# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Complex1
_database_code_depnum_ccdc_archive 'CCDC 1838290'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H44 Fe2 N8 O4 S4'
_chemical_formula_weight         1084.89

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n


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

_cell_length_a                   11.1144(6)
_cell_length_b                   15.7599(7)
_cell_length_c                   14.9052(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.382(3)
_cell_angle_gamma                90.00
_cell_volume                     2517.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5688
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.82

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29928
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         28.72
_reflns_number_total             6489
_reflns_number_gt                5011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v1.0-22 (Bruker, 2004)'
_computing_cell_refinement       'APEX2 v1.0-22'
_computing_data_reduction        'APEX2 v1.0-22'
_computing_structure_solution    'SHELXTL 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL 5.1'
_computing_molecular_graphics    'SHELXTL 5.1'
_computing_publication_material  'SHELXTL 5.1'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6489
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   0.789
_refine_ls_restrained_S_all      0.789
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.46576(2) 0.104964(17) 0.45802(2) 0.01798(9) Uani 1 1 d . . .
S1 S 0.56400(4) 0.04301(3) 0.61023(3) 0.01914(12) Uani 1 1 d . . .
S2 S 0.64139(5) 0.13504(3) 0.40321(4) 0.02431(13) Uani 1 1 d . . .
C21 C 0.35939(19) 0.39058(14) 0.46701(17) 0.0285(5) Uani 1 1 d . . .
H21A H 0.3066 0.3407 0.4427 0.034 Uiso 1 1 calc R . .
H21B H 0.3315 0.4381 0.4230 0.034 Uiso 1 1 calc R . .
N4 N 0.39778(19) 0.48647(12) 0.59878(15) 0.0329(4) Uani 1 1 d . . .
C22 C 0.34193(19) 0.41462(13) 0.56056(17) 0.0272(5) Uani 1 1 d . . .
C24 C 0.2589(3) 0.38824(18) 0.6898(2) 0.0520(8) Uani 1 1 d . . .
H24 H 0.2109 0.3550 0.7207 0.062 Uiso 1 1 calc R . .
C23 C 0.2716(2) 0.36422(16) 0.6038(2) 0.0404(6) Uani 1 1 d . . .
H23 H 0.2328 0.3140 0.5747 0.049 Uiso 1 1 calc R . .
C25 C 0.3168(3) 0.46080(19) 0.7300(2) 0.0544(9) Uani 1 1 d . . .
H25 H 0.3102 0.4785 0.7895 0.065 Uiso 1 1 calc R . .
C26 C 0.3850(3) 0.50778(17) 0.6823(2) 0.0472(7) Uani 1 1 d . . .
H26 H 0.4250 0.5580 0.7106 0.057 Uiso 1 1 calc R . .
C20 C 0.53722(17) 0.29381(12) 0.49584(14) 0.0180(4) Uani 1 1 d . . .
C14 C 0.72812(18) 0.21275(12) 0.47840(15) 0.0215(4) Uani 1 1 d . . .
C15 C 0.8586(2) 0.20624(14) 0.50550(17) 0.0287(5) Uani 1 1 d . . .
H15 H 0.8968 0.1579 0.4867 0.034 Uiso 1 1 calc R . .
C19 C 0.67478(18) 0.28479(12) 0.50931(14) 0.0206(4) Uani 1 1 d . . .
C16 C 0.9334(2) 0.26775(16) 0.55853(18) 0.0329(5) Uani 1 1 d . . .
H16 H 1.0215 0.2609 0.5761 0.040 Uiso 1 1 calc R . .
C18 C 0.75194(19) 0.34729(13) 0.56140(15) 0.0248(4) Uani 1 1 d . . .
H18 H 0.7153 0.3963 0.5802 0.030 Uiso 1 1 calc R . .
C17 C 0.8809(2) 0.33921(16) 0.58615(17) 0.0316(5) Uani 1 1 d . . .
H17 H 0.9322 0.3822 0.6215 0.038 Uiso 1 1 calc R . .
O2 O 0.47063(13) 0.23419(9) 0.51083(10) 0.0212(3) Uani 1 1 d . . .
N3 N 0.48927(16) 0.37058(11) 0.47211(13) 0.0221(4) Uani 1 1 d . . .
C6 C 0.3593(2) 0.10941(13) 0.66830(17) 0.0269(5) Uani 1 1 d . . .
C1 C 0.4771(2) 0.06966(13) 0.69003(15) 0.0245(4) Uani 1 1 d . . .
C5 C 0.3130(3) 0.14239(16) 0.7404(2) 0.0415(6) Uani 1 1 d . . .
H5 H 0.2356 0.1719 0.7253 0.050 Uiso 1 1 calc R . .
C4 C 0.3772(3) 0.1328(2) 0.8320(2) 0.0525(8) Uani 1 1 d . . .
H4 H 0.3452 0.1562 0.8797 0.063 Uiso 1 1 calc R . .
C2 C 0.5392(3) 0.05849(16) 0.78484(16) 0.0355(5) Uani 1 1 d . . .
H2 H 0.6169 0.0296 0.8015 0.043 Uiso 1 1 calc R . .
C3 C 0.4885(3) 0.0892(2) 0.85436(19) 0.0504(8) Uani 1 1 d . . .
H3 H 0.5310 0.0799 0.9178 0.060 Uiso 1 1 calc R . .
N2 N 0.30654(18) 0.15442(11) 0.35701(13) 0.0286(4) Uani 1 1 d . . .
C9 C 0.1907(2) 0.13138(14) 0.35800(17) 0.0328(5) Uani 1 1 d . . .
