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

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

data_Fe-mac
_database_code_depnum_ccdc_archive 'CCDC 1569378'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2018-08-01 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         ?
_chemical_formula_sum            'C32 H28 B2 F8 Fe N4 Se2'
_chemical_formula_weight         855.97

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   17.4674(17)
_cell_length_b                   10.6360(11)
_cell_length_c                   17.9626(19)
_cell_angle_alpha                90
_cell_angle_beta                 106.425(3)
_cell_angle_gamma                90
_cell_volume                     3201.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4615
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.74

_exptl_crystal_description       tabular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.824
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8668
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13474
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         25.149
_diffrn_reflns_theta_full        25.149
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2850
_reflns_number_gt                2286
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0527P)²+16.2373P] 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         2850
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.09724(3) 0.03876(5) 0.24634(3) 0.04710(19) Uani 1 1 d . . . . .
Fe1 Fe 0.0000 -0.11242(10) 0.2500 0.0495(3) Uani 1 2 d S T P . .
C7 C 0.1550(3) -0.0443(6) 0.1833(3) 0.0549(13) Uani 1 1 d . . . . .
N1 N 0.0838(3) -0.2422(5) 0.2672(4) 0.0748(15) Uani 1 1 d . . . . .
C6 C 0.1867(3) 0.0292(7) 0.1361(3) 0.0683(16) Uani 1 1 d . . . . .
H6 H 0.1762 0.1151 0.1318 0.082 Uiso 1 1 calc R U . . .
C13 C -0.0213(3) 0.1001(7) 0.0999(3) 0.0626(15) Uani 1 1 d . . . . .
C8 C 0.0355(3) 0.1479(5) 0.1662(3) 0.0527(12) Uani 1 1 d . . . . .
C14 C -0.0425(3) -0.0314(8) 0.0869(4) 0.0688(17) Uani 1 1 d . . . . .
H14 H -0.0657 -0.0549 0.0356 0.083 Uiso 1 1 calc R U . . .
C2 C 0.1717(3) -0.1740(7) 0.1910(4) 0.0666(16) Uani 1 1 d . . . . .
C5 C 0.2350(4) -0.0263(11) 0.0947(4) 0.096(3) Uani 1 1 d . . . . .
H5 H 0.2547 0.0222 0.0612 0.116 Uiso 1 1 calc R U . . .
C1 C 0.1460(4) -0.2554(6) 0.2437(5) 0.0779(19) Uani 1 1 d . . . . .
H1 H 0.1781 -0.3247 0.2626 0.093 Uiso 1 1 calc R U . . .
C3 C 0.2222(4) -0.2238(9) 0.1511(5) 0.089(2) Uani 1 1 d . . . . .
H3 H 0.2356 -0.3086 0.1568 0.107 Uiso 1 1 calc R U . . .
C9 C 0.0520(4) 0.2752(6) 0.1749(5) 0.0757(18) Uani 1 1 d . . . . .
H9 H 0.0903 0.3049 0.2185 0.091 Uiso 1 1 calc R U . . .
C10 C 0.0113(6) 0.3573(8) 0.1184(7) 0.105(3) Uani 1 1 d . . . . .
H10 H 0.0210 0.4432 0.1245 0.126 Uiso 1 1 calc R U . . .
C4 C 0.2529(4) -0.1504(12) 0.1034(5) 0.108(3) Uani 1 1 d . . . . .
H4 H 0.2861 -0.1862 0.0769 0.130 Uiso 1 1 calc R U . . .
C11 C -0.0446(6) 0.3118(12) 0.0520(6) 0.117(4) Uani 1 1 d . . . . .
H11 H -0.0715 0.3675 0.0135 0.140 Uiso 1 1 calc R U . . .
C12 C -0.0599(4) 0.1864(11) 0.0432(4) 0.095(3) Uani 1 1 d . . . . .
H12 H -0.0968 0.1576 -0.0017 0.114 Uiso 1 1 calc R U . . .
N2 N -0.0330(3) -0.1183(5) 0.1371(3) 0.0623(13) Uani 1 1 d . . . . .
F2 F 0.1905(4) 0.4609(8) 0.1567(3) 0.168(3) Uani 1 1 d . . . . .
C16 C 0.0770(5) -0.3244(7) 0.3315(6) 0.106(3) Uani 1 1 d . . . . .
H16A H 0.1249 -0.3747 0.3500 0.128 Uiso 1 1 calc R U . . .
H16B H 0.0319 -0.3807 0.3134 0.128 Uiso 1 1 calc R U . . .
C15 C -0.0658(5) -0.2436(8) 0.1048(6) 0.105(3) Uani 1 1 d . . . . .
H15A H -0.1165 -0.2322 0.0656 0.126 Uiso 1 1 calc R U . . .
H15B H -0.0291 -0.2839 0.0805 0.126 Uiso 1 1 calc R U . . .
F4 F 0.2201(6) 0.3038(7) 0.0976(7) 0.235(5) Uani 1 1 d . . . . .
