# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Fe(hfac)2(betaDTDA)
_database_code_depnum_ccdc_archive 'CCDC 1886640'
loop_
_audit_author_name
_audit_author_address
'Paul D. Boyle'
;University of Western Ontario
Canada
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H6 F12 Fe N3 O4 S3'
_chemical_formula_weight         708.29
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'
F F 0.0171 0.0103 '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                   17.183(2)
_cell_length_b                   16.421(3)
_cell_length_c                   8.8532(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.124(5)
_cell_angle_gamma                90
_cell_volume                     2494.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9371
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.97
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             1396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.527
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    0.979
_shelx_estimated_absorpt_T_min   0.627
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.458022
_exptl_absorpt_correction_T_max  0.74516
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4485
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.750
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_full        25.045
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.876
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.876
_reflns_number_total             4485
_reflns_number_gt                3069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _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       Apex3
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_refine_special_details          
;Refined as a 2-component twin.  Sample crystal was non-merohedrally
twinned by an approximate 180 degree rotation about the [-100] direction
in reciprocal space.  The twin fraction parameter refined to a value
of 0.4072(15).,Twin,Poorly difracting sample.
;
#orientation matrices for twin domains.
loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Bruker .p4p convention for domain 1' -1.9314697e-03 -5.7712533e-02
3.5654351e-02 5.8128934e-02 -6.6053797e-04 1.4250924e-02 -3.7614924e-03
1.9426765e-02 1.0640558e-01
'Bruker .p4p convention for domain 2' -1.9270423e-03 5.7706360e-02
-3.6097500e-02 5.8124434e-02 6.3094840e-04 -2.0832138e-03 -3.8326040e-03
-1.9446068e-02 -1.0718722e-01

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4485
_refine_ls_number_parameters     381
_refine_ls_number_restraints     429
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.77788(5) 0.54930(5) 0.67986(13) 0.0290(3) Uani 1 1 d . . . . .
O21 O 0.7061(2) 0.5347(2) 0.8566(5) 0.0300(12) Uani 1 1 d . . . . .
O25 O 0.8435(3) 0.4544(3) 0.7857(6) 0.0327(13) Uani 1 1 d . . . . .
O31 O 0.7079(3) 0.4660(2) 0.5630(6) 0.0323(13) Uani 1 1 d . . . . .
O35 O 0.8489(2) 0.5441(3) 0.5039(6) 0.0314(12) Uani 1 1 d . . . . .
N1 N 0.8458(3) 0.6451(3) 0.7933(6) 0.0313(14) Uani 1 1 d . . . . .
S2 S 0.92153(11) 0.64287(11) 0.9142(2) 0.0389(6) Uani 1 1 d . . . . .
S3 S 0.92877(11) 0.76952(10) 0.9343(2) 0.0423(6) Uani 1 1 d . . . . .
N4 N 0.8542(3) 0.7886(3) 0.8186(7) 0.0381(17) Uani 1 1 d . . . . .
C5 C 0.8214(4) 0.7217(4) 0.7587(9) 0.0295(18) Uani 1 1 d . . . . .
C6 C 0.7537(3) 0.7269(3) 0.6546(8) 0.0254(17) Uani 1 1 d . . . . .
N7 N 0.7180(3) 0.6614(3) 0.6029(6) 0.0281(15) Uani 1 1 d . . . . .
C8 C 0.6548(4) 0.6806(4) 0.5073(8) 0.0288(18) Uani 1 1 d . . . . .
C9 C 0.6024(4) 0.6257(4) 0.4388(8) 0.0343(19) Uani 1 1 d . . . . .
H9 H 0.607148 0.568996 0.458088 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5440(4) 0.6551(4) 0.3432(9) 0.042(2) Uani 1 1 d . . . . .
H10 H 0.508594 0.617970 0.293999 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5349(4) 0.7393(5) 0.3157(9) 0.046(2) Uani 1 1 d . . . . .
H11 H 0.493362 0.758009 0.249304 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5853(4) 0.7943(4) 0.3837(9) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.579329 0.851080 0.366232 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6453(3) 0.7646(4) 0.4786(8) 0.0305(18) Uani 1 1 d . . . . .
S14 S 0.71638(12) 0.81851(11) 0.5861(2) 0.0351(6) Uani 1 1 d . . . . .
