.1240(4) 0.12203(15) 0.0688(9) Uani 1 1 d . . . . .
H12 H 0.0189 0.0614 0.1124 0.083 Uiso 1 1 calc R U . . .
C9 C 0.1418(3) 0.1728(3) 0.17409(13) 0.0569(7) Uani 1 1 d . . . . .
C10 C 0.0813(4) 0.1523(4) 0.22011(15) 0.0713(9) Uani 1 1 d . . . . .
H13 H -0.0074 0.0928 0.2278 0.086 Uiso 1 1 calc R U . . .
C11 C 0.1694(6) 0.2562(6) 0.30779(15) 0.0955(14) Uani 1 1 d . . . . .
H14 H 0.1842 0.1617 0.3247 0.143 Uiso 1 1 calc R U . . .
H15 H 0.0642 0.2970 0.3149 0.143 Uiso 1 1 calc R U . . .
H16 H 0.2552 0.3232 0.3200 0.143 Uiso 1 1 calc R U . . .
C12 C 0.6099(3) 0.0160(3) 0.13838(11) 0.0493(6) Uani 1 1 d . . . . .
C13 C 0.2135(3) 0.5809(3) 0.08240(10) 0.0453(6) Uani 1 1 d . . . . .
Fe1 Fe 0.39123(4) 0.29270(4) 0.11809(2) 0.04335(14) Uani 1 1 d . . . . .
N1 N 0.8016(3) 0.5032(3) 0.18098(12) 0.0659(7) Uani 1 1 d . . . . .
N2 N 0.6483(3) 0.4548(3) 0.18849(10) 0.0529(6) Uani 1 1 d . . . . .
N3 N 0.5890(2) 0.4038(2) 0.14434(9) 0.0462(5) Uani 1 1 d . . . . .
N4 N 0.5049(4) 0.3055(3) 0.05469(10) 0.0635(7) Uani 1 1 d . . . . .
N5 N 0.2051(3) 0.1732(3) 0.09032(10) 0.0598(6) Uani 1 1 d . . . . .
N6 N 0.2735(2) 0.2677(2) 0.18069(8) 0.0438(5) Uani 1 1 d . . . . .
N7 N 0.2952(3) 0.3076(3) 0.22860(9) 0.0513(5) Uani 1 1 d . . . . .
N8 N 0.1763(3) 0.2358(3) 0.25253(10) 0.0613(7) Uani 1 1 d . . . . .
N9 N 0.5162(3) 0.1108(3) 0.13447(9) 0.0522(5) Uani 1 1 d . . . . .
N10 N 0.2747(3) 0.4747(3) 0.09895(9) 0.0491(5) Uani 1 1 d . . . . .
S1 S 0.74235(12) -0.11985(11) 0.14405(5) 0.0851(3) Uani 1 1 d . . . . .
S2 S 0.12191(13) 0.73154(12) 0.06085(4) 0.0816(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.459(5) . ?
C1 H3 0.9600 . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C2 N1 1.320(5) . ?
C2 C3 1.364(5) . ?
C2 H4 0.9300 . ?
C3 N3 1.361(3) . ?
C3 C4 1.433(5) . ?
C4 N4 1.283(5) . ?
C4 H5 0.9300 . ?
C5 N4 1.488(5) . ?
C5 C6 1.554(7) . ?
C5 H6 0.9700 . ?
C5 H7 0.9700 . ?
C6 C7 1.413(7) . ?
C6 H9 0.9700 . ?
C6 H8 0.9700 . ?
C7 N5 1.461(4) . ?
C7 H10 0.9700 . ?
C7 H11 0.9700 . ?
C8 N5 1.271(5) . ?
C8 C9 1.444(5) . ?
C8 H12 0.9300 . ?
C9 C10 1.347(5) . ?
C9 N6 1.370(3) . ?
C10 N8 1.339(5) . ?
C10 H13 0.9300 . ?
C11 N8 1.466(5) . ?
C11 H14 0.9600 . ?
C11 H15 0.9600 . ?
C11 H16 0.9600 . ?
C12 N9 1.142(3) . ?
C12 S1 1.627(3) . ?
C13 N10 1.147(3) . ?
C13 S2 1.626(3) . ?
Fe1 N10 1.937(2) . ?
Fe1 N9 1.956(2) . ?
Fe1 N5 1.956(3) . ?
Fe1 N4 1.960(3) . ?
Fe1 N6 1.968(2) . ?
Fe1 N3 1.976(2) . ?
N1 N2 1.347(3) . ?
N2 N3 1.307(3) . ?
N6 N7 1.307(3) . ?
N7 N8 1.351(3) . ?

