# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_d24217
_audit_block_doi                 10.5517/ccdc.csd.cc2gh099
_database_code_depnum_ccdc_archive 'CCDC 2278540'
loop_
_audit_author_name
_audit_author_address
'Jyh-Chien Chen '
;National Taiwan University of Science and Technology Department of Materials Science and Engineering
Taiwan
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(1R,2R,3R,4R,5R)-trimethyl bicyclo[2.2.2]oct-7-ene-2,3,5-tricarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 O6'
_chemical_formula_sum            'C14 H18 O6'
_chemical_formula_weight         282.28

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.158(4)
_cell_length_b                   10.149(7)
_cell_length_c                   11.482(7)
_cell_angle_alpha                76.503(17)
_cell_angle_beta                 79.869(18)
_cell_angle_gamma                89.31(2)
_cell_volume                     686.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2306
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      22.831

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi scan & omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11320
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.11
_reflns_number_total             2424
_reflns_number_gt                1574
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0859P)²+10.5207P] 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         2424
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1887
_refine_ls_R_factor_gt           0.1463
_refine_ls_wR_factor_ref         0.4118
_refine_ls_wR_factor_gt          0.3893
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3591(19) 0.6424(10) 0.1086(11) 0.046(3) Uani 1 1 d . . .
H1A H 0.4551 0.6764 0.0297 0.069 Uiso 1 1 calc R . .
H1B H 0.3694 0.7045 0.1614 0.069 Uiso 1 1 calc R . .
H1C H 0.2062 0.6363 0.0966 0.069 Uiso 1 1 calc R . .
C2 C 0.6462(15) 0.4903(9) 0.1547(8) 0.027(2) Uani 1 1 d . . .
C3 C 0.6872(15) 0.3492(10) 0.2285(8) 0.028(2) Uani 1 1 d . . .
H3 H 0.6022 0.2803 0.2036 0.033 Uiso 1 1 calc R . .
C4 C 0.9308(14) 0.3149(9) 0.2120(9) 0.027(2) Uani 1 1 d . . .
H4 H 1.0160 0.3978 0.1609 0.033 Uiso 1 1 calc R . .
C5 C 0.9790(15) 0.2015(9) 0.1440(8) 0.028(2) Uani 1 1 d . . .
C6 C 1.269(2) 0.0649(11) 0.0783(10) 0.048(3) Uani 1 1 d . . .
H6A H 1.2512 0.0943 -0.0071 0.071 Uiso 1 1 calc R . .
H6B H 1.1820 -0.0193 0.1166 0.071 Uiso 1 1 calc R . .
H6C H 1.4247 0.0492 0.0824 0.071 Uiso 1 1 calc R . .
C7 C 1.0088(15) 0.2808(11) 0.3345(10) 0.037(3) Uani 1 1 d . . .
H7 H 1.1697 0.2613 0.3242 0.044 Uiso 1 1 calc R . .
C8 C 0.9593(16) 0.4007(11) 0.3911(9) 0.036(2) Uani 1 1 d . . .
H8 H 1.0708 0.4493 0.4128 0.043 Uiso 1 1 calc R . .
C9 C 0.7502(16) 0.4326(10) 0.4082(9) 0.033(2) Uani 1 1 d . . .
H9 H 0.6980 0.5054 0.4435 0.040 Uiso 1 1 calc R . .
C10 C 0.6025(14) 0.3442(9) 0.3668(8) 0.027(2) Uani 1 1 d . . .
H10 H 0.4461 0.3730 0.3807 0.032 Uiso 1 1 calc R . .
C11 C 0.6230(16) 0.1962(10) 0.4356(9) 0.035(2) Uani 1 1 d . . .
H11 H 0.5405 0.1362 0.3996 0.043 Uiso 1 1 calc R . .
C12 C 0.8680(18) 0.1576(11) 0.4188(10) 0.040(3) Uani 1 1 d . . .
H12A H 0.8875 0.0783 0.3820 0.049 Uiso 1 1 calc R . .
H12B H 0.9161 0.1333 0.4988 0.049 Uiso 1 1 calc R . .
C13 C 0.5196(18) 0.1773(11) 0.5689(10) 0.040(3) Uani 1 1 d . . .
C14 C 0.188(2) 0.1878(13) 0.7058(10) 0.051(3) Uani 1 1 d . . .
H14A H 0.0286 0.1861 0.7078 0.077 Uiso 1 1 calc R . .
H14B H 0.2292 0.2645 0.7367 0.077 Uiso 1 1 calc R . .
H14C H 0.2299 0.1031 0.7568 0.077 Uiso 1 1 calc R . .
O1 O 0.4281(10) 0.5089(7) 0.1653(7) 0.0397(18) Uani 1 1 d . . .
O2 O 0.7827(12) 0.5742(7) 0.0992(7) 0.0446(19) Uani 1 1 d . . .
O3 O 0.8516(12) 0.1496(8) 0.1006(7) 0.047(2) Uani 1 1 d . . .
O4 O 1.1912(10) 0.1695(7) 0.1420(6) 0.0348(17) Uani 1 1 d . . .
O5 O 0.6148(16) 0.1473(13) 0.6552(8) 0.088(4) Uani 1 1 d . . .
O6 O 0.3036(12) 0.2024(8) 0.5805(6) 0.046(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
C1 O1 1.453(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.189(11) . ?
C2 O1 1.342(11) . ?
C2 C3 1.527(13) . ?
C3 C4 1.525(12) . ?
C3 C10 1.572(12) . ?
C3 H3 1.0000 . ?
C4 C7 1.528(13) . ?
C4 C5 1.533(12) . ?
C4 H4 1.0000 . ?
C5 O3 1.188(11) . ?
C5 O4 1.340(11) . ?
C6 O4 1.455(11) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.512(13) . ?
C7 C12 1.555(16) . ?
C7 H7 1.0000 . ?
C8 C9 1.316(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.493(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.540(13) . ?
C10 H10 1.0000 . ?
C11 C13 1.519(15) . ?
C11 C12 1.544(14) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O5 1.216(13) . ?
C13 O6 1.340(13) . ?
C14 O6 1.463(12) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.1(9) . . ?
O2 C2 C3 126.5(8) . . ?
O1 C2 C3 109.4(8) . . ?
C4 C3 C2 112.7(8) . . ?
C4 C3 C10 108.4(7) . . ?
C2 C3 C10 108.2(7) . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C10 C3 H3 109.2 . . ?
C3 C4 C7 110.7(7) . . ?
C3 C4 C5 111.9(7) . . ?
C7 C4 C5 111.9(7) . . ?
C3 C4 H4 107.4 . . ?
C7 C4 H4 107.4 . . ?
C5 C4 H4 107.4 . . ?
O3 C5 O4 125.2(9) . . ?
O3 C5 C4 126.5(8) . . ?
O4 C5 C4 108.3(8) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 107.2(8) . . ?
C8 C7 C12 107.3(8) . . ?
C4 C7 C12 108.5(8) . . ?
C8 C7 H7 111.2 . . ?
C4 C7 H7 111.2 . . ?
C12 C7 H7 111.2 . . ?
C9 C8 C7 115.0(9) . . ?
C9 C8 H8 122.5 . . ?
C7 C8 H8 122.5 . . ?
C8 C9 C10 113.9(9) . . ?
C8 C9 H9 123.0 . . ?
C10 C9 H9 123.0 . . ?
C9 C10 C11 108.7(8) . . ?
C9 C10 C3 109.0(7) . . ?
C11 C10 C3 106.1(7) . . ?
C9 C10 H10 111.0 . . ?
C11 C10 H10 111.0 . . ?
C3 C10 H10 111.0 . . ?
C13 C11 C10 110.0(8) . . ?
C13 C11 C12 112.2(8) . . ?
C10 C11 C12 109.7(8) . . ?
C13 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C11 C12 C7 108.7(8) . . ?
C11 C12 H12A 110.0 . . ?
C7 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
C7 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
O5 C13 O6 123.0(11) . . ?
O5 C13 C11 126.4(10) . . ?
O6 C13 C11 110.6(8) . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 C1 116.8(8) . . ?
C5 O4 C6 116.1(8) . . ?
C13 O6 C14 114.9(9) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.125
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 2278551'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H28 Cl2 Fe N6'
_chemical_formula_sum            'C12 H28 Cl2 Fe N6'
_chemical_formula_weight         383.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   18.177(4)
_cell_length_b                   7.3979(15)
_cell_length_c                   13.815(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.03(3)
_cell_angle_gamma                90
_cell_volume                     1817.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17367
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      33.67

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.127
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.3864
_exptl_absorpt_correction_T_max  0.9448

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 1196 frames, detector distance = 60 mm
;

_diffrn_reflns_number            21888
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         33.770
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3454
_reflns_number_gt                2590
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0276P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0532
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_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
Fe1 Fe 0.500000 0.75626(3) 0.750000 0.01069(5) Uani 1 2 d S T P . .
Cl1 Cl 0.60150(2) 0.92367(4) 0.82560(2) 0.01855(6) Uani 1 1 d . . . . .
N1 N 0.55250(4) 0.54341(11) 0.69225(6) 0.01171(17) Uani 1 1 d . . . . .
C1 C 0.60273(5) 0.54282(13) 0.63650(7) 0.01195(19) Uani 1 1 d . . . . .
N2 N 0.59747(4) 0.66229(12) 0.56029(6) 0.01354(17) Uani 1 1 d . . . . .
C2 C 0.70206(6) 0.36908(17) 0.74614(9) 0.0203(2) Uani 1 1 d . . . . .
H2A H 0.686283 0.247271 0.760939 0.030 Uiso 1 1 calc R U . . .
H2B H 0.691019 0.454100 0.795626 0.030 Uiso 1 1 calc R U . . .
H2C H 0.756216 0.369357 0.747776 0.030 Uiso 1 1 calc R U . . .
N3 N 0.66142(5) 0.42332(12) 0.64820(7) 0.01521(18) Uani 1 1 d . . . . .
C3 C 0.68716(6) 0.34262(17) 0.56523(9) 0.0221(2) Uani 1 1 d . . . . .
H3A H 0.654587 0.382054 0.503103 0.033 Uiso 1 1 calc R U . . .
H3B H 0.685256 0.210609 0.570100 0.033 Uiso 1 1 calc R U . . .
H3C H 0.738985 0.380775 0.566534 0.033 Uiso 1 1 calc R U . . .
C4 C 0.52819(6) 0.76089(15) 0.52404(8) 0.0189(2) Uani 1 1 d . . . . .
H4A H 0.525880 0.797848 0.455356 0.028 Uiso 1 1 calc R U . . .
H4B H 0.526788 0.868332 0.565115 0.028 Uiso 1 1 calc R U . . .
H4C H 0.485116 0.683082 0.527183 0.028 Uiso 1 1 calc R U . . .
C5 C 0.66410(6) 0.74782(17) 0.53764(9) 0.0226(2) Uani 1 1 d . . . . .
H5A H 0.662760 0.737543 0.466569 0.034 Uiso 1 1 calc R U . . .
H5B H 0.709274 0.687688 0.574839 0.034 Uiso 1 1 calc R U . . .
H5C H 0.665074 0.875753 0.556265 0.034 Uiso 1 1 calc R U . . .
C6 C 0.54083(5) 0.37639(14) 0.74483(8) 0.01314(19) Uani 1 1 d . . . . .
H6A H 0.574839 0.373345 0.810878 0.016 Uiso 1 1 calc R U . . .
H6B H 0.551226 0.269267 0.706869 0.016 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
Fe1 N1 2.0843(9) . ?
Fe1 N1 2.0843(9) 2_656 ?
Fe1 Cl1 2.2859(6) . ?
Fe1 Cl1 2.2859(6) 2_656 ?
N1 C1 1.3114(13) . ?
N1 C6 1.4710(13) . ?
C1 N2 1.3627(13) . ?
C1 N3 1.3688(13) . ?
N2 C4 1.4512(13) . ?
N2 C5 1.4571(13) . ?
C2 N3 1.4564(14) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C3 1.4536(14) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C6 1.5206(19) 2_656 ?
C6 H6A 0.9900 . ?
C6 H6B 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 81.87(5) . 2_656 ?
N1 Fe1 Cl1 101.18(3) . . ?
N1 Fe1 Cl1 128.66(3) 2_656 . ?
N1 Fe1 Cl1 128.66(3) . 2_656 ?
N1 Fe1 Cl1 101.18(3) 2_656 2_656 ?
Cl1 Fe1 Cl1 114.39(3) . 2_656 ?
C1 N1 C6 118.49(8) . . ?
C1 N1 Fe1 131.13(7) . . ?
C6 N1 Fe1 108.71(6) . . ?
N1 C1 N2 120.41(9) . . ?
N1 C1 N3 123.62(9) . . ?
N2 C1 N3 115.95(9) . . ?
C1 N2 C4 120.58(9) . . ?
C1 N2 C5 121.33(9) . . ?
C4 N2 C5 114.08(9) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C3 122.90(9) . . ?
C1 N3 C2 121.30(9) . . ?
C3 N3 C2 115.80(9) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C6 106.89(7) . 2_656 ?
N1 C6 H6A 110.3 . . ?
C6 C6 H6A 110.3 2_656 . ?
N1 C6 H6B 110.3 . . ?
C6 C6 H6B 110.3 2_656 . ?
H6A C6 H6B 108.6 . . ?

