# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1-S_123K
_database_code_depnum_ccdc_archive 'CCDC 1834090'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;
_audit_creation_date             2018-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        Fe(L_Cl)(NCS)2_123K_Pbna
_chemical_formula_moiety         'C16 H16 Cl2 Fe N6 S2'
_chemical_formula_sum            'C16 H16 Cl2 Fe N6 S2'
_chemical_formula_weight         483.22
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.1129(14)
_cell_length_b                   9.5488(7)
_cell_length_c                   13.0274(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2004.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2828
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      123.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1393
_reflns_number_total             2045
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+1.5256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.0000 0.43073(6) 0.7500 0.01334(16) Uani 1 2 d S T P . .
Cl1 Cl 0.39413(5) 0.36327(8) 0.60026(6) 0.0212(2) Uani 1 1 d . . . . .
S1 S 0.09363(6) 0.81005(8) 0.96739(6) 0.0204(2) Uani 1 1 d . . . . .
N1 N 0.12844(15) 0.4193(3) 0.69581(17) 0.0142(6) Uani 1 1 d . . . . .
N2 N 0.05632(16) 0.2494(3) 0.83400(18) 0.0154(6) Uani 1 1 d . . . . .
H2 H 0.0285 0.2377 0.9021 0.018 Uiso 1 1 d R . . . .
N3 N 0.03834(17) 0.5700(3) 0.86468(19) 0.0215(6) Uani 1 1 d . . . . .
C1 C 0.1582(2) 0.4818(3) 0.6113(2) 0.0168(7) Uani 1 1 d . . . . .
H1 H 0.1215 0.5370 0.5711 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2396(2) 0.4697(3) 0.5800(2) 0.0168(7) Uani 1 1 d . . . . .
H2A H 0.2590 0.5166 0.5203 0.020 Uiso 1 1 calc R . . . .
C3 C 0.29192(19) 0.3876(3) 0.6378(2) 0.0155(7) Uani 1 1 d . . . . .
C4 C 0.2633(2) 0.3228(3) 0.7256(2) 0.0179(8) Uani 1 1 d . . . . .
H4 H 0.2991 0.2663 0.7662 0.022 Uiso 1 1 calc R . . . .
C5 C 0.18114(19) 0.3421(3) 0.7529(2) 0.0157(7) Uani 1 1 d . . . . .
C6 C 0.1444(2) 0.2794(3) 0.8492(2) 0.0205(8) Uani 1 1 d . . . . .
H6A H 0.1742 0.1918 0.8666 0.025 Uiso 1 1 calc R . . . .
H6B H 0.1512 0.3456 0.9071 0.025 Uiso 1 1 calc R . . . .
C7 C 0.0435(2) 0.1222(3) 0.7709(2) 0.0198(8) Uani 1 1 d . . . . .
H7A H 0.0525 0.0376 0.8134 0.024 Uiso 1 1 calc R . . . .
H7B H 0.0838 0.1206 0.7136 0.024 Uiso 1 1 calc R . . . .
C8 C 0.0623(2) 0.6693(3) 0.9071(2) 0.0164(7) 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 N1 2.189(2) 4_556 ?
Fe1 N1 2.189(2) . ?
Fe1 N2 2.240(2) 4_556 ?
Fe1 N2 2.240(2) . ?
Fe1 N3 2.093(3) . ?
Fe1 N3 2.093(3) 4_556 ?
Cl1 C3 1.734(3) . ?
S1 C8 1.637(3) . ?
N1 C1 1.341(4) . ?
N1 C5 1.348(4) . ?
N2 H2 1.0002 . ?
N2 C6 1.462(4) . ?
N2 C7 1.481(4) . ?
N3 C8 1.164(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.375(4) . ?
C3 C4 1.379(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 C6 1.511(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C7 1.503(6) 4_556 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Fe1 N1 174.28(13) . 4_556 ?
N1 Fe1 N2 100.77(9) 4_556 . ?
N1 Fe1 N2 100.77(9) . 4_556 ?
N1 Fe1 N2 74.70(9) 4_556 4_556 ?
N1 Fe1 N2 74.70(9) . . ?
N2 Fe1 N2 78.78(13) 4_556 . ?
N3 Fe1 N1 94.62(9) . 4_556 ?
N3 Fe1 N1 89.02(9) . . ?
N3 Fe1 N1 89.02(9) 4_556 4_556 ?
N3 Fe1 N1 94.62(10) 4_556 . ?
N3 Fe1 N2 91.30(10) . . ?
N3 Fe1 N2 163.56(9) 4_556 . ?
