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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_[Fe(III)(mep)Cl2]PF6
_database_code_depnum_ccdc_archive 'CCDC 1880891'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 F6 Fe N4 P'
_chemical_formula_weight         542.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.2912(6)
_cell_length_b                   17.6962(12)
_cell_length_c                   12.8115(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.226(2)
_cell_angle_gamma                90
_cell_volume                     2089.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9066
_cell_measurement_theta_min      2.302
_cell_measurement_theta_max      28.3285

_exptl_crystal_description       prism
_exptl_crystal_colour            brown-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.398
_exptl_absorpt_coefficient_mu    1.118
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.665
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6214
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
Final wR2(int)= 0.0424. The ratio of minimum to maximun
transmission is 0.6214.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44448
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         28.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5220
_reflns_number_gt                4945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WinGX CIF routines'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+4.2408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5220
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7133(2) 0.41713(12) 0.53396(17) 0.0155(4) Uani 1 1 d . . . . .
H1 H 0.625956 0.442193 0.507237 0.019 Uiso 1 1 calc R U . . .
C2 C 0.8375(3) 0.43115(13) 0.48776(19) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.835421 0.465299 0.430374 0.022 Uiso 1 1 calc R U . . .
C3 C 0.9648(3) 0.39465(13) 0.52649(19) 0.0190(4) Uani 1 1 d . . . . .
H3 H 1.051161 0.403118 0.495654 0.023 Uiso 1 1 calc R U . . .
C4 C 0.9647(2) 0.34558(13) 0.61082(19) 0.0170(4) Uani 1 1 d . . . . .
H4 H 1.051193 0.320366 0.639076 0.020 Uiso 1 1 calc R U . . .
C5 C 0.8362(2) 0.33388(12) 0.65334(17) 0.0129(4) Uani 1 1 d . . . . .
C6 C 0.8256(2) 0.28136(13) 0.74369(17) 0.0155(4) Uani 1 1 d . . . . .
H6A H 0.801286 0.229858 0.716872 0.019 Uiso 1 1 calc R U . . .
H6B H 0.920153 0.279070 0.788858 0.019 Uiso 1 1 calc R U . . .
C7 C 0.7636(2) 0.37840(13) 0.86395(18) 0.0171(4) Uani 1 1 d . . . . .
H7A H 0.821443 0.409237 0.819955 0.021 Uiso 1 1 calc R U . . .
H7B H 0.826392 0.364848 0.929526 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6347(2) 0.42332(14) 0.89009(18) 0.0173(4) Uani 1 1 d . . . . .
H8A H 0.580974 0.393833 0.938240 0.021 Uiso 1 1 calc R U . . .
H8B H 0.668415 0.470814 0.926045 0.021 Uiso 1 1 calc R U . . .
C9 C 0.3875(2) 0.45416(13) 0.81752(19) 0.0182(4) Uani 1 1 d . . . . .
H9A H 0.326665 0.476341 0.756148 0.022 Uiso 1 1 calc R U . . .
H9B H 0.390232 0.490088 0.876965 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3234(2) 0.38027(14) 0.84686(18) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.2259(3) 0.37527(16) 0.91983(19) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.197603 0.419329 0.954432 0.026 Uiso 1 1 calc R U . . .
C12 C 0.1702(3) 0.30564(17) 0.94176(19) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.104932 0.300734 0.992821 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2113(3) 0.24285(15) 0.8877(2) 0.0223(5) Uani 1 1 d . . . . .
H13 H 0.172857 0.194415 0.900226 0.027 Uiso 1 1 calc R U . . .
C14 C 0.3086(2) 0.25146(14) 0.81569(19) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.335927 0.208318 0.778655 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6833(3) 0.24792(14) 0.88104(18) 0.0201(5) Uani 1 1 d . . . . .
H15A H 0.641628 0.203886 0.841841 0.030 Uiso 1 1 calc R U . . .
H15B H 0.614871 0.266538 0.927399 0.030 Uiso 1 1 calc R U . . .
H15C H 0.774357 0.233424 0.923374 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5868(3) 0.51057(13) 0.7421(2) 0.0206(5) Uani 1 1 d . . . . .
H16A H 0.525010 0.520199 0.675644 0.031 Uiso 1 1 calc R U . . .
H16B H 0.687446 0.503869 0.728367 0.031 Uiso 1 1 calc R U . . .
H16C H 0.581063 0.553537 0.789645 0.031 Uiso 1 1 calc R U . . .
N1 N 0.71195(19) 0.36928(10) 0.61536(14) 0.0120(3) Uani 1 1 d . . . . .
N2 N 0.7121(2) 0.30836(11) 0.80610(14) 0.0133(3) Uani 1 1 d . . . . .
N3 N 0.5368(2) 0.44117(11) 0.79139(15) 0.0144(4) Uani 1 1 d . . . . .
N4 N 0.3662(2) 0.31909(11) 0.79618(15) 0.0151(4) Uani 1 1 d . . . . .
F1 F 0.9956(3) 0.34154(9) 0.14484(19) 0.0495(6) Uani 1 1 d . . . . .
F2 F 0.8562(3) 0.39880(12) 0.25675(19) 0.0537(6) Uani 1 1 d . . . . .
F3 F 0.8560(2) 0.44245(13) 0.09399(16) 0.0498(5) Uani 1 1 d . . . . .
F4 F 0.9633(2) 0.50992(10) 0.23148(14) 0.0342(4) Uani 1 1 d . . . . .
F5 F 1.1007(2) 0.45379(10) 0.12063(15) 0.0367(4) Uani 1 1 d . . . . .
F6 F 1.0974(3) 0.41100(15) 0.28769(18) 0.0596(6) Uani 1 1 d . . . . .
P1 P 0.97924(7) 0.42548(4) 0.18773(5) 0.01983(14) Uani 1 1 d . . . . .
CL2 Cl 0.51009(6) 0.21898(3) 0.62518(4) 0.01766(12) Uani 1 1 d . . . . .
CL1 Cl 0.36652(6) 0.39756(3) 0.56599(4) 0.01761(12) Uani 1 1 d . . . . .
FE1 Fe 0.52373(3) 0.33840(2) 0.68940(2) 0.01018(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.345(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.349(3) . ?
C5 C6 1.497(3) . ?
C6 N2 1.481(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.492(3) . ?
C7 C8 1.510(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.496(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.485(3) . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N4 1.348(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 N4 1.347(3) . ?
C14 H14 0.9500 . ?
C15 N2 1.484(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N3 1.482(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 FE1 2.1619(18) . ?
N2 FE1 2.2187(18) . ?
N3 FE1 2.2337(19) . ?
N4 FE1 2.1528(19) . ?
F1 P1 1.5976(18) . ?
F2 P1 1.602(2) . ?
F3 P1 1.580(2) . ?
F4 P1 1.6093(18) . ?
F5 P1 1.5837(17) . ?
F6 P1 1.599(2) . ?
CL2 FE1 2.2656(6) . ?
CL1 FE1 2.2691(6) . ?