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
C6 N1 C1 N2 155.70(9) . . . . ?
Fe1 N1 C1 N2 -40.88(14) . . . . ?
C6 N1 C1 N3 -22.59(14) . . . . ?
Fe1 N1 C1 N3 140.83(8) . . . . ?
N1 C1 N2 C4 -15.07(14) . . . . ?
N3 C1 N2 C4 163.34(9) . . . . ?
N1 C1 N2 C5 141.07(10) . . . . ?
N3 C1 N2 C5 -40.52(13) . . . . ?
N1 C1 N3 C3 140.78(11) . . . . ?
N2 C1 N3 C3 -37.58(13) . . . . ?
N1 C1 N3 C2 -39.13(14) . . . . ?
N2 C1 N3 C2 142.51(10) . . . . ?
C1 N1 C6 C6 -150.14(10) . . . 2_656 ?
Fe1 N1 C6 C6 42.98(11) . . . 2_656 ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_C6
_database_code_depnum_ccdc_archive 'CCDC 2278554'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 Cl2 Fe N4'
_chemical_formula_sum            'C12 H20 Cl2 Fe N4'
_chemical_formula_weight         347.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7832(18)
_cell_length_b                   11.895(2)
_cell_length_c                   15.221(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1590.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    42502
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      69.76

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    10.630
_shelx_estimated_absorpt_T_min   0.132
_shelx_estimated_absorpt_T_max   0.339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.0149
_exptl_absorpt_correction_T_max  0.0430

_exptl_absorpt_special_details   ?
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.5 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 5734 frames, detector distance = 60 mm
;

_diffrn_reflns_number            25688
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.718
_diffrn_reflns_theta_max         69.440
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2964
_reflns_number_gt                2903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.998

_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0842P)²+0.2104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.001(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.1016
_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
N1 N 0.2245(4) 0.4108(3) 0.3720(2) 0.0203(7) Uani 1 1 d . . . . .
C1 C 0.1970(5) 0.5168(3) 0.3494(2) 0.0206(8) Uani 1 1 d . . . . .
Cl2 Cl 0.22968(12) 0.23959(9) 0.15807(6) 0.0294(3) Uani 1 1 d . . . . .
Fe1 Fe 0.31924(7) 0.29811(4) 0.28901(4) 0.01790(19) Uani 1 1 d . . . . .
Cl1 Cl 0.57164(10) 0.34518(8) 0.28181(6) 0.0233(2) Uani 1 1 d . . . . .
N2 N 0.1030(4) 0.5370(3) 0.2802(2) 0.0220(7) Uani 1 1 d . . . . .
C2 C -0.0174(5) 0.4584(3) 0.2559(3) 0.0258(9) Uani 1 1 d . . . . .
H2A H 0.012130 0.417909 0.202485 0.039 Uiso 1 1 calc R U . . .
H2B H -0.111911 0.500010 0.245079 0.039 Uiso 1 1 calc R U . . .
H2C H -0.033342 0.404646 0.303768 0.039 Uiso 1 1 calc R U . . .
N3 N 0.2567(4) 0.6059(3) 0.3922(2) 0.0222(7) Uani 1 1 d . . . . .
C3 C 0.1274(6) 0.6291(3) 0.2186(3) 0.0288(9) Uani 1 1 d . . . . .
H3A H 0.132278 0.599287 0.158684 0.043 Uiso 1 1 calc R U . . .
H3B H 0.223234 0.667196 0.232731 0.043 Uiso 1 1 calc R U . . .
H3C H 0.043008 0.682681 0.223129 0.043 Uiso 1 1 calc R U . . .
N4 N 0.3174(4) 0.1648(3) 0.3814(2) 0.0212(7) Uani 1 1 d . . . . .
C4 C 0.1772(5) 0.7140(3) 0.4019(3) 0.0256(8) Uani 1 1 d . . . . .
H4A H 0.230317 0.771686 0.367613 0.038 Uiso 1 1 calc R U . . .
H4B H 0.175904 0.735796 0.463954 0.038 Uiso 1 1 calc R U . . .
H4C H 0.072460 0.706548 0.380476 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4095(5) 0.6021(4) 0.4294(3) 0.0304(9) Uani 1 1 d . . . . .
H5A H 0.460129 0.532570 0.411056 0.046 Uiso 1 1 calc R U . . .
H5B H 0.403037 0.604374 0.493639 0.046 Uiso 1 1 calc R U . . .
H5C H 0.468076 0.666935 0.408461 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2497(5) 0.3852(3) 0.4655(2) 0.0228(8) Uani 1 1 d . . . . .
H6A H 0.208519 0.446819 0.502214 0.027 Uiso 1 1 calc R U . . .
H6B H 0.360209 0.378880 0.477256 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1705(5) 0.2745(3) 0.4893(3) 0.0255(8) Uani 1 1 d . . . . .
H7A H 0.153624 0.272824 0.553584 0.031 Uiso 1 1 calc R U . . .
H7B H 0.069317 0.273033 0.460612 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2562(4) 0.1700(3) 0.4633(2) 0.0211(8) Uani 1 1 d . . . . .
C9 C 0.2740(5) 0.0818(3) 0.5221(3) 0.0249(8) Uani 1 1 d . . . . .
H9 H 0.229096 0.086300 0.578734 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3566(5) -0.0127(3) 0.4988(3) 0.0269(9) Uani 1 1 d . . . . .
H10 H 0.369142 -0.073183 0.538950 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4210(5) -0.0173(3) 0.4152(3) 0.0262(9) Uani 1 1 d . . . . .
H11 H 0.479418 -0.080407 0.397123 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3976(5) 0.0725(3) 0.3595(3) 0.0238(8) Uani 1 1 d . . . . .
H12 H 0.440546 0.068977 0.302322 0.029 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
N1 C1 1.329(5) . ?
N1 C6 1.473(5) . ?
N1 Fe1 2.021(3) . ?
C1 N3 1.350(5) . ?
C1 N2 1.360(5) . ?
Cl2 Fe1 2.2529(11) . ?
Fe1 N4 2.120(3) . ?
Fe1 Cl1 2.2891(12) . ?
N2 C3 1.457(5) . ?
N2 C2 1.459(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C5 1.457(6) . ?
N3 C4 1.471(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C12 1.346(5) . ?
N4 C8 1.358(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.533(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.506(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.388(6) . ?
C9 C10 1.384(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(6) . ?
C11 H11 0.9500 . ?
C12 H12 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
C1 N1 C6 118.2(3) . . ?
C1 N1 Fe1 122.9(3) . . ?
C6 N1 Fe1 113.9(2) . . ?
N1 C1 N3 123.4(4) . . ?
N1 C1 N2 118.5(4) . . ?
N3 C1 N2 118.1(3) . . ?
N1 Fe1 N4 94.49(13) . . ?
N1 Fe1 Cl2 127.88(10) . . ?
N4 Fe1 Cl2 110.67(9) . . ?
N1 Fe1 Cl1 105.47(10) . . ?
N4 Fe1 Cl1 102.84(10) . . ?
Cl2 Fe1 Cl1 111.80(4) . . ?
C1 N2 C3 122.8(4) . . ?
C1 N2 C2 121.5(3) . . ?
C3 N2 C2 115.2(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C5 121.4(3) . . ?
C1 N3 C4 123.4(3) . . ?
C5 N3 C4 115.2(3) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C12 N4 C8 118.1(3) . . ?
C12 N4 Fe1 116.2(3) . . ?
C8 N4 Fe1 125.3(3) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 109.7(3) . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 114.9(3) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
N4 C8 C9 120.8(4) . . ?
N4 C8 C7 118.5(3) . . ?
C9 C8 C7 120.7(3) . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 118.6(4) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N4 C12 C11 123.9(4) . . ?
N4 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?

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
C6 N1 C1 N3 32.2(6) . . . . ?
Fe1 N1 C1 N3 -121.2(4) . . . . ?
C6 N1 C1 N2 -147.3(4) . . . . ?
Fe1 N1 C1 N2 59.3(5) . . . . ?
N1 C1 N2 C3 -143.5(4) . . . . ?
N3 C1 N2 C3 37.0(5) . . . . ?
N1 C1 N2 C2 28.0(5) . . . . ?
N3 C1 N2 C2 -151.4(4) . . . . ?
N1 C1 N3 C5 35.1(6) . . . . ?
N2 C1 N3 C5 -145.4(4) . . . . ?
N1 C1 N3 C4 -147.4(4) . . . . ?
N2 C1 N3 C4 32.1(5) . . . . ?
C1 N1 C6 C7 139.9(4) . . . . ?
Fe1 N1 C6 C7 -64.4(4) . . . . ?
N1 C6 C7 C8 79.9(4) . . . . ?
C12 N4 C8 C9 -1.0(6) . . . . ?
Fe1 N4 C8 C9 -173.6(3) . . . . ?
C12 N4 C8 C7 178.1(4) . . . . ?
Fe1 N4 C8 C7 5.5(5) . . . . ?
C6 C7 C8 N4 -45.7(5) . . . . ?
C6 C7 C8 C9 133.4(4) . . . . ?
N4 C8 C9 C10 1.0(6) . . . . ?
C7 C8 C9 C10 -178.1(4) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C8 N4 C12 C11 0.1(6) . . . . ?
Fe1 N4 C12 C11 173.4(3) . . . . ?
C10 C11 C12 N4 0.7(6) . . . . ?

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
_geom_hbond_publ_flag
C3 H3B Cl1 0.98 2.79 3.687(5) 152.7 3_655 yes
C4 H4C Cl2 0.98 2.75 3.701(4) 164.9 3 yes
C9 H9 Cl1 0.95 2.66 3.581(4) 163.2 4_456 yes

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 2278552'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H30 Cl2 Fe N6'
_chemical_formula_sum            'C13 H30 Cl2 Fe N6'
_chemical_formula_weight         397.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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

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

_cell_length_a                   9.3007(19)
_cell_length_b                   9.830(2)
_cell_length_c                   12.490(3)
_cell_angle_alpha                69.47(3)
_cell_angle_beta                 87.94(3)
_cell_angle_gamma                65.38(3)
_cell_volume                     964.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27644
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      34.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.065
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.3267
_exptl_absorpt_correction_T_max  0.8883

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 2449 frames, detector distance = 60 mm
;