N3 Fe1 N2 163.56(9) . 4_556 ?
N3 Fe1 N2 91.30(10) 4_556 4_556 ?
N3 Fe1 N3 101.14(15) 4_556 . ?
C1 N1 Fe1 125.5(2) . . ?
C1 N1 C5 118.1(3) . . ?
C5 N1 Fe1 116.41(19) . . ?
Fe1 N2 H2 109.8 . . ?
C6 N2 Fe1 107.95(18) . . ?
C6 N2 H2 109.7 . . ?
C6 N2 C7 111.8(2) . . ?
C7 N2 Fe1 107.83(17) . . ?
C7 N2 H2 109.7 . . ?
C8 N3 Fe1 162.6(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.1(3) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 117.9(3) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 Cl1 120.2(2) . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 Cl1 119.4(2) . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 C6 115.4(3) . . ?
C4 C5 C6 122.4(3) . . ?
N2 C6 C5 110.2(2) . . ?
N2 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C7 109.3(2) . 4_556 ?
N2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C7 C7 H7A 109.8 4_556 . ?
C7 C7 H7B 109.8 4_556 . ?
H7A C7 H7B 108.3 . . ?
N3 C8 S1 178.6(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
Fe1 N1 C1 C2 -179.2(2) . . . . ?
Fe1 N1 C5 C4 178.0(2) . . . . ?
Fe1 N1 C5 C6 -2.6(3) . . . . ?
Fe1 N2 C6 C5 -42.3(3) . . . . ?
Fe1 N2 C7 C7 -43.1(3) . . . 4_556 ?
Cl1 C3 C4 C5 -179.0(2) . . . . ?
N1 C1 C2 C3 1.1(5) . . . . ?
N1 C5 C6 N2 30.9(4) . . . . ?
C1 N1 C5 C4 -1.8(4) . . . . ?
C1 N1 C5 C6 177.7(3) . . . . ?
C1 C2 C3 Cl1 177.8(2) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 N1 1.3(4) . . . . ?
C3 C4 C5 C6 -178.1(3) . . . . ?
C4 C5 C6 N2 -149.6(3) . . . . ?
C5 N1 C1 C2 0.6(4) . . . . ?
C6 N2 C7 C7 -161.6(3) . . . 4_556 ?
C7 N2 C6 C5 76.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1-Se_123K
_database_code_depnum_ccdc_archive 'CCDC 1834091'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;
_audit_creation_date             2018-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl2 Fe N6 Se2'
_chemical_formula_sum            'C16 H16 Cl2 Fe N6 Se2'
_chemical_formula_weight         577.02
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.931(12)
_cell_length_b                   9.285(7)
_cell_length_c                   13.394(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1981(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6194
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.619
_cell_measurement_theta_min      2.539
_shelx_estimated_absorpt_T_max   0.852
_shelx_estimated_absorpt_T_min   0.632
_exptl_absorpt_coefficient_mu    4.720
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1318 before and 0.1003 after correction.
The Ratio of minimum to maximum transmission is 0.8410.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28617
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         2.539
_diffrn_ambient_temperature      123.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1898
_reflns_number_total             2471
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0168P)²+3.7540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.09176(2) 0.18047(3) 0.03391(2) 0.01510(8) Uani 1 1 d . . . . .
Fe1 Fe 0.0000 0.57245(6) 0.2500 0.00962(12) Uani 1 2 d S T P . .
Cl1 Cl -0.38569(4) 0.62798(8) 0.10665(6) 0.01866(16) Uani 1 1 d . . . . .
N1 N -0.11678(13) 0.5770(2) 0.19980(16) 0.0110(5) Uani 1 1 d . . . . .
N2 N -0.04668(14) 0.7331(2) 0.33485(17) 0.0142(5) Uani 1 1 d . . . . .
H2 H -0.0147 0.7408 0.3989 0.017 Uiso 1 1 calc R . . . .
N3 N 0.03594(14) 0.4262(2) 0.15652(17) 0.0147(5) Uani 1 1 d . . . . .
C1 C -0.14478(17) 0.5206(3) 0.1146(2) 0.0134(6) Uani 1 1 d . . . . .
H1 H -0.1060 0.4721 0.0725 0.016 Uiso 1 1 calc R . . . .
C2 C -0.22768(17) 0.5293(3) 0.0845(2) 0.0158(6) Uani 1 1 d . . . . .
H2A H -0.2460 0.4851 0.0244 0.019 Uiso 1 1 calc R . . . .
C3 C -0.28266(17) 0.6037(3) 0.1440(2) 0.0142(6) Uani 1 1 d . . . . .
