# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_DPL385TA_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2005421'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 Fe N8 S2 Se2'
_chemical_formula_sum            'C20 H18 Fe N8 S2 Se2'
_chemical_formula_weight         648.31

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.0926(7)
_cell_length_b                   15.8607(10)
_cell_length_c                   7.8392(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.955(2)
_cell_angle_gamma                90
_cell_volume                     1235.97(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.4180
_cell_measurement_theta_max      24.5529

_exptl_crystal_description       plate
_exptl_crystal_colour            'lustrous light bronze-orange'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.6393
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    3.750
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6393
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            33828
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2527
_reflns_number_gt                1820
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'Bruker Instrument Service (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0506P)²+2.2017P] 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_number_reflns         2527
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Se1 Se 0.05592(5) 0.63851(4) 0.33710(10) 0.0799(3) Uani 1 1 d . . . . .
N1 N 0.3714(3) 0.4028(2) 0.3411(4) 0.0366(7) Uani 1 1 d . . . . .
Fe1 Fe 0.500000 0.500000 0.500000 0.0314(2) Uani 1 2 d S . P . .
S1 S 0.57418(11) 0.53835(7) 0.22541(13) 0.0425(3) Uani 1 1 d . . . . .
C1 C 0.2429(4) 0.3948(3) 0.3677(6) 0.0418(9) Uani 1 1 d . . . . .
H1 H 0.217573 0.424160 0.459629 0.050 Uiso 1 1 calc R U . . .
N2 N 0.5353(4) 0.3676(2) 0.1736(5) 0.0429(8) Uani 1 1 d . . . . .
C2 C 0.1488(5) 0.3463(3) 0.2676(6) 0.0499(11) Uani 1 1 d . . . . .
H2 H 0.062242 0.341943 0.292478 0.060 Uiso 1 1 calc R U . . .
C3 C 0.1834(5) 0.3042(3) 0.1306(6) 0.0618(14) Uani 1 1 d . . . . .
H3 H 0.120670 0.271045 0.059752 0.074 Uiso 1 1 calc R U . . .
N3 N 0.7205(4) 0.4151(2) 0.1049(5) 0.0494(9) Uani 1 1 d . . . . .
C4 C 0.3118(5) 0.3115(3) 0.0988(6) 0.0579(13) Uani 1 1 d . . . . .
H4 H 0.337868 0.283350 0.005991 0.070 Uiso 1 1 calc R U . . .
N4 N 0.3365(4) 0.5857(2) 0.4385(5) 0.0447(8) Uani 1 1 d . . . . .
C5 C 0.4017(4) 0.3611(2) 0.2059(5) 0.0396(9) Uani 1 1 d . . . . .
C8 C 0.8279(5) 0.4722(4) 0.0774(8) 0.0705(15) Uani 1 1 d . . . . .
H8A H 0.868855 0.496303 0.186125 0.106 Uiso 1 1 calc R U . . .
H8B H 0.791219 0.516415 -0.000400 0.106 Uiso 1 1 calc R U . . .
H8C H 0.894280 0.441655 0.028299 0.106 Uiso 1 1 calc R U . . .
C7 C 0.7162(5) 0.3303(3) 0.0701(8) 0.0652(14) Uani 1 1 d . . . . .
H7 H 0.780825 0.299266 0.025994 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6017(5) 0.3003(3) 0.1114(7) 0.0604(13) Uani 1 1 d . . . . .
H6 H 0.572022 0.244780 0.100478 0.072 Uiso 1 1 calc R U . . .
C9 C 0.6096(4) 0.4394(3) 0.1681(5) 0.0396(9) Uani 1 1 d . . . . .
C10 C 0.2263(5) 0.6069(3) 0.3986(5) 0.0415(10) 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
Se1 C10 1.776(5) . ?
N1 C5 1.330(5) . ?
N1 C1 1.354(5) . ?
N1 Fe1 2.249(3) . ?
Fe1 N4 2.128(4) . ?
Fe1 N4 2.128(4) 3_666 ?
Fe1 S1 2.4741(10) . ?
Fe1 S1 2.4741(10) 3_666 ?
S1 C9 1.687(4) . ?
C1 C2 1.361(6) . ?
C1 H1 0.9300 . ?
N2 C9 1.369(5) . ?
N2 C6 1.392(6) . ?
N2 C5 1.418(5) . ?
C2 C3 1.360(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9300 . ?
N3 C9 1.357(5) . ?
N3 C7 1.372(6) . ?
N3 C8 1.457(6) . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
N4 C10 1.152(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 C6 1.340(7) . ?
C7 H7 0.9300 . ?
C6 H6 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
C5 N1 C1 115.8(3) . . ?
C5 N1 Fe1 126.3(3) . . ?
C1 N1 Fe1 117.1(3) . . ?
N4 Fe1 N4 180.0 . 3_666 ?
N4 Fe1 N1 87.79(13) . . ?
N4 Fe1 N1 92.21(13) 3_666 . ?
N4 Fe1 N1 92.21(13) . 3_666 ?
N4 Fe1 N1 87.79(13) 3_666 3_666 ?
N1 Fe1 N1 180.00(15) . 3_666 ?
N4 Fe1 S1 89.16(10) . . ?
N4 Fe1 S1 90.84(10) 3_666 . ?
N1 Fe1 S1 85.38(8) . . ?
N1 Fe1 S1 94.62(8) 3_666 . ?
N4 Fe1 S1 90.84(10) . 3_666 ?
N4 Fe1 S1 89.16(10) 3_666 3_666 ?
N1 Fe1 S1 94.63(8) . 3_666 ?
N1 Fe1 S1 85.37(8) 3_666 3_666 ?
S1 Fe1 S1 180.0 . 3_666 ?
C9 S1 Fe1 96.48(14) . . ?
N1 C1 C2 123.7(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C9 N2 C6 109.1(4) . . ?
C9 N2 C5 127.5(3) . . ?
C6 N2 C5 122.4(4) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C9 N3 C7 110.6(4) . . ?
C9 N3 C8 124.0(4) . . ?
C7 N3 C8 125.4(4) . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C10 N4 Fe1 157.4(3) . . ?
N1 C5 C4 123.6(4) . . ?
N1 C5 N2 117.6(3) . . ?
C4 C5 N2 118.8(4) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 N3 107.4(4) . . ?
C6 C7 H7 126.3 . . ?
N3 C7 H7 126.3 . . ?
C7 C6 N2 107.5(4) . . ?
C7 C6 H6 126.3 . . ?
N2 C6 H6 126.3 . . ?
N3 C9 N2 105.4(4) . . ?
N3 C9 S1 126.0(3) . . ?
N2 C9 S1 128.6(3) . . ?
N4 C10 Se1 179.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.4(6) . . . . ?
Fe1 N1 C1 C2 171.8(3) . . . . ?
N1 C1 C2 C3 -1.3(7) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
C1 N1 C5 C4 -0.9(6) . . . . ?
Fe1 N1 C5 C4 -170.3(3) . . . . ?
C1 N1 C5 N2 -179.9(3) . . . . ?
Fe1 N1 C5 N2 10.8(5) . . . . ?
C3 C4 C5 N1 0.3(7) . . . . ?
C3 C4 C5 N2 179.2(5) . . . . ?
C9 N2 C5 N1 -48.2(6) . . . . ?
C6 N2 C5 N1 143.8(4) . . . . ?
C9 N2 C5 C4 132.8(5) . . . . ?
C6 N2 C5 C4 -35.2(6) . . . . ?
C9 N3 C7 C6 0.0(6) . . . . ?
C8 N3 C7 C6 -179.5(5) . . . . ?
N3 C7 C6 N2 -0.5(6) . . . . ?
C9 N2 C6 C7 0.7(6) . . . . ?
C5 N2 C6 C7 170.7(4) . . . . ?
C7 N3 C9 N2 0.4(5) . . . . ?
C8 N3 C9 N2 180.0(4) . . . . ?
C7 N3 C9 S1 -179.3(4) . . . . ?
C8 N3 C9 S1 0.3(6) . . . . ?
C6 N2 C9 N3 -0.7(5) . . . . ?
C5 N2 C9 N3 -170.0(4) . . . . ?
C6 N2 C9 S1 179.0(4) . . . . ?
C5 N2 C9 S1 9.7(6) . . . . ?
Fe1 S1 C9 N3 -135.7(4) . . . . ?
Fe1 S1 C9 N2 44.7(4) . . . . ?

