# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_1-293K
_database_code_depnum_ccdc_archive 'CCDC 1568651'
_audit_update_record             
;
2017-10-20 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H22 Fe N8 O2, Cl O4'
_chemical_formula_sum            'C24 H22 Cl Fe N8 O6'
_chemical_formula_weight         609.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1Fe1Cl1
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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2935(3)
_cell_length_b                   18.4064(5)
_cell_length_c                   15.7629(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.747(3)
_cell_angle_gamma                90
_cell_volume                     2607.58(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3883
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      72.3740
_cell_measurement_theta_min      3.7370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9303
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.996
_diffrn_reflns_theta_min         3.765
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -129.00  20.00   1.00    2.00    --  -41.49   0.00  90.00  149
  2  ω     35.00  60.00   1.00    2.00    --   41.49-125.00  30.00   25
  3  ω     70.00 115.00   1.00    2.00    --   41.49  37.00-120.00   45
  4  ω    133.00 177.00   1.00   10.00    --  107.19  45.00 -90.00   44
  5  ω     75.00 175.00   1.00   10.00    --  107.19  77.00  60.00  100
  6  ω     34.00  92.00   1.00   10.00    --  107.19 -94.00 150.00   58
  7  ω    137.00 163.00   1.00   10.00    --  107.19 125.00 120.00   26
  8  ω     43.00 124.00   1.00   10.00    --  107.19 -45.00 -90.00   81
  9  ω     98.00 124.00   1.00   10.00    --  107.19 125.00 120.00   26
 10  ω     37.00  63.00   1.00   10.00    --  107.19-125.00 -90.00   26
 11  ω     78.00 114.00   1.00   10.00    --  107.19-125.00 -90.00   36
 12  ω    101.00 150.00   1.00   10.00    --  107.19  45.00-180.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0515406000
_diffrn_orient_matrix_UB_12      0.0603661000
_diffrn_orient_matrix_UB_13      0.0686890000
_diffrn_orient_matrix_UB_21      -0.1154306000
_diffrn_orient_matrix_UB_22      -0.0252332000
_diffrn_orient_matrix_UB_23      0.0485760000
_diffrn_orient_matrix_UB_31      0.1156682000
_diffrn_orient_matrix_UB_32      -0.0522120000
_diffrn_orient_matrix_UB_33      0.0560755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3620
_reflns_number_total             4432
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0870
_refine_ls_restrained_S_all      1.227
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+67.9466P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3294
_refine_ls_wR_factor_ref         0.3340
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C20(H20), C22(H22), C23(H23), C24(H24), N3(H3A), N7(H7A)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.8142(2) 0.10807(10) 0.73768(12) 0.0307(5) Uani 1 1 d . . . . .
Cl1 Cl 0.4291(4) 0.2220(2) 0.9374(3) 0.0597(10) Uani 1 1 d . . . . .
C1 C 1.0153(15) -0.0087(7) 0.8328(10) 0.044(3) Uani 1 1 d . . . . .
C2 C 1.0554(18) -0.0834(8) 0.8274(12) 0.059(4) Uani 1 1 d . . . . .
C3 C 1.161(2) -0.1119(10) 0.8982(15) 0.076(6) Uani 1 1 d . . . . .
H3 H 1.1872 -0.1605 0.8960 0.091 Uiso 1 1 calc R . . . .
C4 C 1.229(2) -0.0726(11) 0.9714(14) 0.075(6) Uani 1 1 d . . . . .
H4 H 1.3029 -0.0934 1.0157 0.090 Uiso 1 1 calc R . . . .
C5 C 1.1852(17) -0.0017(10) 0.9781(12) 0.063(5) Uani 1 1 d . . . . .
H5 H 1.2265 0.0250 1.0285 0.076 Uiso 1 1 calc R . . . .
C6 C 1.0784(15) 0.0303(8) 0.9087(9) 0.043(3) Uani 1 1 d . . . . .
C7 C 1.0302(14) 0.1031(7) 0.9236(8) 0.038(3) Uani 1 1 d . . . . .
H7 H 1.0752 0.1254 0.9766 0.046 Uiso 1 1 calc R . . . .
C8 C 0.7840(13) 0.2435(7) 0.8383(7) 0.031(3) Uani 1 1 d . . . . .
C9 C 0.6324(15) 0.3408(7) 0.8098(8) 0.040(3) Uani 1 1 d . . . . .
H9 H 0.5976 0.3844 0.8269 0.048 Uiso 1 1 calc R . . . .
C10 C 0.5693(15) 0.3161(7) 0.7264(9) 0.044(3) Uani 1 1 d . . . . .
H10 H 0.4954 0.3422 0.6873 0.053 Uiso 1 1 calc R . . . .
C11 C 0.6208(14) 0.2510(7) 0.7036(8) 0.037(3) Uani 1 1 d . . . . .
H11 H 0.5785 0.2316 0.6484 0.044 Uiso 1 1 calc R . . . .
C12 C 0.983(2) -0.1251(9) 0.7467(15) 0.082(6) Uani 1 1 d . . . . .
H12A H 1.0162 -0.1747 0.7536 0.122 Uiso 1 1 calc GR . . . .
H12B H 1.0105 -0.1041 0.6971 0.122 Uiso 1 1 calc GR . . . .
H12C H 0.8773 -0.1234 0.7374 0.122 Uiso 1 1 calc GR . . . .
C13 C 0.4039(19) 0.0150(9) 0.8079(12) 0.067(5) Uani 1 1 d . . . . .
H13A H 0.4059 0.0601 0.8389 0.101 Uiso 1 1 calc GR . . . .
H13B H 0.4969 -0.0098 0.8293 0.101 Uiso 1 1 calc GR . . . .
H13C H 0.3244 -0.0148 0.8170 0.101 Uiso 1 1 calc GR . . . .
C14 C 0.4990(14) 0.0568(7) 0.6800(10) 0.040(3) Uani 1 1 d . . . . .
C15 C 0.3795(16) 0.0301(7) 0.7116(12) 0.052(4) Uani 1 1 d . . . . .
C16 C 0.2449(18) 0.0203(8) 0.6532(13) 0.061(5) Uani 1 1 d . . . . .
H16 H 0.1657 0.0037 0.6740 0.073 Uiso 1 1 calc R . . . .
C17 C 0.2210(16) 0.0340(9) 0.5649(14) 0.071(5) Uani 1 1 d . . . . .
H17 H 0.1277 0.0258 0.5272 0.085 Uiso 1 1 calc R . . . .
C18 C 0.3364(16) 0.0599(8) 0.5321(12) 0.058(4) Uani 1 1 d . . . . .
H18 H 0.3208 0.0699 0.4726 0.070 Uiso 1 1 calc R . . . .
C19 C 0.4777(14) 0.0710(7) 0.5900(9) 0.041(3) Uani 1 1 d . . . . .
C20 C 0.5920(13) 0.1003(7) 0.5543(8) 0.037(3) Uani 1 1 d . . . . .
H20 H 0.5692 0.1075 0.4940 0.044 Uiso 1 1 calc R . . . .
C21 C 0.9476(12) 0.1733(6) 0.6010(7) 0.030(3) Uani 1 1 d . . . . .
C22 C 1.1682(14) 0.2275(8) 0.6032(9) 0.047(3) Uani 1 1 d . . . . .
H22 H 1.2311 0.2515 0.5751 0.057 Uiso 1 1 calc R . . . .
C23 C 1.2209(14) 0.2106(8) 0.6910(9) 0.047(3) Uani 1 1 d . . . . .
H23 H 1.3174 0.2220 0.7221 0.056 Uiso 1 1 calc R . . . .
C24 C 1.1240(13) 0.1762(7) 0.7299(8) 0.037(3) Uani 1 1 d . . . . .
H24 H 1.1555 0.1650 0.7892 0.044 Uiso 1 1 calc R . . . .
N1 N 0.7307(11) 0.2146(5) 0.7590(6) 0.031(2) Uani 1 1 d . . . . .
N2 N 0.9293(11) 0.1389(5) 0.8683(6) 0.033(2) Uani 1 1 d . . . . .
N3 N 0.8927(12) 0.2068(6) 0.8946(6) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.9377 0.2247 0.9447 0.046 Uiso 1 1 calc R . . . .
N4 N 0.7395(12) 0.3066(6) 0.8673(7) 0.037(2) Uani 1 1 d . . . . .
N6 N 0.7231(10) 0.1174(5) 0.5986(6) 0.031(2) Uani 1 1 d . . . . .
N5 N 0.9869(10) 0.1582(5) 0.6864(6) 0.031(2) Uani 1 1 d . . . . .
N7 N 0.8150(11) 0.1500(6) 0.5537(6) 0.039(3) Uani 1 1 d . . . . .
H7A H 0.7883 0.1552 0.4977 0.047 Uiso 1 1 calc R . . . .
N8 N 1.0315(11) 0.2110(6) 0.5571(7) 0.044(3) Uani 1 1 d . . . . .
O1 O 0.9208(11) 0.0200(5) 0.7637(7) 0.050(2) Uani 1 1 d . . . . .
O2 O 0.6286(10) 0.0662(5) 0.7368(6) 0.044(2) Uani 1 1 d . . . . .
O3 O 0.360(2) 0.2873(11) 0.9033(13) 0.163(10) Uani 1 1 d . . . . .
O4 O 0.4768(14) 0.1864(7) 0.8706(7) 0.069(3) Uani 1 1 d . . . . .
O5 O 0.552(2) 0.2413(9) 1.0036(9) 0.117(6) Uani 1 1 d . . . . .
O6 O 0.336(3) 0.1800(13) 0.9682(18) 0.223(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N1 2.167(10) . ?
Fe1 N2 2.141(10) . ?
Fe1 N6 2.147(10) . ?
Fe1 N5 2.177(9) . ?
Fe1 O1 1.889(9) . ?
Fe1 O2 1.886(9) . ?
Cl1 O3 1.403(18) . ?
Cl1 O4 1.405(11) . ?
Cl1 O5 1.382(14) . ?
Cl1 O6 1.337(17) . ?
C1 C2 1.433(19) . ?
C1 C6 1.39(2) . ?
C1 O1 1.323(16) . ?
C2 C3 1.39(3) . ?
C2 C12 1.49(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.37(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.38(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.41(2) . ?
C6 C7 1.452(19) . ?
C7 H7 0.9300 . ?
C7 N2 1.287(15) . ?
C8 N1 1.333(15) . ?
C8 N3 1.344(15) . ?
C8 N4 1.350(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(18) . ?
C9 N4 1.323(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(18) . ?
C11 H11 0.9300 . ?
C11 N1 1.341(15) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C15 1.50(2) . ?
C14 C15 1.416(17) . ?
C14 C19 1.406(19) . ?
C14 O2 1.316(16) . ?
C15 C16 1.36(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.38(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.39(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.411(19) . ?
C19 C20 1.428(17) . ?
C20 H20 0.9300 . ?
C20 N6 1.280(15) . ?
C21 N5 1.331(14) . ?