C8 C 0.17911(19) 0.06032(15) 0.42153(18) 0.0332(5) Uani 1 1 d . . .
H8A H 0.0986 0.0654 0.4377 0.040 Uiso 1 1 calc R . .
H8B H 0.1791 0.0056 0.3889 0.040 Uiso 1 1 calc R . .
C13 C 0.3203(3) 0.21669(15) 0.29876(16) 0.0358(6) Uani 1 1 d . . .
H13 H 0.4024 0.2330 0.2982 0.043 Uiso 1 1 calc R . .
C12 C 0.2207(3) 0.25781(17) 0.23987(18) 0.0491(8) Uani 1 1 d . . .
H12 H 0.2335 0.3016 0.1996 0.059 Uiso 1 1 calc R . .
C11 C 0.1022(3) 0.23362(18) 0.2411(2) 0.0548(9) Uani 1 1 d . . .
H11 H 0.0317 0.2604 0.2009 0.066 Uiso 1 1 calc R . .
C10 C 0.0862(3) 0.17043(17) 0.3006(2) 0.0475(7) Uani 1 1 d . . .
H10 H 0.0048 0.1537 0.3025 0.057 Uiso 1 1 calc R . .
N1 N 0.28160(16) 0.06064(12) 0.50731(14) 0.0245(4) Uani 1 1 d . . .
C7 C 0.27284(19) 0.11902(13) 0.57346(18) 0.0275(5) Uani 1 1 d . . .
O1 O 0.19389(16) 0.17505(11) 0.55475(15) 0.0424(5) Uani 1 1 d . . .
H1B H 0.536(2) 0.4141(16) 0.4610(17) 0.024(6) Uiso 1 1 d . . .
H1A H 0.306(2) 0.0156(18) 0.5287(18) 0.030(7) Uiso 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
Fe1 N2 2.1430(18) . ?
Fe1 O2 2.1788(14) . ?
Fe1 S2 2.3555(6) . ?
Fe1 S1 2.4451(6) . ?
Fe1 S1 2.5306(5) 3_656 ?
S1 C1 1.770(2) . ?
S1 Fe1 2.5306(5) 3_656 ?
S2 C14 1.764(2) . ?
C21 N3 1.460(3) . ?
C21 C22 1.506(3) . ?
N4 C26 1.333(3) . ?
N4 C22 1.343(3) . ?
C22 C23 1.387(3) . ?
C24 C25 1.370(5) . ?
C24 C23 1.379(4) . ?
C25 C26 1.384(4) . ?
C20 O2 1.252(2) . ?
C20 N3 1.332(2) . ?
C20 C19 1.495(3) . ?
C14 C15 1.402(3) . ?
C14 C19 1.413(3) . ?
C15 C16 1.381(3) . ?
C19 C18 1.398(3) . ?
C16 C17 1.380(3) . ?
C18 C17 1.388(3) . ?
C6 C1 1.409(3) . ?
C6 C5 1.409(3) . ?
C6 C7 1.492(3) . ?
C1 C2 1.409(3) . ?
C5 C4 1.370(4) . ?
C4 C3 1.377(5) . ?
C2 C3 1.391(4) . ?
N2 C9 1.341(3) . ?
N2 C13 1.346(3) . ?
C9 C10 1.390(3) . ?
C9 C8 1.494(4) . ?
C8 N1 1.470(3) . ?
C13 C12 1.379(3) . ?
C12 C11 1.375(5) . ?
C11 C10 1.377(5) . ?
N1 C7 1.371(3) . ?
C7 O1 1.224(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
N2 Fe1 O2 81.41(6) . . ?
N2 Fe1 S2 106.80(6) . . ?
O2 Fe1 S2 89.64(4) . . ?
N2 Fe1 S1 151.57(6) . . ?
O2 Fe1 S1 94.35(4) . . ?
S2 Fe1 S1 101.25(2) . . ?
N2 Fe1 S1 93.28(5) . 3_656 ?
O2 Fe1 S1 174.05(4) . 3_656 ?
S2 Fe1 S1 94.477(19) . 3_656 ?
S1 Fe1 S1 89.060(18) . 3_656 ?
C1 S1 Fe1 109.87(8) . . ?
C1 S1 Fe1 116.89(7) . 3_656 ?
Fe1 S1 Fe1 90.941(18) . 3_656 ?
C14 S2 Fe1 106.42(7) . . ?
N3 C21 C22 111.99(19) . . ?
C26 N4 C22 117.2(2) . . ?
N4 C22 C23 122.6(2) . . ?
N4 C22 C21 116.49(19) . . ?
C23 C22 C21 120.9(2) . . ?
C25 C24 C23 118.9(2) . . ?
C22 C23 C24 118.9(3) . . ?
C24 C25 C26 118.6(3) . . ?
N4 C26 C25 123.6(3) . . ?
O2 C20 N3 121.02(17) . . ?
O2 C20 C19 122.44(17) . . ?
N3 C20 C19 116.43(17) . . ?
C15 C14 C19 117.14(19) . . ?
C15 C14 S2 118.77(16) . . ?
C19 C14 S2 123.99(15) . . ?
C16 C15 C14 122.2(2) . . ?
C18 C19 C14 119.89(18) . . ?
C18 C19 C20 117.54(17) . . ?
C14 C19 C20 122.34(18) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C18 C19 121.4(2) . . ?
C16 C17 C18 118.9(2) . . ?
C20 O2 Fe1 126.59(12) . . ?
C20 N3 C21 122.06(18) . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C7 126.07(19) . . ?
C5 C6 C7 114.3(2) . . ?
C6 C1 C2 117.6(2) . . ?