B1 B 0.2105(5) 0.4243(8) 0.0930(5) 0.076(2) Uani 1 1 d . . . . .
F1 F 0.1520(3) 0.4446(6) 0.0278(3) 0.1220(18) Uani 1 1 d . . . . .
F3 F 0.2771(3) 0.4849(7) 0.0898(3) 0.137(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
Se1 C8 1.924(5) . ?
Se1 C7 1.930(5) . ?
Se1 Fe1 2.3533(9) . ?
Fe1 N2 1.947(5) . ?
Fe1 N2 1.947(5) 2 ?
Fe1 N1 1.973(5) . ?
Fe1 N1 1.973(5) 2 ?
Fe1 Se1 2.3532(9) 2 ?
C7 C6 1.379(8) . ?
C7 C2 1.409(9) . ?
N1 C1 1.279(8) . ?
N1 C16 1.479(9) . ?
C6 C5 1.402(9) . ?
C6 H6 0.9300 . ?
C13 C12 1.396(9) . ?
C13 C8 1.413(8) . ?
C13 C14 1.448(10) . ?
C8 C9 1.383(9) . ?
C14 N2 1.269(9) . ?
C14 H14 0.9300 . ?
C2 C3 1.389(9) . ?
C2 C1 1.445(10) . ?
C5 C4 1.355(14) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C3 C4 1.375(13) . ?
C3 H3 0.9300 . ?
C9 C10 1.374(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(14) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C11 C12 1.360(14) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N2 C15 1.501(8) . ?
F2 B1 1.345(10) . ?
C16 C15 1.488(13) 2 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 C16 1.488(13) 2 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
F4 B1 1.291(11) . ?
B1 F1 1.336(9) . ?
B1 F3 1.345(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Se1 C7 96.4(2) . . ?
C8 Se1 Fe1 100.20(16) . . ?
C7 Se1 Fe1 101.82(17) . . ?
N2 Fe1 N2 176.3(3) . 2 ?
N2 Fe1 N1 97.4(2) . . ?
N2 Fe1 N1 80.0(2) 2 . ?
N2 Fe1 N1 80.0(2) . 2 ?
N2 Fe1 N1 97.4(2) 2 2 ?
N1 Fe1 N1 91.1(3) . 2 ?
N2 Fe1 Se1 92.72(14) . 2 ?
N2 Fe1 Se1 89.79(15) 2 2 ?
N1 Fe1 Se1 169.65(19) . 2 ?
N1 Fe1 Se1 88.45(15) 2 2 ?
N2 Fe1 Se1 89.79(15) . . ?
N2 Fe1 Se1 92.73(14) 2 . ?
N1 Fe1 Se1 88.45(15) . . ?
N1 Fe1 Se1 169.65(19) 2 . ?
Se1 Fe1 Se1 93.80(4) 2 . ?
C6 C7 C2 120.5(5) . . ?
C6 C7 Se1 118.0(5) . . ?
C2 C7 Se1 121.2(4) . . ?
C1 N1 C16 117.1(6) . . ?
C1 N1 Fe1 133.4(5) . . ?
C16 N1 Fe1 108.4(4) . . ?
C7 C6 C5 119.6(8) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C13 C8 117.2(7) . . ?
C12 C13 C14 118.0(7) . . ?
C8 C13 C14 124.8(5) . . ?
C9 C8 C13 121.4(6) . . ?
C9 C8 Se1 116.8(5) . . ?
C13 C8 Se1 121.7(4) . . ?
N2 C14 C13 127.8(5) . . ?
N2 C14 H14 116.1 . . ?
C13 C14 H14 116.1 . . ?
C3 C2 C7 117.9(7) . . ?
C3 C2 C1 118.0(7) . . ?
C7 C2 C1 123.8(5) . . ?
C4 C5 C6 120.2(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C1 C2 126.9(6) . . ?
N1 C1 H1 116.5 . . ?
C2 C1 H1 116.5 . . ?
C4 C3 C2 121.4(8) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C10 C9 C8 119.5(8) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.0(9) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C12 C11 C10 120.4(8) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.5(9) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 N2 C15 114.5(6) . . ?
C14 N2 Fe1 131.1(4) . . ?
C15 N2 Fe1 113.5(5) . . ?
N1 C16 C15 108.5(6) . 2 ?
N1 C16 H16A 110.0 . . ?
C15 C16 H16A 110.0 2 . ?
N1 C16 H16B 110.0 . . ?
C15 C16 H16B 110.0 2 . ?
H16A C16 H16B 108.4 . . ?
C16 C15 N2 109.5(6) 2 . ?
C16 C15 H15A 109.8 2 . ?
N2 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 2 . ?
N2 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
F4 B1 F1 105.6(8) . . ?
F4 B1 F3 112.4(9) . . ?
F1 B1 F3 110.0(7) . . ?
F4 B1 F2 107.0(9) . . ?
F1 B1 F2 112.3(8) . . ?
F3 B1 F2 109.4(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 C7 C6 C5 1.0(8) . . . . ?