C21 N7 1.338(15) . ?
C21 N8 1.357(15) . ?
C22 H22 0.9300 . ?
C22 C23 1.382(19) . ?
C22 N8 1.328(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(17) . ?
C24 H24 0.9300 . ?
C24 N5 1.326(15) . ?
N2 N3 1.385(14) . ?
N3 H3A 0.8600 . ?
N6 N7 1.378(13) . ?
N7 H7A 0.8600 . ?

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 N5 90.0(4) . . ?
N2 Fe1 N1 73.9(4) . . ?
N2 Fe1 N6 158.7(4) . . ?
N2 Fe1 N5 90.6(4) . . ?
N6 Fe1 N1 91.3(4) . . ?
N6 Fe1 N5 73.9(4) . . ?
O1 Fe1 N1 158.7(4) . . ?
O1 Fe1 N2 85.0(4) . . ?
O1 Fe1 N6 109.8(4) . . ?
O1 Fe1 N5 92.8(4) . . ?
O2 Fe1 N1 90.5(4) . . ?
O2 Fe1 N2 110.4(4) . . ?
O2 Fe1 N6 84.4(4) . . ?
O2 Fe1 N5 158.3(4) . . ?
O2 Fe1 O1 94.5(4) . . ?
O3 Cl1 O4 108.2(10) . . ?
O5 Cl1 O3 106.1(11) . . ?
O5 Cl1 O4 109.2(10) . . ?
O6 Cl1 O3 111.2(16) . . ?
O6 Cl1 O4 110.9(10) . . ?
O6 Cl1 O5 111.1(15) . . ?
C6 C1 C2 119.2(14) . . ?
O1 C1 C2 117.5(15) . . ?
O1 C1 C6 123.3(12) . . ?
C1 C2 C12 118.6(16) . . ?
C3 C2 C1 117.1(17) . . ?
C3 C2 C12 124.3(16) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 C2 123.8(16) . . ?
C4 C3 H3 118.1 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.9(17) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(19) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.9(14) . . ?
C1 C6 C7 122.4(12) . . ?
C5 C6 C7 116.5(14) . . ?
C6 C7 H7 117.8 . . ?
N2 C7 C6 124.4(13) . . ?
N2 C7 H7 117.8 . . ?
N1 C8 N4 125.9(11) . . ?
N3 C8 N1 117.2(10) . . ?
N3 C8 N4 116.9(10) . . ?
C10 C9 H9 117.9 . . ?
N4 C9 H9 117.9 . . ?
N4 C9 C10 124.1(12) . . ?
C9 C10 H10 121.7 . . ?
C9 C10 C11 116.6(12) . . ?
C11 C10 H10 121.7 . . ?
C10 C11 H11 119.2 . . ?
N1 C11 C10 121.7(12) . . ?
N1 C11 H11 119.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C13 H13A 109.5 . . ?
C15 C13 H13B 109.5 . . ?
C15 C13 H13C 109.5 . . ?
C19 C14 C15 119.8(13) . . ?
O2 C14 C15 118.1(13) . . ?
O2 C14 C19 122.1(11) . . ?
C14 C15 C13 119.3(14) . . ?
C16 C15 C13 122.3(13) . . ?
C16 C15 C14 118.4(16) . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C17 122.9(14) . . ?
C17 C16 H16 118.6 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(15) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(17) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 C18 119.7(13) . . ?
C14 C19 C20 122.7(12) . . ?
C18 C19 C20 117.5(13) . . ?
C19 C20 H20 117.3 . . ?
N6 C20 C19 125.3(12) . . ?
N6 C20 H20 117.3 . . ?
N5 C21 N7 118.2(10) . . ?
N5 C21 N8 125.2(11) . . ?
N7 C21 N8 116.5(10) . . ?
C23 C22 H22 118.6 . . ?
N8 C22 H22 118.6 . . ?
N8 C22 C23 122.8(12) . . ?
C22 C23 H23 121.7 . . ?
C24 C23 C22 116.6(12) . . ?
C24 C23 H23 121.7 . . ?
C23 C24 H24 118.6 . . ?
N5 C24 C23 122.7(11) . . ?
N5 C24 H24 118.6 . . ?
C8 N1 Fe1 116.3(8) . . ?
C11 N1 Fe1 126.5(8) . . ?
C11 N1 C8 116.8(11) . . ?
C7 N2 Fe1 127.9(9) . . ?
C7 N2 N3 116.8(10) . . ?
N3 N2 Fe1 115.2(7) . . ?
C8 N3 N2 117.1(10) . . ?
C8 N3 H3A 121.4 . . ?
N2 N3 H3A 121.4 . . ?
C9 N4 C8 114.8(11) . . ?
C20 N6 Fe1 127.6(8) . . ?
C20 N6 N7 117.1(10) . . ?
N7 N6 Fe1 115.1(7) . . ?
C21 N5 Fe1 115.2(7) . . ?
C21 N5 C24 116.8(10) . . ?
C24 N5 Fe1 128.0(8) . . ?
C21 N7 N6 117.2(9) . . ?
C21 N7 H7A 121.4 . . ?
N6 N7 H7A 121.4 . . ?
C22 N8 C21 115.6(11) . . ?
C1 O1 Fe1 136.3(9) . . ?
C14 O2 Fe1 137.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N2 N3 C8 4.0(13) . . . . ?
Fe1 N6 N7 C21 -1.3(14) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C1 C6 C7 N2 -1.9(19) . . . . ?
C2 C1 C6 C5 2.8(19) . . . . ?
C2 C1 C6 C7 -172.3(12) . . . . ?
C2 C1 O1 Fe1 171.6(9) . . . . ?
C2 C3 C4 C5 4(3) . . . . ?
C3 C4 C5 C6 -3(2) . . . . ?
C4 C5 C6 C1 0(2) . . . . ?
C4 C5 C6 C7 175.4(14) . . . . ?
C5 C6 C7 N2 -177.2(13) . . . . ?
C6 C1 C2 C3 -2.4(19) . . . . ?
C6 C1 C2 C12 178.2(13) . . . . ?
C6 C1 O1 Fe1 -10(2) . . . . ?
C6 C7 N2 Fe1 -4.7(18) . . . . ?
C6 C7 N2 N3 177.5(11) . . . . ?
C7 N2 N3 C8 -177.9(11) . . . . ?
C9 C10 C11 N1 -2(2) . . . . ?
C10 C9 N4 C8 -0.4(19) . . . . ?
C10 C11 N1 Fe1 175.2(10) . . . . ?
C10 C11 N1 C8 2.3(18) . . . . ?
C12 C2 C3 C4 178.6(16) . . . . ?
C13 C15 C16 C17 179.9(15) . . . . ?
C14 C15 C16 C17 1(2) . . . . ?
C14 C19 C20 N6 -1(2) . . . . ?
C15 C14 C19 C18 1.2(19) . . . . ?
C15 C14 C19 C20 177.8(12) . . . . ?
C15 C14 O2 Fe1 -171.3(9) . . . . ?
C15 C16 C17 C18 -1(3) . . . . ?
C16 C17 C18 C19 1(2) . . . . ?
C17 C18 C19 C14 -1(2) . . . . ?
C17 C18 C19 C20 -177.7(14) . . . . ?
C18 C19 C20 N6 175.9(13) . . . . ?
C19 C14 C15 C13 180.0(13) . . . . ?
C19 C14 C15 C16 -1(2) . . . . ?
C19 C14 O2 Fe1 10(2) . . . . ?
C19 C20 N6 Fe1 0.1(19) . . . . ?
C19 C20 N6 N7 -175.3(12) . . . . ?
C20 N6 N7 C21 174.7(11) . . . . ?
C22 C23 C24 N5 1(2) . . . . ?
C23 C22 N8 C21 -3(2) . . . . ?
C23 C24 N5 Fe1 -177.0(11) . . . . ?
C23 C24 N5 C21 1.9(19) . . . . ?
N1 Fe1 O1 C1 -4(2) . . . . ?
N1 Fe1 O2 C14 82.9(13) . . . . ?
N1 C8 N3 N2 -6.3(16) . . . . ?
N1 C8 N4 C9 0.5(18) . . . . ?
N2 Fe1 O1 C1 3.2(12) . . . . ?
N2 Fe1 O2 C14 155.8(12) . . . . ?
N3 C8 N1 Fe1 5.4(14) . . . . ?
N3 C8 N1 C11 179.1(11) . . . . ?
N3 C8 N4 C9 -180.0(11) . . . . ?
N4 C8 N1 Fe1 -175.1(9) . . . . ?
N4 C8 N1 C11 -1.4(18) . . . . ?
N4 C8 N3 N2 174.2(10) . . . . ?
N4 C9 C10 C11 1(2) . . . . ?
N6 Fe1 O1 C1 167.4(12) . . . . ?
N6 Fe1 O2 C14 -8.3(12) . . . . ?
N5 Fe1 O1 C1 93.5(12) . . . . ?
N5 Fe1 O2 C14 -8(2) . . . . ?
N5 C21 N7 N6 5.5(17) . . . . ?
N5 C21 N8 C22 6.5(19) . . . . ?
N7 C21 N5 Fe1 -6.8(14) . . . . ?
N7 C21 N5 C24 174.1(12) . . . . ?
N7 C21 N8 C22 -173.7(12) . . . . ?
N8 C21 N5 Fe1 172.9(10) . . . . ?
N8 C21 N5 C24 -6.1(18) . . . . ?
N8 C21 N7 N6 -174.3(11) . . . . ?
N8 C22 C23 C24 -1(2) . . . . ?
O1 Fe1 O2 C14 -117.8(13) . . . . ?
O1 C1 C2 C3 176.5(12) . . . . ?
O1 C1 C2 C12 -3.0(19) . . . . ?
O1 C1 C6 C5 -176.0(13) . . . . ?
O1 C1 C6 C7 8.9(19) . . . . ?
O2 Fe1 O1 C1 -106.9(12) . . . . ?
O2 C14 C15 C13 1.2(19) . . . . ?
O2 C14 C15 C16 179.9(13) . . . . ?
O2 C14 C19 C18 179.9(13) . . . . ?
O2 C14 C19 C20 -3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.218
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1568653'
_audit_update_record             
;
2017-08-13 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H21 Fe N8 O2, Cl, C H4 O'
_chemical_formula_sum            'C25 H25 Cl Fe N8 O3'
_chemical_formula_weight         576.83
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.922(5)
_cell_length_b                   11.751(6)
_cell_length_c                   11.994(6)
_cell_angle_alpha                93.148(8)
_cell_angle_beta                 97.862(9)
_cell_angle_gamma                105.387(8)
_cell_volume                     1329.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2007
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.095
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.1461
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9644
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.050
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1797
_reflns_number_total             4545
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'crystalstructure 3.6.0 (Rigaku, 2004)'
_computing_data_collection       'crystalstructure 3.6.0 (Rigaku, 2004)'
_computing_data_reduction        'crystalstructure 3.6.0 (Rigaku, 2004)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1927
_refine_ls_R_factor_gt           0.1124
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1981P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2726
_refine_ls_wR_factor_ref         0.3647
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Me refined with riding coordinates:
 C12(H12A,H12B,H12C)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), N3(H3A), N7(H7A)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.12269(13) 0.27976(10) -0.26219(12) 0.0669(6) Uani 1 1 d . . . . .