C6 C1 S1 126.17(17) . . ?
C2 C1 S1 115.77(18) . . ?
C4 C5 C6 121.3(3) . . ?
C5 C4 C3 119.6(3) . . ?
C3 C2 C1 121.1(3) . . ?
C4 C3 C2 120.6(3) . . ?
C9 N2 C13 118.6(2) . . ?
C9 N2 Fe1 120.65(16) . . ?
C13 N2 Fe1 120.28(17) . . ?
N2 C9 C10 121.4(3) . . ?
N2 C9 C8 117.04(18) . . ?
C10 C9 C8 121.5(2) . . ?
N1 C8 C9 111.80(18) . . ?
N2 C13 C12 122.9(3) . . ?
C11 C12 C13 118.1(3) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C10 C9 119.1(3) . . ?
C7 N1 C8 116.20(18) . . ?
O1 C7 N1 120.3(2) . . ?
O1 C7 C6 122.1(2) . . ?
N1 C7 C6 117.56(19) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.72
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_LNHS2
_database_code_depnum_ccdc_archive 'CCDC 1838292'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N4 O2 S2'
_chemical_formula_weight         486.60

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.838(2)
_cell_length_b                   19.043(6)
_cell_length_c                   15.788(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.21(2)
_cell_angle_gamma                90.00
_cell_volume                     2342.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2103
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      17.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28384
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_sigmaI/netI    0.1221
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4614
_reflns_number_gt                2227
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4614
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1516
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.2219
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16035(17) 0.10235(6) 0.36534(8) 0.0641(4) Uani 1 1 d . . .
S2 S 0.15599(15) -0.00474(6) 0.35500(8) 0.0634(4) Uani 1 1 d . . .
C7 C 0.1595(6) 0.2576(2) 0.3169(3) 0.0583(11) Uani 1 1 d . . .
C6 C 0.0819(6) 0.2092(2) 0.2496(3) 0.0561(11) Uani 1 1 d . . .
C1 C 0.0751(6) 0.1363(2) 0.2644(3) 0.0582(12) Uani 1 1 d . . .
C2 C 0.0040(7) 0.0928(3) 0.1994(3) 0.0720(14) Uani 1 1 d . . .
H2 H 0.0020 0.0445 0.2081 0.086 Uiso 1 1 calc R . .
C5 C 0.0117(6) 0.2343(3) 0.1711(3) 0.0681(13) Uani 1 1 d . . .
H5 H 0.0144 0.2823 0.1609 0.082 Uiso 1 1 calc R . .
C3 C -0.0631(7) 0.1201(3) 0.1228(3) 0.0799(15) Uani 1 1 d . . .
H3 H -0.1104 0.0901 0.0800 0.096 Uiso 1 1 calc R . .
C4 C -0.0616(7) 0.1910(3) 0.1081(3) 0.0777(15) Uani 1 1 d . . .
H4 H -0.1095 0.2093 0.0563 0.093 Uiso 1 1 calc R . .
O1 O 0.1659(4) 0.24285(17) 0.3929(2) 0.0713(9) Uani 1 1 d . . .
N1 N 0.2226(5) 0.31868(19) 0.2904(2) 0.0693(11) Uani 1 1 d . . .
H1 H 0.2121 0.3277 0.2367 0.083 Uiso 1 1 calc R . .
C8 C 0.3082(7) 0.3701(2) 0.3490(3) 0.0761(15) Uani 1 1 d . . .
H8A H 0.4115 0.3859 0.3261 0.091 Uiso 1 1 calc R . .
H8B H 0.3431 0.3469 0.4028 0.091 Uiso 1 1 calc R . .
C9 C 0.2024(8) 0.4329(3) 0.3658(3) 0.0712(14) Uani 1 1 d . . .
C10 C 0.0502(9) 0.4498(3) 0.3218(4) 0.102(2) Uani 1 1 d . . .
H10 H 0.0016 0.4203 0.2789 0.122 Uiso 1 1 calc R . .
N2 N 0.2794(7) 0.4737(3) 0.4278(3) 0.0976(15) Uani 1 1 d . . .
C19 C -0.0802(6) -0.0969(2) 0.4124(3) 0.0536(11) Uani 1 1 d . . .
C14 C -0.0511(6) -0.0285(2) 0.3835(3) 0.0543(11) Uani 1 1 d . . .
C20 C 0.0636(7) -0.1485(2) 0.4213(3) 0.0593(12) Uani 1 1 d . . .
C18 C -0.2442(7) -0.1157(3) 0.4306(3) 0.0656(13) Uani 1 1 d . . .
H18 H -0.2640 -0.1612 0.4486 0.079 Uiso 1 1 calc R . .
C15 C -0.1862(7) 0.0185(3) 0.3777(3) 0.0723(14) Uani 1 1 d . . .
H15 H -0.1686 0.0645 0.3607 0.087 Uiso 1 1 calc R . .
C16 C -0.3464(7) -0.0017(3) 0.3967(3) 0.0774(15) Uani 1 1 d . . .
H16 H -0.4353 0.0309 0.3917 0.093 Uiso 1 1 calc R . .
C17 C -0.3776(7) -0.0682(3) 0.4225(3) 0.0728(14) Uani 1 1 d . . .
H17 H -0.4867 -0.0813 0.4344 0.087 Uiso 1 1 calc R . .
O2 O 0.1828(4) -0.14609(16) 0.3770(2) 0.0699(9) Uani 1 1 d . . .
N3 N 0.0540(6) -0.1995(2) 0.4804(2) 0.0756(12) Uani 1 1 d . . .