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 C1 H3 109.5 . . ?
N1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C2 C3 106.4(3) . . ?
N1 C2 H4 126.8 . . ?
C3 C2 H4 126.8 . . ?
N3 C3 C2 106.2(3) . . ?
N3 C3 C4 114.6(3) . . ?
C2 C3 C4 139.1(3) . . ?
N4 C4 C3 115.9(3) . . ?
N4 C4 H5 122.1 . . ?
C3 C4 H5 122.1 . . ?
N4 C5 C6 111.9(3) . . ?
N4 C5 H6 109.2 . . ?
C6 C5 H6 109.2 . . ?
N4 C5 H7 109.2 . . ?
C6 C5 H7 109.2 . . ?
H6 C5 H7 107.9 . . ?
C7 C6 C5 114.6(4) . . ?
C7 C6 H9 108.6 . . ?
C5 C6 H9 108.6 . . ?
C7 C6 H8 108.6 . . ?
C5 C6 H8 108.6 . . ?
H9 C6 H8 107.6 . . ?
C6 C7 N5 112.9(4) . . ?
C6 C7 H10 109.0 . . ?
N5 C7 H10 109.0 . . ?
C6 C7 H11 109.0 . . ?
N5 C7 H11 109.0 . . ?
H10 C7 H11 107.8 . . ?
N5 C8 C9 114.9(3) . . ?
N5 C8 H12 122.6 . . ?
C9 C8 H12 122.6 . . ?
C10 C9 N6 107.5(3) . . ?
C10 C9 C8 138.2(3) . . ?
N6 C9 C8 114.3(3) . . ?
N8 C10 C9 105.2(3) . . ?
N8 C10 H13 127.4 . . ?
C9 C10 H13 127.4 . . ?
N8 C11 H14 109.5 . . ?
N8 C11 H15 109.5 . . ?
H14 C11 H15 109.5 . . ?
N8 C11 H16 109.5 . . ?
H14 C11 H16 109.5 . . ?
H15 C11 H16 109.5 . . ?
N9 C12 S1 179.6(3) . . ?
N10 C13 S2 177.7(2) . . ?
N10 Fe1 N9 177.00(10) . . ?
N10 Fe1 N5 90.75(10) . . ?
N9 Fe1 N5 90.09(10) . . ?
N10 Fe1 N4 88.91(10) . . ?
N9 Fe1 N4 88.14(10) . . ?
N5 Fe1 N4 96.52(13) . . ?
N10 Fe1 N6 93.18(9) . . ?
N9 Fe1 N6 89.79(9) . . ?
N5 Fe1 N6 80.82(11) . . ?
N4 Fe1 N6 176.64(11) . . ?
N10 Fe1 N3 92.15(9) . . ?
N9 Fe1 N3 86.89(9) . . ?
N5 Fe1 N3 176.25(10) . . ?
N4 Fe1 N3 81.18(11) . . ?
N6 Fe1 N3 101.37(9) . . ?
C2 N1 N2 111.1(3) . . ?
C2 N1 C1 129.5(3) . . ?
N2 N1 C1 119.4(3) . . ?
N3 N2 N1 105.9(2) . . ?
N2 N3 C3 110.4(2) . . ?
