# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Compound_5c
_database_code_depnum_ccdc_archive 'CCDC 1501496'
_audit_update_record             
;
2016-08-30 deposited with the CCDC.
2017-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 Fe N S2'
_chemical_formula_sum            'C20 H19 Fe N S2'
_chemical_formula_weight         393.33

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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   10.9404(2)
_cell_length_b                   10.9404(2)
_cell_length_c                   13.0885(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1356.71(6)
_cell_formula_units_Z            3
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3557
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.22

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.187
_exptl_absorpt_coefficient_mu    1.065
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11659
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         28.235
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4457
_reflns_number_gt                3785
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.997

_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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0227P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4457
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0569
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.70834(4) 0.61251(5) 0.16122(3) 0.04233(12) Uani 1 1 d . . . . .
S1 S 0.40095(9) 0.32441(9) 0.19922(8) 0.0525(2) Uani 1 1 d . . . . .
C1 C 0.5643(3) 0.6175(3) 0.2568(2) 0.0370(6) Uani 1 1 d . . . . .
C2 C 0.4981(3) 0.5088(3) 0.1801(3) 0.0399(7) Uani 1 1 d . . . . .
C3 C 0.5330(4) 0.5746(4) 0.0823(3) 0.0472(8) Uani 1 1 d . . . . .
H3 H 0.5028 0.5264 0.0162 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6196(4) 0.7225(4) 0.0973(3) 0.0517(9) Uani 1 1 d . . . . .
H4 H 0.6616 0.7938 0.0433 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6399(4) 0.7482(3) 0.2027(3) 0.0440(8) Uani 1 1 d . . . . .
H5 H 0.6984 0.8410 0.2343 0.053 Uiso 1 1 calc R U . . .
C6 C 0.8312(7) 0.5607(11) 0.2441(5) 0.107(2) Uani 1 1 d . . . . .
H6 H 0.8194 0.5344 0.3165 0.128 Uiso 1 1 calc R U . . .
C7 C 0.7718(5) 0.4686(6) 0.1611(8) 0.108(2) Uani 1 1 d . . . . .
H7 H 0.7110 0.3659 0.1645 0.129 Uiso 1 1 calc R U . . .
C8 C 0.8182(7) 0.5497(10) 0.0736(5) 0.110(2) Uani 1 1 d . . . . .
H8 H 0.7956 0.5149 0.0032 0.132 Uiso 1 1 calc R U . . .
C9 C 0.9055(6) 0.6880(8) 0.1028(6) 0.1006(19) Uani 1 1 d . . . . .
H9 H 0.9538 0.7688 0.0565 0.121 Uiso 1 1 calc R U . . .
C10 C 0.9127(5) 0.6938(8) 0.2048(7) 0.106(2) Uani 1 1 d . . . . .
H10 H 0.9670 0.7798 0.2453 0.127 Uiso 1 1 calc R U . . .
S11 S 0.48251(11) 0.44536(9) 0.43363(8) 0.0564(2) Uani 1 1 d . . . . .
C12 C 0.5603(3) 0.6095(3) 0.3682(2) 0.0389(7) Uani 1 1 d . . . . .
N13 N 0.6092(3) 0.7200(3) 0.4225(2) 0.0502(7) Uani 1 1 d . . . . .
C14 C 0.5796(4) 0.6909(4) 0.5319(3) 0.0502(9) Uani 1 1 d . . . . .
H14 H 0.6641 0.7552 0.5710 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5420(5) 0.5382(4) 0.5539(3) 0.0617(10) Uani 1 1 d . . . . .
H15A H 0.4679 0.4961 0.6049 0.074 Uiso 1 1 calc R U . . .
H15B H 0.6239 0.5351 0.5787 0.074 Uiso 1 1 calc R U . . .
C16 C 0.4602(5) 0.7179(5) 0.5603(3) 0.0743(12) Uani 1 1 d . . . . .
H16A H 0.4845 0.8116 0.5398 0.111 Uiso 1 1 calc R U . . .
H16B H 0.4456 0.7085 0.6329 0.111 Uiso 1 1 calc R U . . .
H16C H 0.3752 0.6506 0.5261 0.111 Uiso 1 1 calc R U . . .
C17 C 0.2258(3) 0.2787(4) 0.1669(3) 0.0446(8) Uani 1 1 d . . . . .
C18 C 0.1342(5) 0.1395(4) 0.1420(4) 0.0829(14) Uani 1 1 d . . . . .
H18 H 0.1656 0.0747 0.1421 0.099 Uiso 1 1 calc R U . . .
C19 C -0.0047(5) 0.0963(6) 0.1170(5) 0.1067(19) Uani 1 1 d . . . . .
H19 H -0.0665 0.0026 0.1000 0.128 Uiso 1 1 calc R U . . .
C20 C -0.0507(5) 0.1917(8) 0.1172(5) 0.0981(19) Uani 1 1 d . . . . .
H20 H -0.1443 0.1625 0.1016 0.118 Uiso 1 1 calc R U . . .
C21 C 0.0399(4) 0.3289(6) 0.1403(4) 0.0769(13) Uani 1 1 d . . . . .
H21 H 0.0087 0.3938 0.1386 0.092 Uiso 1 1 calc R U . . .
C22 C 0.1784(4) 0.3729(4) 0.1662(3) 0.0538(9) Uani 1 1 d . . . . .
H22 H 0.2394 0.4668 0.1833 0.065 Uiso 1 1 calc R U . . .