_refine_diff_density_max         0.742
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_DPL019
_database_code_depnum_ccdc_archive 'CCDC 2005422'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2022-07-07 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 H18 Fe N8 S4'
_chemical_formula_sum            'C20 H18 Fe N8 S4'
_chemical_formula_weight         554.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.8211(7)
_cell_length_b                   15.7029(11)
_cell_length_c                   7.7911(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.618(2)
_cell_angle_gamma                90
_cell_volume                     1184.65(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      33.16

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   0.7019
_exptl_transmission_factor_max   0.7465
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.254
_exptl_absorpt_coefficient_mu    1.016
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            36368
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         32.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4290
_reflns_number_gt                3956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'Bruker Instrument Service (Bruker AXS Inc., 2015)'
_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)+(0.0274P)²+0.4383P] 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_number_reflns         4290
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.5000 0.5000 0.5000 0.01380(5) Uani 1 2 d S . P . .
C1 C 0.76366(10) 0.39438(6) 0.62734(13) 0.01908(17) Uani 1 1 d . . . . .
H1 H 0.7886 0.4243 0.5312 0.023 Uiso 1 1 calc R U . . .
N1 N 0.63284(8) 0.40196(5) 0.65800(10) 0.01664(14) Uani 1 1 d . . . . .
S1 S 0.42252(3) 0.53855(2) 0.77696(3) 0.01825(5) Uani 1 1 d . . . . .
N2 N 0.46413(9) 0.36566(5) 0.82950(11) 0.01867(15) Uani 1 1 d . . . . .
C2 C 0.86308(11) 0.34542(7) 0.72842(14) 0.02221(18) Uani 1 1 d . . . . .
H2 H 0.9534 0.3408 0.7007 0.027 Uiso 1 1 calc R U . . .
S2 S 0.94163(3) 0.63699(2) 0.66335(5) 0.03860(9) Uani 1 1 d . . . . .
C6 C 0.39786(12) 0.29747(7) 0.89663(16) 0.0273(2) Uani 1 1 d . . . . .
H6 H 0.4294 0.2402 0.9078 0.033 Uiso 1 1 calc R U . . .
C7 C 0.28165(12) 0.32805(7) 0.94216(17) 0.0294(2) Uani 1 1 d . . . . .
H7 H 0.2153 0.2964 0.9914 0.035 Uiso 1 1 calc R U . . .
N3 N 0.27587(9) 0.41421(6) 0.90429(12) 0.02175(16) Uani 1 1 d . . . . .
C3 C 0.82825(12) 0.30319(7) 0.87114(15) 0.0275(2) Uani 1 1 d . . . . .
H3 H 0.8948 0.2697 0.9441 0.033 Uiso 1 1 calc R U . . .
C5 C 0.60094(10) 0.35999(6) 0.79493(12) 0.01735(16) Uani 1 1 d . . . . .
C4 C 0.69527(12) 0.31050(7) 0.90579(14) 0.0254(2) Uani 1 1 d . . . . .
H4 H 0.6688 0.2824 1.0030 0.030 Uiso 1 1 calc R U . . .
N4 N 0.66750(9) 0.58584(6) 0.55993(12) 0.02155(16) Uani 1 1 d . . . . .
C8 C 0.16758(12) 0.47206(8) 0.93835(18) 0.0317(2) Uani 1 1 d . . . . .
H8A H 0.1210 0.4965 0.8283 0.048 Uiso 1 1 calc R U . . .
H8B H 0.2084 0.5179 1.0156 0.048 Uiso 1 1 calc R U . . .
H8C H 0.1004 0.4407 0.9940 0.048 Uiso 1 1 calc R U . . .
C10 C 0.78176(10) 0.60722(6) 0.60228(13) 0.01990(17) Uani 1 1 d . . . . .
C9 C 0.38764(9) 0.43819(6) 0.83662(12) 0.01660(15) 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
Fe1 N4 2.1177(9) 3_666 ?
Fe1 N4 2.1177(9) . ?
Fe1 N1 2.2474(8) . ?
Fe1 N1 2.2474(8) 3_666 ?
Fe1 S1 2.4800(3) . ?
Fe1 S1 2.4800(3) 3_666 ?
C1 N1 1.3507(12) . ?
C1 C2 1.3812(14) . ?
C1 H1 0.9500 . ?
N1 C5 1.3351(12) . ?
S1 C9 1.6942(10) . ?
N2 C9 1.3705(12) . ?
N2 C6 1.3991(13) . ?
N2 C5 1.4166(13) . ?
C2 C3 1.3857(15) . ?
C2 H2 0.9500 . ?
S2 C10 1.6312(11) . ?
C6 C7 1.3395(16) . ?
C6 H6 0.9500 . ?
C7 N3 1.3840(15) . ?
C7 H7 0.9500 . ?
N3 C9 1.3484(12) . ?
N3 C8 1.4564(14) . ?
C3 C4 1.3818(16) . ?
C3 H3 0.9500 . ?
C5 C4 1.3931(13) . ?
C4 H4 0.9500 . ?
N4 C10 1.1649(13) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
N4 Fe1 N4 180.00(4) 3_666 . ?
N4 Fe1 N1 92.48(3) 3_666 . ?
N4 Fe1 N1 87.52(3) . . ?
N4 Fe1 N1 87.52(3) 3_666 3_666 ?
N4 Fe1 N1 92.48(3) . 3_666 ?
N1 Fe1 N1 180.0 . 3_666 ?
N4 Fe1 S1 90.41(3) 3_666 . ?
N4 Fe1 S1 89.59(3) . . ?
N1 Fe1 S1 85.70(2) . . ?
N1 Fe1 S1 94.30(2) 3_666 . ?
N4 Fe1 S1 89.59(3) 3_666 3_666 ?
N4 Fe1 S1 90.41(3) . 3_666 ?
N1 Fe1 S1 94.30(2) . 3_666 ?
N1 Fe1 S1 85.70(2) 3_666 3_666 ?
S1 Fe1 S1 180.0 . 3_666 ?
N1 C1 C2 123.44(9) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C5 N1 C1 117.06(8) . . ?
C5 N1 Fe1 125.71(6) . . ?
C1 N1 Fe1 116.48(6) . . ?
C9 S1 Fe1 96.73(3) . . ?
C9 N2 C6 109.18(8) . . ?
C9 N2 C5 127.13(8) . . ?
C6 N2 C5 122.56(8) . . ?
C1 C2 C3 118.56(9) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C7 C6 N2 107.15(9) . . ?
C7 C6 H6 126.4 . . ?
N2 C6 H6 126.4 . . ?
C6 C7 N3 107.48(9) . . ?
C6 C7 H7 126.3 . . ?
N3 C7 H7 126.3 . . ?
C9 N3 C7 110.44(9) . . ?
C9 N3 C8 124.34(9) . . ?
C7 N3 C8 125.18(9) . . ?
C4 C3 C2 119.02(9) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N1 C5 C4 123.38(9) . . ?
N1 C5 N2 118.52(8) . . ?
C4 C5 N2 118.09(9) . . ?
C3 C4 C5 118.53(10) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C10 N4 Fe1 157.21(8) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C10 S2 179.50(10) . . ?
N3 C9 N2 105.74(8) . . ?
N3 C9 S1 125.60(7) . . ?
N2 C9 S1 128.65(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 0.67(14) . . . . ?
C2 C1 N1 Fe1 171.28(8) . . . . ?
N1 C1 C2 C3 -1.45(16) . . . . ?
C9 N2 C6 C7 0.68(13) . . . . ?
C5 N2 C6 C7 169.32(10) . . . . ?
N2 C6 C7 N3 -0.16(14) . . . . ?
C6 C7 N3 C9 -0.43(14) . . . . ?
C6 C7 N3 C8 -178.24(11) . . . . ?
C1 C2 C3 C4 0.93(17) . . . . ?
C1 N1 C5 C4 0.62(14) . . . . ?
Fe1 N1 C5 C4 -169.01(8) . . . . ?
C1 N1 C5 N2 -179.19(8) . . . . ?
Fe1 N1 C5 N2 11.18(12) . . . . ?
C9 N2 C5 N1 -48.64(14) . . . . ?
C6 N2 C5 N1 144.85(10) . . . . ?
C9 N2 C5 C4 131.54(11) . . . . ?
C6 N2 C5 C4 -34.97(14) . . . . ?
C2 C3 C4 C5 0.25(17) . . . . ?
N1 C5 C4 C3 -1.08(16) . . . . ?
N2 C5 C4 C3 178.73(10) . . . . ?
C7 N3 C9 N2 0.84(12) . . . . ?
C8 N3 C9 N2 178.66(10) . . . . ?
C7 N3 C9 S1 -178.51(8) . . . . ?
C8 N3 C9 S1 -0.68(15) . . . . ?
C6 N2 C9 N3 -0.92(11) . . . . ?
C5 N2 C9 N3 -168.91(9) . . . . ?
C6 N2 C9 S1 178.39(8) . . . . ?
C5 N2 C9 S1 10.41(15) . . . . ?
Fe1 S1 C9 N3 -137.16(8) . . . . ?
Fe1 S1 C9 N2 43.65(9) . . . . ?