_diffrn_reflns_number            23563
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.429
_diffrn_reflns_theta_max         34.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7566
_reflns_number_gt                5772
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7566
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
Fe1 Fe 0.73575(2) 0.61325(2) 0.73952(2) 0.01251(4) Uani 1 1 d . . . . .
Cl1 Cl 0.61966(3) 0.77559(3) 0.84604(2) 0.02106(6) Uani 1 1 d . . . . .
N1 N 0.81084(10) 0.38330(10) 0.85931(7) 0.01279(16) Uani 1 1 d . . . . .
C1 C 0.95877(11) 0.28444(11) 0.90693(8) 0.01191(17) Uani 1 1 d . . . . .
Cl2 Cl 0.91162(4) 0.69243(4) 0.63255(2) 0.02409(6) Uani 1 1 d . . . . .
N2 N 1.00385(10) 0.21641(10) 1.02298(8) 0.01630(17) Uani 1 1 d . . . . .
C2 C 0.93364(14) 0.30784(16) 1.09583(10) 0.0265(3) Uani 1 1 d . . . . .
H2A H 0.869343 0.421018 1.047497 0.040 Uiso 1 1 calc R U . . .
H2B H 1.018515 0.299804 1.145312 0.040 Uiso 1 1 calc R U . . .
H2C H 0.865610 0.264467 1.143898 0.040 Uiso 1 1 calc R U . . .
N3 N 1.07490(10) 0.24342(11) 0.83942(8) 0.01562(17) Uani 1 1 d . . . . .
C3 C 1.12643(14) 0.05329(14) 1.08070(11) 0.0256(2) Uani 1 1 d . . . . .
H3A H 1.159493 -0.000249 1.025077 0.038 Uiso 1 1 calc R U . . .
H3B H 1.083811 -0.006822 1.142874 0.038 Uiso 1 1 calc R U . . .
H3C H 1.218553 0.057034 1.113045 0.038 Uiso 1 1 calc R U . . .
N4 N 0.53834(10) 0.61196(10) 0.67217(7) 0.01272(16) Uani 1 1 d . . . . .
C4 C 1.23469(12) 0.22563(15) 0.86541(11) 0.0236(2) Uani 1 1 d . . . . .
H4A H 1.313531 0.119975 0.868070 0.035 Uiso 1 1 calc R U . . .
H4B H 1.244565 0.234533 0.940262 0.035 Uiso 1 1 calc R U . . .
H4C H 1.253436 0.310400 0.805388 0.035 Uiso 1 1 calc R U . . .
N5 N 0.30650(10) 0.81153(10) 0.54376(8) 0.01532(17) Uani 1 1 d . . . . .
C5 C 1.03487(13) 0.25943(14) 0.72295(9) 0.0199(2) Uani 1 1 d . . . . .
H5A H 1.030720 0.361166 0.668072 0.030 Uiso 1 1 calc R U . . .
H5B H 0.930684 0.258504 0.716043 0.030 Uiso 1 1 calc R U . . .
H5C H 1.116204 0.169409 0.706137 0.030 Uiso 1 1 calc R U . . .
N6 N 0.54693(10) 0.70976(10) 0.47543(7) 0.01495(17) Uani 1 1 d . . . . .
C6 C 0.46465(11) 0.70911(11) 0.56759(9) 0.01265(18) Uani 1 1 d . . . . .
C7 C 0.22711(13) 0.89499(13) 0.61988(10) 0.0203(2) Uani 1 1 d . . . . .
H7A H 0.173866 1.011131 0.575576 0.030 Uiso 1 1 calc R U . . .
H7B H 0.306097 0.872931 0.680959 0.030 Uiso 1 1 calc R U . . .
H7C H 0.147870 0.857160 0.654398 0.030 Uiso 1 1 calc R U . . .
C8 C 0.20875(13) 0.85583(13) 0.43798(10) 0.0208(2) Uani 1 1 d . . . . .
H8A H 0.169418 0.971734 0.394353 0.031 Uiso 1 1 calc R U . . .
H8B H 0.118088 0.829324 0.456949 0.031 Uiso 1 1 calc R U . . .
H8C H 0.272869 0.796297 0.391360 0.031 Uiso 1 1 calc R U . . .
C9 C 0.69159(13) 0.56969(13) 0.48048(10) 0.0193(2) Uani 1 1 d . . . . .
H9A H 0.696719 0.558186 0.405436 0.029 Uiso 1 1 calc R U . . .
H9B H 0.690903 0.473103 0.539665 0.029 Uiso 1 1 calc R U . . .
H9C H 0.784708 0.583329 0.499763 0.029 Uiso 1 1 calc R U . . .
C10 C 0.52227(14) 0.85924(13) 0.38109(10) 0.0221(2) Uani 1 1 d . . . . .
H10A H 0.492890 0.854800 0.308230 0.033 Uiso 1 1 calc R U . . .
H10B H 0.620850 0.873338 0.377397 0.033 Uiso 1 1 calc R U . . .
H10C H 0.436477 0.950076 0.394213 0.033 Uiso 1 1 calc R U . . .
C11 C 0.68048(12) 0.36565(12) 0.92462(9) 0.01445(18) Uani 1 1 d . . . . .
H11A H 0.639078 0.447631 0.960455 0.017 Uiso 1 1 calc R U . . .
H11B H 0.722010 0.257955 0.987063 0.017 Uiso 1 1 calc R U . . .
C12 C 0.54494(12) 0.38562(12) 0.84598(9) 0.01534(19) Uani 1 1 d . . . . .
H12A H 0.590982 0.315713 0.800968 0.018 Uiso 1 1 calc R U . . .
H12B H 0.473032 0.347283 0.894758 0.018 Uiso 1 1 calc R U . . .
C13 C 0.44595(11) 0.55760(12) 0.76219(9) 0.01496(19) Uani 1 1 d . . . . .
H13A H 0.350305 0.562914 0.725309 0.018 Uiso 1 1 calc R U . . .
H13B H 0.409563 0.630812 0.805403 0.018 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
Fe1 N4 2.0536(10) . ?
Fe1 N1 2.0551(13) . ?
Fe1 Cl2 2.2893(7) . ?
Fe1 Cl1 2.3307(8) . ?
N1 C1 1.3156(14) . ?
N1 C11 1.4731(13) . ?
C1 N3 1.3601(13) . ?
C1 N2 1.3618(14) . ?
N2 C2 1.4504(15) . ?
N2 C3 1.4546(16) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C5 1.4524(14) . ?
N3 C4 1.4570(14) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C6 1.3162(14) . ?
N4 C13 1.4764(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C6 1.3613(14) . ?
N5 C7 1.4538(14) . ?
N5 C8 1.4543(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 C6 1.3588(13) . ?
N6 C9 1.4531(14) . ?
N6 C10 1.4575(15) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5298(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5272(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 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
N4 Fe1 N1 93.35(5) . . ?
N4 Fe1 Cl2 124.73(3) . . ?
N1 Fe1 Cl2 120.79(4) . . ?
N4 Fe1 Cl1 100.88(3) . . ?
N1 Fe1 Cl1 103.66(3) . . ?
Cl2 Fe1 Cl1 109.93(2) . . ?
C1 N1 C11 118.43(9) . . ?
C1 N1 Fe1 125.67(7) . . ?
C11 N1 Fe1 110.79(7) . . ?
N1 C1 N3 119.92(9) . . ?
N1 C1 N2 123.29(9) . . ?
N3 C1 N2 116.78(9) . . ?
C1 N2 C2 120.62(9) . . ?
C1 N2 C3 123.18(10) . . ?
C2 N2 C3 116.17(10) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C5 120.70(9) . . ?
C1 N3 C4 121.89(9) . . ?
C5 N3 C4 115.28(9) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 N4 C13 119.11(9) . . ?
C6 N4 Fe1 122.43(7) . . ?
C13 N4 Fe1 112.42(7) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 N5 C7 121.16(9) . . ?
C6 N5 C8 123.36(9) . . ?
C7 N5 C8 115.29(9) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 N6 C9 120.92(9) . . ?
C6 N6 C10 121.65(9) . . ?
C9 N6 C10 115.36(9) . . ?
N4 C6 N6 119.92(9) . . ?
N4 C6 N5 123.98(10) . . ?
N6 C6 N5 116.10(10) . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 110.98(8) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 114.89(9) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
N4 C13 C12 111.64(8) . . ?
N4 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?

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
C11 N1 C1 N3 149.91(9) . . . . ?
Fe1 N1 C1 N3 -57.78(12) . . . . ?
C11 N1 C1 N2 -28.88(14) . . . . ?
Fe1 N1 C1 N2 123.44(9) . . . . ?
N1 C1 N2 C2 -38.38(15) . . . . ?
N3 C1 N2 C2 142.80(10) . . . . ?
N1 C1 N2 C3 143.78(11) . . . . ?
N3 C1 N2 C3 -35.04(14) . . . . ?
N1 C1 N3 C5 -21.22(14) . . . . ?
N2 C1 N3 C5 157.64(10) . . . . ?
N1 C1 N3 C4 141.36(10) . . . . ?
N2 C1 N3 C4 -39.78(14) . . . . ?
C13 N4 C6 N6 -153.23(9) . . . . ?
Fe1 N4 C6 N6 56.19(12) . . . . ?
C13 N4 C6 N5 26.13(14) . . . . ?
Fe1 N4 C6 N5 -124.45(9) . . . . ?
C9 N6 C6 N4 24.47(15) . . . . ?
C10 N6 C6 N4 -138.43(11) . . . . ?
C9 N6 C6 N5 -154.94(10) . . . . ?
C10 N6 C6 N5 42.16(14) . . . . ?
C7 N5 C6 N4 37.32(15) . . . . ?
C8 N5 C6 N4 -147.98(10) . . . . ?
C7 N5 C6 N6 -143.30(10) . . . . ?
C8 N5 C6 N6 31.41(14) . . . . ?
C1 N1 C11 C12 -138.82(9) . . . . ?
Fe1 N1 C11 C12 64.99(9) . . . . ?
N1 C11 C12 C13 -71.93(11) . . . . ?
C6 N4 C13 C12 145.62(9) . . . . ?
Fe1 N4 C13 C12 -61.03(10) . . . . ?
C11 C12 C13 N4 69.22(11) . . . . ?

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
_geom_hbond_publ_flag
C3 H3C Cl1 0.98 2.82 3.7133(15) 152.3 2_767 yes
C9 H9C Cl2 0.98 2.78 3.6326(15) 145.6 . yes

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_C7
_database_code_depnum_ccdc_archive 'CCDC 2278555'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 Cl2 Fe N6'
_chemical_formula_sum            'C16 H24 Cl2 Fe N6'
_chemical_formula_weight         427.16

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.306(4)
_cell_length_b                   9.4540(19)
_cell_length_c                   36.444(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.32(3)
_cell_angle_gamma                90
_cell_volume                     5914(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2114
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             2664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.048
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens in: F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard,
Copenhagen (1970), 255 - 270. Afterwards scaling of reflection intensities was
performed within STOE LANA. J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta
Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_absorpt_correction_T_min  0.0838
_exptl_absorpt_correction_T_max  0.8471

_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 'Hybrid Pixel Counting Detector'
_diffrn_detector_type            'Dectris Pilatus 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 1329 frames, detector distance = 60 mm
;