H2A H -0.0322 -0.1991 0.5098 0.091 Uiso 1 1 calc R . .
C22 C 0.2664(7) -0.2492(3) 0.5858(4) 0.0793(16) Uani 1 1 d . . .
C21 C 0.1797(8) -0.2542(3) 0.4967(4) 0.0940(19) Uani 1 1 d . . .
H21A H 0.2648 -0.2502 0.4567 0.113 Uiso 1 1 calc R . .
H21B H 0.1244 -0.2996 0.4884 0.113 Uiso 1 1 calc R . .
C23 C 0.3544(9) -0.1917(3) 0.6102(5) 0.0905(17) Uani 1 1 d . . .
H23 H 0.3670 -0.1555 0.5718 0.109 Uiso 1 1 calc R . .
N4 N 0.2472(8) -0.3041(3) 0.6388(4) 0.1170(19) Uani 1 1 d . . .
C25 C 0.4093(9) -0.2383(4) 0.7482(5) 0.116(2) Uani 1 1 d . . .
H25 H 0.4580 -0.2337 0.8043 0.139 Uiso 1 1 calc R . .
C26 C 0.3204(10) -0.2972(5) 0.7213(5) 0.123(3) Uani 1 1 d . . .
H26 H 0.3092 -0.3334 0.7598 0.148 Uiso 1 1 calc R . .
C24 C 0.4243(9) -0.1870(4) 0.6907(6) 0.117(2) Uani 1 1 d . . .
H24 H 0.4857 -0.1467 0.7079 0.141 Uiso 1 1 calc R . .
C12 C 0.0399(12) 0.5528(4) 0.4027(6) 0.131(3) Uani 1 1 d . . .
H12 H -0.0133 0.5942 0.4164 0.157 Uiso 1 1 calc R . .
C11 C -0.0321(10) 0.5103(4) 0.3403(5) 0.127(3) Uani 1 1 d . . .
H11 H -0.1367 0.5221 0.3101 0.153 Uiso 1 1 calc R . .
C13 C 0.1914(12) 0.5331(4) 0.4446(5) 0.121(3) Uani 1 1 d . . .
H13 H 0.2396 0.5621 0.4881 0.145 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.781(5) . ?
S1 S2 2.0459(18) . ?
S2 C14 1.789(5) . ?
C7 O1 1.228(5) . ?
C7 N1 1.348(5) . ?
C7 C6 1.486(6) . ?
C6 C5 1.384(6) . ?
C6 C1 1.410(6) . ?
C1 C2 1.388(6) . ?
C2 C3 1.369(7) . ?
C5 C4 1.371(7) . ?
C3 C4 1.370(7) . ?
N1 C8 1.460(6) . ?
C8 C9 1.496(7) . ?
C9 N2 1.340(7) . ?
C9 C10 1.353(8) . ?
C10 C11 1.366(8) . ?
N2 C13 1.365(8) . ?
C19 C18 1.394(6) . ?
C19 C14 1.407(6) . ?
C19 C20 1.491(6) . ?
C14 C15 1.383(6) . ?
C20 O2 1.227(5) . ?
C20 N3 1.354(5) . ?
C18 C17 1.378(7) . ?
C15 C16 1.377(7) . ?
C16 C17 1.360(7) . ?
N3 C21 1.438(6) . ?
C22 C23 1.330(8) . ?
C22 N4 1.358(7) . ?
C22 C21 1.497(8) . ?
C23 C24 1.331(9) . ?
N4 C26 1.371(9) . ?
C25 C24 1.347(9) . ?
C25 C26 1.363(10) . ?
C12 C13 1.348(10) . ?
C12 C11 1.351(10) . ?

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
C1 S1 S2 106.81(15) . . ?
C14 S2 S1 103.88(15) . . ?
O1 C7 N1 121.5(4) . . ?
O1 C7 C6 121.8(4) . . ?
N1 C7 C6 116.7(4) . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 C7 121.2(4) . . ?
C1 C6 C7 120.8(4) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C1 S1 121.7(4) . . ?
C6 C1 S1 119.3(3) . . ?
C3 C2 C1 120.8(5) . . ?
C4 C5 C6 122.5(5) . . ?
C2 C3 C4 121.0(5) . . ?
C3 C4 C5 118.7(5) . . ?
C7 N1 C8 122.7(4) . . ?
N1 C8 C9 115.1(5) . . ?
N2 C9 C10 122.6(5) . . ?
N2 C9 C8 112.3(5) . . ?
C10 C9 C8 125.0(5) . . ?
C9 C10 C11 120.1(6) . . ?
C9 N2 C13 115.1(6) . . ?
C18 C19 C14 119.4(4) . . ?
C18 C19 C20 121.1(4) . . ?
C14 C19 C20 119.5(4) . . ?
C15 C14 C19 118.1(4) . . ?
C15 C14 S2 121.9(3) . . ?
C19 C14 S2 120.0(3) . . ?
O2 C20 N3 121.5(4) . . ?
O2 C20 C19 122.4(4) . . ?
N3 C20 C19 116.1(4) . . ?
C17 C18 C19 121.3(5) . . ?
C16 C15 C14 120.9(5) . . ?
C17 C16 C15 121.6(5) . . ?
C16 C17 C18 118.7(5) . . ?
C20 N3 C21 123.7(4) . . ?
C23 C22 N4 123.0(6) . . ?
C23 C22 C21 119.5(5) . . ?
N4 C22 C21 117.5(6) . . ?
N3 C21 C22 110.8(4) . . ?
C22 C23 C24 118.6(6) . . ?
C22 N4 C26 116.7(7) . . ?
C24 C25 C26 117.7(8) . . ?