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
C6 H6 N4 0.95 2.63 3.4122(14) 139.7 2_646
C1 H1 S1 0.95 2.96 3.5285(10) 120.0 3_666
C8 H8A S2 0.98 2.98 3.8254(14) 145.5 1_455
C8 H8C S2 0.98 3.03 3.8503(14) 142.6 3_667

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_DPL277
_database_code_depnum_ccdc_archive 'CCDC 2005426'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2022-07-07 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         'C30 H30 B2 Fe N10 S2'
_chemical_formula_sum            'C30 H30 B2 Fe N10 S2'
_chemical_formula_weight         672.23

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'
B B 0.0013 0.0007 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2630(4)
_cell_length_b                   8.4919(4)
_cell_length_c                   13.1039(7)
_cell_angle_alpha                104.846(2)
_cell_angle_beta                 103.820(2)
_cell_angle_gamma                99.454(2)
_cell_volume                     837.79(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.29

_exptl_crystal_description       square
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   0.7265
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            87200
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.1880
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.556
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3569
_reflns_number_gt                3113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0451P)²+0.5042P] 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_number_reflns         3569
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.008
_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 1.0000 0.5000 0.5000 0.02593(13) Uani 1 2 d S . P . .
N1 N 0.9242(2) 0.7480(2) 0.54268(15) 0.0307(4) Uani 1 1 d . . . . .
C1 C 1.0437(3) 0.8786(3) 0.6208(2) 0.0397(5) Uani 1 1 d . . . . .
S1 S 0.69780(7) 0.37039(7) 0.48045(5) 0.03248(15) Uani 1 1 d . . . . .
B1 B 0.8067(6) 0.5197(5) 0.1259(3) 0.0621(10) Uani 1 1 d . . . . .
H1C H 0.708(6) 0.413(6) 0.077(4) 0.126(17) Uiso 1 1 d . . . . .
H1B H 0.749(7) 0.622(7) 0.137(4) 0.16(2) Uiso 1 1 d . . . . .
H1A H 0.900(7) 0.499(7) 0.083(4) 0.144(19) Uiso 1 1 d . . . . .
N2 N 0.6484(2) 0.6465(2) 0.41507(15) 0.0311(4) Uani 1 1 d . . . . .
C2 C 1.0152(4) 1.0344(3) 0.6582(2) 0.0466(6) Uani 1 1 d . . . . .
N3 N 0.5537(3) 0.6955(3) 0.33586(17) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.8565(4) 1.0602(3) 0.6170(3) 0.0506(7) Uani 1 1 d . . . . .
N5 N 0.9334(2) 0.4883(3) 0.32919(16) 0.0363(4) Uani 1 1 d . . . . .
C5 C 0.7726(3) 0.7785(3) 0.50417(18) 0.0317(5) Uani 1 1 d . . . . .
C4 C 0.7312(4) 0.9287(3) 0.5389(2) 0.0460(6) Uani 1 1 d . . . . .
N4 N 0.4535(3) 0.5539(3) 0.26582(17) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.830(4) 1.156(4) 0.638(3) 0.067(10) Uiso 1 1 d . . . . .
C9 C 0.3866(3) 0.2455(3) 0.22662(19) 0.0376(5) Uani 1 1 d . . . . .
H2 H 1.100(4) 1.119(4) 0.715(3) 0.061(9) Uiso 1 1 d . . . . .
C8 C 0.4782(3) 0.4166(3) 0.29591(19) 0.0332(5) Uani 1 1 d . . . . .
H1 H 1.153(4) 0.855(4) 0.647(2) 0.051(8) Uiso 1 1 d . . . . .
C7 C 0.6070(3) 0.4756(3) 0.39582(18) 0.0289(4) Uani 1 1 d . . . . .
C6 C 0.3365(4) 0.5597(4) 0.1637(3) 0.0636(9) Uani 1 1 d . . . . .
H6A H 0.3544 0.4846 0.1011 0.095 Uiso 1 1 calc R U . . .
H6B H 0.3589 0.6719 0.1592 0.095 Uiso 1 1 calc R U . . .
H6C H 0.2199 0.5264 0.1640 0.095 Uiso 1 1 calc R U . . .
H4 H 0.625(4) 0.938(4) 0.509(2) 0.053(8) Uiso 1 1 d . . . . .
C10 C 0.2091(3) 0.1937(4) 0.2027(2) 0.0514(7) Uani 1 1 d . . . . .
H10 H 0.1477 0.2660 0.2329 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4757(4) 0.1367(4) 0.1827(3) 0.0568(7) Uani 1 1 d . . . . .
C12 C 0.2144(5) -0.0728(4) 0.0890(3) 0.0730(11) Uani 1 1 d . . . . .
H12 H 0.1565 -0.1801 0.0423 0.088 Uiso 1 1 calc R U . . .
C11 C 0.1250(5) 0.0333(5) 0.1333(3) 0.0667(10) Uani 1 1 d . . . . .
H14 H 0.591(4) 0.165(4) 0.194(3) 0.060(9) Uiso 1 1 d . . . . .
C13 C 0.3888(6) -0.0230(4) 0.1124(3) 0.0753(10) Uani 1 1 d . . . . .
H13 H 0.454(5) -0.096(6) 0.080(4) 0.101(14) Uiso 1 1 d . . . . .
H11 H 0.010(5) 0.002(5) 0.120(3) 0.082(12) Uiso 1 1 d . . . . .
C15 C 0.8820(3) 0.5012(3) 0.24405(19) 0.0356(5) 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
Fe1 N5 2.1453(19) 2_766 ?
Fe1 N5 2.1453(19) . ?
Fe1 N1 2.2663(18) 2_766 ?
Fe1 N1 2.2663(18) . ?
Fe1 S1 2.4818(5) 2_766 ?
Fe1 S1 2.4818(5) . ?
N1 C5 1.328(3) . ?
N1 C1 1.352(3) . ?
C1 C2 1.368(4) . ?
S1 C7 1.709(2) . ?
B1 C15 1.582(4) . ?
N2 N3 1.343(2) . ?
N2 C7 1.377(3) . ?
N2 C5 1.433(3) . ?
C2 C3 1.369(4) . ?
N3 N4 1.311(3) . ?
C3 C4 1.376(4) . ?
N5 C15 1.135(3) . ?
C5 C4 1.368(3) . ?
N4 C8 1.353(3) . ?
N4 C6 1.470(3) . ?
C9 C14 1.372(4) . ?
C9 C10 1.393(4) . ?
C9 C8 1.464(3) . ?
C8 C7 1.386(3) . ?
C10 C11 1.385(4) . ?
C14 C13 1.388(5) . ?
C12 C11 1.360(6) . ?
C12 C13 1.368(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Fe1 N5 180.0 2_766 . ?
N5 Fe1 N1 89.71(7) 2_766 2_766 ?
N5 Fe1 N1 90.29(7) . 2_766 ?
N5 Fe1 N1 90.29(7) 2_766 . ?
N5 Fe1 N1 89.71(7) . . ?
N1 Fe1 N1 180.0 2_766 . ?
N5 Fe1 S1 90.96(5) 2_766 2_766 ?
N5 Fe1 S1 89.04(5) . 2_766 ?
N1 Fe1 S1 85.47(5) 2_766 2_766 ?
N1 Fe1 S1 94.53(5) . 2_766 ?
N5 Fe1 S1 89.04(5) 2_766 . ?
N5 Fe1 S1 90.96(5) . . ?
N1 Fe1 S1 94.54(5) 2_766 . ?
N1 Fe1 S1 85.47(5) . . ?
S1 Fe1 S1 180.0 2_766 . ?
C5 N1 C1 115.7(2) . . ?
C5 N1 Fe1 127.59(15) . . ?
C1 N1 Fe1 116.60(15) . . ?
N1 C1 C2 123.5(2) . . ?
C7 S1 Fe1 96.00(7) . . ?
N3 N2 C7 113.22(18) . . ?
N3 N2 C5 115.50(18) . . ?
C7 N2 C5 131.28(18) . . ?
C1 C2 C3 118.9(3) . . ?
N4 N3 N2 103.25(17) . . ?
C2 C3 C4 118.9(2) . . ?
C15 N5 Fe1 168.2(2) . . ?
N1 C5 C4 124.8(2) . . ?
N1 C5 N2 116.76(19) . . ?
C4 C5 N2 118.3(2) . . ?
C5 C4 C3 118.1(2) . . ?
N3 N4 C8 114.04(18) . . ?
N3 N4 C6 118.1(2) . . ?
C8 N4 C6 127.8(2) . . ?
C14 C9 C10 119.7(3) . . ?
C14 C9 C8 119.7(2) . . ?
C10 C9 C8 120.5(2) . . ?
N4 C8 C7 105.9(2) . . ?
N4 C8 C9 122.9(2) . . ?
C7 C8 C9 131.1(2) . . ?
N2 C7 C8 103.59(18) . . ?
N2 C7 S1 125.89(16) . . ?
C8 C7 S1 130.52(17) . . ?
C11 C10 C9 119.2(3) . . ?
C9 C14 C13 120.1(3) . . ?
C11 C12 C13 120.6(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C13 C14 119.8(4) . . ?
N5 C15 B1 178.8(3) . . ?