N2 N3 Fe1 136.76(17) . . ?
C3 N3 Fe1 112.5(2) . . ?
C4 N4 C5 122.3(3) . . ?
C4 N4 Fe1 115.6(2) . . ?
C5 N4 Fe1 122.2(3) . . ?
C8 N5 C7 119.0(3) . . ?
C8 N5 Fe1 116.9(2) . . ?
C7 N5 Fe1 124.2(3) . . ?
N7 N6 C9 110.2(2) . . ?
N7 N6 Fe1 136.79(18) . . ?
C9 N6 Fe1 112.7(2) . . ?
N6 N7 N8 105.2(2) . . ?
C10 N8 N7 111.9(3) . . ?
C10 N8 C11 129.7(3) . . ?
N7 N8 C11 118.4(3) . . ?
C12 N9 Fe1 167.2(2) . . ?
C13 N10 Fe1 172.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N3 -0.1(4) . . . . ?
N1 C2 C3 C4 -178.9(4) . . . . ?
N3 C3 C4 N4 -1.9(5) . . . . ?
C2 C3 C4 N4 176.8(4) . . . . ?
N4 C5 C6 C7 69.2(5) . . . . ?
C5 C6 C7 N5 -69.2(5) . . . . ?
N5 C8 C9 C10 -178.5(4) . . . . ?
N5 C8 C9 N6 1.6(4) . . . . ?
N6 C9 C10 N8 0.6(3) . . . . ?
C8 C9 C10 N8 -179.3(4) . . . . ?
C3 C2 N1 N2 -0.1(4) . . . . ?
C3 C2 N1 C1 -178.6(3) . . . . ?
C2 N1 N2 N3 0.3(3) . . . . ?
C1 N1 N2 N3 179.0(3) . . . . ?
N1 N2 N3 C3 -0.4(3) . . . . ?
N1 N2 N3 Fe1 171.7(2) . . . . ?
C2 C3 N3 N2 0.3(3) . . . . ?
C4 C3 N3 N2 179.5(3) . . . . ?
C2 C3 N3 Fe1 -173.8(2) . . . . ?
C4 C3 N3 Fe1 5.3(3) . . . . ?
C3 C4 N4 C5 176.2(3) . . . . ?
C3 C4 N4 Fe1 -2.5(4) . . . . ?
C6 C5 N4 C4 146.1(4) . . . . ?
C6 C5 N4 Fe1 -35.3(5) . . . . ?
C9 C8 N5 C7 -176.2(3) . . . . ?
C9 C8 N5 Fe1 3.9(4) . . . . ?
C6 C7 N5 C8 -142.9(4) . . . . ?
C6 C7 N5 Fe1 37.0(5) . . . . ?
C10 C9 N6 N7 -0.7(3) . . . . ?
C8 C9 N6 N7 179.2(2) . . . . ?
C10 C9 N6 Fe1 173.9(2) . . . . ?
C8 C9 N6 Fe1 -6.2(3) . . . . ?
C9 N6 N7 N8 0.5(3) . . . . ?
Fe1 N6 N7 N8 -172.2(2) . . . . ?
C9 C10 N8 N7 -0.4(4) . . . . ?
C9 C10 N8 C11 -179.4(3) . . . . ?
N6 N7 N8 C10 -0.1(3) . . . . ?
N6 N7 N8 C11 179.1(3) . . . . ?