_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 C2 2.007(3) . ?
Fe1 C7 2.014(5) . ?
Fe1 C8 2.015(5) . ?
Fe1 C6 2.017(5) . ?
Fe1 C3 2.031(3) . ?
Fe1 C10 2.031(5) . ?
Fe1 C9 2.034(4) . ?
Fe1 C1 2.034(3) . ?
Fe1 C5 2.042(3) . ?
Fe1 C4 2.064(4) . ?
S1 C2 1.766(3) . ?
S1 C17 1.773(3) . ?
C1 C5 1.431(4) . ?
C1 C2 1.444(4) . ?
C1 C12 1.460(5) . ?
C2 C3 1.425(5) . ?
C3 C4 1.422(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.403(5) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C10 1.372(9) . ?
C6 C7 1.400(9) . ?
C6 H6 0.9800 . ?
C7 C8 1.382(9) . ?
C7 H7 0.9800 . ?
C8 C9 1.379(9) . ?
C8 H8 0.9800 . ?
C9 C10 1.337(9) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
S11 C12 1.776(3) . ?
S11 C15 1.809(4) . ?
C12 N13 1.267(4) . ?
N13 C14 1.467(5) . ?
C14 C16 1.523(6) . ?
C14 C15 1.534(6) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.366(5) . ?
C17 C18 1.380(5) . ?
C18 C19 1.386(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C2 Fe1 C7 107.70(18) . . ?
C2 Fe1 C8 126.0(2) . . ?
C7 Fe1 C8 40.1(3) . . ?
C2 Fe1 C6 120.8(3) . . ?
C7 Fe1 C6 40.6(3) . . ?
C8 Fe1 C6 67.3(3) . . ?
C2 Fe1 C3 41.31(14) . . ?
C7 Fe1 C3 120.0(2) . . ?
C8 Fe1 C3 107.73(19) . . ?
C6 Fe1 C3 155.6(3) . . ?
C2 Fe1 C10 155.8(3) . . ?
C7 Fe1 C10 66.9(3) . . ?
C8 Fe1 C10 66.1(2) . . ?
C6 Fe1 C10 39.6(3) . . ?
C3 Fe1 C10 162.3(3) . . ?
C2 Fe1 C9 163.5(3) . . ?
C7 Fe1 C9 66.9(3) . . ?
C8 Fe1 C9 39.8(3) . . ?
C6 Fe1 C9 66.1(3) . . ?
C3 Fe1 C9 126.4(3) . . ?
C10 Fe1 C9 38.4(3) . . ?
C2 Fe1 C1 41.86(12) . . ?
C7 Fe1 C1 126.6(3) . . ?
C8 Fe1 C1 164.1(3) . . ?
C6 Fe1 C1 108.1(2) . . ?
C3 Fe1 C1 69.71(13) . . ?
C10 Fe1 C1 120.9(2) . . ?
C9 Fe1 C1 154.0(3) . . ?
C2 Fe1 C5 69.21(13) . . ?
C7 Fe1 C5 164.5(3) . . ?
C8 Fe1 C5 153.8(3) . . ?
C6 Fe1 C5 126.9(3) . . ?
C3 Fe1 C5 68.38(14) . . ?
C10 Fe1 C5 109.3(2) . . ?
C9 Fe1 C5 120.3(2) . . ?
C1 Fe1 C5 41.10(12) . . ?
C2 Fe1 C4 68.85(14) . . ?
C7 Fe1 C4 154.5(3) . . ?
C8 Fe1 C4 120.2(3) . . ?
C6 Fe1 C4 163.0(3) . . ?
C3 Fe1 C4 40.63(14) . . ?
C10 Fe1 C4 126.5(3) . . ?
C9 Fe1 C4 108.9(2) . . ?
C1 Fe1 C4 68.71(14) . . ?
C5 Fe1 C4 39.95(14) . . ?
C2 S1 C17 103.68(16) . . ?
C5 C1 C2 106.3(3) . . ?
C5 C1 C12 122.7(3) . . ?
C2 C1 C12 131.1(3) . . ?
C5 C1 Fe1 69.75(18) . . ?
C2 C1 Fe1 68.07(17) . . ?
C12 C1 Fe1 127.8(2) . . ?
C3 C2 C1 108.2(3) . . ?
C3 C2 S1 124.1(3) . . ?
C1 C2 S1 127.6(3) . . ?
C3 C2 Fe1 70.23(19) . . ?
C1 C2 Fe1 70.06(17) . . ?
S1 C2 Fe1 121.88(16) . . ?
C4 C3 C2 107.9(3) . . ?
C4 C3 Fe1 70.93(19) . . ?
C2 C3 Fe1 68.46(18) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.0 . . ?
C5 C4 C3 108.2(3) . . ?
C5 C4 Fe1 69.2(2) . . ?
C3 C4 Fe1 68.43(19) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C4 C5 C1 109.4(3) . . ?
C4 C5 Fe1 70.9(2) . . ?
C1 C5 Fe1 69.15(18) . . ?
C4 C5 H5 125.3 . . ?
C1 C5 H5 125.3 . . ?
Fe1 C5 H5 125.3 . . ?
C10 C6 C7 107.2(6) . . ?
C10 C6 Fe1 70.8(3) . . ?
C7 C6 Fe1 69.6(3) . . ?
C10 C6 H6 126.4 . . ?
C7 C6 H6 126.4 . . ?
Fe1 C6 H6 126.4 . . ?
C8 C7 C6 107.0(6) . . ?
C8 C7 Fe1 70.0(3) . . ?
C6 C7 Fe1 69.8(3) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
Fe1 C7 H7 126.5 . . ?
C9 C8 C7 107.7(6) . . ?
C9 C8 Fe1 70.8(3) . . ?
C7 C8 Fe1 69.9(3) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
C10 C9 C8 108.7(6) . . ?
C10 C9 Fe1 70.7(3) . . ?
C8 C9 Fe1 69.3(3) . . ?
C10 C9 H9 125.6 . . ?
C8 C9 H9 125.6 . . ?
Fe1 C9 H9 125.6 . . ?
C9 C10 C6 109.4(6) . . ?
C9 C10 Fe1 70.9(3) . . ?
C6 C10 Fe1 69.6(3) . . ?
C9 C10 H10 125.3 . . ?
C6 C10 H10 125.3 . . ?
Fe1 C10 H10 125.3 . . ?
C12 S11 C15 89.75(17) . . ?
N13 C12 C1 121.1(3) . . ?
N13 C12 S11 117.0(3) . . ?
C1 C12 S11 121.8(2) . . ?
C12 N13 C14 113.5(3) . . ?
N13 C14 C16 108.3(3) . . ?
N13 C14 C15 109.2(3) . . ?
C16 C14 C15 112.1(3) . . ?
N13 C14 H14 109.1 . . ?
C16 C14 H14 109.1 . . ?
C15 C14 H14 109.1 . . ?
C14 C15 S11 105.9(2) . . ?
C14 C15 H15A 110.6 . . ?
S11 C15 H15A 110.6 . . ?
C14 C15 H15B 110.6 . . ?
S11 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 119.4(3) . . ?
C22 C17 S1 123.6(3) . . ?
C18 C17 S1 117.0(3) . . ?
C17 C18 C19 120.0(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.5(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.1(4) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