C22 C 0.6930(4) 0.4653(4) 0.9169(8) 0.0284(18) Uani 1 1 d . . . . .
C23 C 0.7429(4) 0.3977(4) 0.9222(8) 0.033(2) Uani 1 1 d . . . . .
H23 H 0.726967 0.349365 0.970700 0.040 Uiso 1 1 calc R U . . .
C24 C 0.8145(4) 0.3996(4) 0.8587(9) 0.0347(19) Uani 1 1 d . . . . .
C26 C 0.6155(4) 0.4616(4) 0.9857(10) 0.0368(18) Uani 1 1 d . . . . .
F21 F 0.5589(2) 0.4911(2) 0.8935(5) 0.0552(14) Uani 1 1 d . . . . .
F22 F 0.6157(2) 0.5058(3) 1.1116(5) 0.0595(14) Uani 1 1 d . . . . .
F23 F 0.5934(3) 0.3865(3) 1.0211(6) 0.0627(15) Uani 1 1 d . . . . .
C27 C 0.8658(4) 0.3226(5) 0.8776(10) 0.048(2) Uani 0.649(8) 1 d D . P A 1
F24 F 0.9379(4) 0.3373(5) 0.8890(17) 0.064(3) Uani 0.649(8) 1 d D . P A 1
F25 F 0.8468(7) 0.2748(7) 0.9903(17) 0.097(4) Uani 0.649(8) 1 d D . P A 1
F26 F 0.8536(8) 0.2761(6) 0.7522(15) 0.095(3) Uani 0.649(8) 1 d D . P A 1
C27' C 0.8658(4) 0.3226(5) 0.8776(10) 0.048(2) Uani 0.351(8) 1 d D . P A 2
F24' F 0.8337(8) 0.2570(10) 0.855(3) 0.064(3) Uani 0.351(8) 1 d D . P A 2
F25' F 0.9259(14) 0.3232(14) 0.789(3) 0.097(4) Uani 0.351(8) 1 d D . P A 2
F26' F 0.8973(15) 0.3217(12) 1.024(2) 0.095(3) Uani 0.351(8) 1 d D . P A 2
C32 C 0.7249(4) 0.4225(4) 0.4546(8) 0.0276(18) Uani 1 1 d . . . . .
C33 C 0.7912(4) 0.4305(4) 0.3683(8) 0.0373(19) Uani 1 1 d . . . . .
H33 H 0.797224 0.394571 0.285669 0.045 Uiso 1 1 calc R U . . .
C34 C 0.8484(4) 0.4898(4) 0.4005(9) 0.0332(18) Uani 1 1 d . . . . .
C36 C 0.6678(5) 0.3547(4) 0.4160(11) 0.047(2) Uani 1 1 d . . . . .
F31 F 0.5952(3) 0.3849(3) 0.3939(5) 0.0617(15) Uani 1 1 d . . . . .
F32 F 0.6660(3) 0.3022(2) 0.5298(6) 0.0694(16) Uani 1 1 d . . . . .
F33 F 0.6820(3) 0.3126(2) 0.2914(6) 0.0640(15) Uani 1 1 d . . . . .
C37 C 0.9188(5) 0.4879(5) 0.3059(11) 0.048(2) Uani 1 1 d . . . . .
F34 F 0.9645(3) 0.5511(3) 0.3255(6) 0.0746(18) Uani 1 1 d . . . . .
F35 F 0.9008(3) 0.4833(4) 0.1611(7) 0.103(2) Uani 1 1 d . . . . .
F36 F 0.9634(3) 0.4235(3) 0.3403(6) 0.088(2) 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 O35 2.033(5) . ?
Fe1 O21 2.058(5) . ?
Fe1 O31 2.062(5) . ?
Fe1 O25 2.112(5) . ?
Fe1 N1 2.172(5) . ?
Fe1 N7 2.199(6) . ?
O21 C22 1.285(7) . ?
O25 C24 1.229(8) . ?
O31 C32 1.244(7) . ?
O35 C34 1.276(8) . ?
N1 C5 1.355(7) . ?
N1 S2 1.640(6) . ?
S2 S3 2.090(2) . ?
S3 N4 1.627(6) . ?
N4 C5 1.330(7) . ?
C5 C6 1.448(9) . ?
C6 N7 1.309(7) . ?