Se1 C7 C6 C5 174.4(5) . . . . ?
C12 C13 C8 C9 0.4(8) . . . . ?
C14 C13 C8 C9 -179.4(5) . . . . ?
C12 C13 C8 Se1 -176.6(4) . . . . ?
C14 C13 C8 Se1 3.6(7) . . . . ?
C12 C13 C14 N2 -158.6(6) . . . . ?
C8 C13 C14 N2 21.2(9) . . . . ?
C6 C7 C2 C3 1.4(8) . . . . ?
Se1 C7 C2 C3 -171.8(4) . . . . ?
C6 C7 C2 C1 175.0(6) . . . . ?
Se1 C7 C2 C1 1.7(8) . . . . ?
C7 C6 C5 C4 -2.6(10) . . . . ?
C16 N1 C1 C2 -169.6(7) . . . . ?
Fe1 N1 C1 C2 -3.1(12) . . . . ?
C3 C2 C1 N1 -157.5(7) . . . . ?
C7 C2 C1 N1 29.0(11) . . . . ?
C7 C2 C3 C4 -2.3(10) . . . . ?
C1 C2 C3 C4 -176.2(6) . . . . ?
C13 C8 C9 C10 1.1(8) . . . . ?
Se1 C8 C9 C10 178.3(5) . . . . ?
C8 C9 C10 C11 -1.7(10) . . . . ?
C6 C5 C4 C3 1.8(12) . . . . ?
C2 C3 C4 C5 0.7(12) . . . . ?
C9 C10 C11 C12 0.9(12) . . . . ?
C10 C11 C12 C13 0.7(11) . . . . ?
C8 C13 C12 C11 -1.3(9) . . . . ?
C14 C13 C12 C11 178.5(6) . . . . ?
C13 C14 N2 C15 176.7(6) . . . . ?
C13 C14 N2 Fe1 8.5(9) . . . . ?
C1 N1 C16 C15 124.7(7) . . . 2 ?
Fe1 N1 C16 C15 -44.9(8) . . . 2 ?
C14 N2 C15 C16 -160.7(6) . . . 2 ?
Fe1 N2 C15 C16 9.6(8) . . . 2 ?

_refine_diff_density_max         1.034
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_d8-0112_a
_database_code_depnum_ccdc_archive 'CCDC 1569379'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2018-08-01 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         ?
_chemical_formula_sum            'C36 H34 B2 F8 Fe N6 Se2'
_chemical_formula_weight         938.08

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.1966(5)
_cell_length_b                   17.7653(7)
_cell_length_c                   16.4051(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.0790(10)
_cell_angle_gamma                90
_cell_volume                     3760.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9771
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      31.38

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    2.413
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8180
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Ius
_diffrn_measurement_device_type  'Bruker Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47301
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7794
_reflns_number_gt                6873
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0517P)²+2.0365P] 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         7794
_refine_ls_number_parameters     498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.87597(2) 0.52660(2) 0.10548(2) 0.01064(8) Uani 1 1 d . . . . .
Se2 Se 0.65116(2) 0.55398(2) 0.17696(2) 0.01296(8) Uani 1 1 d . . . . .
Fe1 Fe 0.82830(3) 0.53201(2) 0.23526(2) 0.00925(9) Uani 1 1 d . . . . .
N1 N 0.97640(16) 0.53670(11) 0.28931(12) 0.0118(4) Uani 1 1 d . . . . .
N3 N 0.78953(16) 0.51881(12) 0.34405(13) 0.0131(4) Uani 1 1 d . . . . .
N4 N 0.84969(16) 0.64121(12) 0.24110(12) 0.0119(4) Uani 1 1 d . . . . .
N2 N 0.81301(15) 0.42213(12) 0.23516(12) 0.0117(4) Uani 1 1 d . . . . .
C7 C 0.99273(19) 0.45796(14) 0.12623(15) 0.0119(5) Uani 1 1 d . . . . .
C25 C 0.5962(2) 0.62228(16) 0.01687(16) 0.0208(6) Uani 1 1 d . . . . .
H25 H 0.5463 0.5830 0.0068 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6003(2) 0.67526(17) -0.04500(17) 0.0249(6) Uani 1 1 d . . . . .
H26 H 0.5545 0.6714 -0.0979 0.030 Uiso 1 1 calc R U . . .
C8 C 0.77851(19) 0.45468(15) 0.04687(15) 0.0140(5) Uani 1 1 d . . . . .
C6 C 1.00818(19) 0.41246(14) 0.06125(15) 0.0140(5) Uani 1 1 d . . . . .
H6 H 0.9597 0.4130 0.0095 0.017 Uiso 1 1 calc R U . . .
C24 C 0.6652(2) 0.62702(15) 0.09332(15) 0.0158(5) Uani 1 1 d . . . . .
C29 C 0.7395(2) 0.68442(14) 0.10964(16) 0.0157(5) Uani 1 1 d . . . . .
C27 C 0.6710(2) 0.73316(17) -0.02920(17) 0.0248(6) Uani 1 1 d . . . . .