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
C5 C1 C2 C3 -0.6(3) . . . . ?
C12 C1 C2 C3 178.1(3) . . . . ?
Fe1 C1 C2 C3 -60.2(2) . . . . ?
C5 C1 C2 S1 175.0(2) . . . . ?
C12 C1 C2 S1 -6.3(5) . . . . ?
Fe1 C1 C2 S1 115.4(3) . . . . ?
C5 C1 C2 Fe1 59.6(2) . . . . ?
C12 C1 C2 Fe1 -121.8(3) . . . . ?
C17 S1 C2 C3 -73.7(3) . . . . ?
C17 S1 C2 C1 111.4(3) . . . . ?
C17 S1 C2 Fe1 -160.2(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
S1 C2 C3 C4 -175.9(2) . . . . ?
Fe1 C2 C3 C4 -60.2(2) . . . . ?
C1 C2 C3 Fe1 60.1(2) . . . . ?
S1 C2 C3 Fe1 -115.7(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
Fe1 C3 C4 C5 -57.8(3) . . . . ?
C2 C3 C4 Fe1 58.6(2) . . . . ?
C3 C4 C5 C1 -1.2(4) . . . . ?
Fe1 C4 C5 C1 -58.6(2) . . . . ?
C3 C4 C5 Fe1 57.4(2) . . . . ?
C2 C1 C5 C4 1.1(4) . . . . ?
C12 C1 C5 C4 -177.7(3) . . . . ?
Fe1 C1 C5 C4 59.6(3) . . . . ?
C2 C1 C5 Fe1 -58.5(2) . . . . ?
C12 C1 C5 Fe1 122.7(3) . . . . ?
C10 C6 C7 C8 -0.7(6) . . . . ?
Fe1 C6 C7 C8 60.4(4) . . . . ?
C10 C6 C7 Fe1 -61.1(4) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
Fe1 C7 C8 C9 61.1(4) . . . . ?
C6 C7 C8 Fe1 -60.3(3) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
Fe1 C8 C9 C10 59.9(4) . . . . ?
C7 C8 C9 Fe1 -60.5(4) . . . . ?
C8 C9 C10 C6 0.1(6) . . . . ?
Fe1 C9 C10 C6 59.2(4) . . . . ?
C8 C9 C10 Fe1 -59.1(4) . . . . ?
C7 C6 C10 C9 0.4(6) . . . . ?
Fe1 C6 C10 C9 -60.0(4) . . . . ?
C7 C6 C10 Fe1 60.3(3) . . . . ?
C5 C1 C12 N13 9.0(5) . . . . ?
C2 C1 C12 N13 -169.5(3) . . . . ?
Fe1 C1 C12 N13 97.7(4) . . . . ?
C5 C1 C12 S11 -172.9(2) . . . . ?
C2 C1 C12 S11 8.7(5) . . . . ?
Fe1 C1 C12 S11 -84.2(3) . . . . ?
C15 S11 C12 N13 -7.3(3) . . . . ?
C15 S11 C12 C1 174.5(3) . . . . ?
C1 C12 N13 C14 172.5(3) . . . . ?
S11 C12 N13 C14 -5.8(4) . . . . ?
C12 N13 C14 C16 -103.5(4) . . . . ?
C12 N13 C14 C15 18.8(4) . . . . ?
N13 C14 C15 S11 -22.5(4) . . . . ?
C16 C14 C15 S11 97.5(3) . . . . ?
C12 S11 C15 C14 16.5(3) . . . . ?
C2 S1 C17 C22 -21.1(4) . . . . ?
C2 S1 C17 C18 159.4(4) . . . . ?
C22 C17 C18 C19 -0.2(8) . . . . ?
S1 C17 C18 C19 179.3(5) . . . . ?
C17 C18 C19 C20 -0.2(10) . . . . ?
C18 C19 C20 C21 1.1(10) . . . . ?
C19 C20 C21 C22 -1.7(8) . . . . ?
C18 C17 C22 C21 -0.4(6) . . . . ?
S1 C17 C22 C21 -179.9(3) . . . . ?
C20 C21 C22 C17 1.3(7) . . . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1501494'
_audit_update_record             
;
2016-08-30 deposited with the CCDC.
2017-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 Fe N O S'
_chemical_formula_sum            'C14 H17 Fe N O S'
_chemical_formula_weight         303.19