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 C1 C2 122.3(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 C6 115.49(18) . . ?
C4 C5 C6 122.6(2) . . ?
N2 C6 C5 109.74(17) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 109.49(18) . . ?
N2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C7 109.81(18) . . ?
N3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 C10 109.41(18) . . ?
N3 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
N3 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
N4 C10 C11 122.1(2) . . ?
N4 C10 C9 115.32(19) . . ?
C11 C10 C9 122.5(2) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 118.7(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 122.1(2) . . ?
N4 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C5 118.75(19) . . ?
C1 N1 FE1 125.90(15) . . ?
C5 N1 FE1 115.29(14) . . ?
C6 N2 C15 108.39(17) . . ?
C6 N2 C7 109.30(18) . . ?
C15 N2 C7 110.50(18) . . ?
C6 N2 FE1 105.58(13) . . ?
C15 N2 FE1 114.68(14) . . ?
C7 N2 FE1 108.21(13) . . ?
C16 N3 C9 108.64(18) . . ?
C16 N3 C8 110.20(18) . . ?
C9 N3 C8 109.16(18) . . ?
C16 N3 FE1 114.98(14) . . ?
C9 N3 FE1 105.91(13) . . ?
C8 N3 FE1 107.77(13) . . ?
C14 N4 C10 118.4(2) . . ?
C14 N4 FE1 125.20(16) . . ?
C10 N4 FE1 116.36(15) . . ?
F3 P1 F5 91.44(12) . . ?
F3 P1 F1 90.38(13) . . ?
F5 P1 F1 90.12(10) . . ?
F3 P1 F6 176.20(13) . . ?
F5 P1 F6 91.20(12) . . ?
F1 P1 F6 92.35(14) . . ?
F3 P1 F2 88.63(14) . . ?
F5 P1 F2 178.65(11) . . ?
F1 P1 F2 91.23(10) . . ?
F6 P1 F2 88.67(14) . . ?
F3 P1 F4 89.91(11) . . ?
F5 P1 F4 89.91(10) . . ?
F1 P1 F4 179.70(14) . . ?
F6 P1 F4 87.36(12) . . ?
F2 P1 F4 88.74(10) . . ?
N4 FE1 N1 166.19(7) . . ?
N4 FE1 N2 94.33(7) . . ?
N1 FE1 N2 75.12(7) . . ?
N4 FE1 N3 75.45(7) . . ?
N1 FE1 N3 93.63(7) . . ?
N2 FE1 N3 79.67(7) . . ?
N4 FE1 CL2 94.09(6) . . ?
N1 FE1 CL2 95.04(5) . . ?
N2 FE1 CL2 91.41(5) . . ?
N3 FE1 CL2 165.54(5) . . ?
N4 FE1 CL1 94.96(5) . . ?
N1 FE1 CL1 93.61(5) . . ?
N2 FE1 CL1 164.62(5) . . ?
N3 FE1 CL1 90.85(5) . . ?
CL2 FE1 CL1 100.11(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
N1 C5 C6 N2 -30.0(3) . . . . ?
C4 C5 C6 N2 150.1(2) . . . . ?
N2 C7 C8 N3 -57.2(2) . . . . ?
N3 C9 C10 N4 -32.9(3) . . . . ?
N3 C9 C10 C11 147.8(2) . . . . ?
N4 C10 C11 C12 0.0(4) . . . . ?
C9 C10 C11 C12 179.2(2) . . . . ?
C10 C11 C12 C13 -1.6(4) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C12 C13 C14 N4 0.4(4) . . . . ?
C2 C1 N1 C5 0.1(3) . . . . ?
C2 C1 N1 FE1 -176.83(16) . . . . ?
C4 C5 N1 C1 0.1(3) . . . . ?
C6 C5 N1 C1 -179.80(19) . . . . ?
C4 C5 N1 FE1 177.35(16) . . . . ?
C6 C5 N1 FE1 -2.5(2) . . . . ?
C5 C6 N2 C15 168.66(18) . . . . ?
C5 C6 N2 C7 -70.8(2) . . . . ?
C5 C6 N2 FE1 45.34(19) . . . . ?
C8 C7 N2 C6 156.89(18) . . . . ?
C8 C7 N2 C15 -83.9(2) . . . . ?
C8 C7 N2 FE1 42.4(2) . . . . ?
C10 C9 N3 C16 168.53(18) . . . . ?
C10 C9 N3 C8 -71.3(2) . . . . ?
C10 C9 N3 FE1 44.5(2) . . . . ?
C7 C8 N3 C16 -85.1(2) . . . . ?
C7 C8 N3 C9 155.65(19) . . . . ?
C7 C8 N3 FE1 41.1(2) . . . . ?
C13 C14 N4 C10 -2.0(3) . . . . ?
C13 C14 N4 FE1 177.93(17) . . . . ?
C11 C10 N4 C14 1.8(3) . . . . ?
C9 C10 N4 C14 -177.5(2) . . . . ?
C11 C10 N4 FE1 -178.11(17) . . . . ?
C9 C10 N4 FE1 2.6(2) . . . . ?

_refine_diff_density_max         1.149
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.097

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

data_'Fe(II)(mep)Cl2'
_database_code_depnum_ccdc_archive 'CCDC 1880892'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Fe N4'
_chemical_formula_weight         397.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   14.1995(7)
_cell_length_b                   8.0887(5)
_cell_length_c                   15.0900(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1733.17(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      2.898
_cell_measurement_theta_max      40.255

_exptl_crystal_description       rhomboid
_exptl_crystal_colour            brown-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.182
_shelx_estimated_absorpt_T_min   0.616
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8484
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0335 after correction.
The Ratio of minimum to maximum transmission is 0.8492.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30851
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.700
_diffrn_reflns_theta_max         40.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5484
_reflns_number_gt                4449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WINGX CIF Routines'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²+0.6275P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5484
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63236(6) 0.19399(9) 0.42098(5) 0.01289(12) Uani 1 1 d . . . . .
H1 H 0.581026 0.138605 0.448334 0.015 Uiso 1 1 calc R U . . .
C2 C 0.71461(6) 0.21632(10) 0.46912(5) 0.01671(14) Uani 1 1 d . . . . .
H2 H 0.719236 0.177977 0.528468 0.020 Uiso 1 1 calc R U . . .
C3 C 0.78996(6) 0.29567(10) 0.42901(6) 0.01889(15) Uani 1 1 d . . . . .
H3 H 0.847224 0.311954 0.460369 0.023 Uiso 1 1 calc R U . . .
C4 C 0.78048(6) 0.35109(10) 0.34217(6) 0.01562(13) Uani 1 1 d . . . . .
H4 H 0.831323 0.404737 0.313055 0.019 Uiso 1 1 calc R U . . .
C5 C 0.69540(5) 0.32657(9) 0.29886(5) 0.01216(11) Uani 1 1 d . . . . .
C6 C 0.67965(6) 0.38652(11) 0.20541(5) 0.01631(13) Uani 1 1 d . . . . .
H6A H 0.718987 0.485452 0.194381 0.020 Uiso 1 1 calc R U . . .
H6B H 0.699012 0.299423 0.163072 0.020 Uiso 1 1 calc R U . . .
C7 C 0.55267(6) 0.57808(9) 0.24136(5) 0.01608(14) Uani 1 1 d . . . . .
H7A H 0.570144 0.678042 0.207266 0.019 Uiso 1 1 calc R U . . .
H7B H 0.587027 0.580627 0.298433 0.019 Uiso 1 1 calc R U . . .
C8 C 0.56362(7) 0.45404(12) 0.09543(5) 0.01942(15) Uani 1 1 d . . . . .
H8A H 0.607876 0.537193 0.073156 0.029 Uiso 1 1 calc R U . . .
H8B H 0.498939 0.492465 0.085973 0.029 Uiso 1 1 calc R U . . .
H8C H 0.573296 0.349718 0.063688 0.029 Uiso 1 1 calc R U . . .
N1 N 0.62238(5) 0.24753(8) 0.33721(4) 0.01109(10) Uani 1 1 d . . . . .
N2 N 0.57975(5) 0.42809(8) 0.19087(4) 0.01221(10) Uani 1 1 d . . . . .
CL1 Cl 0.57435(2) 0.01919(3) 0.14747(2) 0.01657(4) Uani 1 1 d . . . . .
FE1 Fe 0.500000 0.20943(2) 0.250000 0.00814(3) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3437(9) . ?
C1 C2 1.3873(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.3866(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3916(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3877(11) . ?
C4 H4 0.9500 . ?
C5 N1 1.3486(10) . ?
C5 C6 1.5079(11) . ?
C6 N2 1.4742(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.4833(11) . ?
C7 C7 1.5184(18) 3_655 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.4733(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 FE1 2.2015(6) . ?
N2 FE1 2.2819(6) . ?
CL1 FE1 2.4241(2) . ?
FE1 N1 2.2015(6) 3_655 ?
FE1 N2 2.2819(6) 3_655 ?
FE1 CL1 2.4241(2) 3_655 ?

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 C1 C2 122.65(8) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.76(7) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.05(7) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.79(8) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.34(7) . . ?
N1 C5 C6 116.08(6) . . ?
C4 C5 C6 121.57(7) . . ?
N2 C6 C5 110.81(6) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C7 110.10(5) . 3_655 ?
N2 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 3_655 . ?
N2 C7 H7B 109.6 . . ?
C7 C7 H7B 109.6 3_655 . ?
H7A C7 H7B 108.2 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 C5 118.38(7) . . ?
C1 N1 FE1 126.90(5) . . ?
C5 N1 FE1 114.63(5) . . ?
C8 N2 C6 109.13(6) . . ?
C8 N2 C7 110.20(6) . . ?
C6 N2 C7 111.07(6) . . ?
C8 N2 FE1 114.55(5) . . ?
C6 N2 FE1 104.04(5) . . ?
C7 N2 FE1 107.72(5) . . ?
N1 FE1 N1 163.91(3) . 3_655 ?
N1 FE1 N2 74.54(2) . . ?
N1 FE1 N2 92.84(2) 3_655 . ?
N1 FE1 N2 92.84(2) . 3_655 ?
N1 FE1 N2 74.54(2) 3_655 3_655 ?
N2 FE1 N2 78.37(4) . 3_655 ?
N1 FE1 CL1 97.274(18) . . ?
N1 FE1 CL1 92.930(17) 3_655 . ?
N2 FE1 CL1 91.508(18) . . ?
N2 FE1 CL1 163.284(17) 3_655 . ?
N1 FE1 CL1 92.930(17) . 3_655 ?
N1 FE1 CL1 97.274(18) 3_655 3_655 ?
N2 FE1 CL1 163.284(17) . 3_655 ?
N2 FE1 CL1 91.509(18) 3_655 3_655 ?
CL1 FE1 CL1 101.191(12) . 3_655 ?