H27 H 0.6727 0.7698 -0.0710 0.030 Uiso 1 1 calc R U . . .
C13 C 0.75268(19) 0.38986(15) 0.08680(15) 0.0147(5) Uani 1 1 d . . . . .
C4 C 1.1674(2) 0.36653(15) 0.14666(16) 0.0180(5) Uani 1 1 d . . . . .
H4 H 1.2266 0.3349 0.1537 0.022 Uiso 1 1 calc R U . . .
C31 C 0.9311(2) 0.66513(14) 0.31373(16) 0.0169(5) Uani 1 1 d . . . . .
H31A H 0.8987 0.6915 0.3550 0.020 Uiso 1 1 calc R U . . .
H31B H 0.9798 0.7004 0.2951 0.020 Uiso 1 1 calc R U . . .
C2 C 1.06504(19) 0.45880(14) 0.20229(15) 0.0123(5) Uani 1 1 d . . . . .
C28 C 0.7399(2) 0.73863(15) 0.04723(16) 0.0201(6) Uani 1 1 d . . . . .
H28 H 0.7877 0.7793 0.0574 0.024 Uiso 1 1 calc R U . . .
C12 C 0.6934(2) 0.33449(16) 0.03813(17) 0.0200(6) Uani 1 1 d . . . . .
H12 H 0.6776 0.2892 0.0637 0.024 Uiso 1 1 calc R U . . .
C30 C 0.81774(19) 0.69326(14) 0.18714(15) 0.0148(5) Uani 1 1 d . . . . .
H30 H 0.8475 0.7418 0.1985 0.018 Uiso 1 1 calc R U . . .
C22 C 0.55620(19) 0.68684(15) 0.22969(17) 0.0180(5) Uani 1 1 d . . . . .
H22 H 0.5334 0.6955 0.1716 0.022 Uiso 1 1 calc R U . . .
C5 C 1.0948(2) 0.36594(14) 0.07203(16) 0.0164(5) Uani 1 1 d . . . . .
H5 H 1.1043 0.3336 0.0281 0.020 Uiso 1 1 calc R U . . .
C32 C 0.98981(19) 0.59572(14) 0.35388(15) 0.0146(5) Uani 1 1 d . . . . .
H32A H 1.0642 0.6076 0.3736 0.017 Uiso 1 1 calc R U . . .
H32B H 0.9615 0.5787 0.4021 0.017 Uiso 1 1 calc R U . . .
C9 C 0.7418(2) 0.46509(16) -0.03791(16) 0.0198(6) Uani 1 1 d . . . . .
H9 H 0.7592 0.5095 -0.0642 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6573(2) 0.34453(17) -0.04673(18) 0.0251(6) Uani 1 1 d . . . . .
H11 H 0.6175 0.3062 -0.0789 0.030 Uiso 1 1 calc R U . . .
C3 C 1.1533(2) 0.41327(15) 0.21066(16) 0.0164(5) Uani 1 1 d . . . . .
H3 H 1.2042 0.4146 0.2610 0.020 Uiso 1 1 calc R U . . .
C17 C 0.7222(2) 0.55035(15) 0.37830(16) 0.0164(5) Uani 1 1 d . . . . .
H17 H 0.7148 0.5315 0.4309 0.020 Uiso 1 1 calc R U . . .
C16 C 0.8426(2) 0.45092(14) 0.38474(15) 0.0152(5) Uani 1 1 d . . . . .
H16A H 0.8138 0.4366 0.4336 0.018 Uiso 1 1 calc R U . . .
H16B H 0.9178 0.4606 0.4037 0.018 Uiso 1 1 calc R U . . .
C23 C 0.61989(19) 0.62581(14) 0.25754(15) 0.0142(5) Uani 1 1 d . . . . .
C1 C 1.05893(19) 0.50893(15) 0.27218(15) 0.0143(5) Uani 1 1 d . . . . .
H1 H 1.1226 0.5221 0.3083 0.017 Uiso 1 1 calc R U . . .
C19 C 0.6214(2) 0.66160(16) 0.39909(16) 0.0189(6) Uani 1 1 d . . . . .
H19 H 0.6425 0.6527 0.4573 0.023 Uiso 1 1 calc R U . . .
C18 C 0.65542(19) 0.61322(15) 0.34326(16) 0.0156(5) Uani 1 1 d . . . . .
C21 C 0.5256(2) 0.73542(16) 0.28683(17) 0.0205(6) Uani 1 1 d . . . . .
H21 H 0.4828 0.7775 0.2677 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5575(2) 0.72232(16) 0.37132(18) 0.0218(6) Uani 1 1 d . . . . .
H20 H 0.5358 0.7549 0.4103 0.026 Uiso 1 1 calc R U . . .
C14 C 0.78122(19) 0.37449(14) 0.17595(16) 0.0145(5) Uani 1 1 d . . . . .
H14 H 0.7758 0.3236 0.1923 0.017 Uiso 1 1 calc R U . . .
C10 C 0.6794(2) 0.41035(18) -0.08453(17) 0.0260(6) Uani 1 1 d . . . . .