C6 S14 1.731(6) . ?
N7 C8 1.377(8) . ?
C8 C9 1.389(9) . ?
C8 C13 1.411(9) . ?
C9 C10 1.366(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.411(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(9) . ?
C12 H12 0.9500 . ?
C13 S14 1.748(7) . ?
C22 C23 1.400(9) . ?
C22 C26 1.496(10) . ?
C23 C24 1.381(9) . ?
C23 H23 0.9500 . ?
C24 C27' 1.545(10) . ?
C24 C27 1.545(10) . ?
C26 F21 1.327(8) . ?
C26 F22 1.330(8) . ?
C26 F23 1.333(7) . ?
C27 F24 1.261(10) . ?
C27 F25 1.323(10) . ?
C27 F26 1.354(11) . ?
C27' F24' 1.222(14) . ?
C27' F25' 1.332(15) . ?
C27' F26' 1.374(14) . ?
C32 C33 1.412(9) . ?
C32 C36 1.511(10) . ?
C33 C34 1.402(9) . ?
C33 H33 0.9500 . ?
C34 C37 1.508(11) . ?
C36 F32 1.328(9) . ?
C36 F33 1.335(8) . ?
C36 F31 1.347(9) . ?
C37 F35 1.304(9) . ?
C37 F34 1.308(8) . ?
C37 F36 1.331(8) . ?

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
O35 Fe1 O21 170.89(16) . . ?
O35 Fe1 O31 86.85(19) . . ?
O21 Fe1 O31 86.98(19) . . ?
O35 Fe1 O25 88.90(18) . . ?
O21 Fe1 O25 84.51(17) . . ?
O31 Fe1 O25 90.89(18) . . ?
O35 Fe1 N1 93.18(19) . . ?
O21 Fe1 N1 93.54(18) . . ?
O31 Fe1 N1 175.1(2) . . ?
O25 Fe1 N1 93.98(19) . . ?
O35 Fe1 N7 95.07(18) . . ?
O21 Fe1 N7 92.47(18) . . ?
O31 Fe1 N7 98.6(2) . . ?
O25 Fe1 N7 169.9(2) . . ?
N1 Fe1 N7 76.5(2) . . ?
C22 O21 Fe1 123.0(4) . . ?
C24 O25 Fe1 123.5(4) . . ?
C32 O31 Fe1 127.9(5) . . ?
C34 O35 Fe1 126.8(5) . . ?
C5 N1 S2 113.1(5) . . ?
C5 N1 Fe1 114.6(5) . . ?
S2 N1 Fe1 132.3(3) . . ?
N1 S2 S3 94.3(2) . . ?
N4 S3 S2 95.5(2) . . ?
C5 N4 S3 113.2(5) . . ?
N4 C5 N1 123.9(7) . . ?
N4 C5 C6 120.9(5) . . ?
N1 C5 C6 115.2(6) . . ?
N7 C6 C5 121.3(5) . . ?
N7 C6 S14 115.8(5) . . ?
C5 C6 S14 123.0(5) . . ?
C6 N7 C8 111.4(6) . . ?
C6 N7 Fe1 112.2(4) . . ?
C8 N7 Fe1 136.3(4) . . ?
N7 C8 C9 126.2(6) . . ?
N7 C8 C13 114.5(6) . . ?
C9 C8 C13 119.3(6) . . ?
C10 C9 C8 118.6(6) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 121.6(7) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.6(7) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 117.9(7) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C8 122.0(7) . . ?
C12 C13 S14 128.9(5) . . ?
C8 C13 S14 109.0(5) . . ?
C6 S14 C13 89.2(3) . . ?
O21 C22 C23 126.6(7) . . ?
O21 C22 C26 112.6(6) . . ?
C23 C22 C26 120.7(6) . . ?
C24 C23 C22 121.7(7) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
O25 C24 C23 128.7(7) . . ?
O25 C24 C27' 114.3(6) . . ?
C23 C24 C27' 117.0(6) . . ?
O25 C24 C27 114.3(6) . . ?
C23 C24 C27 117.0(6) . . ?
F21 C26 F22 106.5(6) . . ?
F21 C26 F23 105.9(6) . . ?
F22 C26 F23 107.2(7) . . ?
F21 C26 C22 112.0(7) . . ?