_diffrn_reflns_number            28817
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_av_R_equivalents  0.1453
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6436
_reflns_number_gt                4611
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;
_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)+(0.1148P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6436
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1933
_refine_ls_wR_factor_gt          0.1800
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Fe1 Fe 0.41542(3) 0.56942(5) 0.34697(2) 0.03045(18) Uani 1 1 d . . . . .
Cl1 Cl 0.34778(7) 0.36446(11) 0.34050(3) 0.0510(3) Uani 1 1 d . . . . .
Cl2 Cl 0.39150(8) 0.70010(13) 0.39570(3) 0.0545(3) Uani 1 1 d . . . . .
N1 N 0.40408(17) 0.7096(3) 0.30274(8) 0.0293(7) Uani 1 1 d . . . . .
N2 N 0.27318(19) 0.7824(4) 0.29956(9) 0.0394(8) Uani 1 1 d . . . . .
N3 N 0.36127(19) 0.9502(3) 0.30485(10) 0.0381(8) Uani 1 1 d . . . . .
N4 N 0.52887(18) 0.5708(3) 0.33435(8) 0.0283(7) Uani 1 1 d . . . . .
N5 N 0.6444(2) 0.6287(4) 0.37483(9) 0.0441(9) Uani 1 1 d . . . . .
N6 N 0.5983(2) 0.4114(4) 0.37522(10) 0.0469(9) Uani 1 1 d . . . . .
C1 C 0.3503(2) 0.8099(4) 0.30216(9) 0.0314(8) Uani 1 1 d . . . . .
C2 C 0.2393(2) 0.6447(5) 0.29658(12) 0.0461(11) Uani 1 1 d . . . . .
H2A H 0.187019 0.650296 0.282754 0.069 Uiso 1 1 calc R U . . .
H2B H 0.235927 0.607102 0.321379 0.069 Uiso 1 1 calc R U . . .
H2C H 0.271840 0.582045 0.283553 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2297(3) 0.9077(5) 0.30718(17) 0.0597(14) Uani 1 1 d . . . . .
H3AB H 0.214106 0.904451 0.332367 0.072 Uiso 1 1 calc R U . . .
H3A H 0.182646 0.918991 0.288915 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2874(3) 1.0247(5) 0.30373(15) 0.0552(12) Uani 1 1 d . . . . .
H4AB H 0.274786 1.076488 0.280113 0.066 Uiso 1 1 calc R U . . .
H4A H 0.288574 1.092449 0.324517 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4346(2) 1.0186(4) 0.31985(12) 0.0421(9) Uani 1 1 d . . . . .
H5A H 0.423582 1.098595 0.335490 0.063 Uiso 1 1 calc R U . . .
H5B H 0.461424 1.052787 0.299447 0.063 Uiso 1 1 calc R U . . .
H5C H 0.467839 0.950229 0.334639 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4742(2) 0.7366(4) 0.28815(9) 0.0278(7) Uani 1 1 d . . . . .
C7 C 0.4817(2) 0.8219(4) 0.25767(10) 0.0363(9) Uani 1 1 d . . . . .
H7 H 0.437131 0.869762 0.245750 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5521(2) 0.8387(4) 0.24441(10) 0.0374(9) Uani 1 1 d . . . . .
H8 H 0.556217 0.900560 0.224207 0.045 Uiso 1 1 calc R U . . .
C9 C 0.6171(2) 0.7654(4) 0.26047(10) 0.0341(8) Uani 1 1 d . . . . .
H9 H 0.665444 0.775335 0.251010 0.041 Uiso 1 1 calc R U . . .
C10 C 0.6111(2) 0.6773(4) 0.29047(10) 0.0327(8) Uani 1 1 d . . . . .
H10 H 0.655489 0.626305 0.301353 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5404(2) 0.6629(4) 0.30478(9) 0.0277(7) Uani 1 1 d . . . . .
C12 C 0.5890(2) 0.5404(5) 0.36017(9) 0.0342(8) Uani 1 1 d . . . . .
C13 C 0.6398(3) 0.7802(5) 0.37366(12) 0.0529(12) Uani 1 1 d . . . . .
H13A H 0.659313 0.818792 0.398041 0.079 Uiso 1 1 calc R U . . .
H13B H 0.585409 0.809040 0.366919 0.079 Uiso 1 1 calc R U . . .
H13C H 0.671381 0.816209 0.355234 0.079 Uiso 1 1 calc R U . . .
C14 C 0.6976(3) 0.5552(6) 0.40321(11) 0.0582(14) Uani 1 1 d . . . . .
H14A H 0.694176 0.595284 0.428044 0.070 Uiso 1 1 calc R U . . .
H14B H 0.752132 0.562206 0.397842 0.070 Uiso 1 1 calc R U . . .
C15 C 0.6703(3) 0.4057(7) 0.40101(14) 0.0694(17) Uani 1 1 d . . . . .
H15A H 0.709189 0.343324 0.391503 0.083 Uiso 1 1 calc R U . . .
H15B H 0.660124 0.370866 0.425565 0.083 Uiso 1 1 calc R U . . .
C16 C 0.5641(3) 0.2860(5) 0.35836(13) 0.0502(11) Uani 1 1 d . . . . .
H16A H 0.507443 0.290179 0.357877 0.075 Uiso 1 1 calc R U . . .
H16B H 0.584526 0.203238 0.372616 0.075 Uiso 1 1 calc R U . . .
H16C H 0.577011 0.278636 0.333005 0.075 Uiso 1 1 calc R U . . .
Fe2 Fe 0.250000 0.08443(7) 0.500000 0.0291(2) Uani 1 2 d S T P . .
Cl3 Cl 0.33049(6) -0.03138(10) 0.54393(3) 0.0385(3) Uani 1 1 d . . . . .
N21 N 0.30917(17) 0.2520(3) 0.47973(8) 0.0296(6) Uani 1 1 d . . . . .
N22 N 0.40004(19) 0.1286(4) 0.45027(9) 0.0386(8) Uani 1 1 d . . . . .
N23 N 0.44793(19) 0.2907(4) 0.49115(9) 0.0397(8) Uani 1 1 d . . . . .
C21 C 0.3820(2) 0.2288(4) 0.47415(10) 0.0327(8) Uani 1 1 d . . . . .
C22 C 0.3464(3) 0.0818(4) 0.41843(11) 0.0431(10) Uani 1 1 d . . . . .
H22A H 0.293083 0.081978 0.424819 0.065 Uiso 1 1 calc R U . . .
H22B H 0.360354 -0.014092 0.411473 0.065 Uiso 1 1 calc R U . . .
H22C H 0.349742 0.146170 0.397606 0.065 Uiso 1 1 calc R U . . .
C23 C 0.4836(3) 0.1328(6) 0.44696(14) 0.0587(13) Uani 1 1 d . . . . .
H23A H 0.493774 0.183943 0.424351 0.070 Uiso 1 1 calc R U . . .
H23B H 0.505776 0.036390 0.446627 0.070 Uiso 1 1 calc R U . . .
C24 C 0.5162(3) 0.2124(5) 0.48157(14) 0.0532(12) Uani 1 1 d . . . . .
H24A H 0.536537 0.146541 0.501621 0.064 Uiso 1 1 calc R U . . .
H24B H 0.558321 0.277792 0.476577 0.064 Uiso 1 1 calc R U . . .
C25 C 0.4528(3) 0.3480(5) 0.52819(11) 0.0459(11) Uani 1 1 d . . . . .
H25A H 0.436138 0.447127 0.526948 0.069 Uiso 1 1 calc R U . . .
H25B H 0.506663 0.341951 0.540187 0.069 Uiso 1 1 calc R U . . .
H25C H 0.418794 0.293626 0.542509 0.069 Uiso 1 1 calc R U . . .
C26 C 0.2831(2) 0.3859(4) 0.49043(9) 0.0283(7) Uani 1 1 d . . . . .
C27 C 0.3132(2) 0.5140(4) 0.48003(10) 0.0338(8) Uani 1 1 d . . . . .
H27 H 0.355994 0.514368 0.466065 0.041 Uiso 1 1 calc R U . . .
C28 C 0.2815(2) 0.6414(4) 0.48983(10) 0.0352(9) Uani 1 1 d . . . . .
H28 H 0.302712 0.728345 0.482720 0.042 Uiso 1 1 d 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
Fe1 N4 2.073(3) . ?
Fe1 N1 2.076(3) . ?
Fe1 Cl2 2.2447(12) . ?
Fe1 Cl1 2.2605(12) . ?
N1 C1 1.327(5) . ?
N1 C6 1.409(5) . ?
N2 C1 1.352(5) . ?
N2 C2 1.426(5) . ?
N2 C3 1.448(6) . ?
N3 C1 1.342(5) . ?
N3 C4 1.455(5) . ?
N3 C5 1.467(5) . ?
N4 C12 1.343(4) . ?
N4 C11 1.419(5) . ?
N5 C12 1.330(5) . ?
N5 C13 1.435(6) . ?
N5 C14 1.469(5) . ?
N6 C12 1.338(5) . ?
N6 C16 1.429(6) . ?
N6 C15 1.462(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.507(7) . ?
C3 H3AB 0.9900 . ?
C3 H3A 0.9900 . ?
C4 H4AB 0.9900 . ?
C4 H4A 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.392(5) . ?
C6 C11 1.410(5) . ?
C7 C8 1.377(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(5) . ?
C10 H10 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.489(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Fe2 N21 2.073(3) . ?
Fe2 N21 2.073(3) 2_556 ?
Fe2 Cl3 2.2657(11) 2_556 ?
Fe2 Cl3 2.2657(11) . ?
N21 C21 1.320(5) . ?
N21 C26 1.416(5) . ?
N22 C21 1.350(5) . ?
N22 C22 1.459(5) . ?
N22 C23 1.467(6) . ?
N23 C21 1.360(5) . ?
N23 C25 1.447(5) . ?
N23 C24 1.473(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.515(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.390(5) . ?
C26 C26 1.415(7) 2_556 ?
C27 C28 1.389(5) . ?
C27 H27 0.9500 . ?
C28 C28 1.394(8) 2_556 ?
C28 H28 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
N4 Fe1 N1 79.76(12) . . ?
N4 Fe1 Cl2 116.57(9) . . ?
N1 Fe1 Cl2 104.72(9) . . ?
N4 Fe1 Cl1 118.35(9) . . ?
N1 Fe1 Cl1 118.01(9) . . ?
Cl2 Fe1 Cl1 114.15(5) . . ?
C1 N1 C6 120.0(3) . . ?
C1 N1 Fe1 117.7(3) . . ?
C6 N1 Fe1 114.1(2) . . ?
C1 N2 C2 125.0(3) . . ?
C1 N2 C3 111.2(3) . . ?
C2 N2 C3 122.9(4) . . ?
C1 N3 C4 111.2(3) . . ?
C1 N3 C5 124.8(3) . . ?
C4 N3 C5 120.8(3) . . ?
C12 N4 C11 119.5(3) . . ?
C12 N4 Fe1 121.0(2) . . ?
C11 N4 Fe1 113.6(2) . . ?
C12 N5 C13 125.4(4) . . ?
C12 N5 C14 109.9(4) . . ?
C13 N5 C14 121.4(4) . . ?
C12 N6 C16 123.9(3) . . ?
C12 N6 C15 110.2(4) . . ?
C16 N6 C15 121.2(4) . . ?
N1 C1 N3 127.9(3) . . ?
N1 C1 N2 123.2(3) . . ?
N3 C1 N2 108.9(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 102.6(4) . . ?
N2 C3 H3AB 111.2 . . ?
C4 C3 H3AB 111.2 . . ?
N2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
H3AB C3 H3A 109.2 . . ?
N3 C4 C3 103.4(4) . . ?
N3 C4 H4AB 111.1 . . ?
C3 C4 H4AB 111.1 . . ?
N3 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
H4AB C4 H4A 109.1 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 125.3(3) . . ?
C7 C6 C11 118.5(4) . . ?
N1 C6 C11 116.1(3) . . ?
C8 C7 C6 121.5(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.7(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 119.6(3) . . ?
C10 C11 N4 123.9(3) . . ?
C6 C11 N4 116.4(3) . . ?
N5 C12 N6 111.3(3) . . ?
N5 C12 N4 127.0(4) . . ?
N6 C12 N4 121.6(4) . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 C15 104.2(4) . . ?
N5 C14 H14A 110.9 . . ?
C15 C14 H14A 110.9 . . ?
N5 C14 H14B 110.9 . . ?
C15 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
N6 C15 C14 103.7(4) . . ?
N6 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
N6 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
N6 C16 H16A 109.5 . . ?
N6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N21 Fe2 N21 80.33(17) . 2_556 ?
N21 Fe2 Cl3 113.87(8) . 2_556 ?
N21 Fe2 Cl3 109.51(9) 2_556 2_556 ?
N21 Fe2 Cl3 109.51(9) . . ?
N21 Fe2 Cl3 113.87(8) 2_556 . ?
Cl3 Fe2 Cl3 122.21(6) 2_556 . ?
C21 N21 C26 122.4(3) . . ?
C21 N21 Fe2 116.9(2) . . ?
C26 N21 Fe2 113.3(2) . . ?
C21 N22 C22 123.3(3) . . ?
C21 N22 C23 110.2(3) . . ?
C22 N22 C23 118.5(3) . . ?
C21 N23 C25 122.1(4) . . ?
C21 N23 C24 109.2(3) . . ?
C25 N23 C24 117.1(3) . . ?
N21 C21 N22 121.3(3) . . ?
N21 C21 N23 128.4(4) . . ?
N22 C21 N23 110.2(3) . . ?
N22 C22 H22A 109.5 . . ?
N22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N22 C23 C24 102.2(4) . . ?
N22 C23 H23A 111.3 . . ?
C24 C23 H23A 111.3 . . ?
N22 C23 H23B 111.3 . . ?
C24 C23 H23B 111.3 . . ?
H23A C23 H23B 109.2 . . ?
N23 C24 C23 102.8(3) . . ?
N23 C24 H24A 111.2 . . ?
C23 C24 H24A 111.2 . . ?
N23 C24 H24B 111.2 . . ?
C23 C24 H24B 111.2 . . ?
H24A C24 H24B 109.1 . . ?
N23 C25 H25A 109.5 . . ?
N23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C26 119.3(2) . 2_556 ?
C27 C26 N21 124.1(3) . . ?
C26 C26 N21 116.2(2) 2_556 . ?
C28 C27 C26 120.7(4) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C28 119.9(2) . 2_556 ?
C27 C28 H28 120.1 . . ?
C28 C28 H28 120.1 2_556 . ?