H10 H 0.6520 0.4183 -0.1422 0.031 Uiso 1 1 calc R U . . .
C15 C 0.8244(2) 0.38909(15) 0.32021(16) 0.0193(6) Uani 1 1 d . . . . .
H15A H 0.8834 0.3535 0.3308 0.023 Uiso 1 1 calc R U . . .
H15B H 0.7608 0.3609 0.3240 0.023 Uiso 1 1 calc R U . . .
B1 B 0.5212(3) 0.3894(2) 0.2881(2) 0.0302(8) Uani 1 1 d . . . . .
F1 F 0.57301(17) 0.35617(13) 0.23064(14) 0.0499(6) Uani 1 1 d . . . . .
F2 F 0.5522(2) 0.46230(13) 0.29927(18) 0.0681(8) Uani 1 1 d . . . . .
F3 F 0.5460(2) 0.35213(17) 0.36256(17) 0.0773(9) Uani 1 1 d . . . . .
F4 F 0.41722(17) 0.38758(19) 0.25627(18) 0.0754(8) Uani 1 1 d . . . . .
B2 B 0.8654(2) 0.61838(18) 0.56218(18) 0.0193(6) Uani 1 1 d . . . . .
F5 F 0.92912(14) 0.65254(11) 0.63038(10) 0.0334(4) Uani 1 1 d . . . . .
F6 F 0.90740(14) 0.54994(10) 0.54512(11) 0.0310(4) Uani 1 1 d . . . . .
F7 F 0.76798(13) 0.60515(11) 0.57923(10) 0.0334(4) Uani 1 1 d . . . . .
F8 F 0.85616(14) 0.66471(10) 0.49250(10) 0.0291(4) Uani 1 1 d . . . . .
N5 N 1.0572(2) 0.64535(16) 0.14494(17) 0.0354(6) Uani 1 1 d . . . . .
C33 C 1.1165(2) 0.69105(19) 0.1552(2) 0.0302(7) Uani 1 1 d . . . . .
C34 C 1.1951(3) 0.7505(2) 0.1700(4) 0.0677(15) Uani 1 1 d . . . . .
H34A H 1.2578 0.7317 0.2074 0.102 Uiso 1 1 calc R U . . .
H34B H 1.1683 0.7940 0.1957 0.102 Uiso 1 1 calc R U . . .
H34C H 1.2117 0.7657 0.1169 0.102 Uiso 1 1 calc R U . . .
N6 N 0.2697(3) 0.6389(3) 0.3484(3) 0.0871(15) Uani 1 1 d . . . . .
C35 C 0.3299(3) 0.5945(3) 0.3805(3) 0.0618(13) Uani 1 1 d . . . . .
C36 C 0.4039(4) 0.5390(3) 0.4219(4) 0.0731(15) Uani 1 1 d . . . . .
H36A H 0.4299 0.5540 0.4800 0.110 Uiso 1 1 calc R U . . .
H36B H 0.4619 0.5356 0.3932 0.110 Uiso 1 1 calc R U . . .
H36C H 0.3699 0.4898 0.4204 0.110 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C8 1.922(3) . ?
Se1 C7 1.938(2) . ?
Se1 Fe1 2.3448(4) . ?
Se2 C24 1.925(3) . ?
Se2 C23 1.943(2) . ?
Se2 Fe1 2.3657(4) . ?
Fe1 N4 1.960(2) . ?
Fe1 N2 1.962(2) . ?
Fe1 N3 1.971(2) . ?
Fe1 N1 1.972(2) . ?
N1 C1 1.279(3) . ?
N1 C32 1.475(3) . ?
N3 C17 1.276(3) . ?
N3 C16 1.482(3) . ?
N4 C30 1.289(3) . ?
N4 C31 1.489(3) . ?
N2 C14 1.290(3) . ?
N2 C15 1.492(3) . ?
C7 C6 1.387(3) . ?
C7 C2 1.403(3) . ?
C25 C24 1.390(4) . ?
C25 C26 1.394(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9500 . ?
C8 C9 1.386(4) . ?
C8 C13 1.402(4) . ?
C6 C5 1.391(4) . ?
C6 H6 0.9500 . ?
C24 C29 1.401(4) . ?
C29 C28 1.406(4) . ?
C29 C30 1.469(4) . ?
C27 C28 1.390(4) . ?
C27 H27 0.9500 . ?
C13 C12 1.398(4) . ?
C13 C14 1.458(4) . ?
C4 C3 1.381(4) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C31 C32 1.530(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C2 C3 1.401(4) . ?
C2 C1 1.467(3) . ?
C28 H28 0.9500 . ?
C12 C11 1.385(4) . ?
C12 H12 0.9500 . ?
C30 H30 0.9500 . ?
C22 C23 1.389(4) . ?
C22 C21 1.395(4) . ?
C22 H22 0.9500 . ?
C5 H5 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C9 C10 1.395(4) . ?
C9 H9 0.9500 . ?