C4 C -0.25602(17) 0.6611(3) 0.2334(2) 0.0157(6) Uani 1 1 d . . . . .
H4 H -0.2938 0.7106 0.2762 0.019 Uiso 1 1 calc R . . . .
C5 C -0.17258(16) 0.6443(3) 0.2590(2) 0.0132(6) Uani 1 1 d . . . . .
C6 C -0.13590(17) 0.6996(3) 0.3550(2) 0.0180(6) Uani 1 1 d . . . . .
H6A H -0.1660 0.7873 0.3771 0.022 Uiso 1 1 calc R . . . .
H6B H -0.1405 0.6258 0.4080 0.022 Uiso 1 1 calc R . . . .
C7 C -0.04069(18) 0.8692(3) 0.2777(2) 0.0188(6) Uani 1 1 d . . . . .
H7A H -0.0431 0.9525 0.3238 0.023 Uiso 1 1 calc R . . . .
H7B H -0.0881 0.8767 0.2303 0.023 Uiso 1 1 calc R . . . .
C8 C 0.05886(16) 0.3307(3) 0.1083(2) 0.0128(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 C8 1.793(3) . ?
Fe1 N1 1.979(3) 4 ?
Fe1 N1 1.979(3) . ?
Fe1 N2 2.017(2) 4 ?
Fe1 N2 2.017(2) . ?
Fe1 N3 1.934(3) . ?
Fe1 N3 1.934(3) 4 ?
Cl1 C3 1.731(3) . ?
N1 C1 1.333(3) . ?
N1 C5 1.345(3) . ?
N2 H2 1.0000 . ?
N2 C6 1.480(4) . ?
N2 C7 1.480(4) . ?
N3 C8 1.156(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.370(4) . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C5 C6 1.503(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C7 1.494(6) 4 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Fe1 N1 177.54(13) . 4 ?
N1 Fe1 N2 98.01(10) 4 . ?
N1 Fe1 N2 98.01(9) . 4 ?
N1 Fe1 N2 80.15(10) 4 4 ?
N1 Fe1 N2 80.15(10) . . ?
N2 Fe1 N2 84.65(14) 4 . ?
N3 Fe1 N1 94.21(9) 4 4 ?
N3 Fe1 N1 87.52(9) 4 . ?
N3 Fe1 N1 87.52(9) . 4 ?
N3 Fe1 N1 94.21(9) . . ?
N3 Fe1 N2 92.59(10) 4 . ?
N3 Fe1 N2 173.29(9) . . ?
N3 Fe1 N2 173.29(9) 4 4 ?
N3 Fe1 N2 92.60(11) . 4 ?
N3 Fe1 N3 90.78(15) . 4 ?
C1 N1 Fe1 126.68(18) . . ?
C1 N1 C5 117.8(2) . . ?
C5 N1 Fe1 115.54(18) . . ?
Fe1 N2 H2 110.4 . . ?
C6 N2 Fe1 107.57(17) . . ?
C6 N2 H2 110.4 . . ?
C6 N2 C7 109.6(2) . . ?
C7 N2 Fe1 108.44(17) . . ?
C7 N2 H2 110.4 . . ?
C8 N3 Fe1 173.6(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.1(3) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 Cl1 120.2(2) . . ?
C2 C3 C4 120.2(3) . . ?
C4 C3 Cl1 119.5(2) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 C6 114.0(2) . . ?
C4 C5 C6 123.2(2) . . ?
N2 C6 C5 106.8(2) . . ?
N2 C6 H6A 110.4 . . ?
N2 C6 H6B 110.4 . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
N2 C7 C7 108.23(18) . 4 ?
N2 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C7 C7 H7A 110.1 4 . ?
C7 C7 H7B 110.1 4 . ?
H7A C7 H7B 108.4 . . ?
N3 C8 Se1 178.5(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
Fe1 N1 C1 C2 -179.6(2) . . . . ?
Fe1 N1 C5 C4 177.8(2) . . . . ?
Fe1 N1 C5 C6 -2.0(3) . . . . ?
Fe1 N2 C6 C5 -41.9(2) . . . . ?
Fe1 N2 C7 C7 -39.1(3) . . . 4 ?
Cl1 C3 C4 C5 -177.6(2) . . . . ?
N1 C1 C2 C3 2.1(4) . . . . ?
N1 C5 C6 N2 29.3(3) . . . . ?
C1 N1 C5 C4 -2.3(4) . . . . ?
C1 N1 C5 C6 177.9(2) . . . . ?
C1 C2 C3 Cl1 176.0(2) . . . . ?