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
N1 C1 C2 C3 -0.64(12) . . . . ?
C1 C2 C3 C4 0.39(12) . . . . ?
C2 C3 C4 C5 0.67(12) . . . . ?
C3 C4 C5 N1 -1.60(12) . . . . ?
C3 C4 C5 C6 178.75(8) . . . . ?
N1 C5 C6 N2 30.42(10) . . . . ?
C4 C5 C6 N2 -149.91(7) . . . . ?
C2 C1 N1 C5 -0.23(11) . . . . ?
C2 C1 N1 FE1 176.29(6) . . . . ?
C4 C5 N1 C1 1.37(11) . . . . ?
C6 C5 N1 C1 -178.96(7) . . . . ?
C4 C5 N1 FE1 -175.57(6) . . . . ?
C6 C5 N1 FE1 4.10(9) . . . . ?
C5 C6 N2 C8 -168.90(7) . . . . ?
C5 C6 N2 C7 69.42(8) . . . . ?
C5 C6 N2 FE1 -46.22(7) . . . . ?
C7 C7 N2 C8 83.22(9) 3_655 . . . ?
C7 C7 N2 C6 -155.72(7) 3_655 . . . ?
C7 C7 N2 FE1 -42.39(8) 3_655 . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.082

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

data_[Fe(II)(mep(OH)2)]Cl2
_database_code_depnum_ccdc_archive 'CCDC 1880895'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 Cl2 Fe N4 O2'
_chemical_formula_weight         457.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   10.0933(6)
_cell_length_b                   11.4226(7)
_cell_length_c                   17.1223(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.803(2)
_cell_angle_gamma                90
_cell_volume                     1963.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.701
_cell_measurement_theta_max      30.534

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.266
_exptl_absorpt_coefficient_mu    1.062
_shelx_estimated_absorpt_T_min   0.599
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_T_max  0.8384
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1383 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8188.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39656
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.701
_diffrn_reflns_theta_max         30.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3005
_reflns_number_gt                2880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WINGX CIF routines'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+2.1599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21710(9) 0.73209(8) 0.70541(5) 0.00841(15) Uani 1 1 d . . . . .
C2 C 0.09753(9) 0.71758(9) 0.65922(6) 0.01121(17) Uani 1 1 d . . . . .
H2 H 0.030384 0.667705 0.675729 0.013 Uiso 1 1 calc R U . . .
C3 C 0.07735(10) 0.77749(9) 0.58799(6) 0.01244(17) Uani 1 1 d . . . . .
H3 H -0.004847 0.770256 0.556046 0.015 Uiso 1 1 calc R U . . .
C4 C 0.17811(10) 0.84781(9) 0.56400(5) 0.01142(17) Uani 1 1 d . . . . .
H4 H 0.166621 0.888341 0.515339 0.014 Uiso 1 1 calc R U . . .
C5 C 0.29641(9) 0.85733(8) 0.61315(5) 0.00867(16) Uani 1 1 d . . . . .
C6 C 0.41231(10) 0.93072(8) 0.59284(5) 0.01087(17) Uani 1 1 d . . . . .
H6A H 0.445819 0.900425 0.544355 0.013 Uiso 1 1 calc R U . . .
H6B H 0.382978 1.012621 0.583220 0.013 Uiso 1 1 calc R U . . .
C7 C 0.24854(9) 0.67753(8) 0.78542(5) 0.01001(16) Uani 1 1 d . . . . .
H7A H 0.220862 0.731248 0.826139 0.012 Uiso 1 1 calc R U . . .
H7B H 0.198087 0.603587 0.788264 0.012 Uiso 1 1 calc R U . . .
C8 C 0.42945(10) 0.63943(9) 0.88598(5) 0.01204(17) Uani 1 1 d . . . . .
H8A H 0.411812 0.712642 0.912914 0.018 Uiso 1 1 calc R U . . .
H8B H 0.524305 0.620151 0.895618 0.018 Uiso 1 1 calc R U . . .
H8C H 0.376527 0.576213 0.905929 0.018 Uiso 1 1 calc R U . . .
C9 C 0.42676(9) 0.54702(8) 0.75666(6) 0.01034(16) Uani 1 1 d . . . . .
N2 N 0.39273(8) 0.65346(7) 0.80052(4) 0.00804(14) Uani 1 1 d . . . . .
N1 N 0.31399(8) 0.80148(7) 0.68225(5) 0.00795(14) Uani 1 1 d . . . . .
O1 O 0.51632(7) 0.92705(6) 0.65610(4) 0.01074(13) Uani 1 1 d . . . . .
CL1 Cl 0.75720(2) 0.92850(2) 0.57577(2) 0.01502(6) Uani 1 1 d . . . . .
FE1 Fe 0.500000 0.80473(2) 0.750000 0.00632(5) Uani 1 2 d S T P . .
H21 H 0.592(2) 0.9308(17) 0.6352(12) 0.042(5) Uiso 1 1 d . . . . .
H9A H 0.3709(15) 0.5470(13) 0.7056(9) 0.013(3) Uiso 1 1 d . . . . .
H9B H 0.4053(15) 0.4740(13) 0.7853(8) 0.013(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3492(12) . ?
C1 C2 1.3844(13) . ?
C1 C7 1.5093(13) . ?
C2 C3 1.3953(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3902(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3938(13) . ?
C4 H4 0.9500 . ?
C5 N1 1.3401(11) . ?
C5 C6 1.5081(13) . ?
C6 O1 1.4308(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.4780(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.4813(12) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.4875(12) . ?
C9 C9 1.5185(19) 2_656 ?
C9 H9A 0.992(15) . ?
C9 H9B 1.003(15) . ?
N2 FE1 2.2573(8) . ?
N1 FE1 2.1051(8) . ?
O1 FE1 2.1490(7) . ?
O1 H21 0.88(2) . ?
FE1 N1 2.1051(8) 2_656 ?
FE1 O1 2.1490(7) 2_656 ?
FE1 N2 2.2573(8) 2_656 ?

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 C1 C2 121.22(8) . . ?
N1 C1 C7 114.66(8) . . ?
C2 C1 C7 124.07(8) . . ?
C1 C2 C3 118.84(9) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.68(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.32(9) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 121.66(9) . . ?
N1 C5 C6 115.57(8) . . ?
C4 C5 C6 122.77(8) . . ?
O1 C6 C5 109.63(7) . . ?
O1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
O1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C1 110.40(7) . . ?
N2 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C9 110.72(6) . 2_656 ?
N2 C9 H9A 107.8(8) . . ?
C9 C9 H9A 110.1(8) 2_656 . ?
N2 C9 H9B 111.1(8) . . ?
C9 C9 H9B 109.6(8) 2_656 . ?
H9A C9 H9B 107.5(12) . . ?
C7 N2 C8 109.67(7) . . ?
C7 N2 C9 109.71(7) . . ?
C8 N2 C9 111.27(7) . . ?
C7 N2 FE1 107.01(5) . . ?
C8 N2 FE1 112.31(6) . . ?
C9 N2 FE1 106.74(5) . . ?
C5 N1 C1 120.26(8) . . ?
C5 N1 FE1 120.62(6) . . ?
C1 N1 FE1 118.75(6) . . ?
C6 O1 FE1 118.66(6) . . ?
C6 O1 H21 107.0(13) . . ?
FE1 O1 H21 118.2(13) . . ?
N1 FE1 N1 177.98(4) 2_656 . ?
N1 FE1 O1 74.38(3) 2_656 2_656 ?
N1 FE1 O1 106.99(3) . 2_656 ?
N1 FE1 O1 106.99(3) 2_656 . ?
N1 FE1 O1 74.38(3) . . ?
O1 FE1 O1 98.89(4) 2_656 . ?
N1 FE1 N2 76.24(3) 2_656 2_656 ?
N1 FE1 N2 102.18(3) . 2_656 ?
O1 FE1 N2 149.36(3) 2_656 2_656 ?
O1 FE1 N2 97.75(3) . 2_656 ?
N1 FE1 N2 102.18(3) 2_656 . ?
N1 FE1 N2 76.24(3) . . ?
O1 FE1 N2 97.75(3) 2_656 . ?
O1 FE1 N2 149.36(3) . . ?
N2 FE1 N2 80.11(4) 2_656 . ?