C11 C10 1.383(4) . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C17 C18 1.464(4) . ?
C17 H17 0.9500 . ?
C16 C15 1.509(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C23 C18 1.404(3) . ?
C1 H1 0.9500 . ?
C19 C20 1.386(4) . ?
C19 C18 1.397(4) . ?
C19 H19 0.9500 . ?
C21 C20 1.381(4) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
B1 F2 1.359(4) . ?
B1 F4 1.362(4) . ?
B1 F3 1.368(4) . ?
B1 F1 1.405(4) . ?
B2 F6 1.389(4) . ?
B2 F5 1.391(3) . ?
B2 F7 1.391(4) . ?
B2 F8 1.393(3) . ?
N5 C33 1.115(4) . ?
C33 C34 1.465(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
N6 C35 1.164(7) . ?
C35 C36 1.453(7) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C8 Se1 C7 95.38(10) . . ?
C8 Se1 Fe1 101.71(7) . . ?
C7 Se1 Fe1 102.76(7) . . ?
C24 Se2 C23 96.21(11) . . ?
C24 Se2 Fe1 99.49(8) . . ?
C23 Se2 Fe1 99.55(7) . . ?
N4 Fe1 N2 176.76(9) . . ?
N4 Fe1 N3 97.79(8) . . ?
N2 Fe1 N3 80.57(8) . . ?
N4 Fe1 N1 79.46(8) . . ?
N2 Fe1 N1 97.73(8) . . ?
N3 Fe1 N1 91.06(9) . . ?
N4 Fe1 Se1 91.24(6) . . ?
N2 Fe1 Se1 90.32(6) . . ?
N3 Fe1 Se1 170.81(6) . . ?
N1 Fe1 Se1 88.92(6) . . ?
N4 Fe1 Se2 88.65(6) . . ?
N2 Fe1 Se2 94.07(6) . . ?
N3 Fe1 Se2 87.93(6) . . ?
N1 Fe1 Se2 167.83(6) . . ?
Se1 Fe1 Se2 94.002(14) . . ?
C1 N1 C32 116.9(2) . . ?
C1 N1 Fe1 133.96(18) . . ?
C32 N1 Fe1 108.17(15) . . ?
C17 N3 C16 117.8(2) . . ?
C17 N3 Fe1 133.10(18) . . ?
C16 N3 Fe1 108.47(15) . . ?
C30 N4 C31 115.0(2) . . ?
C30 N4 Fe1 130.82(18) . . ?
C31 N4 Fe1 113.20(15) . . ?
C14 N2 C15 113.5(2) . . ?
C14 N2 Fe1 132.08(18) . . ?
C15 N2 Fe1 113.60(16) . . ?
C6 C7 C2 120.5(2) . . ?
C6 C7 Se1 118.11(18) . . ?
C2 C7 Se1 121.14(18) . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C9 C8 C13 120.7(2) . . ?
C9 C8 Se1 118.0(2) . . ?
C13 C8 Se1 121.00(18) . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C25 C24 C29 121.1(2) . . ?
C25 C24 Se2 117.3(2) . . ?
C29 C24 Se2 121.49(19) . . ?
C24 C29 C28 117.9(2) . . ?
C24 C29 C30 125.5(2) . . ?
C28 C29 C30 116.6(2) . . ?
C26 C27 C28 120.8(3) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C12 C13 C8 118.2(2) . . ?
C12 C13 C14 115.9(2) . . ?
C8 C13 C14 125.9(2) . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N4 C31 C32 109.3(2) . . ?
N4 C31 H31A 109.8 . . ?
C32 C31 H31A 109.8 . . ?
N4 C31 H31B 109.8 . . ?
C32 C31 H31B 109.8 . . ?
H31A C31 H31B 108.3 . . ?
C3 C2 C7 118.5(2) . . ?
C3 C2 C1 117.0(2) . . ?
C7 C2 C1 124.3(2) . . ?
C27 C28 C29 120.5(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N4 C30 C29 126.0(2) . . ?
N4 C30 H30 117.0 . . ?
C29 C30 H30 117.0 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N1 C32 C31 106.86(19) . . ?
N1 C32 H32A 110.4 . . ?
C31 C32 H32A 110.3 . . ?
N1 C32 H32B 110.4 . . ?
C31 C32 H32B 110.3 . . ?
H32A C32 H32B 108.6 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
N3 C17 C18 125.4(2) . . ?
N3 C17 H17 117.3 . . ?
C18 C17 H17 117.3 . . ?
N3 C16 C15 106.6(2) . . ?
N3 C16 H16A 110.4 . . ?
C15 C16 H16A 110.4 . . ?
N3 C16 H16B 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C22 C23 C18 120.4(2) . . ?
C22 C23 Se2 119.26(19) . . ?
C18 C23 Se2 120.20(19) . . ?
N1 C1 C2 126.5(2) . . ?
N1 C1 H1 116.8 . . ?
C2 C1 H1 116.8 . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C18 C23 118.2(2) . . ?
C19 C18 C17 117.5(2) . . ?