Cl1 Cl -0.1032(3) 0.22563(19) 0.3557(2) 0.0804(9) Uani 1 1 d . . . . .
C1 C -0.0422(10) 0.1690(8) -0.0907(9) 0.069(3) Uani 1 1 d . . . . .
C2 C -0.1082(11) 0.1937(9) 0.0007(9) 0.080(3) Uani 1 1 d . . . . .
C3 C -0.2054(11) 0.1014(10) 0.0393(9) 0.084(3) Uani 1 1 d . . . . .
H3 H -0.2502 0.1177 0.0990 0.101 Uiso 1 1 calc R . . . .
C4 C -0.2366(11) -0.0137(10) -0.0092(10) 0.088(3) Uani 1 1 d . . . . .
H4 H -0.3029 -0.0737 0.0171 0.105 Uiso 1 1 calc R . . . .
C5 C -0.1696(11) -0.0394(8) -0.0962(10) 0.087(3) Uani 1 1 d . . . . .
H5 H -0.1878 -0.1176 -0.1262 0.104 Uiso 1 1 calc R . . . .
C6 C -0.0745(10) 0.0505(8) -0.1406(8) 0.068(2) Uani 1 1 d . . . . .
C7 C -0.0091(9) 0.0167(7) -0.2290(8) 0.064(2) Uani 1 1 d . . . . .
H7 H -0.0226 -0.0638 -0.2480 0.076 Uiso 1 1 calc R . . . .
C8 C 0.1842(9) 0.1245(8) -0.4417(8) 0.067(3) Uani 1 1 d . . . . .
C9 C 0.3003(10) 0.1637(9) -0.5934(10) 0.082(3) Uani 1 1 d . . . . .
H9 H 0.3457 0.1407 -0.6501 0.099 Uiso 1 1 calc R . . . .
C10 C 0.2942(10) 0.2790(9) -0.5819(10) 0.083(3) Uani 1 1 d . . . . .
H10 H 0.3307 0.3328 -0.6317 0.100 Uiso 1 1 calc R . . . .
C11 C 0.2329(10) 0.3121(8) -0.4953(8) 0.073(3) Uani 1 1 d . . . . .
H11 H 0.2271 0.3897 -0.4864 0.087 Uiso 1 1 calc R . . . .
C12 C -0.0696(10) 0.3180(9) 0.0561(9) 0.083(3) Uani 1 1 d . . . . .
H12A H -0.0016 0.3687 0.0178 0.124 Uiso 1 1 calc R . . . .
H12B H -0.0295 0.3194 0.1339 0.124 Uiso 1 1 calc R . . . .
H12C H -0.1528 0.3455 0.0520 0.124 Uiso 1 1 calc R . . . .
C13 C 0.4226(9) 0.4182(7) -0.1756(8) 0.065(2) Uani 1 1 d . . . . .
C14 C 0.5568(11) 0.4107(9) -0.1273(9) 0.078(3) Uani 1 1 d . . . . .
C15 C 0.6659(11) 0.5111(9) -0.0939(11) 0.099(4) Uani 1 1 d . . . . .
H15 H 0.7533 0.5044 -0.0603 0.119 Uiso 1 1 calc R . . . .
C16 C 0.6478(12) 0.6258(9) -0.1099(11) 0.100(4) Uani 1 1 d . . . . .
H16 H 0.7207 0.6940 -0.0841 0.119 Uiso 1 1 calc R . . . .
C17 C 0.5188(10) 0.6327(8) -0.1647(9) 0.080(3) Uani 1 1 d . . . . .
H17 H 0.5076 0.7067 -0.1801 0.096 Uiso 1 1 calc R . . . .
C18 C 0.4032(9) 0.5311(7) -0.1984(8) 0.066(2) Uani 1 1 d . . . . .
C19 C 0.2732(10) 0.5495(8) -0.2504(9) 0.074(3) Uani 1 1 d . . . . .
C20 C -0.0822(10) 0.4101(8) -0.3631(8) 0.071(3) Uani 1 1 d . . . . .
C21 C -0.3126(12) 0.3513(9) -0.4368(11) 0.098(4) Uani 1 1 d . . . . .
H21 H -0.3935 0.3685 -0.4717 0.117 Uiso 1 1 calc R . . . .
C22 C -0.3192(10) 0.2392(9) -0.4206(9) 0.077(3) Uani 1 1 d . . . . .
H22 H -0.4051 0.1810 -0.4381 0.093 Uiso 1 1 calc R . . . .
C23 C -0.2008(10) 0.2101(9) -0.3787(10) 0.079(3) Uani 1 1 d . . . . .
H23 H -0.2030 0.1310 -0.3734 0.095 Uiso 1 1 calc R . . . .
C24 C 0.5752(11) 0.2882(8) -0.1116(11) 0.103(4) Uani 1 1 d . . . . .
H24A H 0.5435 0.2394 -0.1821 0.154 Uiso 1 1 calc GR . . . .
H24B H 0.5204 0.2532 -0.0559 0.154 Uiso 1 1 calc GR . . . .
H24C H 0.6733 0.2945 -0.0868 0.154 Uiso 1 1 calc GR . . . .
C25 C -0.4664(13) 0.0101(10) 0.2589(13) 0.127(5) Uani 1 1 d . . . . .
H25A H -0.4801 -0.0274 0.3272 0.190 Uiso 1 1 calc GR . . . .
H25B H -0.3917 -0.0116 0.2275 0.190 Uiso 1 1 calc GR . . . .
H25C H -0.5523 -0.0153 0.2054 0.190 Uiso 1 1 calc GR . . . .
N1 N 0.1807(8) 0.2359(6) -0.4224(6) 0.065(2) Uani 1 1 d . . . . .
N2 N 0.0696(7) 0.0922(6) -0.2856(6) 0.063(2) Uani 1 1 d . . . . .
N3 N 0.1247(7) 0.0467(6) -0.3719(7) 0.068(2) Uani 1 1 d . . . . .
H3A H 0.1212 -0.0272 -0.3806 0.082 Uiso 1 1 calc R . . . .
N4 N 0.2425(8) 0.0814(7) -0.5250(7) 0.075(2) Uani 1 1 d . . . . .
N5 N -0.0778(7) 0.2974(6) -0.3441(6) 0.0621(19) Uani 1 1 d . . . . .
N6 N 0.1556(8) 0.4647(6) -0.2810(7) 0.066(2) Uani 1 1 d . . . . .
N7 N 0.0407(8) 0.4967(7) -0.3290(8) 0.081(3) Uani 1 1 d . . . . .
H7A H 0.0455 0.5698 -0.3375 0.097 Uiso 1 1 calc R . . . .
N8 N -0.1950(9) 0.4408(7) -0.4052(8) 0.088(3) Uani 1 1 d . . . . .
O1 O 0.0484(7) 0.2570(5) -0.1268(6) 0.0736(18) Uani 1 1 d . . . . .
O2 O 0.3161(6) 0.3213(5) -0.2024(5) 0.0690(17) Uani 1 1 d . . . . .
O3 O -0.4312(9) 0.1296(8) 0.2824(11) 0.132(3) Uani 1 1 d . . . . .
H3B H -0.3463 0.1543 0.3067 0.197 Uiso 1 1 calc GR . . . .


_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 2.155(7) . ?
Fe1 N2 2.119(6) . ?
Fe1 N5 2.161(7) . ?
Fe1 N6 2.139(7) . ?
Fe1 O1 1.877(6) . ?
Fe1 O2 1.877(6) . ?
C1 C2 1.406(13) . ?
C1 C6 1.421(12) . ?
C1 O1 1.313(10) . ?
C2 C3 1.393(13) . ?
C2 C12 1.499(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(11) . ?
C6 C7 1.409(12) . ?
C7 H7 0.9300 . ?
C7 N2 1.304(10) . ?
C8 N1 1.327(10) . ?
C8 N3 1.349(10) . ?
C8 N4 1.359(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(13) . ?
C9 N4 1.364(12) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(12) . ?
C11 H11 0.9300 . ?
C11 N1 1.341(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.404(12) . ?
C13 C18 1.426(11) . ?
C13 O2 1.320(10) . ?
C14 C15 1.370(13) . ?
C14 C24 1.517(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.426(14) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.413(12) . ?
C18 C19 1.429(12) . ?
C19 N6 1.310(11) . ?
C20 N5 1.368(10) . ?
C20 N7 1.360(11) . ?
C20 N8 1.310(11) . ?
C21 H21 0.9300 . ?
C21 C22 1.328(13) . ?
C21 N8 1.340(12) . ?
C22 H22 0.9300 . ?
C22 C23 1.349(12) . ?
C23 H23 0.9300 . ?
C23 N5 1.366(12) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O3 1.357(12) . ?
N2 N3 1.379(9) . ?
N3 H3A 0.8600 . ?
N6 N7 1.358(9) . ?
N7 H7A 0.8600 . ?
O3 H3B 0.8200 . ?

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 N5 91.4(3) . . ?
N2 Fe1 N1 73.7(3) . . ?
N2 Fe1 N5 96.6(3) . . ?
N2 Fe1 N6 166.1(3) . . ?
N6 Fe1 N1 95.7(3) . . ?
N6 Fe1 N5 74.3(3) . . ?
O1 Fe1 N1 158.8(3) . . ?
O1 Fe1 N2 85.2(3) . . ?
O1 Fe1 N5 89.7(3) . . ?
O1 Fe1 N6 104.9(3) . . ?
O1 Fe1 O2 98.7(3) . . ?
O2 Fe1 N1 87.4(3) . . ?
O2 Fe1 N2 102.8(2) . . ?
O2 Fe1 N5 159.4(2) . . ?
O2 Fe1 N6 85.4(3) . . ?
C2 C1 C6 119.3(8) . . ?
O1 C1 C2 118.5(9) . . ?
O1 C1 C6 122.1(8) . . ?
C1 C2 C12 119.2(9) . . ?
C3 C2 C1 119.1(10) . . ?
C3 C2 C12 121.7(10) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.5(10) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(9) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(10) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.2(9) . . ?
C5 C6 C7 117.5(9) . . ?
C7 C6 C1 123.3(8) . . ?
C6 C7 H7 118.2 . . ?
N2 C7 C6 123.5(8) . . ?
N2 C7 H7 118.2 . . ?
N1 C8 N3 116.9(8) . . ?
N1 C8 N4 126.2(8) . . ?
N3 C8 N4 116.9(8) . . ?
C10 C9 H9 118.7 . . ?
N4 C9 H9 118.7 . . ?
N4 C9 C10 122.6(9) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.8(9) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 H11 119.1 . . ?
N1 C11 C10 121.8(9) . . ?