C1 C2 C3 C4 -3.2(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C3 C4 C5 N1 1.2(4) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C4 C5 C6 N2 -150.5(3) . . . . ?
C5 N1 C1 C2 0.6(4) . . . . ?
C6 N2 C7 C7 -156.3(3) . . . 4 ?
C7 N2 C6 C5 75.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1-Se_298K
_database_code_depnum_ccdc_archive 'CCDC 1834092'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;
_audit_creation_date             2018-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl2 Fe N6 Se2'
_chemical_formula_sum            'C16 H16 Cl2 Fe N6 Se2'
_chemical_formula_weight         577.02
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.384(6)
_cell_length_b                   9.657(3)
_cell_length_c                   13.344(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2111.3(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.308
_cell_measurement_theta_min      2.448
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.649
_exptl_absorpt_coefficient_mu    4.429
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0839 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8533.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25370
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.232
_diffrn_reflns_theta_max         25.232
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      298.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1364
_reflns_number_total             1901
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+4.1724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.09255(3) 0.18077(5) 0.03303(3) 0.04586(15) Uani 1 1 d . . . . .
Fe1 Fe 0.0000 0.56964(8) 0.2500 0.0305(2) Uani 1 2 d S T P . .
Cl1 Cl -0.38673(6) 0.63707(12) 0.10422(10) 0.0542(3) Uani 1 1 d . . . . .
N1 N -0.12653(19) 0.5803(3) 0.1973(2) 0.0322(8) Uani 1 1 d . . . . .
N2 N -0.0550(2) 0.7477(4) 0.3317(2) 0.0401(9) Uani 1 1 d . . . . .
H2 H -0.0279 0.7589 0.3967 0.048 Uiso 1 1 calc R . . . .
N3 N 0.0363(2) 0.4285(4) 0.1395(3) 0.0503(10) Uani 1 1 d . . . . .
C1 C -0.1559(2) 0.5203(4) 0.1154(3) 0.0390(10) Uani 1 1 d . . . . .
H1 H -0.1205 0.4676 0.0765 0.047 Uiso 1 1 calc R . . . .
C2 C -0.2358(2) 0.5318(4) 0.0846(3) 0.0427(11) Uani 1 1 d . . . . .
H2A H -0.2544 0.4864 0.0276 0.051 Uiso 1 1 calc R . . . .
C3 C -0.2867(2) 0.6123(4) 0.1410(3) 0.0379(10) Uani 1 1 d . . . . .
C4 C -0.2582(3) 0.6753(5) 0.2261(3) 0.0432(11) Uani 1 1 d . . . . .
H4 H -0.2926 0.7300 0.2650 0.052 Uiso 1 1 calc R . . . .
C5 C -0.1777(2) 0.6564(4) 0.2533(3) 0.0366(10) Uani 1 1 d . . . . .
C6 C -0.1421(3) 0.7181(5) 0.3472(3) 0.0512(13) Uani 1 1 d . . . . .
H6A H -0.1707 0.8030 0.3639 0.061 Uiso 1 1 calc R . . . .
H6B H -0.1486 0.6539 0.4025 0.061 Uiso 1 1 calc R . . . .
C7 C -0.0423(3) 0.8729(4) 0.2704(3) 0.0513(13) Uani 1 1 d . . . . .
H7A H -0.0508 0.9548 0.3112 0.062 Uiso 1 1 calc R . . . .
H7B H -0.0814 0.8746 0.2158 0.062 Uiso 1 1 calc R . . . .
C8 C 0.0595(2) 0.3313(5) 0.0979(3) 0.0370(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 C8 1.777(5) . ?
Fe1 N1 2.192(3) 4 ?
Fe1 N1 2.192(3) . ?
Fe1 N2 2.226(3) . ?
Fe1 N2 2.226(3) 4 ?
Fe1 N3 2.094(4) 4 ?
Fe1 N3 2.094(4) . ?
Cl1 C3 1.727(4) . ?
N1 C1 1.327(5) . ?
N1 C5 1.342(5) . ?
N2 H2 0.9800 . ?
N2 C6 1.470(5) . ?
N2 C7 1.474(5) . ?
N3 C8 1.155(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.367(6) . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 C6 1.505(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.491(9) 4 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Fe1 N1 174.63(17) . 4 ?
N1 Fe1 N2 74.82(12) 4 4 ?
N1 Fe1 N2 74.82(12) . . ?
N1 Fe1 N2 100.92(12) 4 . ?
N1 Fe1 N2 100.92(12) . 4 ?
N2 Fe1 N2 78.87(19) . 4 ?