F22 C26 C22 110.9(6) . . ?
F23 C26 C22 113.9(6) . . ?
F24 C27 F25 109.5(8) . . ?
F24 C27 F26 106.3(9) . . ?
F25 C27 F26 104.5(8) . . ?
F24 C27 C24 113.9(7) . . ?
F25 C27 C24 113.8(8) . . ?
F26 C27 C24 108.1(7) . . ?
F24' C27' F25' 105.5(13) . . ?
F24' C27' F26' 107.3(12) . . ?
F25' C27' F26' 106.1(13) . . ?
F24' C27' C24 117.0(10) . . ?
F25' C27' C24 112.7(10) . . ?
F26' C27' C24 107.7(9) . . ?
O31 C32 C33 126.4(7) . . ?
O31 C32 C36 114.9(7) . . ?
C33 C32 C36 118.6(7) . . ?
C34 C33 C32 122.2(7) . . ?
C34 C33 H33 118.9 . . ?
C32 C33 H33 118.9 . . ?
O35 C34 C33 127.4(7) . . ?
O35 C34 C37 116.1(7) . . ?
C33 C34 C37 116.5(7) . . ?
F32 C36 F33 107.7(6) . . ?
F32 C36 F31 106.8(7) . . ?
F33 C36 F31 106.3(7) . . ?
F32 C36 C32 110.4(7) . . ?
F33 C36 C32 115.0(7) . . ?
F31 C36 C32 110.3(6) . . ?
F35 C37 F34 106.5(7) . . ?
F35 C37 F36 106.4(7) . . ?
F34 C37 F36 105.4(7) . . ?
F35 C37 C34 113.2(7) . . ?
F34 C37 C34 113.8(7) . . ?
F36 C37 C34 111.1(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
C5 N1 S2 S3 0.3(5) . . . . ?
Fe1 N1 S2 S3 -179.6(3) . . . . ?
S2 S3 N4 C5 -1.2(5) . . . . ?
S3 N4 C5 N1 1.9(9) . . . . ?
S3 N4 C5 C6 179.2(5) . . . . ?
S2 N1 C5 N4 -1.4(9) . . . . ?
Fe1 N1 C5 N4 178.6(5) . . . . ?
S2 N1 C5 C6 -178.8(5) . . . . ?
Fe1 N1 C5 C6 1.1(7) . . . . ?
N4 C5 C6 N7 -175.5(6) . . . . ?
N1 C5 C6 N7 2.0(9) . . . . ?
N4 C5 C6 S14 6.6(10) . . . . ?
N1 C5 C6 S14 -175.9(5) . . . . ?
C5 C6 N7 C8 179.3(6) . . . . ?
S14 C6 N7 C8 -2.6(7) . . . . ?
C5 C6 N7 Fe1 -4.0(8) . . . . ?
S14 C6 N7 Fe1 174.1(3) . . . . ?
C6 N7 C8 C9 -176.8(7) . . . . ?
Fe1 N7 C8 C9 7.7(12) . . . . ?
C6 N7 C8 C13 3.8(9) . . . . ?
Fe1 N7 C8 C13 -171.7(5) . . . . ?
N7 C8 C9 C10 -178.1(7) . . . . ?
C13 C8 C9 C10 1.2(11) . . . . ?
C8 C9 C10 C11 -1.4(12) . . . . ?
C9 C10 C11 C12 0.6(12) . . . . ?
C10 C11 C12 C13 0.5(12) . . . . ?
C11 C12 C13 C8 -0.7(11) . . . . ?
C11 C12 C13 S14 -177.5(6) . . . . ?
N7 C8 C13 C12 179.3(6) . . . . ?
C9 C8 C13 C12 -0.2(11) . . . . ?
N7 C8 C13 S14 -3.3(8) . . . . ?
C9 C8 C13 S14 177.2(5) . . . . ?
N7 C6 S14 C13 0.6(5) . . . . ?
C5 C6 S14 C13 178.6(6) . . . . ?
C12 C13 S14 C6 178.7(7) . . . . ?
C8 C13 S14 C6 1.5(5) . . . . ?
Fe1 O21 C22 C23 27.2(10) . . . . ?
Fe1 O21 C22 C26 -152.8(5) . . . . ?
O21 C22 C23 C24 -0.4(12) . . . . ?