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'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6132(8)
_cell_length_b                   10.3234(11)
_cell_length_c                   17.0932(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1343.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7812
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.38

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    1.264
_shelx_estimated_absorpt_T_min   0.584
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5903
_exptl_absorpt_correction_T_max  0.8154
_exptl_absorpt_process_details   '(Sheldrick, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11096
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.383
_diffrn_reflns_theta_max         25.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2462
_reflns_number_gt                2310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.999

_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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0254P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     217
_refine_ls_number_restraints     233
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0529
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.001
_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 0.73603(5) 0.61250(3) 0.72870(2) 0.03400(13) Uani 1 1 d . . . . .
S1 S 0.86822(12) 0.58897(9) 0.48691(5) 0.0551(2) Uani 1 1 d . . . . .
O1 O 0.2678(4) 0.5052(3) 0.54387(14) 0.0799(10) Uani 0.974(5) 1 d D . P A 1
H1 H 0.2003 0.5662 0.5503 0.120 Uiso 0.974(5) 1 calc R U P A 1
O1B O 0.221(7) 0.505(11) 0.433(5) 0.0799(10) Uani 0.026(5) 1 d D . P A 2
H1B H 0.1514 0.5647 0.4389 0.120 Uiso 0.026(5) 1 calc R U P A 2
N1 N 0.6195(3) 0.4452(3) 0.54960(14) 0.0393(6) Uani 1 1 d . . . . .
H1A H 0.582(4) 0.420(3) 0.5863(18) 0.047 Uiso 1 1 d . U . . .
C1 C 0.8402(3) 0.5087(3) 0.63923(17) 0.0357(6) Uani 1 1 d . . . . .
C2 C 0.7874(4) 0.4246(3) 0.70148(16) 0.0386(7) Uani 1 1 d . . . . .
H2 H 0.7052 0.3582 0.6980 0.046 Uiso 1 1 calc R U . . .
C3 C 0.8823(4) 0.4603(3) 0.7691(2) 0.0484(7) Uani 1 1 d . . . . .
H3 H 0.8731 0.4213 0.8179 0.058 Uiso 1 1 calc R U . . .
C4 C 0.9927(4) 0.5646(3) 0.7502(2) 0.0525(9) Uani 1 1 d . . . . .
H4 H 1.0691 0.6063 0.7843 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9679(4) 0.5953(3) 0.67040(18) 0.0450(7) Uani 1 1 d . . . . .
H5 H 1.0250 0.6607 0.6430 0.054 Uiso 1 1 calc R U . . .
C6 C 0.632(2) 0.7928(17) 0.7076(9) 0.046(3) Uani 0.351(19) 1 d D U P B 1
H6 H 0.6742 0.8521 0.6711 0.055 Uiso 0.351(19) 1 calc R U P B 1
C7 C 0.504(2) 0.698(2) 0.6936(8) 0.046(3) Uani 0.351(19) 1 d D U P B 1
H7 H 0.4456 0.6838 0.6466 0.055 Uiso 0.351(19) 1 calc R U P B 1
C8 C 0.4809(18) 0.6267(12) 0.7631(13) 0.044(3) Uani 0.351(19) 1 d D U P B 1
H8 H 0.4053 0.5569 0.7700 0.052 Uiso 0.351(19) 1 calc R U P B 1
C9 C 0.592(2) 0.6804(17) 0.8205(7) 0.042(3) Uani 0.351(19) 1 d D U P B 1
H9 H 0.6028 0.6525 0.8721 0.051 Uiso 0.351(19) 1 calc R U P B 1
C10 C 0.685(2) 0.7832(16) 0.7861(10) 0.044(2) Uani 0.351(19) 1 d D U P B 1
H10 H 0.7667 0.8359 0.8110 0.052 Uiso 0.351(19) 1 calc R U P B 1
C6B C 0.5478(13) 0.7285(9) 0.6823(4) 0.0439(17) Uani 0.649(19) 1 d D U P B 2
H6B H 0.5234 0.7394 0.6293 0.053 Uiso 0.649(19) 1 calc R U P B 2
C7B C 0.4704(8) 0.6354(7) 0.7325(7) 0.0416(16) Uani 0.649(19) 1 d D U P B 2
H7B H 0.3865 0.5742 0.7185 0.050 Uiso 0.649(19) 1 calc R U P B 2
C8B C 0.5433(14) 0.6524(9) 0.8074(5) 0.0465(18) Uani 0.649(19) 1 d D U P B 2
H8B H 0.5163 0.6041 0.8517 0.056 Uiso 0.649(19) 1 calc R U P B 2
C9B C 0.6638(12) 0.7549(11) 0.8036(5) 0.0504(19) Uani 0.649(19) 1 d D U P B 2
H9B H 0.7299 0.7866 0.8452 0.060 Uiso 0.649(19) 1 calc R U P B 2
C10B C 0.6680(12) 0.8016(8) 0.7266(6) 0.0490(17) Uani 0.649(19) 1 d D U P B 2
H10B H 0.7378 0.8690 0.7082 0.059 Uiso 0.649(19) 1 calc R U P B 2
C11 C 0.7662(4) 0.5109(2) 0.55979(16) 0.0338(6) Uani 1 1 d . . . . .
C12 C 0.5188(4) 0.4318(3) 0.47754(18) 0.0431(8) Uani 1 1 d . . . . .
H12 H 0.5964 0.4519 0.4334 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3714(5) 0.5277(4) 0.4776(2) 0.0626(10) Uani 1 1 d D . . . .
H13A H 0.4177 0.6152 0.4788 0.075 Uiso 0.974(5) 1 calc R U P A 1
H13B H 0.3012 0.5178 0.4306 0.075 Uiso 0.974(5) 1 calc R U P A 1
H13C H 0.3340 0.5386 0.5315 0.075 Uiso 0.026(5) 1 calc R U P A 2
H13D H 0.4194 0.6102 0.4608 0.075 Uiso 0.026(5) 1 calc R U P A 2
C14 C 0.4555(5) 0.2941(3) 0.4686(2) 0.0580(9) Uani 1 1 d . . . . .
H14A H 0.5546 0.2368 0.4665 0.087 Uiso 1 1 calc R U . . .
H14B H 0.3889 0.2864 0.4211 0.087 Uiso 1 1 calc R U . . .
H14C H 0.3826 0.2716 0.5123 0.087 Uiso 1 1 calc R U . . .