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 N1 C1 C2 -1.1(4) . . . . ?
Fe1 N1 C1 C2 -177.7(2) . . . . ?
N1 C1 C2 C3 1.7(4) . . . . ?
C7 N2 N3 N4 -0.7(3) . . . . ?
C5 N2 N3 N4 179.68(19) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 N1 C5 C4 -0.9(3) . . . . ?
Fe1 N1 C5 C4 175.27(19) . . . . ?
C1 N1 C5 N2 175.1(2) . . . . ?
Fe1 N1 C5 N2 -8.8(3) . . . . ?
N3 N2 C5 N1 -140.1(2) . . . . ?
C7 N2 C5 N1 40.3(3) . . . . ?
N3 N2 C5 C4 36.1(3) . . . . ?
C7 N2 C5 C4 -143.5(2) . . . . ?
N1 C5 C4 C3 2.1(4) . . . . ?
N2 C5 C4 C3 -173.8(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
N2 N3 N4 C8 0.2(3) . . . . ?
N2 N3 N4 C6 -176.8(2) . . . . ?
N3 N4 C8 C7 0.3(3) . . . . ?
C6 N4 C8 C7 176.9(3) . . . . ?
N3 N4 C8 C9 -176.5(2) . . . . ?
C6 N4 C8 C9 0.1(4) . . . . ?
C14 C9 C8 N4 114.1(3) . . . . ?
C10 C9 C8 N4 -64.2(3) . . . . ?
C14 C9 C8 C7 -61.8(4) . . . . ?
C10 C9 C8 C7 119.9(3) . . . . ?
N3 N2 C7 C8 0.8(3) . . . . ?
C5 N2 C7 C8 -179.6(2) . . . . ?
N3 N2 C7 S1 -178.52(16) . . . . ?
C5 N2 C7 S1 1.1(3) . . . . ?
N4 C8 C7 N2 -0.6(2) . . . . ?
C9 C8 C7 N2 175.8(2) . . . . ?
N4 C8 C7 S1 178.67(18) . . . . ?
C9 C8 C7 S1 -4.9(4) . . . . ?
Fe1 S1 C7 N2 -51.05(19) . . . . ?
Fe1 S1 C7 C8 129.8(2) . . . . ?
C14 C9 C10 C11 -0.9(4) . . . . ?
C8 C9 C10 C11 177.4(2) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
C8 C9 C14 C13 -176.8(3) . . . . ?
C13 C12 C11 C10 0.2(5) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C9 C14 C13 C12 -1.3(5) . . . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_DPL291
_database_code_depnum_ccdc_archive 'CCDC 2005423'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2022-07-07 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         'C30 H24 Fe N10 S2 Se2'
_chemical_formula_sum            'C30 H24 Fe N10 S2 Se2'
_chemical_formula_weight         802.48

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1749(10)
_cell_length_b                   8.4576(10)
_cell_length_c                   12.8781(16)
_cell_angle_alpha                104.556(4)
_cell_angle_beta                 101.501(4)
_cell_angle_gamma                100.261(4)
_cell_volume                     819.69(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    171(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      29.09