N3 Fe1 N1 89.33(13) . 4 ?
N3 Fe1 N1 94.17(13) . . ?
N3 Fe1 N1 94.17(13) 4 4 ?
N3 Fe1 N1 89.33(13) 4 . ?
N3 Fe1 N2 92.47(14) . 4 ?
N3 Fe1 N2 164.22(14) 4 4 ?
N3 Fe1 N2 164.21(14) . . ?
N3 Fe1 N2 92.48(14) 4 . ?
N3 Fe1 N3 98.8(2) 4 . ?
C1 N1 Fe1 125.9(3) . . ?
C1 N1 C5 118.1(3) . . ?
C5 N1 Fe1 115.9(3) . . ?
Fe1 N2 H2 109.6 . . ?
C6 N2 Fe1 108.2(3) . . ?
C6 N2 H2 109.6 . . ?
C6 N2 C7 111.9(3) . . ?
C7 N2 Fe1 107.8(2) . . ?
C7 N2 H2 109.6 . . ?
C8 N3 Fe1 163.9(4) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.7(4) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 C1 117.6(4) . . ?
C3 C2 H2A 121.2 . . ?
C2 C3 Cl1 120.1(3) . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 Cl1 119.8(3) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 C6 116.0(3) . . ?
C4 C5 C6 122.4(4) . . ?
N2 C6 C5 109.6(3) . . ?
N2 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C7 109.5(3) . 4 ?
N2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C7 C7 H7A 109.8 4 . ?
C7 C7 H7B 109.8 4 . ?
H7A C7 H7B 108.2 . . ?
N3 C8 Se1 178.5(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
Fe1 N1 C1 C2 -179.0(3) . . . . ?
Fe1 N1 C5 C4 177.6(3) . . . . ?
Fe1 N1 C5 C6 -2.9(5) . . . . ?
Fe1 N2 C6 C5 -42.4(4) . . . . ?
Fe1 N2 C7 C7 -42.9(5) . . . 4 ?
Cl1 C3 C4 C5 -178.8(3) . . . . ?
N1 C1 C2 C3 1.6(6) . . . . ?
N1 C5 C6 N2 31.0(5) . . . . ?
C1 N1 C5 C4 -1.5(6) . . . . ?
C1 N1 C5 C6 178.0(4) . . . . ?
C1 C2 C3 Cl1 177.4(3) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 N1 1.4(6) . . . . ?
C3 C4 C5 C6 -178.1(4) . . . . ?
C4 C5 C6 N2 -149.5(4) . . . . ?
C5 N1 C1 C2 0.0(6) . . . . ?
C6 N2 C7 C7 -161.8(4) . . . 4 ?
C7 N2 C6 C5 76.3(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1-BH3_123K
_database_code_depnum_ccdc_archive 'CCDC 1834093'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;
_audit_creation_date             2017-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 B2 Cl2 Fe N6'
_chemical_formula_sum            'C16 H22 B2 Cl2 Fe N6'
_chemical_formula_weight         446.76
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.1811(6)
_cell_length_b                   9.6128(4)
_cell_length_c                   13.8167(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2016.31(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.348
_cell_measurement_theta_min      2.508
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.9072.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Octahedron
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            78861
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_temperature      123.29
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS active pixel sensor detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1954
_reflns_number_total             2334
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 v2016.1-0'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+2.2413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All B(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C2(H2A)
2.d Idealised Me refined as rotating group:
 B1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.42976(4) 0.2500 0.01570(11) Uani 1 2 d S T P . .
Cl3 Cl 0.10488(3) 0.36073(5) 0.08553(4) 0.02927(14) Uani 1 1 d . . . . .
N2 N 0.45547(11) 0.27535(17) 0.33553(12) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.4753 0.2950 0.4032 0.027 Uiso 1 1 calc R . . . .
N1 N 0.38100(10) 0.42009(16) 0.19426(11) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.45669(10) 0.57071(17) 0.33852(12) 0.0194(3) Uani 1 1 d . . . . .
C4 C 0.23838(13) 0.3164(2) 0.21041(15) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.1999 0.2554 0.2441 0.031 Uiso 1 1 calc R . . . .
C6 C 0.35810(14) 0.2757(3) 0.33462(15) 0.0303(5) Uani 1 1 d . . . . .
H6A H 0.3360 0.3303 0.3903 0.036 Uiso 1 1 calc R . . . .
H6B H 0.3362 0.1792 0.3413 0.036 Uiso 1 1 calc R . . . .
C3 C 0.21054(13) 0.3862(2) 0.12876(15) 0.0214(4) Uani 1 1 d . . . . .