C26 C22 C23 C24 179.6(7) . . . . ?
Fe1 O25 C24 C23 -19.2(12) . . . . ?
Fe1 O25 C24 C27' 159.6(5) . . . . ?
Fe1 O25 C24 C27 159.6(5) . . . . ?
C22 C23 C24 O25 -3.8(13) . . . . ?
C22 C23 C24 C27' 177.5(7) . . . . ?
C22 C23 C24 C27 177.5(7) . . . . ?
O21 C22 C26 F21 46.9(9) . . . . ?
C23 C22 C26 F21 -133.1(7) . . . . ?
O21 C22 C26 F22 -72.0(9) . . . . ?
C23 C22 C26 F22 108.0(7) . . . . ?
O21 C22 C26 F23 166.9(6) . . . . ?
C23 C22 C26 F23 -13.0(11) . . . . ?
O25 C24 C27 F24 34.3(13) . . . . ?
C23 C24 C27 F24 -146.8(10) . . . . ?
O25 C24 C27 F25 160.8(11) . . . . ?
C23 C24 C27 F25 -20.3(14) . . . . ?
O25 C24 C27 F26 -83.5(11) . . . . ?
C23 C24 C27 F26 95.4(12) . . . . ?
O25 C24 C27' F24' -134.0(18) . . . . ?
C23 C24 C27' F24' 45(2) . . . . ?
O25 C24 C27' F25' -11.5(19) . . . . ?
C23 C24 C27' F25' 167.4(18) . . . . ?
O25 C24 C27' F26' 105.2(16) . . . . ?
C23 C24 C27' F26' -75.9(16) . . . . ?
Fe1 O31 C32 C33 -12.6(10) . . . . ?
Fe1 O31 C32 C36 166.9(5) . . . . ?
O31 C32 C33 C34 2.0(12) . . . . ?
C36 C32 C33 C34 -177.5(7) . . . . ?
Fe1 O35 C34 C33 12.4(11) . . . . ?
Fe1 O35 C34 C37 -165.5(5) . . . . ?
C32 C33 C34 O35 -1.9(12) . . . . ?
C32 C33 C34 C37 176.0(7) . . . . ?
O31 C32 C36 F32 -63.8(9) . . . . ?
C33 C32 C36 F32 115.8(8) . . . . ?
O31 C32 C36 F33 174.1(6) . . . . ?
C33 C32 C36 F33 -6.3(10) . . . . ?
O31 C32 C36 F31 54.0(9) . . . . ?
C33 C32 C36 F31 -126.4(7) . . . . ?
O35 C34 C37 F35 -133.1(8) . . . . ?
C33 C34 C37 F35 48.8(9) . . . . ?
O35 C34 C37 F34 -11.3(10) . . . . ?
C33 C34 C37 F34 170.6(7) . . . . ?
O35 C34 C37 F36 107.4(8) . . . . ?
C33 C34 C37 F36 -70.7(10) . . . . ?

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
C9 H9 O31 0.95 2.56 3.340(8) 139.7 .
C12 H12 F21 0.95 2.63 3.555(8) 165.2 4_575

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.103

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# 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_betaDTDA
_database_code_depnum_ccdc_archive 'CCDC 1895351'
loop_
_audit_author_name
_audit_author_address
'DV Soldatov'
;University of Guelph
Canada
;
_audit_update_record             
;
2019-02-04 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 N3 S3'
_chemical_formula_sum            'C8 H4 N3 S3'
_chemical_formula_weight         238.32

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'

_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                   9.7286(3)
_cell_length_b                   17.2405(4)
_cell_length_c                   10.7173(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.114(3)
_cell_angle_gamma                90
_cell_volume                     1796.35(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9799
_cell_measurement_theta_min      3.9730
_cell_measurement_theta_max      33.6940

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.779
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            27775
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         33.769
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measured_fraction_theta_full 0.866
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_Laue_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_point_group_measured_fraction_full 0.866
_reflns_number_total             5909
_reflns_number_gt                4469
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+3.3494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5909
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
N1A N 1.0362(3) 0.58162(14) 0.3517(2) 0.0238(4) Uani 1 1 d . . . . .
S2A S 1.14673(8) 0.51045(4) 0.35415(7) 0.02541(15) Uani 1 1 d . . . . .