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
N1 C1 C2 C3 -0.83(14) . . . . ?
C7 C1 C2 C3 176.63(9) . . . . ?
C1 C2 C3 C4 1.57(14) . . . . ?
C2 C3 C4 C5 -0.92(14) . . . . ?
C3 C4 C5 N1 -0.50(14) . . . . ?
C3 C4 C5 C6 179.75(9) . . . . ?
N1 C5 C6 O1 -2.33(11) . . . . ?
C4 C5 C6 O1 177.43(8) . . . . ?
N1 C1 C7 N2 -32.94(11) . . . . ?
C2 C1 C7 N2 149.45(9) . . . . ?
C1 C7 N2 C8 160.62(8) . . . . ?
C1 C7 N2 C9 -76.88(9) . . . . ?
C1 C7 N2 FE1 38.55(8) . . . . ?
C9 C9 N2 C7 157.05(9) 2_656 . . . ?
C9 C9 N2 C8 -81.41(10) 2_656 . . . ?
C9 C9 N2 FE1 41.44(10) 2_656 . . . ?
C4 C5 N1 C1 1.27(13) . . . . ?
C6 C5 N1 C1 -178.98(8) . . . . ?
C4 C5 N1 FE1 174.12(7) . . . . ?
C6 C5 N1 FE1 -6.12(11) . . . . ?
C2 C1 N1 C5 -0.58(13) . . . . ?
C7 C1 N1 C5 -178.27(8) . . . . ?
C2 C1 N1 FE1 -173.56(7) . . . . ?
C7 C1 N1 FE1 8.75(10) . . . . ?
C5 C6 O1 FE1 9.55(10) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.062

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

data_[Fe(II)(mep(COHNBu)2)]Cl2
_database_code_depnum_ccdc_archive 'CCDC 1880893'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H42 Cl2 Fe N6 O3'
_chemical_formula_weight         613.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.2396(6)
_cell_length_b                   10.7040(5)
_cell_length_c                   22.9106(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.493(2)
_cell_angle_gamma                90
_cell_volume                     2975.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.892
_cell_measurement_theta_max      65.1705