_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 C10B 2.020(9) . ?
Fe1 C9B 2.025(8) . ?
Fe1 C1 2.029(3) . ?
Fe1 C6B 2.029(7) . ?
Fe1 C8B 2.032(7) . ?
Fe1 C2 2.033(3) . ?
Fe1 C5 2.035(3) . ?
Fe1 C8 2.035(13) . ?
Fe1 C7B 2.037(6) . ?
Fe1 C9 2.038(14) . ?
Fe1 C3 2.046(3) . ?
Fe1 C4 2.049(3) . ?
S1 C11 1.675(3) . ?
O1 C13 1.400(4) . ?
O1B C13 1.396(15) . ?
N1 C11 1.319(4) . ?
N1 C12 1.457(4) . ?
C1 C5 1.424(4) . ?
C1 C2 1.431(4) . ?
C1 C11 1.470(4) . ?
C2 C3 1.411(4) . ?
C3 C4 1.404(5) . ?
C4 C5 1.413(5) . ?
C6 C7 1.402(8) . ?
C6 C10 1.405(8) . ?
C7 C8 1.408(8) . ?
C8 C9 1.411(8) . ?
C9 C10 1.403(8) . ?
C6B C10B 1.408(7) . ?
C6B C7B 1.417(7) . ?
C7B C8B 1.406(7) . ?
C8B C9B 1.402(7) . ?
C9B C10B 1.401(7) . ?
C12 C13 1.497(5) . ?
C12 C14 1.509(5) . ?