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   0.6205
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    2.846
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      171(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            59596
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.563
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3347
_reflns_number_gt                2976
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0288P)²+0.9950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3347
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
Se1 Se 0.39145(4) 0.11338(3) 0.11300(2) 0.04081(9) Uani 1 1 d . . . . .
S1 S 0.78706(6) 0.61462(6) 0.47882(5) 0.02197(12) Uani 1 1 d . . . . .
Fe1 Fe 0.5000 0.5000 0.5000 0.01853(10) Uani 1 2 d S . P . .
C1 C 0.5553(3) 0.2326(3) 0.62112(19) 0.0269(5) Uani 1 1 d . . . . .
H1 H 0.469(3) 0.283(3) 0.650(2) 0.033(7) Uiso 1 1 d . . . . .
N1 N 0.6116(2) 0.2913(2) 0.54375(15) 0.0220(4) Uani 1 1 d . . . . .
N2 N 0.7846(2) 0.2768(2) 0.41691(15) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.6140(3) 0.1094(3) 0.6601(2) 0.0304(5) Uani 1 1 d . . . . .
H2 H 0.569(4) 0.077(4) 0.713(3) 0.045(8) Uiso 1 1 d . . . . .
N3 N 0.8173(2) 0.1560(2) 0.33945(16) 0.0251(4) Uani 1 1 d . . . . .
C3 C 0.7408(3) 0.0463(3) 0.6196(2) 0.0333(5) Uani 1 1 d . . . . .
H3 H 0.785(3) -0.035(3) 0.646(2) 0.034(7) Uiso 1 1 d . . . . .
C4 C 0.8038(3) 0.1066(3) 0.5419(2) 0.0299(5) Uani 1 1 d . . . . .
H4 H 0.892(4) 0.076(3) 0.510(2) 0.036(7) Uiso 1 1 d . . . . .
N4 N 0.8608(2) 0.2331(2) 0.26943(16) 0.0255(4) Uani 1 1 d . . . . .
C6 C 0.8987(4) 0.1352(4) 0.1700(2) 0.0397(6) Uani 1 1 d . . . . .
H6C H 0.841(5) 0.154(5) 0.112(3) 0.063(11) Uiso 1 1 d . . . . .
H6B H 1.022(5) 0.167(5) 0.179(3) 0.072(11) Uiso 1 1 d . . . . .
H6A H 0.864(5) 0.028(6) 0.165(3) 0.086(13) Uiso 1 1 d . . . . .
C5 C 0.7327(3) 0.2267(3) 0.50571(18) 0.0217(4) Uani 1 1 d . . . . .
N5 N 0.4194(2) 0.3564(2) 0.32820(16) 0.0261(4) Uani 1 1 d . . . . .
C7 C 0.8083(2) 0.4307(2) 0.39630(18) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.8561(3) 0.3982(3) 0.29698(18) 0.0227(4) Uani 1 1 d . . . . .
C10 C 1.0403(3) 0.5424(3) 0.1985(2) 0.0346(5) Uani 1 1 d . . . . .
H10 H 1.129(4) 0.503(3) 0.227(2) 0.035(7) Uiso 1 1 d . . . . .
C11 C 1.0587(4) 0.6398(3) 0.1276(2) 0.0450(7) Uani 1 1 d . . . . .
H11 H 1.165(4) 0.665(4) 0.108(3) 0.049(8) Uiso 1 1 d . . . . .
C12 C 0.9227(5) 0.6983(3) 0.0830(2) 0.0491(8) Uani 1 1 d . . . . .
H12 H 0.937(4) 0.760(4) 0.037(3) 0.062(10) Uiso 1 1 d . . . . .
C13 C 0.7676(5) 0.6614(4) 0.1087(3) 0.0507(7) Uani 1 1 d . . . . .
H13 H 0.669(5) 0.705(5) 0.074(3) 0.073(11) Uiso 1 1 d . . . . .
C14 C 0.7476(4) 0.5656(3) 0.1799(2) 0.0389(6) Uani 1 1 d . . . . .
H14 H 0.642(4) 0.537(4) 0.198(3) 0.051(9) Uiso 1 1 d . . . . .
C15 C 0.4063(3) 0.2615(3) 0.24319(18) 0.0245(4) Uani 1 1 d . . . . .
C9 C 0.8841(3) 0.5050(3) 0.22496(18) 0.0267(5) 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
Se1 C15 1.790(2) . ?
S1 C7 1.708(2) . ?
S1 Fe1 2.4695(6) . ?
Fe1 N5 2.1418(19) . ?
Fe1 N5 2.1418(19) 2_666 ?
Fe1 N1 2.2657(17) . ?
Fe1 N1 2.2657(17) 2_666 ?
Fe1 S1 2.4695(6) 2_666 ?
C1 N1 1.342(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.97(3) . ?
N1 C5 1.331(3) . ?
N2 N3 1.342(2) . ?
N2 C7 1.381(3) . ?
N2 C5 1.428(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.91(3) . ?
N3 N4 1.306(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.94(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.94(3) . ?
N4 C8 1.360(3) . ?
N4 C6 1.463(3) . ?
C6 H6C 0.87(4) . ?
C6 H6B 0.97(4) . ?
C6 H6A 0.88(5) . ?
N5 C15 1.156(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.470(3) . ?
C10 C11 1.388(4) . ?
C10 C9 1.389(3) . ?
C10 H10 0.90(3) . ?
C11 C12 1.377(5) . ?
C11 H11 0.96(3) . ?
C12 C13 1.377(5) . ?
C12 H12 0.89(4) . ?
C13 C14 1.382(4) . ?
C13 H13 1.01(4) . ?
C14 C9 1.393(4) . ?
C14 H14 0.95(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
C7 S1 Fe1 96.38(7) . . ?
N5 Fe1 N5 180.00(10) . 2_666 ?
N5 Fe1 N1 90.55(7) . . ?
N5 Fe1 N1 89.45(7) 2_666 . ?
N5 Fe1 N1 89.45(7) . 2_666 ?
N5 Fe1 N1 90.55(7) 2_666 2_666 ?
N1 Fe1 N1 180.0 . 2_666 ?
N5 Fe1 S1 90.48(5) . . ?
N5 Fe1 S1 89.52(5) 2_666 . ?
N1 Fe1 S1 86.05(5) . . ?
N1 Fe1 S1 93.95(5) 2_666 . ?
N5 Fe1 S1 89.52(5) . 2_666 ?
N5 Fe1 S1 90.48(5) 2_666 2_666 ?
N1 Fe1 S1 93.95(5) . 2_666 ?
N1 Fe1 S1 86.05(5) 2_666 2_666 ?
S1 Fe1 S1 180.0 . 2_666 ?
N1 C1 C2 123.6(2) . . ?
N1 C1 H1 116.1(16) . . ?
C2 C1 H1 120.3(16) . . ?
C5 N1 C1 116.44(18) . . ?
C5 N1 Fe1 127.40(14) . . ?
C1 N1 Fe1 116.06(14) . . ?
N3 N2 C7 113.17(17) . . ?
N3 N2 C5 115.85(16) . . ?
C7 N2 C5 130.98(18) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 123.7(19) . . ?
C1 C2 H2 117.8(19) . . ?
N4 N3 N2 103.59(16) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.2(17) . . ?
C2 C3 H3 120.5(17) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 H4 127.0(17) . . ?
C5 C4 H4 115.2(17) . . ?
N3 N4 C8 113.89(18) . . ?
N3 N4 C6 118.42(19) . . ?
C8 N4 C6 127.6(2) . . ?
N4 C6 H6C 110(2) . . ?
N4 C6 H6B 108(2) . . ?
H6C C6 H6B 112(3) . . ?
N4 C6 H6A 107(3) . . ?
H6C C6 H6A 109(3) . . ?
H6B C6 H6A 112(3) . . ?
N1 C5 C4 124.3(2) . . ?
N1 C5 N2 117.47(17) . . ?
C4 C5 N2 118.07(19) . . ?
C15 N5 Fe1 163.95(17) . . ?
N2 C7 C8 103.45(17) . . ?
N2 C7 S1 126.45(16) . . ?
C8 C7 S1 130.09(16) . . ?
N4 C8 C7 105.88(18) . . ?
N4 C8 C9 123.17(19) . . ?
C7 C8 C9 130.76(19) . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.2(18) . . ?
C9 C10 H10 120.1(18) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.5(19) . . ?
C10 C11 H11 120.2(19) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 121(2) . . ?
C11 C12 H12 119(2) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119(2) . . ?
C14 C13 H13 121(2) . . ?
C13 C14 C9 120.0(3) . . ?
C13 C14 H14 122.0(19) . . ?
C9 C14 H14 118.0(19) . . ?
N5 C15 Se1 178.5(2) . . ?
C10 C9 C14 119.7(2) . . ?
C10 C9 C8 121.8(2) . . ?
C14 C9 C8 118.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 -1.2(3) . . . . ?
C2 C1 N1 Fe1 -177.88(18) . . . . ?
N1 C1 C2 C3 1.8(4) . . . . ?
C7 N2 N3 N4 -0.3(2) . . . . ?
C5 N2 N3 N4 179.90(17) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
N2 N3 N4 C8 -0.7(2) . . . . ?
N2 N3 N4 C6 -177.4(2) . . . . ?
C1 N1 C5 C4 -0.9(3) . . . . ?
Fe1 N1 C5 C4 175.32(17) . . . . ?
C1 N1 C5 N2 174.96(18) . . . . ?
Fe1 N1 C5 N2 -8.8(3) . . . . ?
C3 C4 C5 N1 2.3(4) . . . . ?
C3 C4 C5 N2 -173.6(2) . . . . ?
N3 N2 C5 N1 -141.71(19) . . . . ?
C7 N2 C5 N1 38.6(3) . . . . ?
N3 N2 C5 C4 34.5(3) . . . . ?
C7 N2 C5 C4 -145.2(2) . . . . ?
N3 N2 C7 C8 1.2(2) . . . . ?
C5 N2 C7 C8 -179.1(2) . . . . ?
N3 N2 C7 S1 -177.35(15) . . . . ?
C5 N2 C7 S1 2.4(3) . . . . ?
Fe1 S1 C7 N2 -50.74(18) . . . . ?
Fe1 S1 C7 C8 131.14(19) . . . . ?
N3 N4 C8 C7 1.4(2) . . . . ?
C6 N4 C8 C7 177.8(2) . . . . ?
N3 N4 C8 C9 -174.1(2) . . . . ?
C6 N4 C8 C9 2.3(4) . . . . ?
N2 C7 C8 N4 -1.5(2) . . . . ?
S1 C7 C8 N4 176.98(16) . . . . ?
N2 C7 C8 C9 173.5(2) . . . . ?
S1 C7 C8 C9 -8.0(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C9 -0.6(5) . . . . ?
C11 C10 C9 C14 0.0(4) . . . . ?
C11 C10 C9 C8 178.1(2) . . . . ?
C13 C14 C9 C10 0.4(4) . . . . ?
C13 C14 C9 C8 -177.7(2) . . . . ?
N4 C8 C9 C10 -63.9(3) . . . . ?
C7 C8 C9 C10 121.9(3) . . . . ?
N4 C8 C9 C14 114.2(3) . . . . ?
C7 C8 C9 C14 -60.1(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
C1 H1 S1 0.97(3) 2.81(3) 3.442(2) 123.5(19) 2_666
C2 H2 Se1 0.91(3) 3.07(3) 3.858(2) 145(2) 2_656

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_DPL277BT
_database_code_depnum_ccdc_archive 'CCDC 2005429'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2022-07-07 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         'C30 H30 B2 Fe N10 S2'
_chemical_formula_sum            'C30 H30 B2 Fe N10 S2'
_chemical_formula_weight         672.23

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'
B B 0.0013 0.0007 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2367(7)
_cell_length_b                   8.4429(9)
_cell_length_c                   12.9792(13)
_cell_angle_alpha                104.946(4)
_cell_angle_beta                 103.136(3)
_cell_angle_gamma                99.831(3)
_cell_volume                     823.62(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    166(2)
_cell_measurement_reflns_used    9613
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      25.01