N1 C11 H11 119.1 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.4(9) . . ?
O2 C13 C14 120.4(8) . . ?
O2 C13 C18 120.2(8) . . ?
C13 C14 C24 117.6(9) . . ?
C15 C14 C13 120.8(9) . . ?
C15 C14 C24 121.6(9) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(10) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.1(10) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.2(9) . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C19 124.5(8) . . ?
C17 C18 C13 118.2(9) . . ?
C17 C18 C19 117.2(8) . . ?
N6 C19 C18 124.2(8) . . ?
N7 C20 N5 115.7(8) . . ?
N8 C20 N5 125.5(9) . . ?
N8 C20 N7 118.6(8) . . ?
C22 C21 H21 118.4 . . ?
C22 C21 N8 123.1(10) . . ?
N8 C21 H21 118.4 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(10) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 N5 119.6(8) . . ?
N5 C23 H23 120.2 . . ?
C14 C24 H24A 109.5 . . ?
C14 C24 H24B 109.5 . . ?
C14 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
C8 N1 Fe1 115.4(6) . . ?
C8 N1 C11 117.1(8) . . ?
C11 N1 Fe1 126.7(7) . . ?
C7 N2 Fe1 127.5(6) . . ?
C7 N2 N3 117.4(7) . . ?
N3 N2 Fe1 115.1(5) . . ?
C8 N3 N2 116.3(7) . . ?
C8 N3 H3A 121.8 . . ?
N2 N3 H3A 121.8 . . ?
C8 N4 C9 114.4(8) . . ?
C20 N5 Fe1 115.9(6) . . ?
C23 N5 Fe1 128.1(6) . . ?
C23 N5 C20 116.0(8) . . ?
C19 N6 Fe1 127.1(6) . . ?
C19 N6 N7 117.1(7) . . ?
N7 N6 Fe1 115.8(6) . . ?
C20 N7 H7A 120.9 . . ?
N6 N7 C20 118.2(7) . . ?
N6 N7 H7A 120.9 . . ?
C20 N8 C21 115.6(8) . . ?
C1 O1 Fe1 134.2(7) . . ?
C13 O2 Fe1 138.5(5) . . ?
C25 O3 H3B 109.5 . . ?

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
C7 H7 Cl1 0.93 2.88 3.651(9) 141.6 2
C9 H9 O3 0.93 2.49 3.326(13) 149.4 1_654
C11 H11 N8 0.93 2.50 3.292(11) 142.7 2_564
C23 H23 N4 0.93 2.62 3.453(13) 148.7 2_554
N3 H3A Cl1 0.86 2.33 3.169(7) 165.2 2
N7 H7A Cl1 0.86 2.35 3.198(8) 169.6 2_565

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1568652'
_audit_update_record             
;
2017-08-13 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H22 Fe N8 O2, B F4'
_chemical_formula_sum            'C24 H22 B F4 Fe N8 O2'
_chemical_formula_weight         597.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3037(19)
_cell_length_b                   18.376(4)
_cell_length_c                   15.821(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.58(3)
_cell_angle_gamma                90
_cell_volume                     2605.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22518
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.008
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3368
_reflns_number_total             5661
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'crystalstructure 3.6.0 (Rigaku, 2004)'
_computing_data_collection       'crystalstructure 3.6.0 (Rigaku, 2004)'
_computing_data_reduction        'crystalstructure 3.6.0 (Rigaku, 2004)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0079(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1022P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1994
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), N3(H3A), N7(H7A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.81573(6) 0.89147(3) 0.24033(3) 0.0486(2) Uani 1 1 d . . . . .
B1 B 1.4261(8) 0.7750(4) 0.4403(5) 0.0901(19) Uani 1 1 d . . . . .
F1 F 1.3277(8) 0.8100(4) 0.4664(5) 0.285(5) Uani 1 1 d . . . . .
F2 F 1.3706(6) 0.7082(3) 0.4031(3) 0.180(2) Uani 1 1 d . . . . .
F3 F 1.5435(6) 0.7559(2) 0.5051(3) 0.1656(19) Uani 1 1 d . . . . .
F4 F 1.4696(4) 0.81131(17) 0.3783(2) 0.1052(10) Uani 1 1 d . . . . .
C1 C 0.4985(4) 0.94271(19) 0.1804(3) 0.0584(10) Uani 1 1 d . . . . .
C2 C 0.3783(5) 0.9685(2) 0.2112(4) 0.0695(13) Uani 1 1 d . . . . .
C3 C 0.2417(5) 0.9790(3) 0.1507(4) 0.0825(15) Uani 1 1 d . . . . .
H3 H 0.1620 0.9956 0.1704 0.099 Uiso 1 1 calc R . . . .
C4 C 0.2192(5) 0.9656(3) 0.0619(5) 0.0912(17) Uani 1 1 d . . . . .
H4 H 0.1260 0.9740 0.0232 0.109 Uiso 1 1 calc R . . . .
C5 C 0.3337(5) 0.9400(2) 0.0309(4) 0.0775(13) Uani 1 1 d . . . . .
H5 H 0.3186 0.9305 -0.0286 0.093 Uiso 1 1 calc R . . . .
C6 C 0.4763(4) 0.9280(2) 0.0909(3) 0.0607(11) Uani 1 1 d . . . . .
C7 C 0.5916(4) 0.89933(19) 0.0542(3) 0.0556(10) Uani 1 1 d . . . . .
H7 H 0.5691 0.8928 -0.0063 0.067 Uiso 1 1 calc R . . . .
C8 C 0.9508(4) 0.82603(19) 0.1045(3) 0.0505(9) Uani 1 1 d . . . . .
C9 C 1.1729(4) 0.7733(2) 0.1096(3) 0.0659(11) Uani 1 1 d . . . . .
H9 H 1.2368 0.7498 0.0823 0.079 Uiso 1 1 calc R . . . .
C10 C 1.2248(4) 0.7897(2) 0.1966(3) 0.0639(11) Uani 1 1 d . . . . .
H10 H 1.3223 0.7789 0.2279 0.077 Uiso 1 1 calc R . . . .
C11 C 1.1277(4) 0.8227(2) 0.2364(3) 0.0531(9) Uani 1 1 d . . . . .
H11 H 1.1583 0.8323 0.2963 0.064 Uiso 1 1 calc R . . . .
C12 C 0.4030(6) 0.9823(3) 0.3080(4) 0.0859(16) Uani 1 1 d . . . . .
H12A H 0.3122 0.9998 0.3186 0.129 Uiso 1 1 calc R . . . .
H12B H 0.4801 1.0181 0.3272 0.129 Uiso 1 1 calc R . . . .
H12C H 0.4323 0.9379 0.3398 0.129 Uiso 1 1 calc R . . . .
C13 C 1.0204(5) 1.0089(2) 0.3368(3) 0.0611(11) Uani 1 1 d . . . . .
C14 C 1.0629(5) 1.0827(2) 0.3314(4) 0.0751(14) Uani 1 1 d . . . . .
C15 C 1.1685(7) 1.1117(3) 0.4021(5) 0.0919(19) Uani 1 1 d . . . . .
H15 H 1.1955 1.1602 0.3995 0.110 Uiso 1 1 calc R . . . .
C16 C 1.2349(7) 1.0725(3) 0.4754(5) 0.0954(18) Uani 1 1 d . . . . .
H16 H 1.3081 1.0940 0.5204 0.114 Uiso 1 1 calc R . . . .
C17 C 1.1938(5) 1.0009(3) 0.4832(3) 0.0798(14) Uani 1 1 d . . . . .
H17 H 1.2387 0.9743 0.5333 0.096 Uiso 1 1 calc R . . . .
C18 C 1.0815(5) 0.9680(2) 0.4131(3) 0.0627(11) Uani 1 1 d . . . . .
C19 C 1.0339(4) 0.8974(2) 0.4282(3) 0.0583(10) Uani 1 1 d . . . . .
H19 H 1.0787 0.8755 0.4819 0.070 Uiso 1 1 calc R . . . .
C20 C 0.7852(4) 0.75529(19) 0.3414(2) 0.0496(9) Uani 1 1 d . . . . .
C21 C 0.6316(4) 0.6578(2) 0.3121(3) 0.0603(10) Uani 1 1 d . . . . .
H21 H 0.5959 0.6146 0.3295 0.072 Uiso 1 1 calc R . . . .
C22 C 0.5699(5) 0.6827(2) 0.2270(3) 0.0601(10) Uani 1 1 d . . . . .
H22 H 0.4961 0.6565 0.1873 0.072 Uiso 1 1 calc R . . . .
C23 C 0.6223(4) 0.7470(2) 0.2042(3) 0.0558(9) Uani 1 1 d . . . . .
H23 H 0.5816 0.7656 0.1482 0.067 Uiso 1 1 calc R . . . .
C24 C 0.9882(6) 1.1253(3) 0.2499(4) 0.0982(19) Uani 1 1 d . . . . .
H24A H 1.0268 1.1740 0.2552 0.147 Uiso 1 1 calc R . . . .
H24B H 0.8825 1.1267 0.2430 0.147 Uiso 1 1 calc R . . . .
H24C H 1.0077 1.1023 0.1996 0.147 Uiso 1 1 calc R . . . .
N2 N 0.7250(3) 0.88213(15) 0.1012(2) 0.0501(7) Uani 1 1 d . . . . .
N3 N 0.8161(3) 0.84952(18) 0.0562(2) 0.0593(8) Uani 1 1 d . . . . .
H3A H 0.7884 0.8444 0.0001 0.071 Uiso 1 1 calc R . . . .
N1 N 0.9882(3) 0.84145(16) 0.1900(2) 0.0492(7) Uani 1 1 d . . . . .
N4 N 1.0346(3) 0.78939(18) 0.0615(2) 0.0577(8) Uani 1 1 d . . . . .
N6 N 0.9306(3) 0.86056(16) 0.3714(2) 0.0519(7) Uani 1 1 d . . . . .
N7 N 0.8950(4) 0.79314(17) 0.3982(2) 0.0583(8) Uani 1 1 d . . . . .
H7A H 0.9405 0.7758 0.4488 0.070 Uiso 1 1 calc R . . . .
N5 N 0.7321(3) 0.78451(15) 0.26121(19) 0.0477(7) Uani 1 1 d . . . . .
N8 N 0.7395(4) 0.69324(16) 0.3695(2) 0.0556(8) Uani 1 1 d . . . . .
O1 O 0.6290(3) 0.93276(14) 0.23776(19) 0.0622(7) Uani 1 1 d . . . . .
O2 O 0.9214(3) 0.97969(14) 0.2675(2) 0.0635(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N2 2.143(3) . ?
Fe1 N1 2.177(3) . ?
Fe1 N6 2.139(3) . ?
Fe1 N5 2.171(3) . ?
Fe1 O1 1.886(3) . ?
Fe1 O2 1.885(3) . ?
B1 F1 1.275(8) . ?
B1 F2 1.398(8) . ?
B1 F3 1.328(7) . ?
B1 F4 1.336(7) . ?