C23 C18 C17 124.2(2) . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
N2 C14 C13 127.4(2) . . ?
N2 C14 H14 116.3 . . ?
C13 C14 H14 116.3 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N2 C15 C16 109.9(2) . . ?
N2 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
F2 B1 F4 109.0(3) . . ?
F2 B1 F3 109.4(3) . . ?
F4 B1 F3 111.4(3) . . ?
F2 B1 F1 108.4(3) . . ?
F4 B1 F1 109.0(3) . . ?
F3 B1 F1 109.7(3) . . ?
F6 B2 F5 110.1(2) . . ?
F6 B2 F7 108.5(2) . . ?
F5 B2 F7 109.9(2) . . ?
F6 B2 F8 108.8(2) . . ?
F5 B2 F8 109.7(2) . . ?
F7 B2 F8 109.8(2) . . ?
N5 C33 C34 179.1(5) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N6 C35 C36 178.9(6) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_refine_diff_density_max         0.901
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.227

####################################################################### 
# 
# 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_d8-0603_a
_database_code_depnum_ccdc_archive 'CCDC 1569380'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2018-08-01 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         ?
_chemical_formula_sum            'C32 H38 B2 F8 N4 Se2'
_chemical_formula_weight         810.20

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.941(2)
_cell_length_b                   7.8551(11)
_cell_length_c                   15.1170(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.334(4)
_cell_angle_gamma                90
_cell_volume                     1693.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9525
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.71

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    2.257
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9052
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            80008
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         28.740
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4386
_reflns_number_gt                3962
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0216P)²+1.5023P] 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         4386
_refine_ls_number_parameters     229
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0576
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Se1 Se 0.33136(2) 0.60621(2) 0.56179(2) 0.01666(5) Uani 1 1 d . . . . .
F1 F 0.56756(7) 0.12048(13) 0.56369(7) 0.0257(2) Uani 1 1 d . . . . .
F2 F 0.60556(11) 0.16286(16) 0.71865(8) 0.0434(3) Uani 1 1 d . . . . .
F3 F 0.56551(10) 0.38644(14) 0.61782(9) 0.0401(3) Uani 1 1 d . . . . .
F4 F 0.70435(8) 0.2487(2) 0.64029(9) 0.0527(4) Uani 1 1 d . . . . .
N2 N 0.59067(9) 0.71744(18) 0.56901(9) 0.0155(3) Uani 1 1 d D . . . .
N1 N 0.48518(9) 0.82927(18) 0.68193(10) 0.0179(3) Uani 1 1 d D . . . .
C1 C 0.35012(10) 0.5367(2) 0.68836(11) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.32198(11) 0.3777(2) 0.71127(12) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.2958 0.2971 0.6637 0.023 Uiso 1 1 calc R U . . .
C3 C 0.33198(11) 0.3359(2) 0.80331(12) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.3128 0.2271 0.8184 0.026 Uiso 1 1 calc R U . . .
C4 C 0.36990(12) 0.4531(3) 0.87279(12) 0.0239(4) Uani 1 1 d . . . . .
H4 H 0.3756 0.4262 0.9355 0.029 Uiso 1 1 calc R U . . .
C5 C 0.39958(11) 0.6100(2) 0.85023(12) 0.0223(3) Uani 1 1 d . . . . .
H5 H 0.4266 0.6890 0.8984 0.027 Uiso 1 1 calc R U . . .
C6 C 0.39092(11) 0.6553(2) 0.75871(11) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.42004(12) 0.8310(2) 0.73802(12) 0.0219(3) Uani 1 1 d . . . . .
H7A H 0.3634 0.8964 0.7047 0.026 Uiso 1 1 calc R U . . .
H7B H 0.4502 0.8902 0.7972 0.026 Uiso 1 1 calc R U . . .
C8 C 0.57409(11) 0.7423(2) 0.72707(11) 0.0181(3) Uani 1 1 d . . . . .
H8A H 0.5623 0.6200 0.7348 0.022 Uiso 1 1 calc R U . . .
H8B H 0.6031 0.7918 0.7893 0.022 Uiso 1 1 calc R U . . .
C9 C 0.64031(11) 0.7621(2) 0.66825(10) 0.0169(3) Uani 1 1 d . . . . .
H9A H 0.6631 0.8811 0.6720 0.020 Uiso 1 1 calc R U . . .
H9B H 0.6952 0.6866 0.6924 0.020 Uiso 1 1 calc R U . . .
C10 C 0.63796(11) 0.7797(2) 0.49992(11) 0.0167(3) Uani 1 1 d . . . . .
H10A H 0.6362 0.9056 0.4982 0.020 Uiso 1 1 calc R U . . .
H10B H 0.6029 0.7376 0.4375 0.020 Uiso 1 1 calc R U . . .
C11 C 0.73847(11) 0.7209(2) 0.52328(11) 0.0161(3) Uani 1 1 d . . . . .
C12 C 0.80919(12) 0.8335(2) 0.56992(11) 0.0209(3) Uani 1 1 d . . . . .