C25 C26 N4 121.5(7) . . ?
C23 C24 C25 122.5(8) . . ?
C13 C12 C11 117.9(7) . . ?
C12 C11 C10 119.4(8) . . ?
C12 C13 N2 124.9(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_Complex2
_database_code_depnum_ccdc_archive 'CCDC 1838291'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H42 Fe N5 O3 S2'
_chemical_formula_weight         688.70

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.879(3)
_cell_length_b                   12.862(3)
_cell_length_c                   16.892(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.985(14)
_cell_angle_gamma                90.00
_cell_volume                     3361.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    917
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      16.04

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31974
_diffrn_reflns_av_R_equivalents  0.1746
_diffrn_reflns_av_sigmaI/netI    0.1303
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         24.50
_reflns_number_total             5583
_reflns_number_gt                2670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5583
_refine_ls_number_parameters     418
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.2051
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.70340(6) 0.07551(7) 0.71103(6) 0.0442(3) Uani 1 1 d . . .
S2 S 0.81178(11) 0.14431(14) 0.66058(11) 0.0536(5) Uani 1 1 d . . .
S1 S 0.80331(11) -0.00466(14) 0.80876(10) 0.0536(5) Uani 1 1 d . . .
C7 C 0.7075(4) -0.1494(5) 0.6597(4) 0.0465(17) Uani 1 1 d . . .
C6 C 0.6749(4) -0.0222(5) 0.5564(4) 0.0517(18) Uani 1 1 d . . .
H6 H 0.6452 -0.0798 0.5249 0.062 Uiso 1 1 calc R . .
H5 H 0.7278 -0.0085 0.5386 0.062 Uiso 1 1 calc R . .
C5 C 0.6188(4) 0.0717(5) 0.5450(4) 0.0476(17) Uani 1 1 d . . .
C4 C 0.5688(5) 0.1002(6) 0.4701(4) 0.061(2) Uani 1 1 d . . .
H4 H 0.5734 0.0646 0.4233 0.073 Uiso 1 1 calc R . .
C9 C 0.6815(5) -0.2823(6) 0.7574(5) 0.066(2) Uani 1 1 d . . .
H7 H 0.6571 -0.3221 0.7120 0.079 Uiso 1 1 calc R . .
C8 C 0.7154(4) -0.1842(5) 0.7467(4) 0.0475(17) Uani 1 1 d . . .
C3 C 0.5114(5) 0.1830(6) 0.4658(5) 0.070(2) Uani 1 1 d . . .
H3 H 0.4768 0.2035 0.4163 0.084 Uiso 1 1 calc R . .
C1 C 0.5604(4) 0.2050(6) 0.6085(5) 0.0579(19) Uani 1 1 d . . .
H1 H 0.5576 0.2410 0.6556 0.070 Uiso 1 1 calc R . .
C13 C 0.7535(4) -0.1256(5) 0.8149(4) 0.0496(17) Uani 1 1 d . . .
C11 C 0.7188(6) -0.2620(7) 0.9008(5) 0.080(3) Uani 1 1 d . . .
H9 H 0.7185 -0.2872 0.9524 0.096 Uiso 1 1 calc R . .
C12 C 0.7541(5) -0.1674(6) 0.8921(5) 0.061(2) Uani 1 1 d . . .
H10 H 0.7792 -0.1294 0.9382 0.074 Uiso 1 1 calc R . .
C10 C 0.6834(6) -0.3207(6) 0.8329(5) 0.078(2) Uani 1 1 d . . .
H8 H 0.6610 -0.3863 0.8388 0.093 Uiso 1 1 calc R . .
C2 C 0.5067(5) 0.2332(6) 0.5353(5) 0.067(2) Uani 1 1 d . . .
H2 H 0.4671 0.2869 0.5337 0.080 Uiso 1 1 calc R . .
N2 N 0.6943(3) -0.0474(4) 0.6429(3) 0.0439(13) Uani 1 1 d . . .
N1 N 0.6169(3) 0.1257(4) 0.6120(3) 0.0458(13) Uani 1 1 d . . .
C26 C 0.7820(4) 0.2753(5) 0.6418(4) 0.0525(18) Uani 1 1 d . . .
C20 C 0.7231(4) 0.2982(5) 0.7708(4) 0.0533(18) Uani 1 1 d . . .
C18 C 0.6098(4) 0.0887(5) 0.8351(4) 0.0528(18) Uani 1 1 d . . .
C22 C 0.7323(5) 0.4415(6) 0.6771(5) 0.071(2) Uani 1 1 d . . .
H17 H 0.7097 0.4820 0.7130 0.085 Uiso 1 1 calc R . .
C14 C 0.5484(4) -0.0385(5) 0.7426(4) 0.0538(18) Uani 1 1 d . . .
H11 H 0.5474 -0.0754 0.6951 0.065 Uiso 1 1 calc R . .
C21 C 0.7453(4) 0.3357(5) 0.6943(5) 0.0567(19) Uani 1 1 d . . .
C19 C 0.6756(5) 0.1735(5) 0.8526(4) 0.064(2) Uani 1 1 d . . .
H15 H 0.6515 0.2340 0.8737 0.077 Uiso 1 1 calc R . .
H16 H 0.7258 0.1505 0.8928 0.077 Uiso 1 1 calc R . .
C25 C 0.8034(5) 0.3239(6) 0.5749(5) 0.069(2) Uani 1 1 d . . .
H20 H 0.8294 0.2855 0.5404 0.083 Uiso 1 1 calc R . .
C24 C 0.7864(6) 0.4280(7) 0.5594(6) 0.088(3) Uani 1 1 d . . .