_exptl_crystal_description       plates
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    6.021
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6150
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0376 after correction.
The Ratio of minimum to maximum transmission is 0.8172.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23853
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.892
_diffrn_reflns_theta_max         65.194
_diffrn_reflns_theta_full        65.194
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5075
_reflns_number_gt                4741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WINGX CIF Routines'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+2.0217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5075
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42912(13) 0.30562(15) 0.65751(7) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.52777(14) 0.27106(16) 0.68971(7) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.580238 0.331989 0.705061 0.025 Uiso 1 1 calc R U . . .
C3 C 0.54791(14) 0.14429(16) 0.69898(8) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.615065 0.117339 0.720855 0.027 Uiso 1 1 calc R U . . .
C4 C 0.46988(13) 0.05734(16) 0.67626(7) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.483686 -0.029581 0.681304 0.023 Uiso 1 1 calc R U . . .
C5 C 0.37116(13) 0.09957(15) 0.64600(7) 0.0153(3) Uani 1 1 d . . . . .
C6 C 0.27791(13) 0.01720(15) 0.61906(7) 0.0170(3) Uani 1 1 d . . . . .
H6A H 0.288161 -0.003756 0.578042 0.020 Uiso 1 1 calc R U . . .
H6B H 0.277656 -0.061616 0.641655 0.020 Uiso 1 1 calc R U . . .
C7 C 0.14283(14) 0.08659(15) 0.68091(7) 0.0182(3) Uani 1 1 d . . . . .
H7A H 0.210273 0.101206 0.708945 0.022 Uiso 1 1 calc R U . . .
H7B H 0.111386 0.005076 0.690530 0.022 Uiso 1 1 calc R U . . .
C8 C 0.06010(14) 0.18930(15) 0.68731(7) 0.0191(3) Uani 1 1 d . . . . .
H8A H -0.008123 0.172991 0.660114 0.023 Uiso 1 1 calc R U . . .
H8B H 0.041003 0.188901 0.727988 0.023 Uiso 1 1 calc R U . . .
C9 C 0.08554(14) 0.01838(16) 0.57978(8) 0.0214(4) Uani 1 1 d . . . . .
H9A H 0.105023 0.019763 0.539629 0.032 Uiso 1 1 calc R U . . .
H9B H 0.014781 0.060803 0.580532 0.032 Uiso 1 1 calc R U . . .
H9C H 0.079589 -0.068387 0.592644 0.032 Uiso 1 1 calc R U . . .
C10 C 0.17662(14) 0.36324(17) 0.72579(7) 0.0225(4) Uani 1 1 d . . . . .
H10A H 0.135029 0.368944 0.759459 0.034 Uiso 1 1 calc R U . . .
H10B H 0.203261 0.446395 0.716635 0.034 Uiso 1 1 calc R U . . .
H10C H 0.239525 0.306960 0.735481 0.034 Uiso 1 1 calc R U . . .
C11 C 0.01186(13) 0.40261(15) 0.65823(7) 0.0158(3) Uani 1 1 d . . . . .
H11A H 0.038372 0.489324 0.665416 0.019 Uiso 1 1 calc R U . . .
H11B H -0.046737 0.386777 0.683292 0.019 Uiso 1 1 calc R U . . .
C12 C -0.03462(12) 0.38773(14) 0.59438(7) 0.0135(3) Uani 1 1 d . . . . .
C13 C -0.14029(13) 0.42542(14) 0.57096(7) 0.0162(3) Uani 1 1 d . . . . .
H13 H -0.189903 0.458562 0.595599 0.019 Uiso 1 1 calc R U . . .
C14 C -0.17116(13) 0.41340(15) 0.51097(7) 0.0180(3) Uani 1 1 d . . . . .
H14 H -0.242605 0.439134 0.494045 0.022 Uiso 1 1 calc R U . . .
C15 C -0.09807(13) 0.36370(15) 0.47506(7) 0.0166(3) Uani 1 1 d . . . . .
H15 H -0.118648 0.354233 0.433862 0.020 Uiso 1 1 calc R U . . .
C16 C 0.00540(13) 0.32879(14) 0.50171(7) 0.0138(3) Uani 1 1 d . . . . .
C17 C 0.39280(13) 0.43561(15) 0.63863(7) 0.0151(3) Uani 1 1 d . . . . .
C18 C 0.43939(13) 0.65483(15) 0.62841(7) 0.0173(3) Uani 1 1 d . . . . .
H18A H 0.475022 0.717461 0.656481 0.021 Uiso 1 1 calc R U . . .
H18B H 0.359040 0.670872 0.622904 0.021 Uiso 1 1 calc R U . . .
C19 C 0.48402(14) 0.66748(16) 0.56952(7) 0.0198(3) Uani 1 1 d . . . . .
H19A H 0.563368 0.645993 0.574990 0.024 Uiso 1 1 calc R U . . .
H19B H 0.445587 0.606987 0.541262 0.024 Uiso 1 1 calc R U . . .
C20 C 0.46953(16) 0.79824(17) 0.54364(8) 0.0254(4) Uani 1 1 d . . . . .
H20A H 0.507400 0.859026 0.571941 0.030 Uiso 1 1 calc R U . . .
H20B H 0.390144 0.819542 0.537616 0.030 Uiso 1 1 calc R U . . .
C21 C 0.51558(16) 0.8093(2) 0.48529(8) 0.0320(4) Uani 1 1 d . . . . .
H21A H 0.594401 0.789426 0.491152 0.048 Uiso 1 1 calc R U . . .
H21B H 0.505032 0.894828 0.470314 0.048 Uiso 1 1 calc R U . . .
H21C H 0.476951 0.750856 0.456808 0.048 Uiso 1 1 calc R U . . .
C22 C 0.10024(13) 0.28017(14) 0.47218(7) 0.0141(3) Uani 1 1 d . . . . .
C23 C 0.17506(15) 0.22968(17) 0.38079(8) 0.0238(4) Uani 1 1 d . . . . .
H23A H 0.245730 0.259327 0.402273 0.029 Uiso 1 1 calc R U . . .
H23B H 0.163251 0.273931 0.342543 0.029 Uiso 1 1 calc R U . . .
C24 C 0.18387(16) 0.09047(18) 0.36941(8) 0.0284(4) Uani 1 1 d . . . . .
H24A H 0.109986 0.058392 0.353724 0.034 Uiso 1 1 calc R U . . .
H24B H 0.232774 0.077679 0.338746 0.034 Uiso 1 1 calc R U . . .
C25 C 0.22761(17) 0.01514(18) 0.42300(9) 0.0325(4) Uani 1 1 d . . . . .
H25A H 0.177202 0.024744 0.453165 0.039 Uiso 1 1 calc R U . . .
H25B H 0.300437 0.048682 0.439623 0.039 Uiso 1 1 calc R U . . .
C26 C 0.23941(17) -0.12302(19) 0.40963(11) 0.0398(5) Uani 1 1 d . . . . .
H26A H 0.167453 -0.157067 0.393478 0.060 Uiso 1 1 calc R U . . .
H26B H 0.267033 -0.167550 0.445949 0.060 Uiso 1 1 calc R U . . .
H26C H 0.291343 -0.133470 0.380860 0.060 Uiso 1 1 calc R U . . .
N1 N 0.35241(11) 0.22139(12) 0.63695(6) 0.0141(3) Uani 1 1 d . . . . .
N2 N 0.17172(10) 0.08310(12) 0.61974(6) 0.0150(3) Uani 1 1 d . . . . .
N3 N 0.10432(11) 0.31411(12) 0.67421(6) 0.0152(3) Uani 1 1 d . . . . .
N4 N 0.03527(10) 0.34051(11) 0.56003(5) 0.0128(3) Uani 1 1 d . . . . .
N5 N 0.46111(12) 0.52912(13) 0.65234(6) 0.0174(3) Uani 1 1 d . . . . .
N6 N 0.08565(12) 0.26259(13) 0.41483(6) 0.0166(3) Uani 1 1 d . . . . .
O1 O 0.29918(9) 0.44900(10) 0.60928(5) 0.0165(2) Uani 1 1 d . . . . .
O2 O 0.19052(9) 0.26141(11) 0.50390(5) 0.0172(2) Uani 1 1 d . . . . .
O3 O 0.86969(11) 0.30886(14) 0.77237(6) 0.0292(3) Uani 1 1 d . . . . .
CL1 Cl 0.71414(3) 0.52527(4) 0.70507(2) 0.02221(10) Uani 1 1 d . . . . .
CL2 Cl 0.87261(4) 0.28203(4) 0.32553(2) 0.02497(11) Uani 1 1 d . . . . .
FE1 Fe 0.19695(2) 0.28741(2) 0.59661(2) 0.01239(8) Uani 1 1 d . . . . .
H23 H 0.822(2) 0.354(2) 0.7560(10) 0.036(6) Uiso 1 1 d . . . . .
H24 H 0.836(2) 0.236(3) 0.7714(11) 0.043(7) Uiso 1 1 d . . . . .
H35 H 0.5266(18) 0.5165(18) 0.6692(9) 0.022(5) Uiso 1 1 d . . . . .
H36 H 0.0210(19) 0.2757(19) 0.3942(9) 0.028(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(2) . ?
C1 C2 1.381(2) . ?
C1 C17 1.507(2) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.336(2) . ?
C5 C6 1.509(2) . ?
C6 N2 1.481(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.490(2) . ?
C7 C8 1.515(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.487(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.476(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N3 1.478(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N3 1.485(2) . ?