H12 H 0.7931 0.9435 0.5864 0.025 Uiso 1 1 calc R U . . .
C13 C 0.90282(12) 0.7860(3) 0.59238(12) 0.0238(4) Uani 1 1 d . . . . .
H13 H 0.9504 0.8626 0.6250 0.029 Uiso 1 1 calc R U . . .
C14 C 0.92660(12) 0.6269(3) 0.56717(12) 0.0239(4) Uani 1 1 d . . . . .
H14 H 0.9907 0.5951 0.5818 0.029 Uiso 1 1 calc R U . . .
C15 C 0.85717(12) 0.5136(2) 0.52048(12) 0.0212(3) Uani 1 1 d . . . . .
H15 H 0.8740 0.4044 0.5035 0.025 Uiso 1 1 calc R U . . .
C16 C 0.76277(11) 0.5593(2) 0.49841(11) 0.0165(3) Uani 1 1 d . . . . .
B1 B 0.61196(14) 0.2304(3) 0.63664(13) 0.0224(4) Uani 1 1 d . . . . .
H1A H 0.4972(15) 0.934(2) 0.6717(14) 0.025(5) Uiso 1 1 d D . . . .
H2A H 0.5356(12) 0.762(3) 0.5537(14) 0.027(6) Uiso 1 1 d D . . . .
H2B H 0.5843(14) 0.6063(19) 0.5660(14) 0.020(5) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.9282(16) . ?
Se1 C16 1.9325(16) 3_666 ?
F1 B1 1.402(2) . ?
F2 B1 1.378(2) . ?
F3 B1 1.395(2) . ?
F4 B1 1.373(2) . ?
N2 C9 1.504(2) . ?
N2 C10 1.506(2) . ?
N2 H2A 0.860(15) . ?
N2 H2B 0.878(15) . ?
N1 C8 1.469(2) . ?
N1 C7 1.469(2) . ?
N1 H1A 0.863(15) . ?
C1 C2 1.394(2) . ?
C1 C6 1.408(2) . ?
C2 C3 1.394(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.508(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.522(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.509(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.397(2) . ?
C11 C16 1.402(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(2) . ?
C15 H15 0.9500 . ?
C16 Se1 1.9324(16) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C16 98.46(7) . 3_666 ?
C9 N2 C10 114.98(12) . . ?
C9 N2 H2A 108.7(14) . . ?
C10 N2 H2A 106.8(14) . . ?
C9 N2 H2B 107.3(13) . . ?
C10 N2 H2B 110.7(13) . . ?
H2A N2 H2B 108(2) . . ?
C8 N1 C7 113.53(14) . . ?
C8 N1 H1A 108.5(14) . . ?
C7 N1 H1A 107.7(14) . . ?
C2 C1 C6 119.97(15) . . ?
C2 C1 Se1 122.32(12) . . ?
C6 C1 Se1 117.68(12) . . ?
C3 C2 C1 120.56(16) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.90(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.56(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.85(16) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.13(16) . . ?
C5 C6 C7 119.41(15) . . ?
C1 C6 C7 122.36(15) . . ?
N1 C7 C6 113.16(13) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C9 109.66(13) . . ?
N1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C8 110.22(13) . . ?
N2 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 112.22(13) . . ?
N2 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C16 119.41(15) . . ?
C12 C11 C10 118.34(15) . . ?
C16 C11 C10 122.24(14) . . ?
C13 C12 C11 120.56(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.89(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.31(16) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 120.29(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.53(15) . . ?
C15 C16 Se1 118.74(13) . 3_666 ?
C11 C16 Se1 121.68(11) . 3_666 ?
F4 B1 F2 110.04(16) . . ?
F4 B1 F3 110.45(16) . . ?
F2 B1 F3 110.99(16) . . ?
F4 B1 F1 109.29(16) . . ?
F2 B1 F1 109.10(15) . . ?
F3 B1 F1 106.89(15) . . ?

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
C8 H8A F3 0.99 2.56 3.230(2) 125.0 .
C9 H9A F1 0.99 2.62 3.253(2) 121.9 1_565
C9 H9A F2 0.99 2.55 3.316(2) 134.1 1_565
C9 H9B F4 0.99 2.57 3.126(2) 115.1 2_656
C10 H10B F3 0.99 2.59 3.300(2) 128.3 3_666
C10 H10A F1 0.99 2.34 3.1316(19) 136.1 1_565
N1 H1A F1 0.863(15) 2.636(18) 3.3546(18) 141.5(18) 1_565
N1 H1A F2 0.863(15) 2.384(18) 3.1329(19) 145.4(18) 1_565
N2 H2A F1 0.860(15) 2.178(18) 2.8997(17) 141.3(19) 3_666
N2 H2A N1 0.860(15) 2.34(2) 2.7881(19) 112.8(16) .
N2 H2B Se1 0.878(15) 3.091(19) 3.6198(14) 120.7(15) 3_666
N2 H2B F3 0.878(15) 1.951(16) 2.7589(19) 152.4(19) .

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.064