H19 H 0.7992 0.4579 0.5134 0.105 Uiso 1 1 calc R . .
C17 C 0.5529(6) 0.0656(6) 0.8821(5) 0.071(2) Uani 1 1 d . . .
H14 H 0.5564 0.1010 0.9308 0.086 Uiso 1 1 calc R . .
C15 C 0.4877(5) -0.0596(6) 0.7862(6) 0.075(2) Uani 1 1 d . . .
H12 H 0.4444 -0.1080 0.7671 0.090 Uiso 1 1 calc R . .
C16 C 0.4910(6) -0.0084(7) 0.8589(6) 0.080(3) Uani 1 1 d . . .
H13 H 0.4521 -0.0241 0.8909 0.096 Uiso 1 1 calc R . .
C23 C 0.7506(6) 0.4888(7) 0.6109(6) 0.085(3) Uani 1 1 d . . .
H18 H 0.7396 0.5591 0.6008 0.102 Uiso 1 1 calc R . .
N4 N 0.7003(3) 0.1994(4) 0.7767(3) 0.0485(14) Uani 1 1 d . . .
N3 N 0.6096(3) 0.0339(4) 0.7665(3) 0.0482(14) Uani 1 1 d . . .
O1 O 0.7075(3) -0.2170(4) 0.6067(3) 0.0608(13) Uani 1 1 d . . .
O2 O 0.7212(4) 0.3647(4) 0.8249(3) 0.0764(16) Uani 1 1 d . . .
N5 N 0.0251(4) 0.3053(5) 0.8554(3) 0.0609(16) Uani 1 1 d . . .
C29 C -0.0485(5) 0.3821(6) 0.8287(5) 0.076(2) Uani 1 1 d . . .
H26 H -0.0866 0.3557 0.7797 0.092 Uiso 1 1 calc R . .
H27 H -0.0815 0.3853 0.8705 0.092 Uiso 1 1 calc R . .
C27 C 0.0790(5) 0.2977(7) 0.7923(5) 0.076(2) Uani 1 1 d . . .
H21 H 0.1115 0.3618 0.7935 0.091 Uiso 1 1 calc R . .
H22 H 0.1205 0.2419 0.8081 0.091 Uiso 1 1 calc R . .
C31 C -0.0192(5) 0.2028(6) 0.8654(5) 0.077(2) Uani 1 1 d . . .
H31 H -0.0532 0.1817 0.8127 0.093 Uiso 1 1 calc R . .
H32 H -0.0589 0.2143 0.9005 0.093 Uiso 1 1 calc R . .
C33 C 0.0855(5) 0.3403(7) 0.9330(5) 0.083(3) Uani 1 1 d . . .
H36 H 0.1067 0.4091 0.9242 0.100 Uiso 1 1 calc R . .
H37 H 0.1349 0.2938 0.9442 0.100 Uiso 1 1 calc R . .
C32 C 0.0410(7) 0.1137(7) 0.9003(6) 0.118(4) Uani 1 1 d . . .
H33 H 0.0823 0.1032 0.8674 0.178 Uiso 1 1 calc R . .
H34 H 0.0078 0.0514 0.9007 0.178 Uiso 1 1 calc R . .
H35 H 0.0707 0.1304 0.9548 0.178 Uiso 1 1 calc R . .
C34 C 0.0476(6) 0.3441(8) 1.0077(5) 0.104(3) Uani 1 1 d . . .
H40 H -0.0016 0.3895 0.9976 0.156 Uiso 1 1 calc R . .
H38 H 0.0904 0.3698 1.0530 0.156 Uiso 1 1 calc R . .
H39 H 0.0302 0.2755 1.0197 0.156 Uiso 1 1 calc R . .
C28 C 0.0308(6) 0.2785(7) 0.7058(5) 0.091(3) Uani 1 1 d . . .
H25 H -0.0062 0.2191 0.7041 0.136 Uiso 1 1 calc R . .
H24 H 0.0713 0.2658 0.6725 0.136 Uiso 1 1 calc R . .
H23 H -0.0035 0.3384 0.6859 0.136 Uiso 1 1 calc R . .
C30 C -0.0216(7) 0.4908(7) 0.8123(6) 0.113(3) Uani 1 1 d . . .
H30 H 0.0210 0.5152 0.8582 0.169 Uiso 1 1 calc R . .
H29 H -0.0710 0.5358 0.8033 0.169 Uiso 1 1 calc R . .
H28 H 0.0024 0.4906 0.7650 0.169 Uiso 1 1 calc R . .
O3 O 0.8360(4) 0.4151(7) 0.9686(5) 0.118(2) Uani 1 1 d D . .
H41 H 0.795(4) 0.444(7) 0.920(3) 0.13(4) Uiso 1 1 d D . .
H42 H 0.822(5) 0.386(9) 1.019(4) 0.20(6) Uiso 1 1 d 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
Fe1 N2 1.942(5) . ?
Fe1 N4 1.949(5) . ?
Fe1 N3 2.002(5) . ?
Fe1 N1 2.018(5) . ?
Fe1 S1 2.265(2) . ?
Fe1 S2 2.265(2) . ?
S2 C26 1.760(7) . ?
S1 C13 1.759(7) . ?
C7 O1 1.248(7) . ?
C7 N2 1.349(8) . ?
C7 C8 1.515(9) . ?
C6 N2 1.460(8) . ?
C6 C5 1.487(9) . ?
C5 N1 1.334(8) . ?
C5 C4 1.383(9) . ?
C4 C3 1.394(10) . ?
C9 C10 1.361(10) . ?
C9 C8 1.400(9) . ?