C7 C 0.49719(17) 0.1436(2) 0.30383(17) 0.0341(5) Uani 1 1 d . . . . .
H7A H 0.4617 0.0634 0.3261 0.041 Uiso 1 1 calc R . . . .
H7B H 0.5569 0.1356 0.3321 0.041 Uiso 1 1 calc R . . . .
B1 B 0.38382(15) 0.7848(2) 0.44105(16) 0.0221(5) Uani 1 1 d . . . . .
H1A H 0.3859 0.8694 0.4016 0.033 Uiso 1 1 calc GR . . . .
H1B H 0.4172 0.7995 0.5009 0.033 Uiso 1 1 calc GR . . . .
H1C H 0.3224 0.7630 0.4569 0.033 Uiso 1 1 calc GR . . . .
C8 C 0.42559(12) 0.6597(2) 0.38256(14) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.35174(13) 0.4874(2) 0.11514(14) 0.0213(4) Uani 1 1 d . . . . .
H1 H 0.3916 0.5462 0.0814 0.026 Uiso 1 1 calc R . . . .
C2 C 0.26699(13) 0.4752(2) 0.08071(15) 0.0234(4) Uani 1 1 d . . . . .
H2A H 0.2480 0.5264 0.0257 0.028 Uiso 1 1 calc R . . . .
C5 C 0.32376(13) 0.3376(2) 0.24203(14) 0.0218(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N2 2.0141(16) 3_655 ?
Fe1 N2 2.0141(16) . ?
Fe1 N1 1.9661(16) . ?
Fe1 N1 1.9661(16) 3_655 ?
Fe1 N3 1.9401(16) . ?
Fe1 N3 1.9401(16) 3_655 ?
Cl3 C3 1.729(2) . ?
N2 H2 1.0000 . ?
N2 C6 1.478(3) . ?
N2 C7 1.482(3) . ?
N1 C1 1.346(3) . ?
N1 C5 1.349(2) . ?
N3 C8 1.151(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.379(3) . ?
C4 C5 1.383(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.504(3) . ?
C3 C2 1.381(3) . ?
C7 C7 1.490(5) 3_655 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
B1 H1A 0.9800 . ?
B1 H1B 0.9800 . ?
B1 H1C 0.9800 . ?
B1 C8 1.581(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(3) . ?
C2 H2A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Fe1 N2 85.06(10) . 3_655 ?
N1 Fe1 N2 92.51(7) . 3_655 ?
N1 Fe1 N2 83.49(7) . . ?
N1 Fe1 N2 92.51(7) 3_655 . ?
N1 Fe1 N2 83.49(7) 3_655 3_655 ?
N1 Fe1 N1 174.58(9) . 3_655 ?
N3 Fe1 N2 91.78(7) . . ?
N3 Fe1 N2 176.66(7) . 3_655 ?
N3 Fe1 N2 176.66(7) 3_655 . ?
N3 Fe1 N2 91.78(7) 3_655 3_655 ?
N3 Fe1 N1 95.60(6) 3_655 . ?
N3 Fe1 N1 95.59(6) . 3_655 ?
N3 Fe1 N1 88.19(6) 3_655 3_655 ?
N3 Fe1 N1 88.20(6) . . ?
N3 Fe1 N3 91.41(10) 3_655 . ?
Fe1 N2 H2 108.0 . . ?
C6 N2 Fe1 109.21(13) . . ?
C6 N2 H2 108.0 . . ?
C6 N2 C7 115.26(18) . . ?
C7 N2 Fe1 108.23(12) . . ?
C7 N2 H2 108.0 . . ?
C1 N1 Fe1 126.79(13) . . ?
C1 N1 C5 117.87(17) . . ?
C5 N1 Fe1 115.34(13) . . ?
C8 N3 Fe1 172.43(16) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.31(19) . . ?
C5 C4 H4 120.8 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 C5 110.78(16) . . ?
H6A C6 H6B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C4 C3 Cl3 119.86(16) . . ?
C4 C3 C2 120.30(19) . . ?
C2 C3 Cl3 119.84(16) . . ?
N2 C7 C7 108.63(15) . 3_655 ?
N2 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C7 C7 H7A 110.0 3_655 . ?
C7 C7 H7B 110.0 3_655 . ?
H7A C7 H7B 108.3 . . ?
H1A B1 H1B 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?
C8 B1 H1A 109.5 . . ?
C8 B1 H1B 109.5 . . ?
C8 B1 H1C 109.5 . . ?
N3 C8 B1 178.5(2) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.26(18) . . ?