C11 C12 1.507(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N4 1.335(2) . ?
C12 C13 1.394(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 N4 1.344(2) . ?
C16 C22 1.510(2) . ?
C17 O1 1.2588(19) . ?
C17 N5 1.316(2) . ?
C18 N5 1.464(2) . ?
C18 C19 1.526(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.521(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O2 1.257(2) . ?
C22 N6 1.316(2) . ?
C23 N6 1.467(2) . ?
C23 C24 1.519(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.508(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.521(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 FE1 2.1250(13) . ?
N2 FE1 2.2807(13) . ?
N3 FE1 2.2480(13) . ?
N4 FE1 2.1234(13) . ?
N5 H35 0.85(2) . ?
N6 H36 0.88(2) . ?
O1 FE1 2.1323(11) . ?
O2 FE1 2.1334(11) . ?
O3 H23 0.81(3) . ?
O3 H24 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.04(15) . . ?
N1 C1 C17 110.66(13) . . ?
C2 C1 C17 127.26(15) . . ?
C1 C2 C3 117.92(16) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 119.89(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.78(15) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.09(15) . . ?
N1 C5 C6 113.67(14) . . ?
C4 C5 C6 125.22(14) . . ?
N2 C6 C5 109.61(13) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 110.66(13) . . ?
N2 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N3 C8 C7 111.54(13) . . ?
N3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 110.55(12) . . ?
N3 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N4 C12 C13 121.09(14) . . ?
N4 C12 C11 114.99(13) . . ?
C13 C12 C11 123.85(14) . . ?
C14 C13 C12 118.37(15) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 120.51(15) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 117.54(14) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
N4 C16 C15 121.88(14) . . ?
N4 C16 C22 110.62(13) . . ?
C15 C16 C22 127.44(14) . . ?
O1 C17 N5 123.14(15) . . ?
O1 C17 C1 118.19(14) . . ?
N5 C17 C1 118.65(14) . . ?
N5 C18 C19 110.12(13) . . ?
N5 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
N5 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 112.90(14) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 C21 112.10(15) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 N6 123.29(15) . . ?
O2 C22 C16 117.72(13) . . ?
N6 C22 C16 118.97(14) . . ?
N6 C23 C24 113.67(14) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 114.23(16) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C26 112.90(17) . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
C26 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 N1 C1 120.21(14) . . ?
C5 N1 FE1 121.22(11) . . ?
C1 N1 FE1 118.36(10) . . ?
C9 N2 C6 109.10(12) . . ?
C9 N2 C7 110.92(13) . . ?
C6 N2 C7 109.76(12) . . ?
C9 N2 FE1 114.42(10) . . ?
C6 N2 FE1 107.98(9) . . ?
C7 N2 FE1 104.50(9) . . ?
C10 N3 C11 109.14(12) . . ?
C10 N3 C8 110.74(13) . . ?
C11 N3 C8 109.71(12) . . ?
C10 N3 FE1 111.50(10) . . ?
C11 N3 FE1 109.45(9) . . ?
C8 N3 FE1 106.25(9) . . ?
C12 N4 C16 120.60(13) . . ?
C12 N4 FE1 120.30(10) . . ?
C16 N4 FE1 119.08(10) . . ?
C17 N5 C18 122.07(14) . . ?
C17 N5 H35 121.1(14) . . ?
C18 N5 H35 115.4(14) . . ?
C22 N6 C23 123.47(15) . . ?
C22 N6 H36 120.7(14) . . ?
C23 N6 H36 115.7(14) . . ?
C17 O1 FE1 117.23(10) . . ?
C22 O2 FE1 118.05(10) . . ?
H23 O3 H24 102(2) . . ?
N4 FE1 N1 175.02(5) . . ?
N4 FE1 O1 109.68(5) . . ?
N1 FE1 O1 74.59(4) . . ?
N4 FE1 O2 74.37(4) . . ?
N1 FE1 O2 107.72(5) . . ?
O1 FE1 O2 100.73(4) . . ?
N4 FE1 N3 74.81(5) . . ?
N1 FE1 N3 102.34(5) . . ?
O1 FE1 N3 97.85(5) . . ?
O2 FE1 N3 147.89(5) . . ?
N4 FE1 N2 101.59(5) . . ?
N1 FE1 N2 73.78(5) . . ?
O1 FE1 N2 147.24(4) . . ?
O2 FE1 N2 96.76(5) . . ?
N3 FE1 N2 80.83(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
N1 C1 C2 C3 2.1(2) . . . . ?
C17 C1 C2 C3 -175.67(15) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C3 C4 C5 N1 2.3(2) . . . . ?
C3 C4 C5 C6 -179.58(15) . . . . ?
N1 C5 C6 N2 -32.01(18) . . . . ?
C4 C5 C6 N2 149.72(15) . . . . ?
N2 C7 C8 N3 -60.07(17) . . . . ?
N3 C11 C12 N4 -24.72(18) . . . . ?
N3 C11 C12 C13 158.47(14) . . . . ?
N4 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 176.28(14) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 N4 0.7(2) . . . . ?
C14 C15 C16 C22 -176.21(14) . . . . ?
N1 C1 C17 O1 2.1(2) . . . . ?
C2 C1 C17 O1 -179.94(16) . . . . ?
N1 C1 C17 N5 -176.33(14) . . . . ?
C2 C1 C17 N5 1.6(2) . . . . ?
N5 C18 C19 C20 -177.00(14) . . . . ?
C18 C19 C20 C21 179.40(15) . . . . ?
N4 C16 C22 O2 -1.87(19) . . . . ?
C15 C16 C22 O2 175.30(15) . . . . ?
N4 C16 C22 N6 179.84(13) . . . . ?
C15 C16 C22 N6 -3.0(2) . . . . ?
N6 C23 C24 C25 -71.9(2) . . . . ?
C23 C24 C25 C26 -177.87(16) . . . . ?
C4 C5 N1 C1 -0.5(2) . . . . ?
C6 C5 N1 C1 -178.80(14) . . . . ?
C4 C5 N1 FE1 -175.15(12) . . . . ?
C6 C5 N1 FE1 6.51(18) . . . . ?
C2 C1 N1 C5 -1.8(2) . . . . ?
C17 C1 N1 C5 176.30(13) . . . . ?
C2 C1 N1 FE1 173.06(12) . . . . ?
C17 C1 N1 FE1 -8.86(17) . . . . ?
C5 C6 N2 C9 164.86(13) . . . . ?
C5 C6 N2 C7 -73.41(16) . . . . ?
C5 C6 N2 FE1 39.94(14) . . . . ?
C8 C7 N2 C9 -79.58(16) . . . . ?
C8 C7 N2 C6 159.78(13) . . . . ?
C8 C7 N2 FE1 44.20(14) . . . . ?
C12 C11 N3 C10 156.23(13) . . . . ?
C12 C11 N3 C8 -82.27(15) . . . . ?
C12 C11 N3 FE1 33.95(14) . . . . ?
C7 C8 N3 C10 -81.23(16) . . . . ?
C7 C8 N3 C11 158.23(13) . . . . ?
C7 C8 N3 FE1 40.01(15) . . . . ?
C13 C12 N4 C16 0.4(2) . . . . ?
C11 C12 N4 C16 -176.54(13) . . . . ?
C13 C12 N4 FE1 178.69(11) . . . . ?
C11 C12 N4 FE1 1.79(17) . . . . ?
C15 C16 N4 C12 -0.5(2) . . . . ?
C22 C16 N4 C12 176.82(13) . . . . ?
C15 C16 N4 FE1 -178.89(11) . . . . ?
C22 C16 N4 FE1 -1.53(16) . . . . ?
O1 C17 N5 C18 -7.6(2) . . . . ?
C1 C17 N5 C18 170.70(14) . . . . ?
C19 C18 N5 C17 -87.36(18) . . . . ?
O2 C22 N6 C23 -5.5(2) . . . . ?
C16 C22 N6 C23 172.72(14) . . . . ?
C24 C23 N6 C22 96.53(19) . . . . ?
N5 C17 O1 FE1 -176.10(12) . . . . ?
C1 C17 O1 FE1 5.54(18) . . . . ?
N6 C22 O2 FE1 -177.42(11) . . . . ?
C16 C22 O2 FE1 4.37(17) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_mep(OH)2
_database_code_depnum_ccdc_archive 'CCDC 1880897'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 N4 O2'
_chemical_formula_weight         330.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.5565(3)
_cell_length_b                   11.9424(5)
_cell_length_c                   8.8195(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.2960(10)
_cell_angle_gamma                90
_cell_volume                     869.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9535
_cell_measurement_theta_min      3.701
_cell_measurement_theta_max      72.411