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6



_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/n
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1A_280K
_database_code_depnum_ccdc_archive 'CCDC 1428206'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Fe N10 S2'
_chemical_formula_weight         432.33

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'
N N 0.0061 0.0033 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.324(8)
_cell_length_b                   8.928(4)
_cell_length_c                   13.831(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.685(6)
_cell_angle_gamma                90
_cell_volume                     1940.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    280(2)

_cell_measurement_reflns_used    2242

_cell_measurement_theta_min      3.0595

_cell_measurement_theta_max      27.4825


_exptl_crystal_description       block

_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.012
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.7703

_exptl_absorpt_correction_T_max  0.8791

_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'


_exptl_special_details           
;
????
;

_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'

_diffrn_measurement_method       dtprofit.ref

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            7105
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.060
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2206
_reflns_number_gt                1549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1245P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2206
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1842
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.0000 0.34747(7) 0.2500 0.0609(3) Uani 1 2 d S T P . .
S1 S 0.26787(5) 0.41522(15) 0.17107(7) 0.0893(4) Uani 1 1 d . . . . .
N5 N 0.1152(2) 0.3462(3) 0.2117(2) 0.0782(8) Uani 1 1 d . . . . .
N3 N 0.06231(15) 0.2175(3) 0.38857(16) 0.0636(6) Uani 1 1 d . . . . .
N2 N 0.07701(16) 0.0801(3) 0.41905(18) 0.0715(7) Uani 1 1 d . . . . .
N1 N 0.12993(17) 0.0883(3) 0.51208(18) 0.0744(7) Uani 1 1 d . . . . .
N4 N 0.05031(15) 0.5214(3) 0.36138(19) 0.0698(7) Uani 1 1 d . . . . .
C7 C 0.1797(2) 0.3748(4) 0.1962(2) 0.0645(8) Uani 1 1 d . . . . .
C2 C 0.1479(2) 0.2285(5) 0.5396(2) 0.0807(10) Uani 1 1 d . . . . .
H4 H 0.1833 0.2616 0.6004 0.097 Uiso 1 1 calc R U . . .
C3 C 0.1048(2) 0.3146(4) 0.4621(2) 0.0712(8) Uani 1 1 d . . . . .
C1 C 0.1592(3) -0.0489(5) 0.5676(3) 0.1020(13) Uani 1 1 d . . . . .
H1 H 0.1110 -0.1053 0.5745 0.153 Uiso 1 1 calc R U . . .
H2 H 0.1950 -0.0242 0.6330 0.153 Uiso 1 1 calc R U . . .
H3 H 0.1908 -0.1076 0.5320 0.153 Uiso 1 1 calc R U . . .
C4 C 0.0946(2) 0.4741(4) 0.4441(3) 0.0838(10) Uani 1 1 d . . . . .
H5 H 0.1209 0.5414 0.4941 0.101 Uiso 1 1 calc R U . . .
C5 C 0.0382(3) 0.6824(4) 0.3429(4) 0.0998(13) Uani 1 1 d . . . . .
H6 H 0.0381 0.7304 0.4059 0.120 Uiso 1 1 calc R U . . .
H7 H 0.0870 0.7205 0.3233 0.120 Uiso 1 1 calc R U . . .
C6 C -0.0302(4) 0.7239(8) 0.2754(5) 0.085(2) Uani 0.5 1 d . . P . .
H8 H -0.0527 0.8213 0.2858 0.101 Uiso 0.5 1 calc R U P . .
H9 H -0.0742 0.6483 0.2551 0.101 Uiso 0.5 1 calc R U P . .


_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 N5 2.087(3) . ?
Fe1 N5 2.087(3) 2 ?
Fe1 N4 2.185(3) . ?
Fe1 N4 2.185(3) 2 ?
Fe1 N3 2.236(3) 2 ?
Fe1 N3 2.236(3) . ?
S1 C7 1.610(4) . ?
N5 C7 1.159(5) . ?
N3 N2 1.298(4) . ?
N3 C3 1.373(4) . ?
N2 N1 1.344(3) . ?
N1 C2 1.318(5) . ?
N1 C1 1.456(4) . ?
N4 C4 1.250(4) . ?
N4 C5 1.464(5) . ?
C2 C3 1.352(5) . ?
C2 H4 0.9300 . ?
C3 C4 1.448(5) . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
C4 H5 0.9300 . ?
C5 C6 1.300(8) . ?
C5 C6 1.649(9) 2 ?
C5 H6 0.9700 . ?
C5 H7 0.9700 . ?
C6 C6 1.357(15) 2 ?
C6 C5 1.649(9) 2 ?
C6 H8 0.9700 . ?
C6 H9 0.9700 . ?