C2 C1 H1 118.4 . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 C3 117.80(19) . . ?
C1 C2 H2A 121.1 . . ?
N1 C5 C4 122.38(19) . . ?
N1 C5 C6 115.17(17) . . ?
C4 C5 C6 122.38(18) . . ?

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
Fe1 N2 C6 C5 26.4(2) . . . . ?
Fe1 N2 C7 C7 -38.4(3) . . . 3_655 ?
Fe1 N1 C1 C2 -179.86(15) . . . . ?
Fe1 N1 C5 C4 -178.00(16) . . . . ?
Fe1 N1 C5 C6 4.8(2) . . . . ?
Cl3 C3 C2 C1 -177.04(15) . . . . ?
N2 C6 C5 N1 -21.1(3) . . . . ?
N2 C6 C5 C4 161.71(19) . . . . ?
N1 C1 C2 C3 -1.9(3) . . . . ?
C4 C3 C2 C1 2.2(3) . . . . ?
C6 N2 C7 C7 84.1(3) . . . 3_655 ?
C3 C4 C5 N1 -2.1(3) . . . . ?
C3 C4 C5 C6 174.88(19) . . . . ?
C7 N2 C6 C5 -95.7(2) . . . . ?
C1 N1 C5 C4 2.5(3) . . . . ?
C1 N1 C5 C6 -174.72(18) . . . . ?
C5 N1 C1 C2 -0.4(3) . . . . ?
C5 C4 C3 Cl3 178.94(16) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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data_1-BH3_298K
_database_code_depnum_ccdc_archive 'CCDC 1834094'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;
_audit_creation_date             2017-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 B2 Cl2 Fe N6'
_chemical_formula_sum            'C16 H22 B2 Cl2 Fe N6'
_chemical_formula_weight         446.76
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.9885(7)
_cell_length_b                   9.8134(5)
_cell_length_c                   13.5420(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2124.76(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.709
_cell_measurement_theta_min      2.435
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1106 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.9226.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Octahedron
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1130
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            73854
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_min         3.267
_diffrn_ambient_temperature      298.06
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS active pixel sensor detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1687
_reflns_number_total             2459
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 v2016.1-0'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+1.6465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All B(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4)
2.d Idealised Me refined as rotating group:
 B1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.56352(5) 0.7500 0.03663(14) Uani 1 2 d S T P . .
Cl1 Cl 0.10538(4) 0.63179(8) 0.60202(6) 0.0676(2) Uani 1 1 d . . . . .
N1 N 0.37053(11) 0.5714(2) 0.69819(15) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.44340(13) 0.7388(2) 0.82987(14) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.4705 0.7496 0.8943 0.056 Uiso 1 1 calc R . . . .
N3 N 0.53823(14) 0.4226(2) 0.64093(18) 0.0564(6) Uani 1 1 d . . . . .
C1 C 0.33979(15) 0.5080(3) 0.61871(19) 0.0476(6) Uani 1 1 d . . . . .
H1 H 0.3755 0.4522 0.5825 0.057 Uiso 1 1 calc R . . . .
C2 C 0.25845(16) 0.5206(3) 0.5876(2) 0.0516(6) Uani 1 1 d . . . . .
H2A H 0.2389 0.4734 0.5327 0.062 Uiso 1 1 calc R . . . .
C7 C 0.45666(17) 0.8628(3) 0.7699(2) 0.0600(8) Uani 1 1 d . . . . .
H7A H 0.4480 0.9431 0.8104 0.072 Uiso 1 1 calc R . . . .
H7B H 0.4168 0.8651 0.7160 0.072 Uiso 1 1 calc R . . . .
C6 C 0.35451(17) 0.7110(3) 0.84366(19) 0.0581(7) Uani 1 1 d . . . . .
H6A H 0.3254 0.7951 0.8592 0.070 Uiso 1 1 calc R . . . .
H6B H 0.3470 0.6486 0.8985 0.070 Uiso 1 1 calc R . . . .
B1 B 0.60531(19) 0.2102(3) 0.5422(2) 0.0521(8) Uani 1 1 d . . . . .
H1A H 0.5754 0.1961 0.4816 0.078 Uiso 1 1 calc GR . . . .
H1B H 0.6012 0.1300 0.5825 0.078 Uiso 1 1 calc GR . . . .
H1C H 0.6630 0.2285 0.5278 0.078 Uiso 1 1 calc GR . . . .
C8 C 0.56668(14) 0.3343(3) 0.59862(19) 0.0438(6) Uani 1 1 d . . . . .