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7156
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0625 after correction.
The ratio of minimum to maximum apparent transmission was 0.716.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11133
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.359
_diffrn_reflns_theta_max         72.490
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1710
_reflns_number_gt                1611
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELX-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WinGX CIF Routines'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.3744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1710
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.40876(12) 0.29332(9) 0.26599(12) 0.0170(2) Uani 1 1 d . . . . .
H1A H 0.431407 0.215748 0.305231 0.020 Uiso 1 1 calc R U . . .
H1B H 0.309521 0.318797 0.293364 0.020 Uiso 1 1 calc R U . . .
C2 C 0.54875(12) 0.36760(9) 0.34881(12) 0.0148(2) Uani 1 1 d . . . . .
C3 C 0.62669(13) 0.43866(9) 0.26772(13) 0.0182(2) Uani 1 1 d . . . . .
H3 H 0.594109 0.442038 0.156172 0.022 Uiso 1 1 calc R U . . .
C4 C 0.75331(13) 0.50476(9) 0.35294(13) 0.0202(2) Uani 1 1 d . . . . .
H4 H 0.808787 0.554163 0.300565 0.024 Uiso 1 1 calc R U . . .
C5 C 0.79719(13) 0.49745(9) 0.51502(13) 0.0185(2) Uani 1 1 d . . . . .
H5 H 0.883406 0.541807 0.575629 0.022 Uiso 1 1 calc R U . . .
C6 C 0.71346(12) 0.42419(8) 0.58868(12) 0.0152(2) Uani 1 1 d . . . . .
C7 C 0.75766(12) 0.41636(9) 0.76602(12) 0.0168(2) Uani 1 1 d . . . . .
H7A H 0.724414 0.486124 0.809558 0.020 Uiso 1 1 calc R U . . .
H7B H 0.697813 0.353365 0.797473 0.020 Uiso 1 1 calc R U . . .
C8 C 0.97318(15) 0.28197(10) 0.81622(15) 0.0256(3) Uani 1 1 d . . . . .
H8A H 0.915568 0.234829 0.874725 0.038 Uiso 1 1 calc R U . . .
H8B H 1.090243 0.271573 0.858359 0.038 Uiso 1 1 calc R U . . .
H8C H 0.941346 0.260768 0.704943 0.038 Uiso 1 1 calc R U . . .
C9 C 0.98709(13) 0.43689(8) 0.99549(12) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.59139(10) 0.35989(7) 0.50686(10) 0.0143(2) Uani 1 1 d . . . . .
N2 N 0.93207(10) 0.39921(7) 0.83205(10) 0.0154(2) Uani 1 1 d . . . . .
O1 O 0.37947(9) 0.29288(7) 0.10105(9) 0.0210(2) Uani 1 1 d . . . . .
H9B H 1.0915(17) 0.3977(11) 1.0443(15) 0.020(3) Uiso 1 1 d . . . . .
H9A H 0.9094(17) 0.4151(11) 1.0587(16) 0.022(3) Uiso 1 1 d . . . . .
H1 H 0.449(2) 0.2445(15) 0.0781(19) 0.037(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4094(12) . ?
C1 C2 1.5145(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.3477(13) . ?
C2 C3 1.3885(15) . ?
C3 C4 1.3900(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3817(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3951(15) . ?
C5 H5 0.9500 . ?
C6 N1 1.3430(13) . ?
C6 C7 1.5120(14) . ?
C7 N2 1.4661(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.4593(14) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.4643(13) . ?
C9 C9 1.523(2) 3_767 ?
C9 H9B 1.000(14) . ?
C9 H9A 1.007(14) . ?
O1 H1 0.888(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 113.74(9) . . ?
O1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
O1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 C3 122.60(9) . . ?
N1 C2 C1 115.01(9) . . ?
C3 C2 C1 122.40(9) . . ?
C2 C3 C4 118.71(10) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.94(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 119.25(10) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 122.04(10) . . ?
N1 C6 C7 117.86(9) . . ?
C5 C6 C7 120.09(9) . . ?
N2 C7 C6 111.72(8) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C9 111.11(11) . 3_767 ?
N2 C9 H9B 107.4(8) . . ?
C9 C9 H9B 109.9(8) 3_767 . ?
N2 C9 H9A 112.2(8) . . ?
C9 C9 H9A 109.6(8) 3_767 . ?
H9B C9 H9A 106.6(11) . . ?
C6 N1 C2 118.47(9) . . ?
C8 N2 C9 111.47(8) . . ?
C8 N2 C7 109.99(8) . . ?
C9 N2 C7 112.16(8) . . ?
C1 O1 H1 106.9(11) . . ?

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
O1 C1 C2 N1 -172.76(8) . . . . ?
O1 C1 C2 C3 7.52(14) . . . . ?
N1 C2 C3 C4 -0.23(16) . . . . ?
C1 C2 C3 C4 179.46(9) . . . . ?
C2 C3 C4 C5 0.03(16) . . . . ?
C3 C4 C5 C6 -0.03(16) . . . . ?
C4 C5 C6 N1 0.25(16) . . . . ?
C4 C5 C6 C7 -178.96(9) . . . . ?
N1 C6 C7 N2 129.86(9) . . . . ?
C5 C6 C7 N2 -50.89(13) . . . . ?
C5 C6 N1 C2 -0.45(15) . . . . ?
C7 C6 N1 C2 178.78(8) . . . . ?
C3 C2 N1 C6 0.44(15) . . . . ?
C1 C2 N1 C6 -179.27(9) . . . . ?
C9 C9 N2 C8 155.15(11) 3_767 . . . ?
C9 C9 N2 C7 -81.01(13) 3_767 . . . ?
C6 C7 N2 C8 -79.08(11) . . . . ?
C6 C7 N2 C9 156.25(9) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046

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

data_[Fe(II)(mep(COHNBu)2)](PF6)2
_database_code_depnum_ccdc_archive 'CCDC 1880894'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H40 F12 Fe N6 O2 P2'
_chemical_formula_weight         814.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.9740(19)
_cell_length_b                   12.663(2)
_cell_length_c                   13.902(3)
_cell_angle_alpha                107.517(2)
_cell_angle_beta                 108.430(2)
_cell_angle_gamma                96.563(2)
_cell_volume                     1700.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5494
_cell_measurement_theta_min      2.3315
_cell_measurement_theta_max      26.2785