_exptl_crystal_description       square
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   0.6934
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      166(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            64134
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         25.124
_diffrn_reflns_theta_full        25.124
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2923
_reflns_number_gt                2536
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0215P)²+0.4975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2923
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0606
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 1.0000 0.5000 0.5000 0.01700(11) Uani 1 2 d S . P . .
C1 C 1.0449(2) 0.8803(2) 0.62126(16) 0.0254(4) Uani 1 1 d . . . . .
N1 N 0.92509(18) 0.74912(18) 0.54360(12) 0.0200(3) Uani 1 1 d . . . . .
S1 S 0.69743(5) 0.36804(6) 0.48079(4) 0.02101(12) Uani 1 1 d . . . . .
B1 B 1.2016(4) 0.4819(4) 0.8757(2) 0.0382(6) Uani 1 1 d . . . . .
H1A H 1.106(4) 0.475(4) 0.916(2) 0.086(10) Uiso 1 1 d . . . . .
H1B H 1.307(4) 0.586(4) 0.924(2) 0.080(9) Uiso 1 1 d . . . . .
H1C H 1.262(4) 0.373(4) 0.864(2) 0.081(9) Uiso 1 1 d . . . . .
N2 N 0.64827(18) 0.64647(18) 0.41607(12) 0.0200(3) Uani 1 1 d . . . . .
C2 C 1.0165(3) 1.0382(2) 0.65938(17) 0.0296(4) Uani 1 1 d . . . . .
C4 C 0.7311(3) 0.9314(2) 0.54100(18) 0.0298(5) Uani 1 1 d . . . . .
N4 N 0.4524(2) 0.5531(2) 0.26653(13) 0.0255(4) Uani 1 1 d . . . . .
N3 N 0.55333(19) 0.6955(2) 0.33695(13) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.8569(3) 1.0634(3) 0.61897(18) 0.0328(5) Uani 1 1 d . . . . .
N5 N 1.06593(19) 0.51280(19) 0.67206(13) 0.0235(3) Uani 1 1 d . . . . .
C5 C 0.7726(2) 0.7785(2) 0.50505(15) 0.0205(4) Uani 1 1 d . . . . .
H4 H 0.623(3) 0.940(3) 0.5109(18) 0.042(6) Uiso 1 1 d . . . . .
C10 C 0.2071(3) 0.1897(3) 0.20131(17) 0.0324(5) Uani 1 1 d . . . . .
C12 C 0.2138(3) -0.0789(3) 0.0860(2) 0.0463(6) Uani 1 1 d . . . . .
C11 C 0.1225(3) 0.0283(3) 0.13124(18) 0.0416(6) Uani 1 1 d . . . . .
H14 H 0.600(3) 0.171(3) 0.1975(18) 0.041(6) Uiso 1 1 d . . . . .
C13 C 0.3900(3) -0.0279(3) 0.1104(2) 0.0458(6) Uani 1 1 d . . . . .
H13 H 0.455(4) -0.102(4) 0.077(2) 0.070(9) Uiso 1 1 d . . . . .
H12 H 0.157(3) -0.189(3) 0.039(2) 0.060(8) Uiso 1 1 d . . . . .
C14 C 0.4765(3) 0.1323(3) 0.18105(18) 0.0350(5) Uani 1 1 d . . . . .
H11 H 0.001(3) -0.002(3) 0.1148(19) 0.047(7) Uiso 1 1 d . . . . .
C15 C 1.1216(2) 0.5001(2) 0.75799(15) 0.0227(4) Uani 1 1 d . . . . .
H10 H 0.145(3) 0.264(3) 0.2291(18) 0.038(6) Uiso 1 1 d . . . . .
H6C H 0.347(4) 0.484(4) 0.105(3) 0.080(11) Uiso 1 1 d . . . . .
H6B H 0.218(4) 0.530(4) 0.169(3) 0.091(11) Uiso 1 1 d . . . . .
H6A H 0.361(4) 0.665(4) 0.163(2) 0.075(10) Uiso 1 1 d . . . . .
H3 H 0.835(3) 1.170(3) 0.6436(19) 0.044(6) Uiso 1 1 d . . . . .
C9 C 0.3851(2) 0.2423(2) 0.22619(15) 0.0243(4) Uani 1 1 d . . . . .
H2 H 1.105(3) 1.122(3) 0.7111(18) 0.037(6) Uiso 1 1 d . . . . .
C8 C 0.4777(2) 0.4147(2) 0.29644(15) 0.0219(4) Uani 1 1 d . . . . .
H1 H 1.156(3) 0.861(2) 0.6488(16) 0.028(5) Uiso 1 1 d . . . . .
C7 C 0.6065(2) 0.4740(2) 0.39640(14) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.3355(3) 0.5582(4) 0.1645(2) 0.0424(6) 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
Fe1 N5 2.1443(16) . ?
Fe1 N5 2.1443(16) 2_766 ?
Fe1 N1 2.2611(14) 2_766 ?
Fe1 N1 2.2611(14) . ?
Fe1 S1 2.4780(5) 2_766 ?
Fe1 S1 2.4780(5) . ?
C1 N1 1.347(2) . ?
C1 C2 1.376(3) . ?
C1 H1 0.96(2) . ?
N1 C5 1.332(2) . ?
S1 C7 1.7094(17) . ?
B1 C15 1.579(3) . ?
B1 H1A 1.04(3) . ?
B1 H1B 1.06(3) . ?
B1 H1C 1.11(3) . ?
N2 N3 1.343(2) . ?
N2 C7 1.379(2) . ?
N2 C5 1.426(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.92(2) . ?
C4 C3 1.374(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.91(2) . ?
N4 N3 1.311(2) . ?
N4 C8 1.356(2) . ?
N4 C6 1.466(3) . ?
C3 H3 0.94(2) . ?
N5 C15 1.145(2) . ?
C10 C11 1.385(3) . ?
C10 C9 1.393(3) . ?
C10 H10 0.93(2) . ?
C12 C11 1.374(4) . ?
C12 C13 1.378(4) . ?
C12 H12 0.94(3) . ?
C11 H11 0.95(2) . ?
C13 C14 1.382(3) . ?
C13 H13 0.97(3) . ?
C14 C9 1.390(3) . ?
C14 H14 0.97(2) . ?
C9 C8 1.467(3) . ?
C8 C7 1.385(2) . ?
C6 H6C 0.90(3) . ?
C6 H6B 0.97(3) . ?
C6 H6A 0.90(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
N5 Fe1 N5 180.0 . 2_766 ?
N5 Fe1 N1 89.86(5) . 2_766 ?
N5 Fe1 N1 90.14(5) 2_766 2_766 ?
N5 Fe1 N1 90.14(5) . . ?
N5 Fe1 N1 89.86(5) 2_766 . ?
N1 Fe1 N1 180.00(7) 2_766 . ?
N5 Fe1 S1 90.68(4) . 2_766 ?
N5 Fe1 S1 89.32(4) 2_766 2_766 ?
N1 Fe1 S1 85.76(4) 2_766 2_766 ?
N1 Fe1 S1 94.24(4) . 2_766 ?
N5 Fe1 S1 89.32(4) . . ?
N5 Fe1 S1 90.68(4) 2_766 . ?
N1 Fe1 S1 94.24(4) 2_766 . ?
N1 Fe1 S1 85.76(4) . . ?
S1 Fe1 S1 180.0 2_766 . ?
N1 C1 C2 123.33(18) . . ?
N1 C1 H1 117.1(12) . . ?
C2 C1 H1 119.5(12) . . ?
C5 N1 C1 116.30(15) . . ?
C5 N1 Fe1 127.11(12) . . ?
C1 N1 Fe1 116.50(12) . . ?
C7 S1 Fe1 96.26(6) . . ?
C15 B1 H1A 108.4(17) . . ?
C15 B1 H1B 110.8(16) . . ?
H1A B1 H1B 110(2) . . ?
C15 B1 H1C 108.7(15) . . ?
H1A B1 H1C 115(2) . . ?
H1B B1 H1C 103(2) . . ?
N3 N2 C7 113.10(14) . . ?
N3 N2 C5 115.78(14) . . ?
C7 N2 C5 131.12(14) . . ?
C3 C2 C1 118.83(19) . . ?
C3 C2 H2 122.5(14) . . ?
C1 C2 H2 118.6(14) . . ?
C3 C4 C5 117.97(19) . . ?
C3 C4 H4 123.6(14) . . ?
C5 C4 H4 118.5(15) . . ?
N3 N4 C8 113.74(15) . . ?
N3 N4 C6 118.49(17) . . ?
C8 N4 C6 127.67(18) . . ?
N4 N3 N2 103.50(14) . . ?
C4 C3 C2 119.23(19) . . ?
C4 C3 H3 120.6(14) . . ?
C2 C3 H3 120.2(14) . . ?
C15 N5 Fe1 166.69(15) . . ?
N1 C5 C4 124.30(17) . . ?
N1 C5 N2 117.47(15) . . ?
C4 C5 N2 118.11(16) . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2(14) . . ?
C9 C10 H10 120.1(14) . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 120.2(16) . . ?
C13 C12 H12 119.2(16) . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 122.5(14) . . ?
C10 C11 H11 117.4(14) . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 121.1(17) . . ?
C14 C13 H13 118.9(17) . . ?
C13 C14 C9 119.8(2) . . ?
C13 C14 H14 121.0(13) . . ?
C9 C14 H14 119.1(13) . . ?
N5 C15 B1 178.9(2) . . ?
C14 C9 C10 119.81(19) . . ?
C14 C9 C8 119.19(17) . . ?
C10 C9 C8 120.97(18) . . ?
N4 C8 C7 106.06(16) . . ?
N4 C8 C9 122.50(16) . . ?
C7 C8 C9 131.36(16) . . ?
N2 C7 C8 103.59(15) . . ?
N2 C7 S1 125.85(13) . . ?
C8 C7 S1 130.56(14) . . ?
N4 C6 H6C 110(2) . . ?
N4 C6 H6B 108.3(19) . . ?
H6C C6 H6B 110(3) . . ?
N4 C6 H6A 106.7(19) . . ?
H6C C6 H6A 113(3) . . ?
H6B C6 H6A 109(3) . . ?