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
N5 Fe1 N5 179.39(15) . 2 ?
N5 Fe1 N4 89.44(11) . . ?
N5 Fe1 N4 91.00(10) 2 . ?
N5 Fe1 N4 91.00(10) . 2 ?
N5 Fe1 N4 89.43(11) 2 2 ?
N4 Fe1 N4 89.41(16) . 2 ?
N5 Fe1 N3 90.67(11) . 2 ?
N5 Fe1 N3 89.01(10) 2 2 ?
N4 Fe1 N3 165.97(10) . 2 ?
N4 Fe1 N3 76.56(11) 2 2 ?
N5 Fe1 N3 89.01(10) . . ?
N5 Fe1 N3 90.67(11) 2 . ?
N4 Fe1 N3 76.56(11) . . ?
N4 Fe1 N3 165.97(10) 2 . ?
N3 Fe1 N3 117.47(13) 2 . ?
C7 N5 Fe1 166.5(3) . . ?
N2 N3 C3 110.1(2) . . ?
N2 N3 Fe1 140.36(18) . . ?
C3 N3 Fe1 109.2(2) . . ?
N3 N2 N1 105.9(2) . . ?
C2 N1 N2 111.3(3) . . ?
C2 N1 C1 129.1(3) . . ?
N2 N1 C1 119.6(3) . . ?
C4 N4 C5 120.6(3) . . ?
C4 N4 Fe1 114.8(3) . . ?
C5 N4 Fe1 124.6(3) . . ?
N5 C7 S1 178.2(3) . . ?
N1 C2 C3 106.4(3) . . ?
N1 C2 H4 126.8 . . ?
C3 C2 H4 126.8 . . ?
C2 C3 N3 106.2(3) . . ?
C2 C3 C4 135.0(3) . . ?
N3 C3 C4 118.8(3) . . ?
N1 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
N4 C4 C3 120.1(3) . . ?
N4 C4 H5 119.9 . . ?
C3 C4 H5 119.9 . . ?
C6 C5 N4 117.0(4) . . ?
C6 C5 C6 53.2(6) . 2 ?
N4 C5 C6 111.3(4) . 2 ?
C6 C5 H6 108.0 . . ?
N4 C5 H6 108.0 . . ?
C6 C5 H6 140.6 2 . ?
C6 C5 H7 108.0 . . ?
N4 C5 H7 108.0 . . ?
C6 C5 H7 59.6 2 . ?
H6 C5 H7 107.3 . . ?
C5 C6 C6 76.7(6) . 2 ?
C5 C6 C5 118.1(6) . 2 ?
C6 C6 C5 50.1(5) 2 2 ?
C5 C6 H8 115.7 . . ?
C6 C6 H8 115.7 2 . ?
C5 C6 H8 114.7 2 . ?
C5 C6 H9 115.7 . . ?
C6 C6 H9 115.7 2 . ?
C5 C6 H9 72.7 2 . ?
H8 C6 H9 112.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 N2 N1 -0.7(3) . . . . ?
Fe1 N3 N2 N1 171.6(2) . . . . ?
N3 N2 N1 C2 0.2(4) . . . . ?
N3 N2 N1 C1 -179.8(3) . . . . ?
N2 N1 C2 C3 0.4(4) . . . . ?
C1 N1 C2 C3 -179.6(4) . . . . ?
N1 C2 C3 N3 -0.8(4) . . . . ?
N1 C2 C3 C4 178.0(4) . . . . ?
N2 N3 C3 C2 1.0(4) . . . . ?
Fe1 N3 C3 C2 -173.8(2) . . . . ?
N2 N3 C3 C4 -178.1(3) . . . . ?
Fe1 N3 C3 C4 7.1(4) . . . . ?
C5 N4 C4 C3 178.8(3) . . . . ?
Fe1 N4 C4 C3 -3.7(4) . . . . ?
C2 C3 C4 N4 178.6(4) . . . . ?
N3 C3 C4 N4 -2.7(5) . . . . ?
C4 N4 C5 C6 -154.8(5) . . . . ?
Fe1 N4 C5 C6 28.0(6) . . . . ?
C4 N4 C5 C6 146.7(4) . . . 2 ?
Fe1 N4 C5 C6 -30.5(5) . . . 2 ?
N4 C5 C6 C6 -97.4(4) . . . 2 ?
N4 C5 C6 C5 -68.3(7) . . . 2 ?
C6 C5 C6 C5 29.1(6) 2 . . 2 ?

_refine_diff_density_max         0.793
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4



_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1A_250K
_database_code_depnum_ccdc_archive 'CCDC 1428207'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Fe N10 S2'
_chemical_formula_weight         432.33

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'
N N 0.0061 0.0033 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.27(3)
_cell_length_b                   9.786(18)
_cell_length_c                   13.27(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.53(2)
_cell_angle_gamma                90
_cell_volume                     1857(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)

_cell_measurement_reflns_used    2480

_cell_measurement_theta_min      3.2693

_cell_measurement_theta_max      27.6236


_exptl_crystal_description       block

_exptl_crystal_colour            'dark red-purple'

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3790

_exptl_crystal_size_mid          0.2910

_exptl_crystal_size_min          0.1490

_exptl_absorpt_coefficient_mu    1.058
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4211

_exptl_absorpt_correction_T_max  1.0000

_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'


_exptl_special_details           
;
????
;

_diffrn_ambient_temperature      250(2)

_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'