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
C10B Fe1 C9B 40.5(2) . . ?
C10B Fe1 C1 126.7(3) . . ?
C9B Fe1 C1 165.0(4) . . ?
C10B Fe1 C6B 40.7(2) . . ?
C9B Fe1 C6B 68.1(3) . . ?
C1 Fe1 C6B 107.0(2) . . ?
C10B Fe1 C8B 68.3(3) . . ?
C9B Fe1 C8B 40.4(2) . . ?
C1 Fe1 C8B 152.6(4) . . ?
C6B Fe1 C8B 68.2(2) . . ?
C10B Fe1 C2 165.4(3) . . ?
C9B Fe1 C2 152.8(3) . . ?
C1 Fe1 C2 41.24(11) . . ?
C6B Fe1 C2 127.6(3) . . ?
C8B Fe1 C2 118.9(3) . . ?
C10B Fe1 C5 107.3(2) . . ?
C9B Fe1 C5 127.5(3) . . ?
C1 Fe1 C5 41.03(11) . . ?
C6B Fe1 C5 118.2(3) . . ?
C8B Fe1 C5 165.5(4) . . ?
C2 Fe1 C5 68.75(13) . . ?
C1 Fe1 C8 129.0(5) . . ?
C2 Fe1 C8 108.6(4) . . ?
C5 Fe1 C8 167.4(6) . . ?
C10B Fe1 C7B 68.5(3) . . ?
C9B Fe1 C7B 68.0(3) . . ?
C1 Fe1 C7B 118.3(3) . . ?
C6B Fe1 C7B 40.8(2) . . ?
C8B Fe1 C7B 40.4(2) . . ?
C2 Fe1 C7B 108.0(2) . . ?
C5 Fe1 C7B 152.5(4) . . ?
C1 Fe1 C9 166.5(6) . . ?
C2 Fe1 C9 127.4(5) . . ?
C5 Fe1 C9 150.8(6) . . ?
C8 Fe1 C9 40.5(3) . . ?
C10B Fe1 C3 152.6(3) . . ?
C9B Fe1 C3 119.5(3) . . ?
C1 Fe1 C3 68.64(13) . . ?
C6B Fe1 C3 165.8(3) . . ?
C8B Fe1 C3 109.0(2) . . ?
C2 Fe1 C3 40.49(12) . . ?
C5 Fe1 C3 68.04(14) . . ?
C8 Fe1 C3 118.5(5) . . ?
C7B Fe1 C3 128.2(3) . . ?
C9 Fe1 C3 107.2(3) . . ?
C10B Fe1 C4 118.8(3) . . ?
C9B Fe1 C4 108.7(2) . . ?
C1 Fe1 C4 68.57(12) . . ?
C6B Fe1 C4 152.4(4) . . ?
C8B Fe1 C4 128.2(3) . . ?
C2 Fe1 C4 68.10(13) . . ?
C5 Fe1 C4 40.47(14) . . ?
C8 Fe1 C4 151.2(6) . . ?
C7B Fe1 C4 165.7(4) . . ?
C9 Fe1 C4 117.2(5) . . ?
C3 Fe1 C4 40.10(13) . . ?
C11 N1 C12 127.3(3) . . ?
C5 C1 C2 107.1(3) . . ?
C5 C1 C11 126.7(3) . . ?
C2 C1 C11 126.1(3) . . ?
C5 C1 Fe1 69.70(15) . . ?
C2 C1 Fe1 69.51(15) . . ?
C11 C1 Fe1 122.56(19) . . ?
C3 C2 C1 107.9(3) . . ?
C3 C2 Fe1 70.25(16) . . ?
C1 C2 Fe1 69.24(15) . . ?
C4 C3 C2 108.6(3) . . ?
C4 C3 Fe1 70.08(18) . . ?
C2 C3 Fe1 69.26(16) . . ?
C3 C4 C5 108.3(3) . . ?
C3 C4 Fe1 69.82(17) . . ?
C5 C4 Fe1 69.23(18) . . ?
C4 C5 C1 108.1(3) . . ?
C4 C5 Fe1 70.30(19) . . ?
C1 C5 Fe1 69.27(15) . . ?
C7 C6 C10 108.2(5) . . ?
C7 C6 Fe1 70.3(7) . . ?
C10 C6 Fe1 70.0(8) . . ?
C6 C7 C8 108.0(5) . . ?
C6 C7 Fe1 69.9(8) . . ?
C8 C7 Fe1 68.9(7) . . ?
C7 C8 C9 107.9(5) . . ?
C7 C8 Fe1 70.9(7) . . ?
C9 C8 Fe1 69.8(7) . . ?
C10 C9 C8 107.9(5) . . ?
C10 C9 Fe1 70.6(8) . . ?
C8 C9 Fe1 69.6(7) . . ?
C9 C10 C6 108.1(5) . . ?
C9 C10 Fe1 69.3(7) . . ?
C6 C10 Fe1 70.0(8) . . ?
C10B C6B C7B 107.9(5) . . ?
C10B C6B Fe1 69.3(4) . . ?
C7B C6B Fe1 69.9(3) . . ?
C8B C7B C6B 107.6(5) . . ?
C8B C7B Fe1 69.6(3) . . ?
C6B C7B Fe1 69.3(3) . . ?
C9B C8B C7B 108.1(5) . . ?
C9B C8B Fe1 69.5(4) . . ?
C7B C8B Fe1 70.0(3) . . ?
C10B C9B C8B 108.5(5) . . ?
C10B C9B Fe1 69.5(4) . . ?
C8B C9B Fe1 70.1(4) . . ?
C9B C10B C6B 107.8(5) . . ?
C9B C10B Fe1 69.9(4) . . ?
C6B C10B Fe1 70.0(3) . . ?
N1 C11 C1 116.0(2) . . ?
N1 C11 S1 122.8(2) . . ?
C1 C11 S1 121.1(2) . . ?
N1 C12 C13 109.4(3) . . ?
N1 C12 C14 110.1(3) . . ?
C13 C12 C14 112.5(3) . . ?
O1B C13 C12 120(4) . . ?
O1 C13 C12 108.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 S1 0.82 2.76 3.309(3) 125.9 1_455
O1B H1B S1 0.82 2.32 2.97(8) 136.4 1_455

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_Compuesto_4
_database_code_depnum_ccdc_archive 'CCDC 1501495'
_audit_update_record             
;