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
C6 N1 C1 N3 -32.2(5) . . . . ?
Fe1 N1 C1 N3 114.5(4) . . . . ?
C6 N1 C1 N2 149.6(3) . . . . ?
Fe1 N1 C1 N2 -63.7(4) . . . . ?
C4 N3 C1 N1 -178.9(4) . . . . ?
C5 N3 C1 N1 -19.2(6) . . . . ?
C4 N3 C1 N2 -0.5(5) . . . . ?
C5 N3 C1 N2 159.2(4) . . . . ?
C2 N2 C1 N1 -1.0(6) . . . . ?
C3 N2 C1 N1 168.2(4) . . . . ?
C2 N2 C1 N3 -179.5(4) . . . . ?
C3 N2 C1 N3 -10.4(5) . . . . ?
C1 N2 C3 C4 16.2(5) . . . . ?
C2 N2 C3 C4 -174.5(4) . . . . ?
C1 N3 C4 C3 10.3(5) . . . . ?
C5 N3 C4 C3 -150.3(4) . . . . ?
N2 C3 C4 N3 -15.1(5) . . . . ?
C1 N1 C6 C7 -34.8(5) . . . . ?
Fe1 N1 C6 C7 177.3(3) . . . . ?
C1 N1 C6 C11 149.5(3) . . . . ?
Fe1 N1 C6 C11 1.6(4) . . . . ?
N1 C6 C7 C8 -177.6(4) . . . . ?
C11 C6 C7 C8 -2.0(6) . . . . ?
C6 C7 C8 C9 2.6(6) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C11 -0.6(6) . . . . ?
C9 C10 C11 C6 1.1(5) . . . . ?
C9 C10 C11 N4 177.4(3) . . . . ?
C7 C6 C11 C10 0.1(5) . . . . ?
N1 C6 C11 C10 176.1(3) . . . . ?
C7 C6 C11 N4 -176.4(3) . . . . ?
N1 C6 C11 N4 -0.4(4) . . . . ?
C12 N4 C11 C10 29.3(5) . . . . ?
Fe1 N4 C11 C10 -177.4(3) . . . . ?
C12 N4 C11 C6 -154.4(3) . . . . ?
Fe1 N4 C11 C6 -1.1(4) . . . . ?
C13 N5 C12 N6 -160.2(4) . . . . ?
C14 N5 C12 N6 -0.5(5) . . . . ?
C13 N5 C12 N4 18.1(6) . . . . ?
C14 N5 C12 N4 177.8(4) . . . . ?
C16 N6 C12 N5 -160.4(4) . . . . ?
C15 N6 C12 N5 -4.5(5) . . . . ?
C16 N6 C12 N4 21.2(6) . . . . ?
C15 N6 C12 N4 177.1(4) . . . . ?
C11 N4 C12 N5 39.1(6) . . . . ?
Fe1 N4 C12 N5 -112.3(4) . . . . ?
C11 N4 C12 N6 -142.8(4) . . . . ?
Fe1 N4 C12 N6 65.8(5) . . . . ?
C12 N5 C14 C15 5.1(5) . . . . ?
C13 N5 C14 C15 165.7(4) . . . . ?
C12 N6 C15 C14 7.4(5) . . . . ?
C16 N6 C15 C14 164.0(4) . . . . ?
N5 C14 C15 N6 -7.2(5) . . . . ?
C26 N21 C21 N22 -151.7(3) . . . . ?
Fe2 N21 C21 N22 60.4(4) . . . . ?
C26 N21 C21 N23 31.6(6) . . . . ?
Fe2 N21 C21 N23 -116.3(4) . . . . ?
C22 N22 C21 N21 27.0(6) . . . . ?
C23 N22 C21 N21 175.3(4) . . . . ?
C22 N22 C21 N23 -155.7(4) . . . . ?
C23 N22 C21 N23 -7.5(5) . . . . ?
C25 N23 C21 N21 26.8(6) . . . . ?
C24 N23 C21 N21 168.8(4) . . . . ?
C25 N23 C21 N22 -150.2(4) . . . . ?
C24 N23 C21 N22 -8.2(5) . . . . ?
C21 N22 C23 C24 19.1(5) . . . . ?
C22 N22 C23 C24 169.1(4) . . . . ?
C21 N23 C24 C23 19.6(5) . . . . ?
C25 N23 C24 C23 163.7(4) . . . . ?
N22 C23 C24 N23 -22.3(5) . . . . ?
C21 N21 C26 C27 31.6(5) . . . . ?
Fe2 N21 C26 C27 -179.4(3) . . . . ?
C21 N21 C26 C26 -155.2(4) . . . 2_556 ?
Fe2 N21 C26 C26 -6.3(4) . . . 2_556 ?
C26 C26 C27 C28 3.2(6) 2_556 . . . ?
N21 C26 C27 C28 176.2(3) . . . . ?
C26 C27 C28 C28 -0.3(6) . . . 2_556 ?

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
_geom_hbond_publ_flag
C4 H4A Cl1 0.99 2.80 3.584(5) 136.3 1_565 yes
C22 H22A Cl3 0.98 2.76 3.670(5) 154.0 2_556 yes
C22 H22B Cl2 0.98 2.83 3.806(4) 174.9 1_545 yes
C23 H23B Cl3 0.99 2.81 3.333(5) 113.6 5_656 yes
C25 H25B Cl2 0.98 2.77 3.641(4) 148.4 5_666 yes

_refine_diff_density_max         1.619
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_C5
_database_code_depnum_ccdc_archive 'CCDC 2278553'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Cl Fe N8, Cl'
_chemical_formula_sum            'C22 H36 Cl2 Fe N8'
_chemical_formula_weight         539.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.769(3)
_cell_length_b                   13.649(3)
_cell_length_c                   15.343(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2674.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29755
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      33.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.790
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.5013
_exptl_absorpt_correction_T_max  0.7323
_exptl_absorpt_special_details   ?
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 1181 frames, detector distance = 60 mm
;

_diffrn_reflns_number            35928
_diffrn_reflns_av_unetI/netI     0.1168
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.997
_diffrn_reflns_theta_max         33.762
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             9889
_reflns_number_gt                6846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.989

_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0382P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9889
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.29655(3) 0.34504(3) 0.65531(3) 0.01186(9) Uani 1 1 d . . . . .
Cl1 Cl 0.18943(6) 0.47454(5) 0.61316(5) 0.02161(17) Uani 1 1 d . . . . .
N1 N 0.4123(2) 0.33906(19) 0.75170(16) 0.0144(5) Uani 1 1 d . . . . .
C1 C 0.3991(3) 0.3216(2) 0.8360(2) 0.0207(7) Uani 1 1 d . . . . .
N2 N 0.4638(3) 0.2649(2) 0.8849(2) 0.0299(8) Uani 1 1 d . . . . .
C2 C 0.2767(3) 0.4582(2) 0.8499(2) 0.0275(8) Uani 1 1 d . . . . .
H2A H 0.324001 0.486484 0.806276 0.041 Uiso 1 1 calc R U . . .
H2B H 0.272564 0.501983 0.900386 0.041 Uiso 1 1 calc R U . . .
H2C H 0.206858 0.450156 0.824469 0.041 Uiso 1 1 calc R U . . .
N3 N 0.3164(2) 0.3635(2) 0.87724(18) 0.0257(7) Uani 1 1 d . . . . .
C3 C 0.2569(3) 0.3135(3) 0.9457(2) 0.0432(12) Uani 1 1 d . . . . .
H3A H 0.183062 0.309735 0.928726 0.065 Uiso 1 1 calc R U . . .
H3B H 0.263231 0.350202 1.000364 0.065 Uiso 1 1 calc R U . . .
H3C H 0.284735 0.247237 0.953797 0.065 Uiso 1 1 calc R U . . .
N4 N 0.4360(2) 0.40657(18) 0.58882(17) 0.0136(5) Uani 1 1 d . . . . .
C4 C 0.4857(4) 0.2852(3) 0.9768(3) 0.0515(14) Uani 1 1 d . . . . .
H4A H 0.561514 0.290794 0.985374 0.077 Uiso 1 1 calc R U . . .
H4B H 0.458454 0.231579 1.012727 0.077 Uiso 1 1 calc R U . . .
H4C H 0.451803 0.346697 0.993737 0.077 Uiso 1 1 calc R U . . .
N5 N 0.3087(2) 0.20295(17) 0.60892(15) 0.0132(5) Uani 1 1 d . . . . .
C5 C 0.5256(4) 0.1844(2) 0.8476(3) 0.0402(11) Uani 1 1 d . . . . .
H5A H 0.494786 0.164380 0.791892 0.060 Uiso 1 1 calc R U . . .
H5B H 0.525475 0.128738 0.887921 0.060 Uiso 1 1 calc R U . . .
H5C H 0.597740 0.206468 0.838114 0.060 Uiso 1 1 calc R U . . .
N6 N 0.3220(2) 0.2184(2) 0.45991(17) 0.0187(6) Uani 1 1 d . . . . .
C6 C 0.5191(2) 0.3377(2) 0.7170(2) 0.0171(6) Uani 1 1 d . . . . .
H6A H 0.539876 0.269511 0.703359 0.021 Uiso 1 1 calc R U . . .
H6B H 0.568339 0.363803 0.761098 0.021 Uiso 1 1 calc R U . . .
N7 N 0.4042(2) 0.08665(19) 0.52659(18) 0.0178(6) Uani 1 1 d . . . . .
C7 C 0.5242(2) 0.3992(2) 0.6357(2) 0.0153(6) Uani 1 1 d . . . . .
N8 N 0.1702(2) 0.26485(18) 0.72353(17) 0.0157(5) Uani 1 1 d . . . . .
C8 C 0.6180(3) 0.4416(2) 0.6082(2) 0.0232(7) Uani 1 1 d . . . . .
H8 H 0.679075 0.437003 0.643221 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6208(3) 0.4902(3) 0.5291(2) 0.0246(8) Uani 1 1 d . . . . .
H9 H 0.683765 0.519864 0.509238 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5312(3) 0.4949(2) 0.4800(2) 0.0228(7) Uani 1 1 d . . . . .
H10 H 0.531820 0.525316 0.424328 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4405(3) 0.4549(2) 0.5127(2) 0.0185(7) Uani 1 1 d . . . . .
H11 H 0.377862 0.461905 0.479825 0.022 Uiso 1 1 calc R U . . .
C12 C 0.3446(2) 0.1691(2) 0.5346(2) 0.0143(6) Uani 1 1 d . . . . .
C13 C 0.4744(3) 0.0552(3) 0.5949(2) 0.0253(8) Uani 1 1 d . . . . .
H13A H 0.541205 0.034713 0.569178 0.038 Uiso 1 1 calc R U . . .
H13B H 0.443196 0.000015 0.626394 0.038 Uiso 1 1 calc R U . . .
H13C H 0.486599 0.109542 0.635380 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3980(3) 0.0209(3) 0.4521(2) 0.0269(8) Uani 1 1 d . . . . .
H14A H 0.347707 0.046881 0.409691 0.040 Uiso 1 1 calc R U . . .
H14B H 0.374880 -0.043989 0.471600 0.040 Uiso 1 1 calc R U . . .
H14C H 0.467089 0.015454 0.424758 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2268(3) 0.2778(2) 0.4538(2) 0.0219(7) Uani 1 1 d . . . . .
H15A H 0.201167 0.277312 0.393626 0.033 Uiso 1 1 calc R U . . .
H15B H 0.242496 0.345276 0.471347 0.033 Uiso 1 1 calc R U . . .
H15C H 0.173008 0.250628 0.492451 0.033 Uiso 1 1 calc R U . . .
C16 C 0.3939(3) 0.2288(3) 0.3874(2) 0.0290(8) Uani 1 1 d . . . . .
H16A H 0.365129 0.195556 0.336120 0.043 Uiso 1 1 calc R U . . .
H16B H 0.461465 0.199490 0.402749 0.043 Uiso 1 1 calc R U . . .
H16C H 0.403677 0.298510 0.374348 0.043 Uiso 1 1 calc R U . . .
C17 C 0.2816(3) 0.1322(2) 0.6772(2) 0.0174(7) Uani 1 1 d . . . . .
H17A H 0.338926 0.127638 0.720457 0.021 Uiso 1 1 calc R U . . .
H17B H 0.270476 0.066475 0.651470 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1826(2) 0.1673(2) 0.72061(19) 0.0153(6) Uani 1 1 d . . . . .
C19 C 0.1091(3) 0.1031(3) 0.7547(2) 0.0217(7) Uani 1 1 d . . . . .
H19 H 0.120534 0.034395 0.752156 0.026 Uiso 1 1 calc R U . . .
C20 C 0.0187(3) 0.1403(3) 0.7927(2) 0.0234(8) Uani 1 1 d . . . . .
H20 H -0.032900 0.097365 0.815862 0.028 Uiso 1 1 calc R U . . .
C21 C 0.0049(3) 0.2409(3) 0.7962(2) 0.0213(7) Uani 1 1 d . . . . .
H21 H -0.055666 0.268684 0.822416 0.026 Uiso 1 1 calc R U . . .
C22 C 0.0820(2) 0.2998(3) 0.7604(2) 0.0180(7) Uani 1 1 d . . . . .
H22 H 0.072127 0.368798 0.761798 0.022 Uiso 1 1 calc R U . . .
Cl2 Cl 0.76248(7) 0.37090(6) 0.85020(7) 0.0216(2) Uani 0.869(2) 1 d . . P A 1
Cl2' Cl 0.7489(4) 0.1611(4) 0.7597(3) 0.0140(13) Uani 0.131(2) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N5 2.072(2) . ?
Fe1 N1 2.092(3) . ?
Fe1 N8 2.213(3) . ?
Fe1 N4 2.218(3) . ?
Fe1 Cl1 2.3266(9) . ?
N1 C1 1.325(4) . ?
N1 C6 1.465(4) . ?
C1 N3 1.357(4) . ?
C1 N2 1.359(4) . ?
N2 C4 1.463(5) . ?
N2 C5 1.469(5) . ?
C2 N3 1.450(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C3 1.465(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C7 1.340(4) . ?
N4 C11 1.343(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C12 1.312(4) . ?
N5 C17 1.467(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 C12 1.360(4) . ?
N6 C16 1.449(4) . ?
N6 C15 1.464(4) . ?
C6 C7 1.504(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C12 1.364(4) . ?
N7 C13 1.445(4) . ?
N7 C14 1.456(4) . ?
C7 C8 1.395(4) . ?
N8 C18 1.342(4) . ?
N8 C22 1.348(4) . ?
C8 C9 1.383(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.507(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.386(4) . ?
C19 C20 1.390(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9500 . ?
C22 H22 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
N5 Fe1 N1 98.83(10) . . ?
N5 Fe1 N8 75.76(10) . . ?
N1 Fe1 N8 99.27(10) . . ?
N5 Fe1 N4 97.84(10) . . ?
N1 Fe1 N4 76.87(10) . . ?
N8 Fe1 N4 172.07(10) . . ?
N5 Fe1 Cl1 131.28(8) . . ?
N1 Fe1 Cl1 129.89(8) . . ?
N8 Fe1 Cl1 94.52(7) . . ?
N4 Fe1 Cl1 93.24(7) . . ?
C1 N1 C6 118.1(3) . . ?
C1 N1 Fe1 127.4(2) . . ?
C6 N1 Fe1 113.66(19) . . ?
N1 C1 N3 118.6(3) . . ?
N1 C1 N2 124.4(3) . . ?
N3 C1 N2 117.1(3) . . ?
C1 N2 C4 122.8(3) . . ?
C1 N2 C5 122.5(3) . . ?
C4 N2 C5 114.5(3) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C2 120.8(3) . . ?
C1 N3 C3 122.8(3) . . ?
C2 N3 C3 116.2(3) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 N4 C11 117.9(3) . . ?
C7 N4 Fe1 113.5(2) . . ?
C11 N4 Fe1 128.3(2) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C12 N5 C17 118.1(2) . . ?
C12 N5 Fe1 130.9(2) . . ?
C17 N5 Fe1 110.70(18) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 N6 C16 124.1(3) . . ?
C12 N6 C15 120.3(3) . . ?
C16 N6 C15 115.0(3) . . ?
N1 C6 C7 109.5(2) . . ?
N1 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C12 N7 C13 121.7(3) . . ?
C12 N7 C14 123.3(3) . . ?
C13 N7 C14 114.8(3) . . ?
N4 C7 C8 121.8(3) . . ?
N4 C7 C6 116.8(3) . . ?
C8 C7 C6 121.3(3) . . ?
C18 N8 C22 117.6(3) . . ?
C18 N8 Fe1 112.9(2) . . ?
C22 N8 Fe1 129.2(2) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N4 C11 C10 123.2(3) . . ?
N4 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N5 C12 N6 118.9(3) . . ?
N5 C12 N7 124.3(3) . . ?
N6 C12 N7 116.8(3) . . ?
N7 C13 H13A 109.5 . . ?
N7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N6 C15 H15A 109.5 . . ?
N6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N6 C16 H16A 109.5 . . ?
N6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 C18 107.7(2) . . ?
N5 C17 H17A 110.2 . . ?
C18 C17 H17A 110.2 . . ?
N5 C17 H17B 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
N8 C18 C19 122.4(3) . . ?
N8 C18 C17 115.4(3) . . ?
C19 C18 C17 122.2(3) . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 118.0(3) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
N8 C22 C21 123.7(3) . . ?
N8 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?