C1 C2 1.416(5) . ?
C1 C6 1.401(6) . ?
C1 O1 1.319(5) . ?
C2 C3 1.383(7) . ?
C2 C12 1.508(7) . ?
C3 C4 1.386(8) . ?
C4 C5 1.371(7) . ?
C5 C6 1.426(6) . ?
C6 C7 1.449(6) . ?
C7 N2 1.303(5) . ?
C8 N3 1.352(4) . ?
C8 N1 1.333(5) . ?
C8 N4 1.345(5) . ?
C9 C10 1.365(6) . ?
C9 N4 1.340(5) . ?
C10 C11 1.373(5) . ?
C11 N1 1.352(5) . ?
C13 C14 1.420(6) . ?
C13 C18 1.406(6) . ?
C13 O2 1.341(5) . ?
C14 C15 1.381(7) . ?
C14 C24 1.509(8) . ?
C15 C16 1.364(8) . ?
C16 C17 1.386(7) . ?
C17 C18 1.437(6) . ?
C18 C19 1.412(6) . ?
C19 N6 1.313(5) . ?
C20 N7 1.358(4) . ?
C20 N5 1.343(5) . ?
C20 N8 1.335(5) . ?
C21 C22 1.392(6) . ?
C21 N8 1.329(5) . ?
C22 C23 1.363(5) . ?
C23 N5 1.356(4) . ?
N2 N3 1.381(4) . ?
N6 N7 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Fe1 N1 73.50(11) . . ?
N2 Fe1 N5 91.46(11) . . ?
N6 Fe1 N2 158.65(12) . . ?
N6 Fe1 N1 90.99(12) . . ?
N6 Fe1 N5 73.64(11) . . ?
N5 Fe1 N1 90.17(11) . . ?
O1 Fe1 N2 84.48(12) . . ?
O1 Fe1 N1 157.98(12) . . ?
O1 Fe1 N6 110.18(12) . . ?
O1 Fe1 N5 90.11(12) . . ?
O2 Fe1 N2 109.89(12) . . ?
O2 Fe1 N1 93.20(12) . . ?
O2 Fe1 N6 85.03(12) . . ?
O2 Fe1 N5 158.46(12) . . ?
O2 Fe1 O1 94.58(12) . . ?
F1 B1 F2 111.3(7) . . ?
F1 B1 F3 113.4(7) . . ?
F1 B1 F4 111.8(5) . . ?
F3 B1 F2 103.1(5) . . ?
F3 B1 F4 110.5(6) . . ?
F4 B1 F2 106.3(6) . . ?
C6 C1 C2 119.8(4) . . ?
O1 C1 C2 118.4(4) . . ?
O1 C1 C6 121.8(3) . . ?
C1 C2 C12 119.2(4) . . ?
C3 C2 C1 118.1(5) . . ?
C3 C2 C12 122.7(4) . . ?
C2 C3 C4 122.5(4) . . ?
C5 C4 C3 120.2(5) . . ?
C4 C5 C6 119.2(5) . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 C7 123.5(4) . . ?
C5 C6 C7 116.4(4) . . ?
N2 C7 C6 123.6(4) . . ?
N1 C8 N3 117.1(3) . . ?
N1 C8 N4 126.2(3) . . ?
N4 C8 N3 116.7(4) . . ?
N4 C9 C10 123.3(4) . . ?
C9 C10 C11 117.5(4) . . ?
N1 C11 C10 121.2(4) . . ?
C18 C13 C14 120.5(4) . . ?
O2 C13 C14 118.3(4) . . ?
O2 C13 C18 121.2(3) . . ?
C13 C14 C24 118.3(5) . . ?
C15 C14 C13 117.9(5) . . ?
C15 C14 C24 123.7(5) . . ?
C16 C15 C14 123.1(5) . . ?
C15 C16 C17 120.2(5) . . ?
C16 C17 C18 119.5(6) . . ?
C13 C18 C17 118.7(4) . . ?
C13 C18 C19 124.4(4) . . ?
C19 C18 C17 116.9(5) . . ?
N6 C19 C18 124.2(4) . . ?
N5 C20 N7 116.2(3) . . ?
N8 C20 N7 117.8(3) . . ?
N8 C20 N5 126.0(3) . . ?
N8 C21 C22 122.7(3) . . ?
C23 C22 C21 117.1(4) . . ?
N5 C23 C22 121.7(4) . . ?
C7 N2 Fe1 128.2(3) . . ?
C7 N2 N3 115.7(3) . . ?
N3 N2 Fe1 115.9(2) . . ?
C8 N3 N2 116.8(3) . . ?
C8 N1 Fe1 116.3(2) . . ?
C8 N1 C11 116.6(3) . . ?
C11 N1 Fe1 127.1(3) . . ?
C9 N4 C8 115.0(3) . . ?
C19 N6 Fe1 127.6(3) . . ?
C19 N6 N7 116.4(3) . . ?
N7 N6 Fe1 116.0(2) . . ?
C20 N7 N6 117.2(3) . . ?
C20 N5 Fe1 116.7(2) . . ?
C20 N5 C23 116.4(3) . . ?
C23 N5 Fe1 126.6(2) . . ?
C21 N8 C20 116.1(3) . . ?
C1 O1 Fe1 138.0(3) . . ?
C13 O2 Fe1 137.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-100K
_database_code_depnum_ccdc_archive 'CCDC 1581049'
_audit_update_record             
;
2017-10-20 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H22 Fe N8 O2, Cl O4'
_chemical_formula_sum            'C24 H22 Cl Fe N8 O6'
_chemical_formula_weight         609.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1Fe1Cl1
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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2382(2)
_cell_length_b                   18.0876(4)
_cell_length_c                   15.7870(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.325(3)
_cell_angle_gamma                90
_cell_volume                     2555.94(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3958
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9910
_cell_measurement_theta_min      4.8910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9644
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.244
_diffrn_reflns_theta_min         3.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  32.00   1.00    1.00    --  -41.49  57.00  90.00   99
  2  ω    -94.00 -19.00   1.00    1.00    --  -41.49 -37.00 -90.00   75
  3  ω     24.00  75.00   1.00    1.00    --   41.49-125.00-180.00   51
  4  ω     75.00 170.00   1.00    3.00    --  107.19  77.00  60.00   95
  5  ω     79.00 158.00   1.00    3.00    --  107.19  61.00 150.00   79
  6  ω     39.00 123.00   1.00    3.00    --  107.19 -45.00 -90.00   84
  7  ω     28.00  80.00   1.00    3.00    --  107.19 -94.00 120.00   52
  8  ω     94.00 127.00   1.00    3.00    --  107.19 125.00-120.00   33
  9  ω     36.00 107.00   1.00    3.00    --  107.19 -94.00-150.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0556384000
_diffrn_orient_matrix_UB_12      0.0593351000
_diffrn_orient_matrix_UB_13      0.0707630000
_diffrn_orient_matrix_UB_21      -0.1167689000
_diffrn_orient_matrix_UB_22      -0.0256399000
_diffrn_orient_matrix_UB_23      0.0484201000
_diffrn_orient_matrix_UB_31      0.1132490000
_diffrn_orient_matrix_UB_32      -0.0555140000
_diffrn_orient_matrix_UB_33      0.0529626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4159
_reflns_number_total             4989
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.196
_refine_diff_density_min         -1.127
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0780
_refine_ls_restrained_S_all      1.213
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+40.9619P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2386
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C20(H20), C22(H22), C23(H23), C24(H24), N3(H3A), N7(H7A)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.82388(12) 0.10731(6) 0.74634(8) 0.0118(3) Uani 1 1 d . . . . .
Cl1 Cl 0.4315(2) 0.23088(10) 0.93584(13) 0.0214(4) Uani 1 1 d . . . . .
C1 C 1.0256(8) -0.0121(4) 0.8402(5) 0.0154(15) Uani 1 1 d . . . . .
C2 C 1.0658(8) -0.0874(4) 0.8359(6) 0.0193(16) Uani 1 1 d . . . . .
C3 C 1.1715(9) -0.1178(4) 0.9049(6) 0.0254(19) Uani 1 1 d . . . . .
H3 H 1.1983 -0.1670 0.9014 0.031 Uiso 1 1 calc R . . . .
C4 C 1.2394(9) -0.0773(5) 0.9794(6) 0.0251(19) Uani 1 1 d . . . . .
H4 H 1.3125 -0.0986 1.0240 0.030 Uiso 1 1 calc R . . . .
C5 C 1.1958(8) -0.0047(5) 0.9856(6) 0.0226(17) Uani 1 1 d . . . . .
H5 H 1.2381 0.0227 1.0354 0.027 Uiso 1 1 calc R . . . .
C6 C 1.0874(8) 0.0283(4) 0.9167(5) 0.0154(15) Uani 1 1 d . . . . .
C7 C 1.0402(7) 0.1020(4) 0.9317(5) 0.0145(15) Uani 1 1 d . . . . .
H7 H 1.0847 0.1244 0.9848 0.017 Uiso 1 1 calc R . . . .
C8 C 0.7936(7) 0.2453(4) 0.8477(5) 0.0111(13) Uani 1 1 d . . . . .
C9 C 0.6386(8) 0.3442(4) 0.8196(5) 0.0175(16) Uani 1 1 d . . . . .
H9 H 0.6022 0.3880 0.8374 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5773(8) 0.3192(4) 0.7357(5) 0.0177(16) Uani 1 1 d . . . . .
H10 H 0.5033 0.3457 0.6969 0.021 Uiso 1 1 calc R . . . .
C11 C 0.6308(8) 0.2531(4) 0.7121(5) 0.0170(15) Uani 1 1 d . . . . .
H11 H 0.5900 0.2340 0.6566 0.020 Uiso 1 1 calc R . . . .
C12 C 0.9940(10) -0.1309(4) 0.7543(6) 0.0266(19) Uani 1 1 d . . . . .
H12A H 1.0280 -0.1812 0.7612 0.040 Uiso 1 1 calc GR . . . .
H12B H 1.0212 -0.1093 0.7048 0.040 Uiso 1 1 calc GR . . . .
H12C H 0.8874 -0.1297 0.7451 0.040 Uiso 1 1 calc GR . . . .
C13 C 0.4136(9) 0.0145(4) 0.8220(6) 0.0237(18) Uani 1 1 d . . . . .
H13A H 0.4204 0.0604 0.8533 0.035 Uiso 1 1 calc GR . . . .
H13B H 0.5053 -0.0124 0.8416 0.035 Uiso 1 1 calc GR . . . .
H13C H 0.3326 -0.0143 0.8327 0.035 Uiso 1 1 calc GR . . . .
C14 C 0.5066(8) 0.0559(4) 0.6931(5) 0.0156(15) Uani 1 1 d . . . . .
C15 C 0.3859(8) 0.0299(4) 0.7255(5) 0.0175(16) Uani 1 1 d . . . . .
C16 C 0.2482(8) 0.0195(4) 0.6678(6) 0.0220(18) Uani 1 1 d . . . . .