_diffrn_measurement_method       dtprofit.ref

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            6219
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2112
_reflns_number_gt                1656
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1233P)²+2.5915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2112
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2260
_refine_ls_wR_factor_gt          0.2082
_refine_ls_goodness_of_fit_ref   1.092
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.0000 0.33222(9) 0.2500 0.0531(3) Uani 1 2 d S T P . .
S1 S 0.27473(8) 0.39153(19) 0.17420(10) 0.0803(5) Uani 1 1 d . . . . .
N5 N 0.1118(3) 0.3359(4) 0.2138(3) 0.0592(9) Uani 1 1 d . . . . .
N3 N 0.0597(2) 0.2057(4) 0.3711(2) 0.0534(8) Uani 1 1 d . . . . .
N1 N 0.1146(3) 0.0605(5) 0.4917(3) 0.0685(10) Uani 1 1 d . . . . .
N4 N 0.0583(3) 0.4652(4) 0.3625(4) 0.0726(11) Uani 1 1 d . . . . .
N2 N 0.0632(3) 0.0759(4) 0.3886(3) 0.0603(9) Uani 1 1 d . . . . .
C7 C 0.1791(3) 0.3571(5) 0.1966(3) 0.0555(10) Uani 1 1 d . . . . .
C3 C 0.1084(3) 0.2724(6) 0.4628(3) 0.0698(13) Uani 1 1 d . . . . .
C1 C 0.1331(5) -0.0751(7) 0.5398(4) 0.0923(19) Uani 1 1 d . . . . .
H3 H 0.1816 -0.1190 0.5199 0.138 Uiso 1 1 calc R U . . .
H1 H 0.0764 -0.1295 0.5140 0.138 Uiso 1 1 calc R U . . .
H2 H 0.1535 -0.0673 0.6175 0.138 Uiso 1 1 calc R U . . .
C2 C 0.1431(4) 0.1786(7) 0.5393(4) 0.0854(18) Uani 1 1 d . . . . .
H4 H 0.1800 0.1937 0.6118 0.102 Uiso 1 1 calc R U . . .
C4 C 0.1058(4) 0.4180(6) 0.4540(4) 0.0802(15) Uani 1 1 d . . . . .
H5 H 0.1374 0.4750 0.5125 0.096 Uiso 1 1 calc R U . . .
C5 C 0.0488(7) 0.6134(7) 0.3459(7) 0.118(3) Uani 1 1 d . . . . .
H6 H 0.0595 0.6548 0.4165 0.141 Uiso 1 1 calc R U . . .
H7 H 0.1004 0.6431 0.3233 0.141 Uiso 1 1 calc R U . . .
C6 C -0.0207(12) 0.6634(11) 0.2849(12) 0.095(4) Uani 0.5 1 d . . P . .
H8 H -0.0345 0.7547 0.3058 0.114 Uiso 0.5 1 calc R U P . .
H9 H -0.0758 0.6040 0.2660 0.114 Uiso 0.5 1 calc R U P . .


_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 N5 1.929(5) . ?
Fe1 N5 1.929(5) 2 ?
Fe1 N4 1.945(5) . ?
Fe1 N4 1.945(5) 2 ?
Fe1 N3 1.979(4) 2 ?
Fe1 N3 1.979(4) . ?
S1 C7 1.625(5) . ?
N5 C7 1.147(6) . ?
N3 N2 1.289(6) . ?
N3 C3 1.351(6) . ?
N1 C2 1.316(8) . ?
N1 N2 1.326(5) . ?
N1 C1 1.457(8) . ?
N4 C4 1.263(7) . ?
N4 C5 1.467(9) . ?
C3 C2 1.333(8) . ?
C3 C4 1.430(9) . ?
C1 H3 0.9700 . ?
C1 H1 0.9700 . ?
C1 H2 0.9700 . ?
C2 H4 0.9400 . ?
C4 H5 0.9400 . ?
C5 C6 1.191(15) . ?
C5 C6 1.707(17) 2 ?
C5 H6 0.9800 . ?
C5 H7 0.9800 . ?
C6 C6 1.29(3) 2 ?
C6 C5 1.707(17) 2 ?
C6 H8 0.9800 . ?
C6 H9 0.9800 . ?