2016-08-30 deposited with the CCDC.
2017-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Fe N S'
_chemical_formula_sum            'C14 H15 Fe N S'
_chemical_formula_weight         285.18

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.2026(6)
_cell_length_b                   15.2374(9)
_cell_length_c                   8.0026(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1244.09(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      36.55

_exptl_crystal_description       box
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.354
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45112
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.673
_diffrn_reflns_theta_max         40.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7873
_reflns_number_gt                6729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.998

_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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0374P)²+0.0373P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7873
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_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 0.51456(2) 0.57980(2) 0.30953(2) 0.01997(4) Uani 1 1 d . . . . .
S1 S 0.33529(4) 0.36669(3) 0.48865(6) 0.03386(9) Uani 1 1 d . . . . .
N1 N 0.59027(12) 0.34688(8) 0.49721(17) 0.0247(2) Uani 1 1 d . . . . .
C1 C 0.52010(14) 0.44701(8) 0.28137(15) 0.0211(2) Uani 1 1 d . . . . .
C2 C 0.64433(14) 0.48472(9) 0.23774(17) 0.0226(2) Uani 1 1 d . . . . .
H2 H 0.7261 0.4720 0.2891 0.027 Uiso 1 1 calc R U . . .
C3 C 0.62328(15) 0.54469(10) 0.10369(17) 0.0265(2) Uani 1 1 d . . . . .
H3 H 0.6887 0.5787 0.0496 0.032 Uiso 1 1 calc R U . . .
C4 C 0.48694(16) 0.54464(10) 0.06494(16) 0.0273(2) Uani 1 1 d . . . . .
H4 H 0.4458 0.5788 -0.0194 0.033 Uiso 1 1 calc R U . . .
C5 C 0.42293(14) 0.48477(9) 0.17408(18) 0.0256(2) Uani 1 1 d . . . . .
H5 H 0.3318 0.4721 0.1756 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4738(2) 0.60504(10) 0.55458(18) 0.0355(4) Uani 1 1 d . . . . .
H6 H 0.4608 0.5625 0.6397 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5958(2) 0.64322(10) 0.5097(2) 0.0339(3) Uani 1 1 d . . . . .
H7 H 0.6784 0.6308 0.5592 0.041 Uiso 1 1 calc R U . . .
C8 C 0.57196(17) 0.70360(10) 0.3767(2) 0.0294(3) Uani 1 1 d . . . . .
H8 H 0.6360 0.7384 0.3216 0.035 Uiso 1 1 calc R U . . .
C9 C 0.43516(16) 0.70239(9) 0.34148(19) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.3919 0.7366 0.2590 0.033 Uiso 1 1 calc R U . . .
C10 C 0.37454(19) 0.64126(10) 0.4508(2) 0.0320(3) Uani 1 1 d . . . . .
H10 H 0.2839 0.6271 0.4541 0.038 Uiso 1 1 calc R U . . .
C11 C 0.49845(12) 0.38621(7) 0.41949(16) 0.0209(2) Uani 1 1 d . . . . .
C12 C 0.39639(18) 0.27720(10) 0.6156(3) 0.0359(4) Uani 1 1 d . . . . .
H12A H 0.3484 0.2738 0.7229 0.043 Uiso 1 1 calc R U . . .
H12B H 0.3871 0.2205 0.5563 0.043 Uiso 1 1 calc R U . . .
C13 C 0.54141(15) 0.29909(9) 0.6449(2) 0.0282(3) Uani 1 1 d . . . . .
H13 H 0.5920 0.2433 0.6579 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5625(2) 0.35617(12) 0.7986(2) 0.0377(3) Uani 1 1 d . . . . .
H14A H 0.6556 0.3713 0.8078 0.057 Uiso 1 1 calc R U . . .
H14B H 0.5351 0.3240 0.8986 0.057 Uiso 1 1 calc R U . . .
H14C H 0.5106 0.4100 0.7882 0.057 Uiso 1 1 calc R U . . .