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
C2 C1 N1 C5 -0.9(3) . . . . ?
C2 C1 N1 Fe1 -177.66(15) . . . . ?
N1 C1 C2 C3 1.9(3) . . . . ?
C8 N4 N3 N2 0.0(2) . . . . ?
C6 N4 N3 N2 -176.64(19) . . . . ?
C7 N2 N3 N4 -0.62(19) . . . . ?
C5 N2 N3 N4 179.66(14) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 N1 C5 C4 -1.1(3) . . . . ?
Fe1 N1 C5 C4 175.19(14) . . . . ?
C1 N1 C5 N2 174.73(15) . . . . ?
Fe1 N1 C5 N2 -8.9(2) . . . . ?
C3 C4 C5 N1 2.2(3) . . . . ?
C3 C4 C5 N2 -173.66(17) . . . . ?
N3 N2 C5 N1 -140.27(16) . . . . ?
C7 N2 C5 N1 40.1(3) . . . . ?
N3 N2 C5 C4 35.9(2) . . . . ?
C7 N2 C5 C4 -143.79(19) . . . . ?
C13 C12 C11 C10 0.5(4) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C13 C14 C9 C10 0.9(3) . . . . ?
C13 C14 C9 C8 -176.91(19) . . . . ?
C11 C10 C9 C14 -0.3(3) . . . . ?
C11 C10 C9 C8 177.48(18) . . . . ?
N3 N4 C8 C7 0.5(2) . . . . ?
C6 N4 C8 C7 176.8(2) . . . . ?
N3 N4 C8 C9 -176.47(16) . . . . ?
C6 N4 C8 C9 -0.2(3) . . . . ?
C14 C9 C8 N4 114.8(2) . . . . ?
C10 C9 C8 N4 -63.1(3) . . . . ?
C14 C9 C8 C7 -61.4(3) . . . . ?
C10 C9 C8 C7 120.7(2) . . . . ?
N3 N2 C7 C8 0.94(19) . . . . ?
C5 N2 C7 C8 -179.39(17) . . . . ?
N3 N2 C7 S1 -178.53(12) . . . . ?
C5 N2 C7 S1 1.1(3) . . . . ?
N4 C8 C7 N2 -0.85(19) . . . . ?
C9 C8 C7 N2 175.80(18) . . . . ?
N4 C8 C7 S1 178.58(14) . . . . ?
C9 C8 C7 S1 -4.8(3) . . . . ?
Fe1 S1 C7 N2 -50.65(15) . . . . ?
Fe1 S1 C7 C8 130.03(17) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_DPL290
_database_code_depnum_ccdc_archive 'CCDC 2005428'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Fe N10 S4'
_chemical_formula_sum            'C30 H24 Fe N10 S4'
_chemical_formula_weight         708.68

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2200(8)
_cell_length_b                   8.4119(8)
_cell_length_c                   13.0015(13)
_cell_angle_alpha                106.039(3)
_cell_angle_beta                 102.841(4)
_cell_angle_gamma                99.914(3)
_cell_volume                     815.80(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9601
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.91