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
N5 Fe1 N5 177.8(2) . 2 ?
N5 Fe1 N4 88.39(19) . . ?
N5 Fe1 N4 90.16(19) 2 . ?
N5 Fe1 N4 90.16(19) . 2 ?
N5 Fe1 N4 88.39(19) 2 2 ?
N4 Fe1 N4 96.0(3) . 2 ?
N5 Fe1 N3 90.33(17) . 2 ?
N5 Fe1 N3 91.03(17) 2 2 ?
N4 Fe1 N3 176.48(17) . 2 ?
N4 Fe1 N3 80.7(2) 2 2 ?
N5 Fe1 N3 91.03(17) . . ?
N5 Fe1 N3 90.33(17) 2 . ?
N4 Fe1 N3 80.7(2) . . ?
N4 Fe1 N3 176.48(17) 2 . ?
N3 Fe1 N3 102.6(2) 2 . ?
C7 N5 Fe1 170.3(4) . . ?
N2 N3 C3 109.8(4) . . ?
N2 N3 Fe1 137.8(3) . . ?
C3 N3 Fe1 112.4(4) . . ?
C2 N1 N2 111.9(5) . . ?
C2 N1 C1 127.6(5) . . ?
N2 N1 C1 120.6(5) . . ?
C4 N4 C5 119.9(6) . . ?
C4 N4 Fe1 116.5(4) . . ?
C5 N4 Fe1 123.5(5) . . ?
N3 N2 N1 105.7(4) . . ?
N5 C7 S1 178.3(5) . . ?
C2 C3 N3 107.5(5) . . ?
C2 C3 C4 137.8(5) . . ?
N3 C3 C4 114.7(5) . . ?
N1 C1 H3 109.5 . . ?
N1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C2 C3 105.2(5) . . ?
N1 C2 H4 127.4 . . ?
C3 C2 H4 127.4 . . ?
N4 C4 C3 115.7(4) . . ?
N4 C4 H5 122.2 . . ?
C3 C4 H5 122.2 . . ?
C6 C5 N4 121.7(10) . . ?
C6 C5 C6 49.1(12) . 2 ?
N4 C5 C6 114.3(6) . 2 ?
C6 C5 H6 106.9 . . ?
N4 C5 H6 106.9 . . ?
C6 C5 H6 138.7 2 . ?
C6 C5 H7 106.9 . . ?
N4 C5 H7 106.9 . . ?
C6 C5 H7 63.0 2 . ?
H6 C5 H7 106.7 . . ?
C5 C6 C6 86.7(16) . 2 ?
C5 C6 C5 114.8(11) . 2 ?
C6 C6 C5 44.2(10) 2 2 ?
C5 C6 H8 114.2 . . ?
C6 C6 H8 114.2 2 . ?
C5 C6 H8 123.1 2 . ?
C5 C6 H9 114.2 . . ?
C6 C6 H9 114.2 2 . ?
C5 C6 H9 71.6 2 . ?
H8 C6 H9 111.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 N2 N1 -0.3(4) . . . . ?
Fe1 N3 N2 N1 -177.6(3) . . . . ?
C2 N1 N2 N3 0.3(5) . . . . ?
C1 N1 N2 N3 179.9(4) . . . . ?
N2 N3 C3 C2 0.2(5) . . . . ?
Fe1 N3 C3 C2 178.2(4) . . . . ?
N2 N3 C3 C4 -177.3(4) . . . . ?
Fe1 N3 C3 C4 0.7(5) . . . . ?
N2 N1 C2 C3 -0.2(6) . . . . ?
C1 N1 C2 C3 -179.7(5) . . . . ?
N3 C3 C2 N1 0.0(6) . . . . ?
C4 C3 C2 N1 176.6(6) . . . . ?
C5 N4 C4 C3 178.1(5) . . . . ?
Fe1 N4 C4 C3 -1.4(6) . . . . ?
C2 C3 C4 N4 -176.0(6) . . . . ?
N3 C3 C4 N4 0.4(7) . . . . ?
C4 N4 C5 C6 -146.7(11) . . . . ?
Fe1 N4 C5 C6 32.8(13) . . . . ?
C4 N4 C5 C6 157.8(8) . . . 2 ?
Fe1 N4 C5 C6 -22.8(11) . . . 2 ?
N4 C5 C6 C6 -96.1(9) . . . 2 ?
N4 C5 C6 C5 -60.9(14) . . . 2 ?
C6 C5 C6 C5 35.1(8) 2 . . 2 ?

_refine_diff_density_max         1.185
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.115

_shelxl_version_number           2013-4



_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'

#===END
_exptl_crystal_preparation       'Magnetic properties'