S3A S 1.15986(8) 0.50537(4) 0.15938(7) 0.02570(16) Uani 1 1 d . . . . .
N4A N 1.0519(3) 0.57612(15) 0.1329(2) 0.0242(5) Uani 1 1 d . . . . .
C5A C 1.0021(3) 0.60723(16) 0.2368(2) 0.0208(5) Uani 1 1 d . . . . .
C6A C 0.9084(3) 0.67326(15) 0.2202(2) 0.0200(4) Uani 1 1 d . . . . .
N7A N 0.8295(3) 0.69962(14) 0.3062(2) 0.0226(4) Uani 1 1 d . . . . .
C8A C 0.7523(3) 0.76170(16) 0.2596(2) 0.0205(5) Uani 1 1 d . . . . .
C9A C 0.6534(3) 0.80199(18) 0.3271(3) 0.0251(5) Uani 1 1 d . . . . .
H9A H 0.6353 0.7880 0.4106 0.030 Uiso 1 1 calc R U . . .
C10A C 0.5832(3) 0.86265(19) 0.2685(3) 0.0274(6) Uani 1 1 d . . . . .
H10A H 0.5152 0.8900 0.3123 0.033 Uiso 1 1 calc R U . . .
C11A C 0.6108(3) 0.88462(17) 0.1449(3) 0.0256(5) Uani 1 1 d . . . . .
H11A H 0.5628 0.9272 0.1075 0.031 Uiso 1 1 calc R U . . .
C12A C 0.7078(3) 0.84445(16) 0.0771(3) 0.0232(5) Uani 1 1 d . . . . .
H12A H 0.7260 0.8585 -0.0064 0.028 Uiso 1 1 calc R U . . .
C13A C 0.7772(3) 0.78304(15) 0.1360(2) 0.0204(5) Uani 1 1 d . . . . .
S14A S 0.89895(7) 0.72076(4) 0.07626(6) 0.02168(15) Uani 1 1 d . . . . .
N1B N 0.8088(3) 0.45046(15) 0.3615(2) 0.0266(5) Uani 1 1 d . . . . .
S2B S 0.93426(9) 0.38816(4) 0.35795(7) 0.02845(17) Uani 1 1 d . . . . .
S3B S 0.93362(9) 0.38120(4) 0.16199(7) 0.02910(17) Uani 1 1 d . . . . .
N4B N 0.8098(3) 0.44469(17) 0.1419(2) 0.0279(5) Uani 1 1 d . . . . .
C5B C 0.7618(3) 0.47234(16) 0.2483(3) 0.0231(5) Uani 1 1 d . . . . .
C6B C 0.6514(3) 0.53020(16) 0.2366(3) 0.0214(5) Uani 1 1 d . . . . .
N7B N 0.5800(3) 0.55537(15) 0.3289(2) 0.0249(5) Uani 1 1 d . . . . .
C8B C 0.4867(3) 0.61049(17) 0.2851(3) 0.0258(5) Uani 1 1 d . . . . .
C9B C 0.3922(3) 0.6492(2) 0.3588(3) 0.0320(6) Uani 1 1 d . . . . .
H9B H 0.3887 0.6391 0.4458 0.038 Uiso 1 1 calc R U . . .
C10B C 0.3033(4) 0.7029(2) 0.3010(4) 0.0386(8) Uani 1 1 d . . . . .
H10B H 0.2392 0.7301 0.3494 0.046 Uiso 1 1 calc R U . . .
C11B C 0.3076(4) 0.7170(2) 0.1732(4) 0.0410(8) Uani 1 1 d . . . . .
H11B H 0.2456 0.7537 0.1361 0.049 Uiso 1 1 calc R U . . .
C12B C 0.3996(4) 0.6792(2) 0.0986(4) 0.0368(7) Uani 1 1 d . . . . .
H12B H 0.4019 0.6891 0.0115 0.044 Uiso 1 1 calc R U . . .
C13B C 0.4894(3) 0.62561(18) 0.1571(3) 0.0270(6) Uani 1 1 d . . . . .
S14B S 0.61334(8) 0.56930(5) 0.08969(7) 0.02696(16) 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
N1A C5A 1.339(4) . ?
N1A S2A 1.631(3) . ?
S2A S3A 2.0979(10) . ?
S3A N4A 1.628(3) . ?