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
C6 N1 C1 N3 150.5(3) . . . . ?
Fe1 N1 C1 N3 -41.1(4) . . . . ?
C6 N1 C1 N2 -28.7(5) . . . . ?
Fe1 N1 C1 N2 139.7(3) . . . . ?
N1 C1 N2 C4 146.0(4) . . . . ?
N3 C1 N2 C4 -33.2(5) . . . . ?
N1 C1 N2 C5 -27.6(5) . . . . ?
N3 C1 N2 C5 153.2(3) . . . . ?
N1 C1 N3 C2 -31.5(4) . . . . ?
N2 C1 N3 C2 147.8(3) . . . . ?
N1 C1 N3 C3 143.1(3) . . . . ?
N2 C1 N3 C3 -37.7(4) . . . . ?
C1 N1 C6 C7 -155.5(3) . . . . ?
Fe1 N1 C6 C7 34.5(3) . . . . ?
C11 N4 C7 C8 1.1(4) . . . . ?
Fe1 N4 C7 C8 -174.2(2) . . . . ?
C11 N4 C7 C6 -175.1(3) . . . . ?
Fe1 N4 C7 C6 9.5(3) . . . . ?
N1 C6 C7 N4 -28.6(4) . . . . ?
N1 C6 C7 C8 155.1(3) . . . . ?
N4 C7 C8 C9 -1.8(5) . . . . ?
C6 C7 C8 C9 174.3(3) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C11 2.9(5) . . . . ?
C7 N4 C11 C10 1.6(5) . . . . ?
Fe1 N4 C11 C10 176.1(2) . . . . ?
C9 C10 C11 N4 -3.6(5) . . . . ?
C17 N5 C12 N6 147.3(3) . . . . ?
Fe1 N5 C12 N6 -40.2(4) . . . . ?
C17 N5 C12 N7 -32.8(4) . . . . ?
Fe1 N5 C12 N7 139.7(3) . . . . ?
C16 N6 C12 N5 143.4(3) . . . . ?
C15 N6 C12 N5 -27.0(4) . . . . ?
C16 N6 C12 N7 -36.5(4) . . . . ?
C15 N6 C12 N7 153.0(3) . . . . ?
C13 N7 C12 N5 -30.6(5) . . . . ?
C14 N7 C12 N5 145.7(3) . . . . ?
C13 N7 C12 N6 149.3(3) . . . . ?
C14 N7 C12 N6 -34.4(4) . . . . ?
C12 N5 C17 C18 -140.2(3) . . . . ?
Fe1 N5 C17 C18 45.9(3) . . . . ?
C22 N8 C18 C19 -0.8(5) . . . . ?
Fe1 N8 C18 C19 -176.1(2) . . . . ?
C22 N8 C18 C17 178.9(3) . . . . ?
Fe1 N8 C18 C17 3.6(3) . . . . ?
N5 C17 C18 N8 -31.6(4) . . . . ?
N5 C17 C18 C19 148.0(3) . . . . ?
N8 C18 C19 C20 0.7(5) . . . . ?
C17 C18 C19 C20 -179.0(3) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C18 N8 C22 C21 1.0(5) . . . . ?
Fe1 N8 C22 C21 175.4(2) . . . . ?
C20 C21 C22 N8 -1.1(5) . . . . ?

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
_geom_hbond_publ_flag
C2 H2A Cl2'^b 0.98 2.75 3.256(7) 112.6 3_656 yes
C5 H5C Cl2'^b 0.98 2.36 3.170(7) 139.9 . yes
C6 H6B Cl2^a 0.99 2.83 3.747(3) 153.9 . yes
C15 H15A Cl2'^b 0.98 2.57 3.393(6) 141.3 4_456 yes
C17 H17B Cl2^a 0.99 2.70 3.634(3) 157.0 3_646 yes
C21 H21 Cl2^a 0.95 2.74 3.662(4) 163.2 1_455 yes

_refine_diff_density_max         0.784
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_C8
_database_code_depnum_ccdc_archive 'CCDC 2278556'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 Cl2 Fe N6'
_chemical_formula_sum            'C20 H26 Cl2 Fe N6'
_chemical_formula_weight         477.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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

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

_cell_length_a                   15.712(3)
_cell_length_b                   9.2900(19)
_cell_length_c                   16.520(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.37(3)
_cell_angle_gamma                90
_cell_volume                     2160.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    70768
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      36.40

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.965
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.3483
_exptl_absorpt_correction_T_max  0.8663

_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 'Hybrid Pixel Counting Detector'
_diffrn_detector_type            'Dectris Pilatus 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 2046 frames, detector distance = 60 mm
;

_diffrn_reflns_number            109748
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.1128
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.476
_diffrn_reflns_theta_max         35.629
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9941
_reflns_number_gt                7830
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;