H16 H 0.1691 0.0026 0.6893 0.026 Uiso 1 1 calc R . . . .
C17 C 0.2236(8) 0.0337(4) 0.5783(6) 0.0256(19) Uani 1 1 d . . . . .
H17 H 0.1295 0.0264 0.5412 0.031 Uiso 1 1 calc R . . . .
C18 C 0.3404(8) 0.0588(4) 0.5453(6) 0.0241(18) Uani 1 1 d . . . . .
H18 H 0.3247 0.0681 0.4858 0.029 Uiso 1 1 calc R . . . .
C19 C 0.4831(8) 0.0703(4) 0.6018(5) 0.0178(16) Uani 1 1 d . . . . .
C20 C 0.5979(8) 0.0992(4) 0.5645(5) 0.0152(15) Uani 1 1 d . . . . .
H20 H 0.5745 0.1060 0.5043 0.018 Uiso 1 1 calc R . . . .
C21 C 0.9565(8) 0.1729(4) 0.6073(5) 0.0119(14) Uani 1 1 d . . . . .
C22 C 1.1783(8) 0.2284(4) 0.6093(5) 0.0184(16) Uani 1 1 d . . . . .
H22 H 1.2405 0.2537 0.5811 0.022 Uiso 1 1 calc R . . . .
C23 C 1.2326(8) 0.2105(4) 0.6967(5) 0.0153(15) Uani 1 1 d . . . . .
H23 H 1.3301 0.2215 0.7268 0.018 Uiso 1 1 calc R . . . .
C24 C 1.1349(8) 0.1756(4) 0.7367(5) 0.0135(14) Uani 1 1 d . . . . .
H24 H 1.1670 0.1644 0.7959 0.016 Uiso 1 1 calc R . . . .
N1 N 0.7402(6) 0.2156(3) 0.7670(4) 0.0136(12) Uani 1 1 d . . . . .
N2 N 0.9402(6) 0.1392(3) 0.8762(4) 0.0128(12) Uani 1 1 d . . . . .
N3 N 0.9031(6) 0.2078(3) 0.9031(4) 0.0147(13) Uani 1 1 d . . . . .
H3A H 0.9480 0.2258 0.9532 0.018 Uiso 1 1 calc R . . . .
N4 N 0.7469(6) 0.3090(3) 0.8763(4) 0.0145(13) Uani 1 1 d . . . . .
N6 N 0.7307(6) 0.1165(3) 0.6077(4) 0.0130(12) Uani 1 1 d . . . . .
N5 N 0.9968(6) 0.1572(3) 0.6943(4) 0.0139(12) Uani 1 1 d . . . . .
N7 N 0.8223(6) 0.1497(4) 0.5622(4) 0.0165(13) Uani 1 1 d . . . . .
H7A H 0.7940 0.1554 0.5065 0.020 Uiso 1 1 calc R . . . .
N8 N 1.0409(6) 0.2110(3) 0.5639(4) 0.0160(13) Uani 1 1 d . . . . .
O1 O 0.9294(6) 0.0173(3) 0.7727(4) 0.0187(11) Uani 1 1 d . . . . .
O2 O 0.6375(5) 0.0653(3) 0.7475(4) 0.0167(11) Uani 1 1 d . . . . .
O3 O 0.3751(7) 0.3020(4) 0.8996(5) 0.0371(16) Uani 1 1 d . . . . .
O4 O 0.4888(6) 0.1914(3) 0.8724(4) 0.0219(12) Uani 1 1 d . . . . .
O5 O 0.5498(8) 0.2437(4) 1.0118(4) 0.0371(16) Uani 1 1 d . . . . .
O6 O 0.3148(9) 0.1891(4) 0.9567(5) 0.055(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N1 2.161(6) . ?
Fe1 N2 2.145(6) . ?
Fe1 N6 2.151(6) . ?
Fe1 N5 2.166(6) . ?
Fe1 O1 1.890(5) . ?
Fe1 O2 1.886(5) . ?
Cl1 O3 1.451(7) . ?
Cl1 O4 1.434(6) . ?
Cl1 O5 1.428(6) . ?
Cl1 O6 1.420(7) . ?
C1 C2 1.418(10) . ?
C1 C6 1.405(11) . ?
C1 O1 1.319(9) . ?
C2 C3 1.383(12) . ?
C2 C12 1.516(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.415(11) . ?
C6 C7 1.441(10) . ?
C7 H7 0.9300 . ?
C7 N2 1.293(10) . ?
C8 N1 1.357(9) . ?
C8 N3 1.346(9) . ?
C8 N4 1.347(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(11) . ?
C9 N4 1.328(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(10) . ?
C11 H11 0.9300 . ?
C11 N1 1.341(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C15 1.508(12) . ?
C14 C15 1.417(10) . ?
C14 C19 1.427(11) . ?
C14 O2 1.310(9) . ?
C15 C16 1.382(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.398(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(11) . ?
C18 H18 0.9300 . ?
C18 C19 1.412(11) . ?
C19 C20 1.433(10) . ?
C20 H20 0.9300 . ?
C20 N6 1.286(9) . ?
C21 N5 1.362(9) . ?
C21 N7 1.334(9) . ?
C21 N8 1.348(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(11) . ?
C22 N8 1.331(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(10) . ?
C24 H24 0.9300 . ?
C24 N5 1.328(9) . ?
N2 N3 1.383(8) . ?
N3 H3A 0.8600 . ?
N6 N7 1.376(8) . ?
N7 H7A 0.8600 . ?

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 N5 90.2(2) . . ?
N2 Fe1 N1 74.1(2) . . ?
N2 Fe1 N6 158.7(2) . . ?
N2 Fe1 N5 90.5(2) . . ?
N6 Fe1 N1 90.9(2) . . ?
N6 Fe1 N5 74.3(2) . . ?
O1 Fe1 N1 158.7(3) . . ?
O1 Fe1 N2 84.9(2) . . ?
O1 Fe1 N6 110.2(2) . . ?
O1 Fe1 N5 93.1(2) . . ?
O2 Fe1 N1 90.1(2) . . ?
O2 Fe1 N2 110.0(2) . . ?
O2 Fe1 N6 84.5(2) . . ?
O2 Fe1 N5 158.8(2) . . ?
O2 Fe1 O1 94.2(2) . . ?
O4 Cl1 O3 109.0(4) . . ?
O5 Cl1 O3 108.2(4) . . ?
O5 Cl1 O4 109.2(4) . . ?
O6 Cl1 O3 110.1(5) . . ?
O6 Cl1 O4 109.2(4) . . ?
O6 Cl1 O5 111.0(5) . . ?
C6 C1 C2 119.0(7) . . ?
O1 C1 C2 118.7(7) . . ?
O1 C1 C6 122.3(7) . . ?
C1 C2 C12 118.3(7) . . ?
C3 C2 C1 119.1(8) . . ?
C3 C2 C12 122.5(7) . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.5(8) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(8) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(9) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.1(7) . . ?
C1 C6 C7 123.2(7) . . ?
C5 C6 C7 116.6(7) . . ?
C6 C7 H7 117.8 . . ?
N2 C7 C6 124.3(7) . . ?
N2 C7 H7 117.8 . . ?
N3 C8 N1 116.8(6) . . ?
N3 C8 N4 117.7(6) . . ?
N4 C8 N1 125.5(7) . . ?
C10 C9 H9 118.3 . . ?
N4 C9 H9 118.3 . . ?
N4 C9 C10 123.4(7) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 C9 117.0(7) . . ?
C11 C10 H10 121.5 . . ?
C10 C11 H11 119.2 . . ?
N1 C11 C10 121.7(7) . . ?
N1 C11 H11 119.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C13 H13A 109.5 . . ?
C15 C13 H13B 109.5 . . ?
C15 C13 H13C 109.5 . . ?
C15 C14 C19 119.3(7) . . ?
O2 C14 C15 119.2(7) . . ?
O2 C14 C19 121.5(6) . . ?
C14 C15 C13 118.4(7) . . ?
C16 C15 C13 122.6(7) . . ?
C16 C15 C14 119.0(8) . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.2(7) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(8) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(9) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C20 122.5(7) . . ?
C18 C19 C14 119.7(7) . . ?
C18 C19 C20 117.7(8) . . ?
C19 C20 H20 117.4 . . ?
N6 C20 C19 125.3(7) . . ?
N6 C20 H20 117.4 . . ?
N7 C21 N5 117.3(6) . . ?
N7 C21 N8 117.9(6) . . ?
N8 C21 N5 124.8(7) . . ?
C23 C22 H22 118.5 . . ?
N8 C22 H22 118.5 . . ?
N8 C22 C23 122.9(7) . . ?
C22 C23 H23 121.7 . . ?
C24 C23 C22 116.6(7) . . ?
C24 C23 H23 121.7 . . ?
C23 C24 H24 118.6 . . ?
N5 C24 C23 122.7(7) . . ?
N5 C24 H24 118.6 . . ?
C8 N1 Fe1 116.1(5) . . ?
C11 N1 Fe1 126.9(5) . . ?
C11 N1 C8 116.6(6) . . ?
C7 N2 Fe1 127.8(5) . . ?
C7 N2 N3 116.7(6) . . ?
N3 N2 Fe1 115.5(4) . . ?
C8 N3 N2 117.2(6) . . ?
C8 N3 H3A 121.4 . . ?
N2 N3 H3A 121.4 . . ?
C9 N4 C8 115.8(7) . . ?
C20 N6 Fe1 127.6(5) . . ?
C20 N6 N7 117.3(6) . . ?
N7 N6 Fe1 114.9(4) . . ?
C21 N5 Fe1 115.2(5) . . ?
C24 N5 Fe1 128.3(5) . . ?
C24 N5 C21 116.4(6) . . ?
C21 N7 N6 118.0(6) . . ?
C21 N7 H7A 121.0 . . ?
N6 N7 H7A 121.0 . . ?
C22 N8 C21 116.2(7) . . ?
C1 O1 Fe1 137.1(5) . . ?
C14 O2 Fe1 138.0(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N2 N3 C8 3.5(7) . . . . ?
Fe1 N6 N7 C21 -0.3(8) . . . . ?
C1 C2 C3 C4 0.7(11) . . . . ?
C1 C6 C7 N2 -1.9(11) . . . . ?
C2 C1 C6 C5 4.4(10) . . . . ?
C2 C1 C6 C7 -172.2(6) . . . . ?
C2 C1 O1 Fe1 172.5(5) . . . . ?
C2 C3 C4 C5 2.0(12) . . . . ?
C3 C4 C5 C6 -1.6(12) . . . . ?
C4 C5 C6 C1 -1.6(11) . . . . ?
C4 C5 C6 C7 175.2(7) . . . . ?
C5 C6 C7 N2 -178.6(7) . . . . ?
C6 C1 C2 C3 -3.9(10) . . . . ?
C6 C1 C2 C12 177.9(7) . . . . ?
C6 C1 O1 Fe1 -6.4(11) . . . . ?
C6 C7 N2 Fe1 -3.3(10) . . . . ?