N4A C5A 1.342(3) . ?
C5A C6A 1.466(4) . ?
C6A N7A 1.302(3) . ?
C6A S14A 1.746(3) . ?
N7A C8A 1.390(4) . ?
C8A C13A 1.404(4) . ?
C8A C9A 1.408(4) . ?
C9A C10A 1.387(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.413(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.396(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.394(4) . ?
C12A H12A 0.9500 . ?
C13A S14A 1.739(3) . ?
N1B C5B 1.335(4) . ?
N1B S2B 1.627(3) . ?
S2B S3B 2.1033(11) . ?
S3B N4B 1.636(3) . ?
N4B C5B 1.336(4) . ?
C5B C6B 1.468(4) . ?
C6B N7B 1.304(4) . ?
C6B S14B 1.740(3) . ?
N7B C8B 1.384(4) . ?
C8B C13B 1.398(4) . ?
C8B C9B 1.403(4) . ?
C9B C10B 1.396(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.394(6) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.386(6) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.403(5) . ?
C12B H12B 0.9500 . ?
C13B S14B 1.727(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
C5A N1A S2A 113.8(2) . . ?
N1A S2A S3A 94.56(9) . . ?
N4A S3A S2A 94.57(9) . . ?
C5A N4A S3A 113.9(2) . . ?
N1A C5A N4A 123.1(3) . . ?
N1A C5A C6A 120.0(2) . . ?
N4A C5A C6A 116.9(2) . . ?
N7A C6A C5A 124.4(2) . . ?
N7A C6A S14A 116.7(2) . . ?
C5A C6A S14A 118.90(19) . . ?
C6A N7A C8A 109.8(2) . . ?
N7A C8A C13A 115.5(2) . . ?
N7A C8A C9A 124.5(2) . . ?
C13A C8A C9A 120.0(3) . . ?
C10A C9A C8A 118.3(3) . . ?
C10A C9A H9A 120.8 . . ?
C8A C9A H9A 120.8 . . ?
C9A C10A C11A 121.3(3) . . ?
C9A C10A H10A 119.4 . . ?
C11A C10A H10A 119.4 . . ?
C12A C11A C10A 120.7(3) . . ?
C12A C11A H11A 119.7 . . ?
C10A C11A H11A 119.7 . . ?
C13A C12A C11A 117.8(3) . . ?
C13A C12A H12A 121.1 . . ?
C11A C12A H12A 121.1 . . ?
C12A C13A C8A 121.9(2) . . ?
C12A C13A S14A 128.8(2) . . ?
C8A C13A S14A 109.2(2) . . ?
C13A S14A C6A 88.76(13) . . ?
C5B N1B S2B 113.4(2) . . ?
N1B S2B S3B 94.96(10) . . ?
N4B S3B S2B 93.91(10) . . ?
C5B N4B S3B 113.9(2) . . ?
N1B C5B N4B 123.8(3) . . ?
N1B C5B C6B 119.7(3) . . ?
N4B C5B C6B 116.5(3) . . ?
N7B C6B C5B 124.7(3) . . ?
N7B C6B S14B 117.1(2) . . ?
C5B C6B S14B 118.1(2) . . ?
C6B N7B C8B 109.4(3) . . ?
N7B C8B C13B 115.2(3) . . ?
N7B C8B C9B 124.8(3) . . ?
C13B C8B C9B 120.1(3) . . ?
C10B C9B C8B 118.3(3) . . ?
C10B C9B H9B 120.9 . . ?
C8B C9B H9B 120.9 . . ?
C11B C10B C9B 120.8(3) . . ?
C11B C10B H10B 119.6 . . ?
C9B C10B H10B 119.6 . . ?
C12B C11B C10B 121.9(3) . . ?
C12B C11B H11B 119.1 . . ?
C10B C11B H11B 119.1 . . ?
C11B C12B C13B 117.2(3) . . ?
C11B C12B H12B 121.4 . . ?
C13B C12B H12B 121.4 . . ?
C8B C13B C12B 121.8(3) . . ?
C8B C13B S14B 110.2(2) . . ?
C12B C13B S14B 128.0(3) . . ?
C13B S14B C6B 88.16(14) . . ?

_refine_diff_density_max         0.659
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.119

_shelxl_version_number           2013-4