_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)+(0.0539P)²+0.0264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9941
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.69428(2) 0.65095(2) 0.41696(2) 0.01092(4) Uani 1 1 d . . . . .
C1 C 0.84422(7) 0.85047(12) 0.42829(7) 0.01490(18) Uani 1 1 d . . . . .
N1 N 0.81627(6) 0.71493(10) 0.41050(6) 0.01430(15) Uani 1 1 d . . . . .
Cl1 Cl 0.72416(2) 0.48782(3) 0.52817(2) 0.01887(6) Uani 1 1 d . . . . .
Cl2 Cl 0.60632(2) 0.85203(3) 0.40371(2) 0.02186(6) Uani 1 1 d . . . . .
C2 C 0.84230(9) 0.86077(14) 0.57770(8) 0.0229(2) Uani 1 1 d . . . . .
H2A H 0.786424 0.895607 0.583570 0.034 Uiso 1 1 calc R U . . .
H2B H 0.900002 0.888138 0.631477 0.034 Uiso 1 1 calc R U . . .
H2C H 0.839282 0.755710 0.571746 0.034 Uiso 1 1 calc R U . . .
N2 N 0.84404(8) 0.92406(12) 0.49841(7) 0.0221(2) Uani 1 1 d . . . . .
N4 N 0.64598(6) 0.58122(10) 0.28718(6) 0.01251(15) Uani 1 1 d . . . . .
C4 C 0.87613(9) 1.08937(13) 0.40938(9) 0.0222(2) Uani 1 1 d . . . . .
H4A H 0.821388 1.144799 0.365196 0.027 Uiso 1 1 calc R U . . .
H4AB H 0.935711 1.137824 0.418076 0.027 Uiso 1 1 calc R U . . .
N3 N 0.87376(7) 0.93989(11) 0.37944(7) 0.01810(17) Uani 1 1 d . . . . .
C3 C 0.87064(9) 1.07364(13) 0.49907(8) 0.0207(2) Uani 1 1 d . . . . .
H3A H 0.932784 1.094128 0.550898 0.025 Uiso 1 1 calc R U . . .
H3AB H 0.822090 1.138792 0.501747 0.025 Uiso 1 1 calc R U . . .
N6 N 0.48134(6) 0.62840(10) 0.23377(6) 0.01449(16) Uani 1 1 d . . . . .
C6 C 0.56183(7) 0.62549(11) 0.22342(7) 0.01203(16) Uani 1 1 d . . . . .
N5 N 0.54463(7) 0.68143(11) 0.14239(6) 0.01599(16) Uani 1 1 d . . . . .
C5 C 0.84430(10) 0.92002(14) 0.28312(8) 0.0233(2) Uani 1 1 d . . . . .
H5A H 0.884934 0.977898 0.264778 0.035 Uiso 1 1 calc R U . . .
H5B H 0.778077 0.950619 0.248928 0.035 Uiso 1 1 calc R U . . .
H5C H 0.850090 0.818172 0.270910 0.035 Uiso 1 1 calc R U . . .
C9 C 0.40349(8) 0.69576(14) 0.15608(8) 0.0191(2) Uani 1 1 d . . . . .
H9A H 0.387944 0.791737 0.171939 0.023 Uiso 1 1 calc R U . . .
H9AB H 0.345804 0.634822 0.132707 0.023 Uiso 1 1 calc R U . . .
C8 C 0.44373(8) 0.70799(13) 0.08730(7) 0.01828(19) Uani 1 1 d . . . . .
H8A H 0.415418 0.635006 0.038943 0.022 Uiso 1 1 calc R U . . .
H8AB H 0.432609 0.805038 0.059728 0.022 Uiso 1 1 calc R U . . .
C7 C 0.61508(9) 0.72709(16) 0.11448(9) 0.0252(2) Uani 1 1 d . . . . .
H7A H 0.597910 0.822029 0.085903 0.038 Uiso 1 1 calc R U . . .
H7B H 0.618118 0.657623 0.071200 0.038 Uiso 1 1 calc R U . . .
H7C H 0.677181 0.732719 0.167341 0.038 Uiso 1 1 calc R U . . .
C10 C 0.46470(8) 0.55207(13) 0.30115(8) 0.0189(2) Uani 1 1 d . . . . .
H10A H 0.446420 0.620511 0.335797 0.028 Uiso 1 1 calc R U . . .
H10B H 0.522828 0.501719 0.341950 0.028 Uiso 1 1 calc R U . . .
H10C H 0.413509 0.481978 0.271607 0.028 Uiso 1 1 calc R U . . .
C11 C 0.70536(7) 0.50297(11) 0.25924(7) 0.01235(16) Uani 1 1 d . . . . .
C12 C 0.66405(8) 0.40082(12) 0.19164(7) 0.01597(18) Uani 1 1 d . . . . .
H12 H 0.596870 0.391091 0.163173 0.019 Uiso 1 1 calc R U . . .
C13 C 0.71812(9) 0.31147(12) 0.16392(7) 0.01818(19) Uani 1 1 d . . . . .
H13 H 0.687452 0.243076 0.117129 0.022 Uiso 1 1 calc R U . . .
C14 C 0.81473(8) 0.32269(12) 0.20409(8) 0.01733(19) Uani 1 1 d . . . . .
H14 H 0.851103 0.261679 0.185263 0.021 Uiso 1 1 calc R U . . .
C15 C 0.86122(8) 0.42470(12) 0.27369(7) 0.01524(18) Uani 1 1 d . . . . .
C16 C 0.96187(8) 0.43439(13) 0.31289(8) 0.0202(2) Uani 1 1 d . . . . .
H16 H 0.996251 0.372713 0.292118 0.024 Uiso 1 1 calc R U . . .
C17 C 1.00986(8) 0.53132(14) 0.38010(9) 0.0217(2) Uani 1 1 d . . . . .
H17 H 1.077209 0.536472 0.406335 0.026 Uiso 1 1 calc R U . . .
C18 C 0.95867(8) 0.62324(13) 0.41001(8) 0.0187(2) Uani 1 1 d . . . . .
H18 H 0.992707 0.689082 0.457473 0.022 Uiso 1 1 calc R U . . .
C19 C 0.86039(7) 0.62144(12) 0.37286(7) 0.01341(17) Uani 1 1 d . . . . .
C20 C 0.80752(7) 0.51839(11) 0.30313(7) 0.01269(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N4 2.0363(10) . ?
Fe1 N1 2.0543(10) . ?
Fe1 Cl1 2.2641(5) . ?
Fe1 Cl2 2.2758(5) . ?
C1 N1 1.3229(14) . ?
C1 N2 1.3463(14) . ?
C1 N3 1.3744(14) . ?
N1 C19 1.4159(14) . ?
C2 N2 1.4471(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C3 1.4497(16) . ?
N4 C6 1.3378(14) . ?
N4 C11 1.4124(13) . ?
C4 N3 1.4690(16) . ?
C4 C3 1.5290(17) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
N3 C5 1.4582(16) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
N6 C6 1.3496(13) . ?
N6 C10 1.4383(14) . ?
N6 C9 1.4631(15) . ?
C6 N5 1.3466(13) . ?
N5 C7 1.4391(15) . ?
N5 C8 1.4563(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C9 C8 1.5304(16) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3874(15) . ?
C11 C20 1.4452(15) . ?
C12 C13 1.4022(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3639(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.4170(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.4208(16) . ?
C15 C20 1.4388(15) . ?
C16 C17 1.3669(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.4047(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3854(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.4434(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Fe1 N1 87.56(4) . . ?
N4 Fe1 Cl1 119.17(3) . . ?
N1 Fe1 Cl1 111.95(4) . . ?
N4 Fe1 Cl2 103.50(4) . . ?
N1 Fe1 Cl2 107.35(3) . . ?
Cl1 Fe1 Cl2 121.71(2) . . ?
N1 C1 N2 123.16(10) . . ?
N1 C1 N3 127.61(10) . . ?
N2 C1 N3 109.18(10) . . ?
C1 N1 C19 120.16(9) . . ?
C1 N1 Fe1 119.29(7) . . ?
C19 N1 Fe1 119.70(7) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N2 C2 125.50(11) . . ?
C1 N2 C3 112.48(9) . . ?
C2 N2 C3 120.26(10) . . ?
C6 N4 C11 117.79(8) . . ?
C6 N4 Fe1 120.47(7) . . ?
C11 N4 Fe1 121.10(7) . . ?
N3 C4 C3 103.41(10) . . ?
N3 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N3 C4 H4AB 111.1 . . ?
C3 C4 H4AB 111.1 . . ?
H4A C4 H4AB 109.0 . . ?
C1 N3 C5 122.54(10) . . ?
C1 N3 C4 109.78(9) . . ?
C5 N3 C4 115.81(10) . . ?
N2 C3 C4 102.97(9) . . ?
N2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
N2 C3 H3AB 111.2 . . ?
C4 C3 H3AB 111.2 . . ?
H3A C3 H3AB 109.1 . . ?
C6 N6 C10 126.22(10) . . ?
C6 N6 C9 111.27(9) . . ?
C10 N6 C9 121.41(9) . . ?
N4 C6 N5 126.38(10) . . ?
N4 C6 N6 124.08(10) . . ?
N5 C6 N6 109.43(10) . . ?
C6 N5 C7 126.08(10) . . ?
C6 N5 C8 111.63(9) . . ?
C7 N5 C8 121.91(9) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C9 C8 102.88(9) . . ?
N6 C9 H9A 111.2 . . ?
C8 C9 H9A 111.2 . . ?
N6 C9 H9AB 111.2 . . ?
C8 C9 H9AB 111.2 . . ?
H9A C9 H9AB 109.1 . . ?
N5 C8 C9 102.56(9) . . ?
N5 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
N5 C8 H8AB 111.3 . . ?
C9 C8 H8AB 111.3 . . ?
H8A C8 H8AB 109.2 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N4 118.31(9) . . ?
C12 C11 C20 119.34(9) . . ?
N4 C11 C20 122.19(9) . . ?
C11 C12 C13 122.21(10) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 120.04(10) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.47(10) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 118.71(10) . . ?
C14 C15 C20 120.70(10) . . ?
C16 C15 C20 120.58(10) . . ?
C17 C16 C15 120.84(11) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.39(11) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 122.44(11) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 N1 117.70(10) . . ?
C18 C19 C20 119.65(10) . . ?
N1 C19 C20 122.47(9) . . ?
C15 C20 C19 117.06(9) . . ?
C15 C20 C11 117.24(9) . . ?
C19 C20 C11 125.69(9) . . ?

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
N2 C1 N1 C19 -146.46(11) . . . . ?
N3 C1 N1 C19 36.23(17) . . . . ?
N2 C1 N1 Fe1 44.12(14) . . . . ?
N3 C1 N1 Fe1 -133.19(10) . . . . ?
N1 C1 N2 C2 19.78(18) . . . . ?
N3 C1 N2 C2 -162.47(11) . . . . ?
N1 C1 N2 C3 -175.39(11) . . . . ?
N3 C1 N2 C3 2.36(14) . . . . ?
N1 C1 N3 C5 25.21(18) . . . . ?
N2 C1 N3 C5 -152.41(11) . . . . ?
N1 C1 N3 C4 166.32(11) . . . . ?
N2 C1 N3 C4 -11.31(13) . . . . ?
C3 C4 N3 C1 14.97(12) . . . . ?
C3 C4 N3 C5 158.95(10) . . . . ?
C1 N2 C3 C4 6.93(13) . . . . ?
C2 N2 C3 C4 172.65(11) . . . . ?
N3 C4 C3 N2 -12.66(12) . . . . ?
C11 N4 C6 N5 -41.58(15) . . . . ?
Fe1 N4 C6 N5 129.29(10) . . . . ?
C11 N4 C6 N6 142.69(10) . . . . ?
Fe1 N4 C6 N6 -46.44(13) . . . . ?
C10 N6 C6 N4 -17.79(17) . . . . ?
C9 N6 C6 N4 174.14(10) . . . . ?
C10 N6 C6 N5 165.85(10) . . . . ?
C9 N6 C6 N5 -2.22(12) . . . . ?
N4 C6 N5 C7 -11.27(18) . . . . ?
N6 C6 N5 C7 164.98(11) . . . . ?
N4 C6 N5 C8 175.74(10) . . . . ?
N6 C6 N5 C8 -8.01(12) . . . . ?
C6 N6 C9 C8 10.60(12) . . . . ?
C10 N6 C9 C8 -158.13(10) . . . . ?
C6 N5 C8 C9 14.04(12) . . . . ?
C7 N5 C8 C9 -159.29(11) . . . . ?
N6 C9 C8 N5 -14.03(11) . . . . ?
C6 N4 C11 C12 -40.75(14) . . . . ?
Fe1 N4 C11 C12 148.44(8) . . . . ?
C6 N4 C11 C20 143.93(10) . . . . ?
Fe1 N4 C11 C20 -26.88(13) . . . . ?
N4 C11 C12 C13 -175.61(10) . . . . ?
C20 C11 C12 C13 -0.16(16) . . . . ?
C11 C12 C13 C14 0.40(18) . . . . ?
C12 C13 C14 C15 -0.25(17) . . . . ?
C13 C14 C15 C16 -179.10(11) . . . . ?
C13 C14 C15 C20 -0.13(16) . . . . ?
C14 C15 C16 C17 179.87(11) . . . . ?
C20 C15 C16 C17 0.90(17) . . . . ?
C15 C16 C17 C18 -0.60(18) . . . . ?
C16 C17 C18 C19 -1.09(18) . . . . ?
C17 C18 C19 N1 177.64(10) . . . . ?
C17 C18 C19 C20 2.42(17) . . . . ?
C1 N1 C19 C18 45.33(14) . . . . ?
Fe1 N1 C19 C18 -145.29(8) . . . . ?
C1 N1 C19 C20 -139.58(11) . . . . ?
Fe1 N1 C19 C20 29.79(13) . . . . ?
C14 C15 C20 C19 -178.54(10) . . . . ?
C16 C15 C20 C19 0.40(15) . . . . ?
C14 C15 C20 C11 0.36(15) . . . . ?
C16 C15 C20 C11 179.31(10) . . . . ?
C18 C19 C20 C15 -2.00(15) . . . . ?
N1 C19 C20 C15 -177.00(9) . . . . ?
C18 C19 C20 C11 179.19(10) . . . . ?
N1 C19 C20 C11 4.20(16) . . . . ?
C12 C11 C20 C15 -0.22(14) . . . . ?
N4 C11 C20 C15 175.06(9) . . . . ?
C12 C11 C20 C19 178.58(10) . . . . ?
N4 C11 C20 C19 -6.14(16) . . . . ?