C6 C7 N2 N3 176.8(6) . . . . ?
C7 N2 N3 C8 -176.6(6) . . . . ?
C9 C10 C11 N1 -1.7(11) . . . . ?
C10 C9 N4 C8 -1.1(10) . . . . ?
C10 C11 N1 Fe1 173.9(5) . . . . ?
C10 C11 N1 C8 1.2(10) . . . . ?
C12 C2 C3 C4 178.9(7) . . . . ?
C13 C15 C16 C17 -179.8(7) . . . . ?
C14 C15 C16 C17 0.1(11) . . . . ?
C14 C19 C20 N6 -1.5(12) . . . . ?
C15 C14 C19 C18 0.2(11) . . . . ?
C15 C14 C19 C20 177.7(7) . . . . ?
C15 C14 O2 Fe1 -170.6(5) . . . . ?
C15 C16 C17 C18 0.2(12) . . . . ?
C16 C17 C18 C19 -0.3(12) . . . . ?
C17 C18 C19 C14 0.1(11) . . . . ?
C17 C18 C19 C20 -177.5(7) . . . . ?
C18 C19 C20 N6 176.0(7) . . . . ?
C19 C14 C15 C13 179.6(7) . . . . ?
C19 C14 C15 C16 -0.3(10) . . . . ?
C19 C14 O2 Fe1 10.1(11) . . . . ?
C19 C20 N6 Fe1 0.6(11) . . . . ?
C19 C20 N6 N7 -174.3(7) . . . . ?
C20 N6 N7 C21 175.2(7) . . . . ?
C22 C23 C24 N5 2.2(11) . . . . ?
C23 C22 N8 C21 -1.5(11) . . . . ?
C23 C24 N5 Fe1 -176.8(5) . . . . ?
C23 C24 N5 C21 1.8(10) . . . . ?
N1 Fe1 O1 C1 -6.8(11) . . . . ?
N1 Fe1 O2 C14 82.2(7) . . . . ?
N1 C8 N3 N2 -6.5(9) . . . . ?
N1 C8 N4 C9 0.6(10) . . . . ?
N2 Fe1 O1 C1 1.7(7) . . . . ?
N2 Fe1 O2 C14 155.3(7) . . . . ?
N3 C8 N1 Fe1 6.3(8) . . . . ?
N3 C8 N1 C11 179.8(6) . . . . ?
N3 C8 N4 C9 -179.9(6) . . . . ?
N4 C8 N1 Fe1 -174.1(5) . . . . ?
N4 C8 N1 C11 -0.7(10) . . . . ?
N4 C8 N3 N2 174.0(6) . . . . ?
N4 C9 C10 C11 1.7(11) . . . . ?
N6 Fe1 O1 C1 166.3(6) . . . . ?
N6 Fe1 O2 C14 -8.7(7) . . . . ?
N5 Fe1 O1 C1 91.9(7) . . . . ?
N5 Fe1 O2 C14 -8.7(11) . . . . ?
N5 C21 N7 N6 4.4(9) . . . . ?
N5 C21 N8 C22 6.1(10) . . . . ?
N7 C21 N5 Fe1 -6.3(8) . . . . ?
N7 C21 N5 C24 174.9(6) . . . . ?
N7 C21 N8 C22 -175.1(7) . . . . ?
N8 C21 N5 Fe1 172.5(5) . . . . ?
N8 C21 N5 C24 -6.2(10) . . . . ?
N8 C21 N7 N6 -174.5(6) . . . . ?
N8 C22 C23 C24 -2.4(11) . . . . ?
O1 Fe1 O2 C14 -118.6(7) . . . . ?
O1 C1 C2 C3 177.2(7) . . . . ?
O1 C1 C2 C12 -1.0(10) . . . . ?
O1 C1 C6 C5 -176.8(7) . . . . ?
O1 C1 C6 C7 6.6(11) . . . . ?
O2 Fe1 O1 C1 -108.1(7) . . . . ?
O2 C14 C15 C13 0.3(10) . . . . ?
O2 C14 C15 C16 -179.6(7) . . . . ?
O2 C14 C19 C18 179.5(7) . . . . ?
O2 C14 C19 C20 -3.0(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.211
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1568654'
_audit_update_record             
;
2017-08-13 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H21 Fe N8 O2, C O, O'
_chemical_formula_sum            'C25 H29 Fe N8 O4'
_chemical_formula_weight         561.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Fe Fe 0.3460 0.8440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.2328(3)
_cell_length_b                   16.0054(7)
_cell_length_c                   19.3465(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.848(4)
_cell_angle_gamma                90
_cell_volume                     2536.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8550
_cell_measurement_theta_min      3.5450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.73396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14841
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.545
_diffrn_reflns_theta_min         3.349
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4552
_reflns_number_total             6073
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0734P)²+3.0543P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1733
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O4A)=1-FVAR(1)
 Sof(O4)=FVAR(1)
3.a Riding coordinates:
 N3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16),
  C17(H17), C19(H19), C21(H21), C22(H22), C23(H23)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.60118(5) 0.17013(3) 0.17897(2) 0.02399(15) Uani 1 1 d . . . . .
O1 O 0.5825(3) 0.19612(16) 0.27267(13) 0.0386(6) Uani 1 1 d . . . . .
O2 O 0.6331(3) 0.27926(15) 0.14678(15) 0.0398(6) Uani 1 1 d . . . . .
N2 N 0.8412(3) 0.1486(2) 0.20129(15) 0.0356(7) Uani 1 1 d . . . . .
N1 N 0.6667(4) 0.12590(18) 0.08737(16) 0.0353(7) Uani 1 1 d . . . . .
N3 N 0.9266(4) 0.1288(2) 0.14547(16) 0.0377(7) Uani 1 1 d . . . . .
H3 H 1.0348 0.1244 0.1442 0.27(6) Uiso 1 1 d R . . . .
N4 N 0.9031(4) 0.0949(2) 0.02916(18) 0.0474(8) Uani 1 1 d . . . . .
N6 N 0.3583(3) 0.18131(16) 0.15420(16) 0.0311(6) Uani 1 1 d . . . . .
N5 N 0.5191(4) 0.05225(18) 0.19562(17) 0.0386(7) Uani 1 1 d . . . . .
N7 N 0.2653(3) 0.11199(18) 0.16535(17) 0.0344(7) Uani 1 1 d . . . . .
N8 N 0.2707(5) -0.0258(2) 0.19877(19) 0.0535(10) Uani 1 1 d . . . . .
C1 C 0.6894(5) 0.1892(2) 0.32875(18) 0.0366(8) Uani 1 1 d . . . . .
C2 C 0.6300(5) 0.2031(2) 0.3944(2) 0.0415(9) Uani 1 1 d . . . . .
C3 C 0.7407(6) 0.2014(3) 0.4538(2) 0.0516(11) Uani 1 1 d . . . . .
H3A H 0.7032 0.2107 0.4969 0.062 Uiso 1 1 calc R . . . .
C4 C 0.9049(6) 0.1861(4) 0.4504(2) 0.0646(14) Uani 1 1 d . . . . .
H4 H 0.9765 0.1863 0.4908 0.077 Uiso 1 1 calc R . . . .
C5 C 0.9624(6) 0.1707(4) 0.3879(2) 0.0687(16) Uani 1 1 d . . . . .
H5 H 1.0728 0.1598 0.3862 0.082 Uiso 1 1 calc R . . . .
C6 C 0.8558(5) 0.1711(3) 0.3257(2) 0.0507(12) Uani 1 1 d . . . . .
C7 C 0.9241(5) 0.1524(3) 0.2617(2) 0.0544(12) Uani 1 1 d . . . . .
H7 H 1.0358 0.1424 0.2640 0.065 Uiso 1 1 calc R . . . .
C8 C 0.8010(6) 0.0781(3) -0.0273(2) 0.0559(12) Uani 1 1 d . . . . .
H8 H 0.8461 0.0613 -0.0672 0.067 Uiso 1 1 calc R . . . .
C9 C 0.6353(6) 0.0838(3) -0.0303(2) 0.0553(12) Uani 1 1 d . . . . .
H9 H 0.5690 0.0708 -0.0708 0.066 Uiso 1 1 calc R . . . .
C10 C 0.8302(4) 0.1165(2) 0.0859(2) 0.0377(9) Uani 1 1 d . . . . .
C11 C 0.5708(5) 0.1092(2) 0.0282(2) 0.0454(10) Uani 1 1 d . . . . .
H11 H 0.4583 0.1152 0.0273 0.055 Uiso 1 1 calc R . . . .
C12 C 0.4519(6) 0.2183(3) 0.3976(2) 0.0519(11) Uani 1 1 d . . . . .
H12A H 0.4242 0.2732 0.3802 0.078 Uiso 1 1 calc GR . . . .
H12B H 0.4270 0.2140 0.4449 0.078 Uiso 1 1 calc GR . . . .
H12C H 0.3900 0.1774 0.3698 0.078 Uiso 1 1 calc GR . . . .
C13 C 0.5279(5) 0.3385(2) 0.1239(2) 0.0370(8) Uani 1 1 d . . . . .
C14 C 0.5904(5) 0.4175(2) 0.1070(2) 0.0413(9) Uani 1 1 d . . . . .
C15 C 0.4821(6) 0.4809(2) 0.0869(3) 0.0543(11) Uani 1 1 d . . . . .
H15 H 0.5236 0.5328 0.0761 0.065 Uiso 1 1 calc R . . . .
C16 C 0.3155(6) 0.4706(3) 0.0822(3) 0.0585(12) Uani 1 1 d . . . . .
H16 H 0.2460 0.5153 0.0702 0.070 Uiso 1 1 calc R . . . .
C17 C 0.2539(5) 0.3939(3) 0.0955(3) 0.0533(11) Uani 1 1 d . . . . .
H17 H 0.1414 0.3860 0.0906 0.064 Uiso 1 1 calc R . . . .
C18 C 0.3573(5) 0.3257(2) 0.1166(2) 0.0407(9) Uani 1 1 d . . . . .
C19 C 0.2812(4) 0.2482(2) 0.1309(2) 0.0387(9) Uani 1 1 d . . . . .
H19 H 0.1680 0.2453 0.1229 0.046 Uiso 1 1 calc R . . . .
C20 C 0.3532(5) 0.0456(2) 0.18705(19) 0.0349(8) Uani 1 1 d . . . . .
C21 C 0.3642(9) -0.0915(3) 0.2171(3) 0.077(2) Uani 1 1 d . . . . .
H21 H 0.3123 -0.1413 0.2262 0.093 Uiso 1 1 calc R . . . .
C22 C 0.5331(8) -0.0909(3) 0.2237(3) 0.0743(19) Uani 1 1 d . . . . .
H22 H 0.5932 -0.1392 0.2346 0.089 Uiso 1 1 calc R . . . .
C23 C 0.6072(6) -0.0167(3) 0.2137(2) 0.0553(13) Uani 1 1 d . . . . .