C5 C 0.31826(14) 0.6497(2) 0.75114(18) 0.0437(6) Uani 1 1 d . . . . .
C4 C 0.23623(15) 0.6698(3) 0.72317(19) 0.0487(6) Uani 1 1 d . . . . .
H4 H 0.2012 0.7261 0.7598 0.058 Uiso 1 1 calc R . . . .
C3 C 0.20736(15) 0.6049(3) 0.6401(2) 0.0467(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 N1 2.1871(19) 3_656 ?
Fe1 N1 2.1870(19) . ?
Fe1 N2 2.224(2) . ?
Fe1 N2 2.224(2) 3_656 ?
Fe1 N3 2.114(2) 3_656 ?
Fe1 N3 2.114(2) . ?
Cl1 C3 1.731(2) . ?
N1 C1 1.337(3) . ?
N1 C5 1.343(3) . ?
N2 H2 0.9800 . ?
N2 C7 1.478(3) . ?
N2 C6 1.459(3) . ?
N3 C8 1.134(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.363(4) . ?
C7 C7 1.487(6) 3_656 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.506(3) . ?
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?
B1 C8 1.565(4) . ?
C5 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Fe1 N1 175.96(10) . 3_656 ?
N1 Fe1 N2 101.64(7) . 3_656 ?
N1 Fe1 N2 75.14(7) . . ?
N1 Fe1 N2 75.14(7) 3_656 3_656 ?
N1 Fe1 N2 101.64(7) 3_656 . ?
N2 Fe1 N2 78.70(11) . 3_656 ?
N3 Fe1 N1 94.16(8) 3_656 3_656 ?
N3 Fe1 N1 88.49(8) 3_656 . ?
N3 Fe1 N1 88.49(8) . 3_656 ?
N3 Fe1 N1 94.16(8) . . ?
N3 Fe1 N2 92.78(9) . 3_656 ?
N3 Fe1 N2 164.45(8) . . ?
N3 Fe1 N2 164.46(8) 3_656 3_656 ?
N3 Fe1 N2 92.78(9) 3_656 . ?
N3 Fe1 N3 98.26(13) . 3_656 ?
C1 N1 Fe1 126.14(16) . . ?
C1 N1 C5 117.9(2) . . ?
C5 N1 Fe1 115.98(16) . . ?
Fe1 N2 H2 109.7 . . ?
C7 N2 Fe1 108.14(15) . . ?
C7 N2 H2 109.7 . . ?
C6 N2 Fe1 108.31(16) . . ?
C6 N2 H2 109.7 . . ?
C6 N2 C7 111.3(2) . . ?
C8 N3 Fe1 165.7(2) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.6(2) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 H2A 121.2 . . ?
N2 C7 C7 109.45(18) . 3_656 ?
N2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C7 C7 H7A 109.8 3_656 . ?
C7 C7 H7B 109.8 3_656 . ?
H7A C7 H7B 108.2 . . ?
N2 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
N2 C6 C5 110.1(2) . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H1A B1 H1B 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?
C8 B1 H1A 109.5 . . ?
C8 B1 H1B 109.5 . . ?
C8 B1 H1C 109.5 . . ?
N3 C8 B1 178.7(3) . . ?
N1 C5 C6 115.7(2) . . ?
N1 C5 C4 121.8(2) . . ?
C4 C5 C6 122.5(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C2 C3 Cl1 120.1(2) . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 Cl1 119.4(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
Fe1 N1 C1 C2 -177.5(2) . . . . ?
Fe1 N1 C5 C6 -5.1(3) . . . . ?
Fe1 N1 C5 C4 176.16(19) . . . . ?
Fe1 N2 C7 C7 -42.6(3) . . . 3_656 ?
Fe1 N2 C6 C5 -41.8(3) . . . . ?
N1 C1 C2 C3 1.4(4) . . . . ?
N1 C5 C4 C3 1.6(4) . . . . ?
N2 C6 C5 N1 32.2(3) . . . . ?
N2 C6 C5 C4 -149.1(2) . . . . ?
C1 N1 C5 C6 176.0(2) . . . . ?
C1 N1 C5 C4 -2.7(4) . . . . ?
C1 C2 C3 Cl1 177.1(2) . . . . ?
C1 C2 C3 C4 -2.5(4) . . . . ?
C7 N2 C6 C5 77.0(3) . . . . ?
C6 N2 C7 C7 -161.5(3) . . . 3_656 ?
C6 C5 C4 C3 -177.0(2) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
C5 C4 C3 Cl1 -178.50(19) . . . . ?
C5 C4 C3 C2 1.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'