C8 C13 1.395(9) . ?
C3 C2 1.355(10) . ?
C1 N1 1.351(8) . ?
C1 C2 1.383(9) . ?
C13 C12 1.409(9) . ?
C11 C12 1.362(10) . ?
C11 C10 1.383(11) . ?
C26 C25 1.398(9) . ?
C26 C21 1.400(9) . ?
C20 O2 1.257(7) . ?
C20 N4 1.332(8) . ?
C20 C21 1.494(9) . ?
C18 N3 1.356(8) . ?
C18 C17 1.363(9) . ?
C18 C19 1.493(9) . ?
C22 C23 1.360(11) . ?
C22 C21 1.398(9) . ?
C14 N3 1.341(8) . ?
C14 C15 1.366(10) . ?
C19 N4 1.460(8) . ?
C25 C24 1.379(10) . ?
C24 C23 1.384(11) . ?
C17 C16 1.362(11) . ?
C15 C16 1.384(11) . ?
N5 C33 1.509(9) . ?
N5 C27 1.514(9) . ?
N5 C29 1.519(9) . ?
N5 C31 1.522(9) . ?
C29 C30 1.506(11) . ?
C27 C28 1.509(10) . ?
C31 C32 1.523(11) . ?
C33 C34 1.515(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Fe1 N4 174.4(2) . . ?
N2 Fe1 N3 95.5(2) . . ?
N4 Fe1 N3 80.5(2) . . ?
N2 Fe1 N1 79.8(2) . . ?
N4 Fe1 N1 96.4(2) . . ?
N3 Fe1 N1 92.0(2) . . ?
N2 Fe1 S1 90.45(16) . . ?
N4 Fe1 S1 93.45(16) . . ?
N3 Fe1 S1 90.59(16) . . ?
N1 Fe1 S1 170.11(17) . . ?
N2 Fe1 S2 93.24(16) . . ?
N4 Fe1 S2 90.77(17) . . ?
N3 Fe1 S2 171.26(17) . . ?
N1 Fe1 S2 89.78(15) . . ?
S1 Fe1 S2 89.15(7) . . ?
C26 S2 Fe1 104.2(2) . . ?
C13 S1 Fe1 101.2(2) . . ?
O1 C7 N2 123.5(6) . . ?
O1 C7 C8 118.5(6) . . ?
N2 C7 C8 117.8(6) . . ?
N2 C6 C5 107.2(5) . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 C6 116.1(6) . . ?
C4 C5 C6 122.6(7) . . ?
C5 C4 C3 119.0(7) . . ?
C10 C9 C8 121.3(7) . . ?
C13 C8 C9 119.2(7) . . ?
C13 C8 C7 124.6(6) . . ?
C9 C8 C7 116.2(6) . . ?
C2 C3 C4 118.8(7) . . ?
N1 C1 C2 120.4(7) . . ?
C8 C13 C12 118.1(6) . . ?
C8 C13 S1 123.1(5) . . ?
C12 C13 S1 118.8(5) . . ?
C12 C11 C10 119.9(8) . . ?
C11 C12 C13 121.6(7) . . ?
C9 C10 C11 120.0(7) . . ?
C3 C2 C1 120.4(7) . . ?
C7 N2 C6 114.5(5) . . ?
C7 N2 Fe1 132.9(4) . . ?
C6 N2 Fe1 112.5(4) . . ?
C5 N1 C1 119.9(6) . . ?
C5 N1 Fe1 113.3(4) . . ?
C1 N1 Fe1 126.8(5) . . ?
C25 C26 C21 118.3(7) . . ?
C25 C26 S2 118.0(6) . . ?
C21 C26 S2 123.4(5) . . ?
O2 C20 N4 122.9(7) . . ?
O2 C20 C21 117.3(6) . . ?
N4 C20 C21 119.6(6) . . ?
N3 C18 C17 120.7(7) . . ?
N3 C18 C19 114.6(6) . . ?
C17 C18 C19 124.7(7) . . ?
C23 C22 C21 123.9(8) . . ?
N3 C14 C15 121.9(7) . . ?
C22 C21 C26 118.2(7) . . ?
C22 C21 C20 116.2(7) . . ?
C26 C21 C20 125.6(6) . . ?
N4 C19 C18 107.9(6) . . ?
C24 C25 C26 121.0(8) . . ?
C25 C24 C23 121.3(8) . . ?
C16 C17 C18 121.0(8) . . ?
C14 C15 C16 119.5(8) . . ?
C17 C16 C15 118.0(7) . . ?
C22 C23 C24 117.3(8) . . ?
C20 N4 C19 114.5(6) . . ?
C20 N4 Fe1 134.1(5) . . ?
C19 N4 Fe1 111.1(4) . . ?
C14 N3 C18 118.7(6) . . ?
C14 N3 Fe1 127.6(5) . . ?
C18 N3 Fe1 113.7(4) . . ?
C33 N5 C27 106.4(5) . . ?
C33 N5 C29 111.2(6) . . ?
C27 N5 C29 110.6(6) . . ?
C33 N5 C31 112.4(6) . . ?
C27 N5 C31 111.7(6) . . ?
C29 N5 C31 104.6(5) . . ?
C30 C29 N5 115.2(7) . . ?
C28 C27 N5 116.6(6) . . ?
N5 C31 C32 115.4(7) . . ?