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   0.6653
_exptl_transmission_factor_max   0.7273
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_T_max  0.7273
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            84766
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3732
_reflns_number_gt                3425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0373P)²+0.3214P] 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_number_reflns         3732
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 1.000000 0.500000 0.500000 0.01872(8) Uani 1 2 d S . P . .
S1 S 0.69485(4) 0.36849(4) 0.48009(3) 0.02232(9) Uani 1 1 d . . . . .
N1 N 0.92833(14) 0.75379(14) 0.54520(9) 0.0222(2) Uani 1 1 d . . . . .
C1 C 1.05006(19) 0.88605(18) 0.62325(12) 0.0273(3) Uani 1 1 d . . . . .
H1 H 1.158(2) 0.862(2) 0.6490(14) 0.027(4) Uiso 1 1 d . . . . .
N2 N 0.65026(14) 0.65016(14) 0.41821(9) 0.0224(2) Uani 1 1 d . . . . .
S2 S 0.80083(9) 0.51408(6) 0.12233(3) 0.05835(16) Uani 1 1 d . . . . .
C2 C 1.0244(2) 1.04740(18) 0.66317(13) 0.0313(3) Uani 1 1 d . . . . .
H2 H 1.116(3) 1.129(3) 0.7155(17) 0.044(5) Uiso 1 1 d . . . . .
N3 N 0.55537(16) 0.69980(15) 0.34031(10) 0.0285(3) Uani 1 1 d . . . . .
C3 C 0.8641(2) 1.07375(19) 0.62433(14) 0.0342(3) Uani 1 1 d . . . . .
H3 H 0.845(2) 1.185(2) 0.6487(16) 0.041(5) Uiso 1 1 d . . . . .
C4 C 0.7362(2) 0.93982(18) 0.54584(13) 0.0317(3) Uani 1 1 d . . . . .
H4 H 0.619(3) 0.947(3) 0.5129(17) 0.049(5) Uiso 1 1 d . . . . .
N4 N 0.45277(16) 0.55586(15) 0.26923(10) 0.0282(3) Uani 1 1 d . . . . .
C5 C 0.77632(17) 0.78428(16) 0.50792(11) 0.0221(3) Uani 1 1 d . . . . .
N5 N 0.93488(15) 0.47831(15) 0.32865(10) 0.0265(2) Uani 1 1 d . . . . .
C6 C 0.3349(3) 0.5614(2) 0.16824(15) 0.0468(4) Uani 1 1 d . . . . .
H6A H 0.354656 0.486392 0.102165 0.070 Uiso 1 1 calc R U . . .
H6B H 0.355516 0.678696 0.166385 0.070 Uiso 1 1 calc R U . . .
H6C H 0.215587 0.522772 0.168647 0.070 Uiso 1 1 calc R U . . .
C8 C 0.47689(17) 0.41595(17) 0.29696(11) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.60699(16) 0.47623(16) 0.39747(11) 0.0207(2) Uani 1 1 d . . . . .
C9 C 0.38261(18) 0.24138(17) 0.22540(11) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.2046(2) 0.1886(2) 0.20190(13) 0.0336(3) Uani 1 1 d . . . . .
H10 H 0.145(3) 0.267(3) 0.2352(17) 0.047(5) Uiso 1 1 d . . . . .
C11 C 0.1178(2) 0.0253(2) 0.13042(14) 0.0427(4) Uani 1 1 d . . . . .
H11 H -0.008(3) -0.013(3) 0.1120(18) 0.058(6) Uiso 1 1 d . . . . .
C12 C 0.2072(3) -0.0843(2) 0.08173(14) 0.0463(4) Uani 1 1 d . . . . .
H12 H 0.149(3) -0.195(3) 0.0309(19) 0.060(6) Uiso 1 1 d . . . . .
C13 C 0.3831(3) -0.0325(2) 0.10455(16) 0.0465(4) Uani 1 1 d . . . . .
H13 H 0.450(3) -0.105(3) 0.072(2) 0.068(7) Uiso 1 1 d . . . . .
C14 C 0.4725(2) 0.1303(2) 0.17691(14) 0.0365(3) Uani 1 1 d . . . . .
H14 H 0.597(3) 0.168(2) 0.1928(16) 0.041(5) Uiso 1 1 d . . . . .
C15 C 0.87962(19) 0.49225(17) 0.24246(11) 0.0263(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N5 2.1200(12) 2_766 ?
Fe1 N5 2.1201(12) . ?
Fe1 N1 2.2680(11) 2_766 ?
Fe1 N1 2.2680(11) . ?
Fe1 S1 2.4860(4) 2_766 ?
Fe1 S1 2.4860(4) . ?
S1 C7 1.7074(13) . ?
N1 C5 1.3311(17) . ?
N1 C1 1.3455(18) . ?
C1 C2 1.383(2) . ?
C1 H1 0.954(17) . ?
N2 N3 1.3429(15) . ?
N2 C7 1.3785(16) . ?
N2 C5 1.4283(17) . ?
S2 C15 1.6256(14) . ?
C2 C3 1.381(2) . ?
C2 H2 0.91(2) . ?
N3 N4 1.3096(17) . ?
C3 C4 1.377(2) . ?
C3 H3 0.957(19) . ?
C4 C5 1.3886(18) . ?
C4 H4 0.99(2) . ?
N4 C8 1.3555(17) . ?
N4 C6 1.4660(18) . ?
N5 C15 1.1577(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C7 1.3909(18) . ?
C8 C9 1.4680(19) . ?
C9 C10 1.391(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.96(2) . ?
C11 C12 1.382(3) . ?
C11 H11 0.98(2) . ?
C12 C13 1.375(3) . ?
C12 H12 0.95(2) . ?
C13 C14 1.391(2) . ?
C13 H13 0.96(3) . ?
C14 H14 0.974(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Fe1 N5 180.0 2_766 . ?
N5 Fe1 N1 90.99(4) 2_766 2_766 ?
N5 Fe1 N1 89.01(4) . 2_766 ?
N5 Fe1 N1 89.01(4) 2_766 . ?
N5 Fe1 N1 90.99(4) . . ?
N1 Fe1 N1 180.0 2_766 . ?
N5 Fe1 S1 90.29(3) 2_766 2_766 ?
N5 Fe1 S1 89.71(3) . 2_766 ?
N1 Fe1 S1 85.93(3) 2_766 2_766 ?
N1 Fe1 S1 94.06(3) . 2_766 ?
N5 Fe1 S1 89.71(3) 2_766 . ?
N5 Fe1 S1 90.29(3) . . ?
N1 Fe1 S1 94.07(3) 2_766 . ?
N1 Fe1 S1 85.93(3) . . ?
S1 Fe1 S1 180.0 2_766 . ?
C7 S1 Fe1 95.91(4) . . ?
C5 N1 C1 116.35(11) . . ?
C5 N1 Fe1 127.27(9) . . ?
C1 N1 Fe1 116.26(9) . . ?
N1 C1 C2 123.39(14) . . ?
N1 C1 H1 115.1(10) . . ?
C2 C1 H1 121.5(10) . . ?
N3 N2 C7 113.44(11) . . ?
N3 N2 C5 115.47(11) . . ?
C7 N2 C5 131.08(11) . . ?
C3 C2 C1 118.73(14) . . ?
C3 C2 H2 124.7(13) . . ?
C1 C2 H2 116.5(13) . . ?
N4 N3 N2 103.28(10) . . ?
C4 C3 C2 119.08(13) . . ?
C4 C3 H3 120.8(12) . . ?
C2 C3 H3 120.0(12) . . ?
C3 C4 C5 117.90(14) . . ?
C3 C4 H4 124.6(12) . . ?
C5 C4 H4 117.5(12) . . ?
N3 N4 C8 114.05(11) . . ?
N3 N4 C6 118.18(12) . . ?
C8 N4 C6 127.67(13) . . ?
N1 C5 C4 124.48(13) . . ?
N1 C5 N2 117.23(11) . . ?
C4 C5 N2 118.18(12) . . ?
C15 N5 Fe1 165.11(11) . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C8 C7 105.91(12) . . ?
N4 C8 C9 122.84(12) . . ?
C7 C8 C9 131.18(12) . . ?
N2 C7 C8 103.29(11) . . ?
N2 C7 S1 126.53(10) . . ?
C8 C7 S1 130.18(10) . . ?
C10 C9 C14 119.86(14) . . ?
C10 C9 C8 120.89(13) . . ?
C14 C9 C8 119.20(13) . . ?
C11 C10 C9 119.78(16) . . ?
C11 C10 H10 121.5(12) . . ?
C9 C10 H10 118.7(12) . . ?
C12 C11 C10 120.23(17) . . ?
C12 C11 H11 119.0(13) . . ?
C10 C11 H11 120.8(13) . . ?
C13 C12 C11 120.18(16) . . ?
C13 C12 H12 118.9(14) . . ?
C11 C12 H12 120.9(14) . . ?
C12 C13 C14 120.37(17) . . ?
C12 C13 H13 122.9(15) . . ?
C14 C13 H13 116.8(15) . . ?
C13 C14 C9 119.58(16) . . ?
C13 C14 H14 120.9(11) . . ?
C9 C14 H14 119.5(11) . . ?
N5 C15 S2 179.15(13) . . ?

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 N1 C1 C2 -1.1(2) . . . . ?
Fe1 N1 C1 C2 -177.40(11) . . . . ?
N1 C1 C2 C3 2.4(2) . . . . ?
C7 N2 N3 N4 -0.69(15) . . . . ?
C5 N2 N3 N4 179.81(11) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
N2 N3 N4 C8 -0.23(15) . . . . ?
N2 N3 N4 C6 -176.86(14) . . . . ?
C1 N1 C5 C4 -1.4(2) . . . . ?
Fe1 N1 C5 C4 174.37(11) . . . . ?
C1 N1 C5 N2 174.67(12) . . . . ?
Fe1 N1 C5 N2 -9.51(16) . . . . ?
C3 C4 C5 N1 2.6(2) . . . . ?
C3 C4 C5 N2 -173.50(13) . . . . ?
N3 N2 C5 N1 -140.52(12) . . . . ?
C7 N2 C5 N1 40.09(19) . . . . ?
N3 N2 C5 C4 35.84(17) . . . . ?
C7 N2 C5 C4 -143.55(14) . . . . ?
N3 N4 C8 C7 1.01(16) . . . . ?
C6 N4 C8 C7 177.26(15) . . . . ?
N3 N4 C8 C9 -176.28(13) . . . . ?
C6 N4 C8 C9 0.0(2) . . . . ?
N3 N2 C7 C8 1.27(15) . . . . ?
C5 N2 C7 C8 -179.33(12) . . . . ?
N3 N2 C7 S1 -177.82(10) . . . . ?
C5 N2 C7 S1 1.6(2) . . . . ?
N4 C8 C7 N2 -1.29(14) . . . . ?
C9 C8 C7 N2 175.68(14) . . . . ?
N4 C8 C7 S1 177.75(10) . . . . ?
C9 C8 C7 S1 -5.3(2) . . . . ?
Fe1 S1 C7 N2 -50.75(11) . . . . ?
Fe1 S1 C7 C8 130.41(12) . . . . ?
N4 C8 C9 C10 -63.44(19) . . . . ?
C7 C8 C9 C10 120.03(17) . . . . ?
N4 C8 C9 C14 113.81(16) . . . . ?
C7 C8 C9 C14 -62.7(2) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?
C8 C9 C10 C11 177.35(14) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C9 -0.6(3) . . . . ?
C10 C9 C14 C13 0.5(2) . . . . ?
C8 C9 C14 C13 -176.78(15) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.059