H23 H 0.7206 -0.0134 0.2193 0.066 Uiso 1 1 calc R . . . .
C24 C 0.7723(5) 0.4304(3) 0.1133(2) 0.0492(10) Uani 1 1 d . . . . .
H24A H 0.8135 0.4318 0.1616 0.074 Uiso 1 1 calc GR . . . .
H24B H 0.7967 0.4822 0.0917 0.074 Uiso 1 1 calc GR . . . .
H24C H 0.8228 0.3852 0.0908 0.074 Uiso 1 1 calc GR . . . .
O3 O 0.0361(8) 0.4325(5) 0.3062(5) 0.174(3) Uani 1 1 d . . . . .
C25 C 0.0444(15) 0.3485(7) 0.2811(10) 0.226(8) Uani 1 1 d . . . . .
O4 O 0.1969(7) 0.3736(5) 0.4865(4) 0.058(3) Uani 0.491(11) 1 d . . P A 1
O4A O 0.1930(9) 0.3978(5) 0.4295(5) 0.087(4) Uani 0.509(11) 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 O1 1.881(3) . ?
Fe1 O2 1.882(2) . ?
Fe1 N2 2.009(3) . ?
Fe1 N1 2.032(3) . ?
Fe1 N6 2.016(3) . ?
Fe1 N5 2.041(3) . ?
O1 C1 1.330(4) . ?
O2 C13 1.329(4) . ?
N2 N3 1.385(4) . ?
N2 C7 1.293(5) . ?
N1 C10 1.358(5) . ?
N1 C11 1.350(4) . ?
N3 C10 1.346(5) . ?
N4 C8 1.336(5) . ?
N4 C10 1.348(5) . ?
N6 N7 1.378(4) . ?
N6 C19 1.301(5) . ?
N5 C20 1.363(5) . ?
N5 C23 1.347(5) . ?
N7 C20 1.329(5) . ?
N8 C20 1.360(5) . ?
N8 C21 1.330(7) . ?
C1 C2 1.425(5) . ?
C1 C6 1.407(6) . ?
C2 C3 1.392(6) . ?
C2 C12 1.494(6) . ?
C3 C4 1.382(7) . ?
C4 C5 1.365(7) . ?
C5 C6 1.415(5) . ?
C6 C7 1.442(6) . ?
C8 C9 1.363(7) . ?
C9 C11 1.361(7) . ?
C13 C14 1.416(5) . ?
C13 C18 1.412(5) . ?
C14 C15 1.379(6) . ?
C14 C24 1.505(6) . ?
C15 C16 1.375(7) . ?
C16 C17 1.364(6) . ?
C17 C18 1.418(6) . ?
C18 C19 1.430(5) . ?
C21 C22 1.384(8) . ?
C22 C23 1.359(7) . ?
O3 C25 1.434(12) . ?

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 Fe1 O2 98.14(12) . . ?
O1 Fe1 N2 90.33(12) . . ?
O1 Fe1 N1 166.54(12) . . ?
O1 Fe1 N6 91.90(12) . . ?
O1 Fe1 N5 89.52(12) . . ?
O2 Fe1 N2 93.58(12) . . ?
O2 Fe1 N1 88.63(11) . . ?
O2 Fe1 N6 90.43(11) . . ?
O2 Fe1 N5 165.95(13) . . ?
N2 Fe1 N1 77.58(12) . . ?
N2 Fe1 N6 175.09(12) . . ?
N2 Fe1 N5 98.17(13) . . ?
N1 Fe1 N5 86.40(11) . . ?
N6 Fe1 N1 99.71(12) . . ?
N6 Fe1 N5 77.48(12) . . ?
C1 O1 Fe1 130.9(3) . . ?
C13 O2 Fe1 131.6(2) . . ?
N3 N2 Fe1 116.0(2) . . ?
C7 N2 Fe1 127.1(3) . . ?
C7 N2 N3 116.9(3) . . ?
C10 N1 Fe1 114.2(2) . . ?
C11 N1 Fe1 128.7(3) . . ?
C11 N1 C10 117.1(4) . . ?
C10 N3 N2 113.5(3) . . ?
C8 N4 C10 114.9(4) . . ?
N7 N6 Fe1 116.4(2) . . ?
C19 N6 Fe1 126.3(2) . . ?
C19 N6 N7 117.2(3) . . ?
C20 N5 Fe1 113.4(2) . . ?
C23 N5 Fe1 128.3(3) . . ?
C23 N5 C20 118.3(4) . . ?
C20 N7 N6 113.5(3) . . ?
C21 N8 C20 115.0(4) . . ?
O1 C1 C2 117.1(4) . . ?
O1 C1 C6 123.3(3) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 C12 119.3(4) . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 C12 122.1(4) . . ?
C4 C3 C2 121.7(4) . . ?
C5 C4 C3 120.3(4) . . ?
C4 C5 C6 120.8(5) . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 C7 123.0(3) . . ?
C5 C6 C7 117.8(4) . . ?
N2 C7 C6 124.7(4) . . ?
N4 C8 C9 124.5(5) . . ?
C11 C9 C8 117.2(4) . . ?
N3 C10 N1 117.7(4) . . ?
N3 C10 N4 117.5(3) . . ?
N4 C10 N1 124.8(3) . . ?
N1 C11 C9 121.4(4) . . ?
O2 C13 C14 118.3(3) . . ?
O2 C13 C18 122.5(3) . . ?
C18 C13 C14 119.1(3) . . ?
C13 C14 C24 119.0(4) . . ?
C15 C14 C13 118.8(4) . . ?
C15 C14 C24 122.2(4) . . ?
C16 C15 C14 122.9(4) . . ?
C17 C16 C15 118.8(4) . . ?
C16 C17 C18 121.6(4) . . ?
C13 C18 C17 118.6(4) . . ?
C13 C18 C19 123.9(3) . . ?
C17 C18 C19 117.5(4) . . ?
N6 C19 C18 124.9(3) . . ?
N7 C20 N5 118.9(3) . . ?
N7 C20 N8 117.3(3) . . ?
N8 C20 N5 123.8(3) . . ?
N8 C21 C22 124.7(4) . . ?
C23 C22 C21 117.0(4) . . ?
N5 C23 C22 121.0(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 -171.2(2) . . . . ?
Fe1 O1 C1 C6 10.5(5) . . . . ?
Fe1 O2 C13 C14 176.1(3) . . . . ?
Fe1 O2 C13 C18 -3.3(6) . . . . ?
Fe1 N2 N3 C10 -8.1(4) . . . . ?
Fe1 N2 C7 C6 1.8(7) . . . . ?
Fe1 N1 C10 N3 6.5(4) . . . . ?
Fe1 N1 C10 N4 -174.2(3) . . . . ?
Fe1 N1 C11 C9 176.5(3) . . . . ?
Fe1 N6 N7 C20 -4.1(4) . . . . ?
Fe1 N6 C19 C18 2.1(6) . . . . ?
Fe1 N5 C20 N7 4.1(4) . . . . ?
Fe1 N5 C20 N8 -176.6(3) . . . . ?
Fe1 N5 C23 C22 179.1(3) . . . . ?
O1 Fe1 O2 C13 -86.5(3) . . . . ?
O1 C1 C2 C3 -176.1(3) . . . . ?
O1 C1 C2 C12 4.4(5) . . . . ?
O1 C1 C6 C5 175.6(4) . . . . ?
O1 C1 C6 C7 -4.7(7) . . . . ?
O2 Fe1 O1 C1 -101.7(3) . . . . ?
O2 C13 C14 C15 -176.4(4) . . . . ?
O2 C13 C14 C24 1.9(6) . . . . ?
O2 C13 C18 C17 176.5(4) . . . . ?
O2 C13 C18 C19 -1.8(6) . . . . ?
N2 Fe1 O1 C1 -8.1(3) . . . . ?
N2 Fe1 O2 C13 -177.3(3) . . . . ?
N2 N3 C10 N1 0.9(5) . . . . ?
N2 N3 C10 N4 -178.5(3) . . . . ?
N1 Fe1 O1 C1 17.9(7) . . . . ?
N1 Fe1 O2 C13 105.2(3) . . . . ?
N3 N2 C7 C6 -179.2(4) . . . . ?
N4 C8 C9 C11 0.7(7) . . . . ?
N6 Fe1 O1 C1 167.6(3) . . . . ?
N6 Fe1 O2 C13 5.5(3) . . . . ?
N6 N7 C20 N5 -0.1(5) . . . . ?
N6 N7 C20 N8 -179.5(3) . . . . ?
N5 Fe1 O1 C1 90.1(3) . . . . ?
N5 Fe1 O2 C13 35.9(7) . . . . ?
N7 N6 C19 C18 179.7(3) . . . . ?
N8 C21 C22 C23 3.1(7) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C1 C6 C7 N2 -1.4(8) . . . . ?
C2 C1 C6 C5 -2.6(6) . . . . ?
C2 C1 C6 C7 177.1(4) . . . . ?
C2 C3 C4 C5 -1.2(8) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C4 C5 C6 C7 -178.6(5) . . . . ?
C5 C6 C7 N2 178.3(5) . . . . ?
C6 C1 C2 C3 2.3(5) . . . . ?
C6 C1 C2 C12 -177.2(4) . . . . ?
C7 N2 N3 C10 172.7(4) . . . . ?
C8 N4 C10 N1 -3.6(6) . . . . ?
C8 N4 C10 N3 175.7(4) . . . . ?
C8 C9 C11 N1 -1.8(6) . . . . ?
C10 N1 C11 C9 0.2(5) . . . . ?
C10 N4 C8 C9 1.8(6) . . . . ?
C11 N1 C10 N3 -176.7(3) . . . . ?
C11 N1 C10 N4 2.7(5) . . . . ?
C12 C2 C3 C4 179.1(4) . . . . ?
C13 C14 C15 C16 -0.4(7) . . . . ?
C13 C18 C19 N6 2.2(7) . . . . ?
C14 C13 C18 C17 -2.9(6) . . . . ?
C14 C13 C18 C19 178.7(4) . . . . ?
C14 C15 C16 C17 -2.4(8) . . . . ?
C15 C16 C17 C18 2.5(8) . . . . ?
C16 C17 C18 C13 0.1(7) . . . . ?
C16 C17 C18 C19 178.6(4) . . . . ?
C17 C18 C19 N6 -176.2(4) . . . . ?
C18 C13 C14 C15 3.0(6) . . . . ?
C18 C13 C14 C24 -178.7(4) . . . . ?
C19 N6 N7 C20 178.0(3) . . . . ?
C20 N5 C23 C22 -0.6(6) . . . . ?
C20 N8 C21 C22 -0.8(6) . . . . ?
C21 N8 C20 N5 -2.5(6) . . . . ?
C21 N8 C20 N7 176.9(4) . . . . ?
C21 C22 C23 N5 -2.3(7) . . . . ?
C23 N5 C20 N7 -176.1(3) . . . . ?
C23 N5 C20 N8 3.2(5) . . . . ?
C24 C14 C15 C16 -178.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