_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 C5 2.0361(14) . ?
Fe1 C1 2.0366(12) . ?
Fe1 C6 2.0411(14) . ?
Fe1 C2 2.0449(13) . ?
Fe1 C7 2.0463(16) . ?
Fe1 C8 2.0472(15) . ?
Fe1 C10 2.0486(15) . ?
Fe1 C4 2.0488(13) . ?
Fe1 C9 2.0520(14) . ?
Fe1 C3 2.0568(14) . ?
S1 C11 1.7793(13) . ?
S1 C12 1.8110(18) . ?
N1 C11 1.2742(18) . ?
N1 C13 1.475(2) . ?
C1 C5 1.432(2) . ?
C1 C2 1.4348(19) . ?
C1 C11 1.4591(18) . ?
C2 C3 1.425(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.422(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.420(3) . ?
C6 C10 1.421(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.428(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.424(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C13 1.535(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.522(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C5 Fe1 C1 41.18(6) . . ?
C5 Fe1 C6 123.50(7) . . ?
C1 Fe1 C6 107.41(6) . . ?
C5 Fe1 C2 69.14(6) . . ?
C1 Fe1 C2 41.16(6) . . ?
C6 Fe1 C2 122.36(6) . . ?
C5 Fe1 C7 159.83(7) . . ?
C1 Fe1 C7 122.99(6) . . ?
C6 Fe1 C7 40.67(8) . . ?
C2 Fe1 C7 106.98(7) . . ?
C5 Fe1 C8 157.90(7) . . ?
C1 Fe1 C8 159.49(6) . . ?
C6 Fe1 C8 68.42(7) . . ?
C2 Fe1 C8 122.78(6) . . ?
C7 Fe1 C8 40.82(7) . . ?
C5 Fe1 C10 107.38(7) . . ?
C1 Fe1 C10 122.31(6) . . ?
C6 Fe1 C10 40.67(8) . . ?
C2 Fe1 C10 158.50(6) . . ?
C7 Fe1 C10 68.57(8) . . ?
C8 Fe1 C10 68.48(7) . . ?
C5 Fe1 C4 40.74(6) . . ?
C1 Fe1 C4 68.80(6) . . ?
C6 Fe1 C4 159.90(8) . . ?
C2 Fe1 C4 68.62(6) . . ?
C7 Fe1 C4 157.98(7) . . ?
C8 Fe1 C4 122.09(6) . . ?
C10 Fe1 C4 123.43(7) . . ?
C5 Fe1 C9 122.17(6) . . ?
C1 Fe1 C9 158.29(6) . . ?
C6 Fe1 C9 68.18(6) . . ?
C2 Fe1 C9 159.31(6) . . ?
C7 Fe1 C9 68.44(7) . . ?
C8 Fe1 C9 40.66(7) . . ?
C10 Fe1 C9 40.52(6) . . ?
C4 Fe1 C9 107.62(6) . . ?
C5 Fe1 C3 68.67(6) . . ?
C1 Fe1 C3 68.78(6) . . ?
C6 Fe1 C3 158.17(8) . . ?
C2 Fe1 C3 40.67(6) . . ?
C7 Fe1 C3 122.09(7) . . ?
C8 Fe1 C3 107.21(7) . . ?
C10 Fe1 C3 159.58(7) . . ?
C4 Fe1 C3 40.63(6) . . ?
C9 Fe1 C3 123.33(6) . . ?
C11 S1 C12 88.75(7) . . ?
C11 N1 C13 112.01(12) . . ?
C5 C1 C2 107.74(12) . . ?
C5 C1 C11 127.19(13) . . ?
C2 C1 C11 124.92(12) . . ?
C5 C1 Fe1 69.39(8) . . ?
C2 C1 Fe1 69.73(7) . . ?
C11 C1 Fe1 122.87(8) . . ?
C3 C2 C1 107.87(12) . . ?
C3 C2 Fe1 70.11(8) . . ?
C1 C2 Fe1 69.11(7) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
Fe1 C2 H2 126.3 . . ?
C4 C3 C2 108.08(13) . . ?
C4 C3 Fe1 69.39(8) . . ?
C2 C3 Fe1 69.22(8) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 127.0 . . ?
C5 C4 C3 108.36(13) . . ?
C5 C4 Fe1 69.15(8) . . ?
C3 C4 Fe1 69.99(8) . . ?
C5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
Fe1 C4 H4 126.6 . . ?
C4 C5 C1 107.94(13) . . ?
C4 C5 Fe1 70.11(8) . . ?
C1 C5 Fe1 69.43(7) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 108.55(13) . . ?
C7 C6 Fe1 69.86(9) . . ?
C10 C6 Fe1 69.95(9) . . ?
C7 C6 H6 125.7 . . ?
C10 C6 H6 125.7 . . ?
Fe1 C6 H6 126.0 . . ?
C6 C7 C8 107.63(15) . . ?
C6 C7 Fe1 69.47(9) . . ?
C8 C7 Fe1 69.63(9) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
Fe1 C7 H7 126.3 . . ?
C9 C8 C7 107.86(15) . . ?
C9 C8 Fe1 69.85(9) . . ?
C7 C8 Fe1 69.56(9) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
C10 C9 C8 108.25(15) . . ?
C10 C9 Fe1 69.61(8) . . ?
C8 C9 Fe1 69.49(9) . . ?
C10 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
Fe1 C9 H9 126.6 . . ?
C9 C10 C6 107.71(16) . . ?
C9 C10 Fe1 69.87(9) . . ?
C6 C10 Fe1 69.38(9) . . ?
C9 C10 H10 126.1 . . ?
C6 C10 H10 126.1 . . ?
Fe1 C10 H10 126.2 . . ?
N1 C11 C1 123.86(12) . . ?
N1 C11 S1 117.22(10) . . ?
C1 C11 S1 118.91(10) . . ?
C13 C12 S1 104.72(10) . . ?
C13 C12 H12A 110.8 . . ?
S1 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
S1 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
N1 C13 C14 108.51(12) . . ?
N1 C13 C12 108.09(14) . . ?
C14 C13 C12 112.61(15) . . ?
N1 C13 H13 109.2 . . ?
C14 C13 H13 109.2 . . ?
C12 C13 H13 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
C5 C1 C2 C3 -0.43(15) . . . . ?
C11 C1 C2 C3 -176.23(11) . . . . ?
Fe1 C1 C2 C3 -59.63(9) . . . . ?
C5 C1 C2 Fe1 59.20(9) . . . . ?
C11 C1 C2 Fe1 -116.60(12) . . . . ?
C1 C2 C3 C4 0.33(16) . . . . ?
Fe1 C2 C3 C4 -58.67(10) . . . . ?
C1 C2 C3 Fe1 59.00(9) . . . . ?
C2 C3 C4 C5 -0.10(16) . . . . ?
Fe1 C3 C4 C5 -58.67(10) . . . . ?
C2 C3 C4 Fe1 58.56(10) . . . . ?
C3 C4 C5 C1 -0.16(16) . . . . ?
Fe1 C4 C5 C1 -59.35(9) . . . . ?
C3 C4 C5 Fe1 59.18(10) . . . . ?
C2 C1 C5 C4 0.37(15) . . . . ?
C11 C1 C5 C4 176.04(12) . . . . ?
Fe1 C1 C5 C4 59.77(10) . . . . ?
C2 C1 C5 Fe1 -59.41(9) . . . . ?
C11 C1 C5 Fe1 116.27(12) . . . . ?
C10 C6 C7 C8 -0.06(17) . . . . ?
Fe1 C6 C7 C8 59.40(10) . . . . ?
C10 C6 C7 Fe1 -59.46(10) . . . . ?
C6 C7 C8 C9 0.28(17) . . . . ?
Fe1 C7 C8 C9 59.58(11) . . . . ?
C6 C7 C8 Fe1 -59.30(10) . . . . ?
C7 C8 C9 C10 -0.40(17) . . . . ?
Fe1 C8 C9 C10 59.00(10) . . . . ?
C7 C8 C9 Fe1 -59.40(11) . . . . ?
C8 C9 C10 C6 0.37(17) . . . . ?
Fe1 C9 C10 C6 59.29(10) . . . . ?
C8 C9 C10 Fe1 -58.92(11) . . . . ?
C7 C6 C10 C9 -0.19(17) . . . . ?
Fe1 C6 C10 C9 -59.59(11) . . . . ?
C7 C6 C10 Fe1 59.40(10) . . . . ?
C13 N1 C11 C1 172.24(11) . . . . ?
C13 N1 C11 S1 -6.33(15) . . . . ?
C5 C1 C11 N1 171.20(13) . . . . ?
C2 C1 C11 N1 -13.83(19) . . . . ?
Fe1 C1 C11 N1 -100.85(14) . . . . ?
C5 C1 C11 S1 -10.26(17) . . . . ?
C2 C1 C11 S1 164.72(10) . . . . ?
Fe1 C1 C11 S1 77.70(12) . . . . ?
C12 S1 C11 N1 -11.56(12) . . . . ?
C12 S1 C11 C1 169.80(11) . . . . ?
C11 S1 C12 C13 23.74(12) . . . . ?
C11 N1 C13 C14 -97.24(16) . . . . ?
C11 N1 C13 C12 25.17(17) . . . . ?
S1 C12 C13 N1 -31.54(16) . . . . ?
S1 C12 C13 C14 88.32(15) . . . . ?

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.083