N5 C33 C34 116.0(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_LN-S
_database_code_depnum_ccdc_archive 'CCDC 1838293'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O S'
_chemical_formula_weight         242.30

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.9938(16)
_cell_length_b                   13.994(2)
_cell_length_c                   8.1879(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.361(11)
_cell_angle_gamma                90.00
_cell_volume                     1135.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3505
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13677
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.79
_reflns_number_total             2935
_reflns_number_gt                2234
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v1.0-22 (Bruker, 2004)'
_computing_cell_refinement       'APEX2 v1.0-22'
_computing_data_reduction        'APEX2 v1.0-22'
_computing_structure_solution    'SHELXTL 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL 5.1'
_computing_molecular_graphics    'SHELXTL 5.1'
_computing_publication_material  'SHELXTL 5.1'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2935
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.00005(4) 0.08142(3) 0.14935(5) 0.04609(17) Uani 1 1 d . . .
C7 C 0.19445(18) 0.14160(11) 0.3715(2) 0.0489(4) Uani 1 1 d . . .
C6 C 0.07272(18) 0.13780(11) 0.45017(19) 0.0471(4) Uani 1 1 d . . .
C9 C 0.33465(15) 0.00918(12) 0.1074(2) 0.0477(4) Uani 1 1 d . . .
C1 C -0.03923(18) 0.10647(10) 0.34564(19) 0.0448(4) Uani 1 1 d . . .
C5 C 0.0607(2) 0.16055(11) 0.6135(2) 0.0612(5) Uani 1 1 d . . .
H5 H 0.1354 0.1815 0.6836 0.073 Uiso 1 1 calc R . .
C8 C 0.26437(18) 0.10441(13) 0.0974(2) 0.0535(4) Uani 1 1 d . . .
H8A H 0.3307 0.1547 0.1216 0.064 Uiso 1 1 calc R . .
H8B H 0.2201 0.1141 -0.0138 0.064 Uiso 1 1 calc R . .
C4 C -0.0609(3) 0.15190(13) 0.6694(2) 0.0707(6) Uani 1 1 d . . .
H4 H -0.0697 0.1676 0.7779 0.085 Uiso 1 1 calc R . .
C3 C -0.1720(3) 0.11968(14) 0.5652(3) 0.0722(6) Uani 1 1 d . . .
H3 H -0.2543 0.1135 0.6060 0.087 Uiso 1 1 calc R . .
C2 C -0.1644(2) 0.09643(13) 0.4024(3) 0.0593(5) Uani 1 1 d . . .
H2 H -0.2396 0.0750 0.3335 0.071 Uiso 1 1 calc R . .
C11 C 0.5034(2) -0.0980(2) 0.2293(3) 0.0813(7) Uani 1 1 d . . .
H11 H 0.5781 -0.1114 0.3057 0.098 Uiso 1 1 calc R . .
C10 C 0.44505(18) -0.00922(17) 0.2229(2) 0.0659(5) Uani 1 1 d . . .
H10 H 0.4796 0.0383 0.2957 0.079 Uiso 1 1 calc R . .
C12 C 0.4492(2) -0.16703(16) 0.1207(4) 0.0821(7) Uani 1 1 d . . .
H12 H 0.4856 -0.2282 0.1225 0.098 Uiso 1 1 calc R . .
C13 C 0.3400(2) -0.14285(15) 0.0101(3) 0.0756(6) Uani 1 1 d . . .
H13 H 0.3038 -0.1894 -0.0638 0.091 Uiso 1 1 calc R . .
O1 O 0.30878(14) 0.16809(10) 0.43059(18) 0.0708(4) Uani 1 1 d . . .
N1 N 0.16428(13) 0.11084(10) 0.21271(16) 0.0459(3) Uani 1 1 d . . .
N2 N 0.28248(15) -0.05700(11) 0.0015(2) 0.0599(4) 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
S1 N1 1.7081(14) . ?
S1 C1 1.7380(16) . ?
C7 O1 1.239(2) . ?
C7 N1 1.366(2) . ?
C7 C6 1.448(2) . ?
C6 C1 1.390(2) . ?
C6 C5 1.395(2) . ?
C9 N2 1.329(2) . ?
C9 C10 1.382(2) . ?
C9 C8 1.504(2) . ?
C1 C2 1.396(2) . ?
C5 C4 1.357(3) . ?
C8 N1 1.463(2) . ?
C4 C3 1.386(3) . ?
C3 C2 1.384(3) . ?
C11 C12 1.376(4) . ?
C11 C10 1.371(3) . ?
C12 C13 1.368(4) . ?
C13 N2 1.330(2) . ?

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 S1 C1 89.55(7) . . ?
O1 C7 N1 123.07(17) . . ?
O1 C7 C6 128.50(16) . . ?
N1 C7 C6 108.42(15) . . ?
C1 C6 C5 120.06(17) . . ?
C1 C6 C7 113.18(14) . . ?
C5 C6 C7 126.76(17) . . ?
N2 C9 C10 121.92(17) . . ?
N2 C9 C8 116.13(14) . . ?
C10 C9 C8 121.93(17) . . ?
C6 C1 C2 120.78(17) . . ?
C6 C1 S1 111.98(13) . . ?
C2 C1 S1 127.24(15) . . ?
C4 C5 C6 119.6(2) . . ?
N1 C8 C9 111.87(13) . . ?
C3 C4 C5 120.16(18) . . ?
C4 C3 C2 122.0(2) . . ?
C3 C2 C1 117.3(2) . . ?
C12 C11 C10 118.8(2) . . ?
C9 C10 C11 119.6(2) . . ?
C11 C12 C13 118.0(2) . . ?
N2 C13 C12 124.1(2) . . ?
C7 N1 C8 123.20(15) . . ?
C7 N1 S1 116.83(12) . . ?
C8 N1 S1 119.95(11) . . ?
C9 N2 C13 117.65(17) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.79
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.042