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
_geom_hbond_publ_flag
C8 H8AB Cl1 0.99 2.81 3.5896(14) 136.4 2_655 yes
C7 H7B Cl2 0.98 2.69 3.5011(15) 140.2 4_575 yes

_refine_diff_density_max         0.622
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_C1
_database_code_depnum_ccdc_archive 'CCDC 2278549'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H28 Cl2 Fe N6'
_chemical_formula_sum            'C16 H28 Cl2 Fe N6'
_chemical_formula_weight         431.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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

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

_cell_length_a                   12.011(2)
_cell_length_b                   10.508(2)
_cell_length_c                   16.725(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.09(3)
_cell_angle_gamma                90
_cell_volume                     2028.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    50590
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      34.21

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.019
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2862
_exptl_absorpt_correction_T_max  0.7387
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
;
_exptl_absorpt_special_details   
;
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Genix Mo'
_diffrn_radiation_probe          x-ray
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 2297 frames, detector distance = 60 mm
;

_diffrn_reflns_number            38281
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         34.092
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7950
_reflns_number_gt                7217
_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       
;
X-Area Pilatus3_SV 1.31.131.0 (STOE, 2017)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.71.4.0 (STOE, 2017)
;

_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.77, Darmstadt 2016
;

_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)+(0.0237P)²+1.4402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7950
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
Fe1 Fe 0.74623(2) 0.64968(2) 0.61226(2) 0.01143(4) Uani 1 1 d . . . . .
C1 C 0.71470(9) 0.36398(10) 0.56786(6) 0.01271(16) Uani 1 1 d . . . . .
N1 N 0.69131(8) 0.46065(8) 0.61208(5) 0.01237(15) Uani 1 1 d . . . . .
Cl1 Cl 0.61882(2) 0.78565(3) 0.52876(2) 0.01929(5) Uani 1 1 d . . . . .
C2 C 0.81167(10) 0.22766(11) 0.68701(7) 0.01778(19) Uani 1 1 d . . . . .
H2A H 0.873595 0.165050 0.691590 0.027 Uiso 1 1 calc R U . . .
H2B H 0.757565 0.196657 0.716983 0.027 Uiso 1 1 calc R U . . .
H2C H 0.845321 0.308632 0.711216 0.027 Uiso 1 1 calc R U . . .
N2 N 0.75019(8) 0.24643(9) 0.59989(6) 0.01511(16) Uani 1 1 d . . . . .
Cl2 Cl 0.93912(2) 0.67585(3) 0.62707(2) 0.01975(6) Uani 1 1 d . . . . .
C3 C 0.70484(12) 0.13013(11) 0.55508(8) 0.0230(2) Uani 1 1 d . . . . .
H3A H 0.769262 0.078105 0.548189 0.035 Uiso 1 1 calc R U . . .
H3B H 0.653484 0.151971 0.500253 0.035 Uiso 1 1 calc R U . . .
H3C H 0.661279 0.082149 0.586674 0.035 Uiso 1 1 calc R U . . .
N3 N 0.70784(8) 0.38117(9) 0.48643(6) 0.01488(16) Uani 1 1 d . . . . .
C4 C 0.63383(11) 0.47825(12) 0.43631(7) 0.0196(2) Uani 1 1 d . . . . .
H4A H 0.595220 0.443385 0.381258 0.029 Uiso 1 1 calc R U . . .
H4B H 0.681047 0.551730 0.430199 0.029 Uiso 1 1 calc R U . . .
H4C H 0.575405 0.504977 0.463752 0.029 Uiso 1 1 calc R U . . .
N4 N 0.73673(8) 0.63444(8) 0.73345(5) 0.01164(14) Uani 1 1 d . . . . .
C5 C 0.78495(11) 0.31779(12) 0.44564(7) 0.0209(2) Uani 1 1 d . . . . .
H5A H 0.826902 0.381744 0.422667 0.031 Uiso 1 1 calc R U . . .
H5B H 0.739412 0.263817 0.400577 0.031 Uiso 1 1 calc R U . . .
H5C H 0.840474 0.265138 0.486205 0.031 Uiso 1 1 calc R U . . .
N5 N 0.87451(8) 0.61468(9) 0.86470(6) 0.01444(15) Uani 1 1 d . . . . .
C6 C 0.64636(8) 0.43607(10) 0.68047(6) 0.01188(16) Uani 1 1 d . . . . .
N6 N 0.83258(8) 0.81182(9) 0.80278(6) 0.01458(16) Uani 1 1 d . . . . .
C7 C 0.57297(9) 0.33430(10) 0.68453(7) 0.01495(17) Uani 1 1 d . . . . .
H7 H 0.552659 0.274463 0.640280 0.018 Uiso 1 1 calc R U . . .
C8 C 0.52963(9) 0.32026(11) 0.75290(7) 0.01705(19) Uani 1 1 d . . . . .
H8 H 0.481847 0.249423 0.755988 0.020 Uiso 1 1 calc R U . . .
C9 C 0.55593(9) 0.40958(11) 0.81697(7) 0.01673(19) Uani 1 1 d . . . . .
H9 H 0.526174 0.399654 0.863637 0.020 Uiso 1 1 calc R U . . .
C10 C 0.62577(9) 0.51321(11) 0.81243(6) 0.01445(17) Uani 1 1 d . . . . .
H10 H 0.642128 0.575159 0.855489 0.017 Uiso 1 1 calc R U . . .
C12 C 0.81161(9) 0.68565(10) 0.79951(6) 0.01161(16) Uani 1 1 d . . . . .
C13 C 0.88795(11) 0.65126(13) 0.95056(7) 0.0221(2) Uani 1 1 d . . . . .
H13A H 0.970575 0.656703 0.980083 0.033 Uiso 1 1 calc R U . . .
H13B H 0.850943 0.587486 0.977489 0.033 Uiso 1 1 calc R U . . .
H13C H 0.851403 0.734274 0.952067 0.033 Uiso 1 1 calc R U . . .
C14 C 0.90897(10) 0.48595(11) 0.85119(8) 0.0197(2) Uani 1 1 d . . . . .
H14A H 0.987896 0.470372 0.886165 0.030 Uiso 1 1 calc R U . . .
H14B H 0.906578 0.475165 0.792532 0.030 Uiso 1 1 calc R U . . .
H14C H 0.855706 0.425331 0.865733 0.030 Uiso 1 1 calc R U . . .
C15 C 0.75842(11) 0.89892(11) 0.74422(8) 0.0198(2) Uani 1 1 d . . . . .
H15A H 0.749826 0.978108 0.772899 0.030 Uiso 1 1 calc R U . . .
H15B H 0.682121 0.859913 0.721226 0.030 Uiso 1 1 calc R U . . .
H15C H 0.793234 0.917557 0.699007 0.030 Uiso 1 1 calc R U . . .
C16 C 0.94189(11) 0.86643(12) 0.85142(9) 0.0228(2) Uani 1 1 d . . . . .
H16A H 0.971670 0.924556 0.816393 0.034 Uiso 1 1 calc R U . . .
H16B H 0.998152 0.798107 0.871770 0.034 Uiso 1 1 calc R U . . .
H16C H 0.929376 0.913359 0.898829 0.034 Uiso 1 1 calc R U . . .
C11 C 0.67216(8) 0.52690(9) 0.74484(6) 0.01138(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N4 2.0675(10) . ?
Fe1 N1 2.0926(10) . ?
Fe1 Cl1 2.2692(6) . ?
Fe1 Cl2 2.2775(6) . ?
C1 N1 1.3315(13) . ?
C1 N3 1.3535(14) . ?
C1 N2 1.3666(14) . ?
N1 C6 1.4175(13) . ?
C2 N2 1.4529(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C3 1.4578(15) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N3 C5 1.4549(15) . ?
N3 C4 1.4562(15) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N4 C12 1.3298(13) . ?
N4 C11 1.4130(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N5 C12 1.3635(14) . ?
N5 C14 1.4505(15) . ?
N5 C13 1.4517(15) . ?
C6 C7 1.3994(14) . ?
C6 C11 1.4074(14) . ?
N6 C12 1.3478(13) . ?
N6 C15 1.4514(15) . ?
N6 C16 1.4571(15) . ?
C7 C8 1.3893(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3932(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3894(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3995(14) . ?
C10 H10 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Fe1 N1 79.92(3) . . ?
N4 Fe1 Cl1 116.18(3) . . ?
N1 Fe1 Cl1 115.99(3) . . ?
N4 Fe1 Cl2 103.51(4) . . ?
N1 Fe1 Cl2 115.18(3) . . ?
Cl1 Fe1 Cl2 118.89(2) . . ?
N1 C1 N3 119.58(9) . . ?
N1 C1 N2 124.24(9) . . ?
N3 C1 N2 116.13(9) . . ?
C1 N1 C6 119.70(9) . . ?
C1 N1 Fe1 127.59(7) . . ?
C6 N1 Fe1 111.23(6) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N2 C2 122.16(9) . . ?
C1 N2 C3 121.64(9) . . ?
C2 N2 C3 114.55(9) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N3 C5 122.79(9) . . ?
C1 N3 C4 122.00(9) . . ?
C5 N3 C4 114.66(9) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C12 N4 C11 118.80(8) . . ?
C12 N4 Fe1 125.09(7) . . ?
C11 N4 Fe1 112.06(6) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 N5 C14 120.28(9) . . ?
C12 N5 C13 122.09(10) . . ?
C14 N5 C13 116.28(10) . . ?
C7 C6 C11 119.29(9) . . ?
C7 C6 N1 124.36(9) . . ?
C11 C6 N1 116.19(9) . . ?
C12 N6 C15 121.34(9) . . ?
C12 N6 C16 122.64(10) . . ?
C15 N6 C16 114.71(10) . . ?
C8 C7 C6 120.38(10) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.31(10) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.84(10) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.42(10) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
N4 C12 N6 120.50(9) . . ?
N4 C12 N5 122.71(9) . . ?
N6 C12 N5 116.72(9) . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N6 C15 H15A 109.5 . . ?
N6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N6 C16 H16A 109.5 . . ?
N6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C11 C6 119.70(9) . . ?
C10 C11 N4 123.19(9) . . ?
C6 C11 N4 116.87(9) . . ?

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
N3 C1 N1 C6 151.07(10) . . . . ?
N2 C1 N1 C6 -31.44(15) . . . . ?
N3 C1 N1 Fe1 -44.08(13) . . . . ?
N2 C1 N1 Fe1 133.40(9) . . . . ?
N1 C1 N2 C2 -26.51(16) . . . . ?
N3 C1 N2 C2 151.05(10) . . . . ?
N1 C1 N2 C3 138.06(12) . . . . ?
N3 C1 N2 C3 -44.38(15) . . . . ?
N1 C1 N3 C5 145.43(11) . . . . ?
N2 C1 N3 C5 -32.26(15) . . . . ?
N1 C1 N3 C4 -25.53(15) . . . . ?
N2 C1 N3 C4 156.78(10) . . . . ?
C1 N1 C6 C7 -32.78(15) . . . . ?
Fe1 N1 C6 C7 160.06(8) . . . . ?
C1 N1 C6 C11 151.94(9) . . . . ?
Fe1 N1 C6 C11 -15.22(11) . . . . ?
C11 C6 C7 C8 -2.49(15) . . . . ?
N1 C6 C7 C8 -177.64(10) . . . . ?
C6 C7 C8 C9 1.99(17) . . . . ?
C7 C8 C9 C10 0.03(17) . . . . ?
C8 C9 C10 C11 -1.51(16) . . . . ?
C11 N4 C12 N6 -147.96(10) . . . . ?
Fe1 N4 C12 N6 56.56(13) . . . . ?
C11 N4 C12 N5 35.24(14) . . . . ?
Fe1 N4 C12 N5 -120.24(9) . . . . ?
C15 N6 C12 N4 13.14(16) . . . . ?
C16 N6 C12 N4 -153.06(11) . . . . ?
C15 N6 C12 N5 -169.87(10) . . . . ?
C16 N6 C12 N5 23.93(15) . . . . ?
C14 N5 C12 N4 31.01(15) . . . . ?
C13 N5 C12 N4 -135.23(11) . . . . ?
C14 N5 C12 N6 -145.91(10) . . . . ?
C13 N5 C12 N6 47.85(14) . . . . ?
C9 C10 C11 C6 0.98(15) . . . . ?
C9 C10 C11 N4 175.27(10) . . . . ?
C7 C6 C11 C10 1.01(15) . . . . ?
N1 C6 C11 C10 176.54(9) . . . . ?
C7 C6 C11 N4 -173.63(9) . . . . ?
N1 C6 C11 N4 1.90(13) . . . . ?
C12 N4 C11 C10 39.70(14) . . . . ?
Fe1 N4 C11 C10 -161.80(8) . . . . ?
C12 N4 C11 C6 -145.86(10) . . . . ?
Fe1 N4 C11 C6 12.64(11) . . . . ?

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.066