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012/1) was used for absorption correction.
wR2(int) was 0.0456 after correction.
The ratio of minimum to maximum apparent transmission was 0.7379.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17141
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.653
_diffrn_reflns_theta_max         26.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6772
_reflns_number_gt                5571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker APEX'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    'SHELX-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WinGX CIF Routines'
_refine_special_details          
;
A DFIX restraint was used to model the N-H distance in one of the
amide groups. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+1.4461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6772
_refine_ls_number_parameters     454
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8937(3) 0.6390(2) 0.8731(2) 0.0188(6) Uani 1 1 d . . . . .
C2 C 0.9199(3) 0.7556(2) 0.9555(2) 0.0191(6) Uani 1 1 d . . . . .
C3 C 1.0239(3) 0.8058(3) 1.0532(2) 0.0236(6) Uani 1 1 d . . . . .
H3 H 1.092257 0.768075 1.074054 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0270(3) 0.9136(3) 1.1213(2) 0.0264(7) Uani 1 1 d . . . . .
H4 H 1.097223 0.949873 1.189692 0.032 Uiso 1 1 calc R U . . .
C5 C 0.9270(3) 0.9673(3) 1.0883(2) 0.0241(6) Uani 1 1 d . . . . .
H5 H 0.928093 1.040841 1.133418 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8253(3) 0.9120(2) 0.9882(2) 0.0201(6) Uani 1 1 d . . . . .
C7 C 0.7123(3) 0.9612(2) 0.9412(2) 0.0235(6) Uani 1 1 d . . . . .
H7A H 0.693529 1.013802 1.000889 0.028 Uiso 1 1 calc R U . . .
H7B H 0.737061 1.005285 0.899626 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5282(3) 0.8308(2) 0.9351(2) 0.0214(6) Uani 1 1 d . . . . .
H8A H 0.473246 0.883288 0.956451 0.026 Uiso 1 1 calc R U . . .
H8B H 0.596815 0.832061 1.002108 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4426(3) 0.7113(2) 0.8722(2) 0.0211(6) Uani 1 1 d . . . . .
H9A H 0.397559 0.688340 0.916720 0.025 Uiso 1 1 calc R U . . .
H9B H 0.374132 0.710000 0.805140 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4351(3) 0.5255(2) 0.7532(2) 0.0199(6) Uani 1 1 d . . . . .
H10A H 0.353734 0.504726 0.766515 0.024 Uiso 1 1 calc R U . . .
H10B H 0.479904 0.461635 0.749820 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3993(3) 0.5442(2) 0.6468(2) 0.0170(5) Uani 1 1 d . . . . .
C12 C 0.2861(3) 0.4834(2) 0.5564(2) 0.0203(6) Uani 1 1 d . . . . .
H12 H 0.221593 0.429635 0.560206 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2690(3) 0.5025(2) 0.4611(2) 0.0209(6) Uani 1 1 d . . . . .
H13 H 0.192934 0.460826 0.397970 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3637(3) 0.5832(2) 0.4571(2) 0.0195(6) Uani 1 1 d . . . . .
H14 H 0.353649 0.596943 0.391859 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4717(3) 0.6420(2) 0.5505(2) 0.0175(6) Uani 1 1 d . . . . .
C16 C 0.5866(3) 0.7320(2) 0.5667(2) 0.0176(6) Uani 1 1 d . . . . .
C17 C 0.5013(3) 0.9134(2) 0.7943(2) 0.0227(6) Uani 1 1 d . . . . .
H17A H 0.420779 0.853774 0.747979 0.034 Uiso 1 1 calc R U . . .
H17B H 0.544318 0.935152 0.748935 0.034 Uiso 1 1 calc R U . . .
H17C H 0.478524 0.979925 0.836572 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5945(3) 0.5989(2) 0.9371(2) 0.0228(6) Uani 1 1 d . . . . .
H18A H 0.530658 0.562127 0.959831 0.034 Uiso 1 1 calc R U . . .
H18B H 0.651575 0.667855 0.997366 0.034 Uiso 1 1 calc R U . . .
H18C H 0.648428 0.546337 0.916158 0.034 Uiso 1 1 calc R U . . .
C19 C 0.9658(3) 0.4667(2) 0.8059(2) 0.0212(6) Uani 1 1 d . . . . .
H19A H 0.949097 0.473047 0.733815 0.025 Uiso 1 1 calc R U . . .
H19B H 0.887259 0.415204 0.800867 0.025 Uiso 1 1 calc R U . . .
C20 C 1.0852(3) 0.4160(2) 0.8356(3) 0.0249(6) Uani 1 1 d . . . . .
H20A H 1.098888 0.404706 0.905364 0.030 Uiso 1 1 calc R U . . .
H20B H 1.165017 0.469082 0.844627 0.030 Uiso 1 1 calc R U . . .
C21 C 1.0644(3) 0.3020(3) 0.7467(3) 0.0308(7) Uani 1 1 d . . . . .
H21A H 0.982202 0.250948 0.736400 0.037 Uiso 1 1 calc R U . . .
H21B H 1.051969 0.314728 0.677732 0.037 Uiso 1 1 calc R U . . .
C22 C 1.1776(3) 0.2424(3) 0.7704(3) 0.0372(8) Uani 1 1 d . . . . .
H22A H 1.259720 0.292274 0.781242 0.056 Uiso 1 1 calc R U . . .
H22B H 1.158640 0.171497 0.709051 0.056 Uiso 1 1 calc R U . . .
H22C H 1.187320 0.225017 0.836196 0.056 Uiso 1 1 calc R U . . .
C23 C 0.7016(3) 0.8430(2) 0.4917(2) 0.0220(6) Uani 1 1 d . . . . .
H23A H 0.717006 0.820205 0.422669 0.026 Uiso 1 1 calc R U . . .
H23B H 0.782935 0.845192 0.550132 0.026 Uiso 1 1 calc R U . . .
C24 C 0.6735(3) 0.9611(2) 0.5159(3) 0.0243(6) Uani 1 1 d . . . . .
H24A H 0.586940 0.956856 0.462116 0.029 Uiso 1 1 calc R U . . .
H24B H 0.667906 0.987163 0.588690 0.029 Uiso 1 1 calc R U . . .
C25 C 0.7787(3) 1.0475(3) 0.5126(3) 0.0290(7) Uani 1 1 d . . . . .
H25A H 0.790491 1.018146 0.442424 0.035 Uiso 1 1 calc R U . . .
H25B H 0.863655 1.057573 0.571271 0.035 Uiso 1 1 calc R U . . .
C26 C 0.7425(3) 1.1622(3) 0.5262(3) 0.0312(7) Uani 1 1 d . . . . .
H26A H 0.657572 1.152363 0.469074 0.047 Uiso 1 1 calc R U . . .
H26B H 0.810922 1.214659 0.520990 0.047 Uiso 1 1 calc R U . . .
H26C H 0.735563 1.193554 0.597438 0.047 Uiso 1 1 calc R U . . .
N1 N 0.8221(2) 0.80802(19) 0.92433(19) 0.0177(5) Uani 1 1 d . . . . .
N2 N 0.5922(2) 0.87008(19) 0.86899(19) 0.0190(5) Uani 1 1 d . . . . .
N3 N 0.5231(2) 0.62940(19) 0.84349(18) 0.0179(5) Uani 1 1 d . . . . .
N4 N 0.4890(2) 0.62192(18) 0.64275(18) 0.0161(5) Uani 1 1 d . . . . .
N5 N 0.9851(2) 0.5795(2) 0.8861(2) 0.0208(5) Uani 1 1 d D . . . .
N6 N 0.5922(2) 0.7581(2) 0.4833(2) 0.0202(5) Uani 1 1 d . . . . .
O1 O 0.78515(18) 0.60067(16) 0.79550(15) 0.0192(4) Uani 1 1 d . . . . .
O2 O 0.67444(18) 0.77751(16) 0.65956(16) 0.0197(4) Uani 1 1 d . . . . .
F1 F 0.9866(2) 0.6852(2) 0.56895(18) 0.0586(7) Uani 1 1 d . . . . .
F2 F 1.20853(18) 0.73161(16) 0.65117(15) 0.0320(4) Uani 1 1 d . . . . .
F3 F 1.18817(19) 0.80480(18) 0.81375(15) 0.0384(5) Uani 1 1 d . . . . .
F4 F 1.0869(3) 0.62384(18) 0.7038(2) 0.0613(7) Uani 1 1 d . . . . .
F5 F 0.9674(2) 0.7561(2) 0.73258(19) 0.0513(6) Uani 1 1 d . . . . .
F6 F 1.0891(2) 0.86523(18) 0.67952(19) 0.0474(6) Uani 1 1 d . . . . .
F7 F 0.3630(2) 0.80781(16) 0.08753(16) 0.0383(5) Uani 1 1 d . . . . .
F8 F 0.4662(2) 0.67222(17) 0.12323(17) 0.0380(5) Uani 1 1 d . . . . .
F9 F 0.2937(2) 0.82132(17) 0.22468(15) 0.0396(5) Uani 1 1 d . . . . .
F10 F 0.24776(17) 0.65019(14) 0.08953(14) 0.0290(4) Uani 1 1 d . . . . .
F11 F 0.39263(18) 0.68219(15) 0.25958(14) 0.0298(4) Uani 1 1 d . . . . .
F12 F 0.5096(2) 0.84038(17) 0.25705(17) 0.0432(5) Uani 1 1 d . . . . .
P1 P 1.08731(7) 0.74414(7) 0.69069(7) 0.02475(19) Uani 1 1 d . . . . .
P2 P 0.37872(8) 0.74547(6) 0.17366(6) 0.02265(19) Uani 1 1 d . . . . .
FE1 Fe 0.65655(4) 0.71774(3) 0.78203(3) 0.01647(12) Uani 1 1 d . . . . .
H5N H 1.057(2) 0.611(3) 0.9392(19) 0.018(8) Uiso 1 1 d D . . . .
H6 H 0.534(3) 0.730(3) 0.424(3) 0.012(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.248(3) . ?
C1 N5 1.321(4) . ?
C1 C2 1.501(4) . ?
C2 N1 1.350(4) . ?
C2 C3 1.373(4) . ?
C3 C4 1.397(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.337(4) . ?
C6 C7 1.504(4) . ?
C7 N2 1.481(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.479(4) . ?
C8 C9 1.516(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.483(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.480(3) . ?
C10 C11 1.505(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.337(3) . ?
C11 C12 1.388(4) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9500 . ?
C15 N4 1.341(3) . ?
C15 C16 1.509(4) . ?
C16 O2 1.252(3) . ?
C16 N6 1.315(4) . ?
C17 N2 1.479(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N3 1.478(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N5 1.466(4) . ?
C19 C20 1.520(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.528(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.526(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N6 1.466(3) . ?
C23 C24 1.520(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.518(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.523(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 FE1 2.100(2) . ?
N2 FE1 2.265(2) . ?
N3 FE1 2.262(2) . ?
N4 FE1 2.104(2) . ?
N5 H5N 0.839(18) . ?
N6 H6 0.81(3) . ?
O1 FE1 2.1685(19) . ?
O2 FE1 2.1126(19) . ?
F1 P1 1.585(2) . ?
F2 P1 1.5983(19) . ?
F3 P1 1.600(2) . ?
F4 P1 1.588(2) . ?
F5 P1 1.603(2) . ?
F6 P1 1.586(2) . ?
F7 P2 1.599(2) . ?
F8 P2 1.585(2) . ?
F9 P2 1.584(2) . ?
F10 P2 1.6064(18) . ?
F11 P2 1.6066(18) . ?
F12 P2 1.602(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N5 122.2(3) . . ?
O1 C1 C2 118.8(2) . . ?
N5 C1 C2 119.0(2) . . ?
N1 C2 C3 121.6(3) . . ?
N1 C2 C1 111.0(2) . . ?
C3 C2 C1 127.3(3) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 121.1(3) . . ?
N1 C6 C7 114.3(2) . . ?
C5 C6 C7 124.6(3) . . ?
N2 C7 C6 111.0(2) . . ?
N2 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 111.0(2) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 C8 110.9(2) . . ?
N3 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 C11 110.7(2) . . ?
N3 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C12 121.0(3) . . ?
N4 C11 C10 114.8(2) . . ?
C12 C11 C10 124.2(2) . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
N4 C15 C14 121.8(2) . . ?
N4 C15 C16 110.2(2) . . ?
C14 C15 C16 128.0(3) . . ?
O2 C16 N6 122.6(3) . . ?
O2 C16 C15 118.1(2) . . ?
N6 C16 C15 119.3(2) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 C20 111.9(2) . . ?
N5 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N5 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 C21 110.2(2) . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C22 C21 C20 114.2(3) . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N6 C23 C24 111.9(2) . . ?
N6 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N6 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 112.7(2) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 111.9(3) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C6 N1 C2 120.3(2) . . ?
C6 N1 FE1 120.52(19) . . ?
C2 N1 FE1 118.94(18) . . ?
C17 N2 C8 111.1(2) . . ?
C17 N2 C7 109.5(2) . . ?
C8 N2 C7 109.6(2) . . ?
C17 N2 FE1 113.30(18) . . ?
C8 N2 FE1 105.29(16) . . ?
C7 N2 FE1 107.89(17) . . ?
C18 N3 C10 109.4(2) . . ?
C18 N3 C9 111.4(2) . . ?
C10 N3 C9 108.9(2) . . ?
C18 N3 FE1 114.05(17) . . ?
C10 N3 FE1 108.59(16) . . ?
C9 N3 FE1 104.28(16) . . ?
C11 N4 C15 120.4(2) . . ?
C11 N4 FE1 120.55(19) . . ?
C15 N4 FE1 119.00(17) . . ?
C1 N5 C19 121.0(2) . . ?
C1 N5 H5N 118(2) . . ?
C19 N5 H5N 121(2) . . ?
C16 N6 C23 122.7(3) . . ?
C16 N6 H6 122(2) . . ?
C23 N6 H6 115(2) . . ?
C1 O1 FE1 116.08(17) . . ?
C16 O2 FE1 117.68(17) . . ?
F1 P1 F6 90.11(14) . . ?
F1 P1 F4 90.79(15) . . ?
F6 P1 F4 179.10(15) . . ?
F1 P1 F2 90.30(12) . . ?
F6 P1 F2 91.12(12) . . ?
F4 P1 F2 88.96(12) . . ?
F1 P1 F3 179.34(14) . . ?
F6 P1 F3 89.36(12) . . ?
F4 P1 F3 89.74(14) . . ?
F2 P1 F3 90.10(10) . . ?
F1 P1 F5 90.68(13) . . ?
F6 P1 F5 89.65(13) . . ?
F4 P1 F5 90.26(13) . . ?
F2 P1 F5 178.76(13) . . ?
F3 P1 F5 88.93(12) . . ?
F9 P2 F8 178.67(12) . . ?
F9 P2 F7 89.18(11) . . ?
F8 P2 F7 90.14(11) . . ?
F9 P2 F12 89.21(12) . . ?
F8 P2 F12 89.65(12) . . ?
F7 P2 F12 90.65(11) . . ?
F9 P2 F10 91.01(11) . . ?
F8 P2 F10 90.12(11) . . ?
F7 P2 F10 89.16(10) . . ?
F12 P2 F10 179.70(12) . . ?
F9 P2 F11 90.52(11) . . ?
F8 P2 F11 90.18(10) . . ?
F7 P2 F11 179.29(11) . . ?
F12 P2 F11 89.98(11) . . ?
F10 P2 F11 90.21(10) . . ?
N1 FE1 N4 177.39(9) . . ?
N1 FE1 O2 107.56(8) . . ?
N4 FE1 O2 74.97(8) . . ?
N1 FE1 O1 74.85(8) . . ?
N4 FE1 O1 103.92(8) . . ?
O2 FE1 O1 106.58(8) . . ?
N1 FE1 N3 102.49(9) . . ?
N4 FE1 N3 75.17(9) . . ?
O2 FE1 N3 147.85(8) . . ?
O1 FE1 N3 91.93(8) . . ?
N1 FE1 N2 75.53(9) . . ?
N4 FE1 N2 105.07(9) . . ?
O2 FE1 N2 95.53(8) . . ?
O1 FE1 N2 147.19(8) . . ?
N3 FE1 N2 80.99(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
O1 C1 C2 N1 -7.1(4) . . . . ?
N5 C1 C2 N1 174.2(2) . . . . ?
O1 C1 C2 C3 170.3(3) . . . . ?
N5 C1 C2 C3 -8.5(4) . . . . ?
N1 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -176.9(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 N1 0.6(4) . . . . ?
C4 C5 C6 C7 -178.6(3) . . . . ?
N1 C6 C7 N2 30.1(3) . . . . ?
C5 C6 C7 N2 -150.7(3) . . . . ?
N2 C8 C9 N3 61.8(3) . . . . ?
N3 C10 C11 N4 27.6(3) . . . . ?
N3 C10 C11 C12 -155.4(3) . . . . ?
N4 C11 C12 C13 1.6(4) . . . . ?
C10 C11 C12 C13 -175.2(3) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 N4 1.5(4) . . . . ?
C13 C14 C15 C16 179.6(3) . . . . ?
N4 C15 C16 O2 -3.3(3) . . . . ?
C14 C15 C16 O2 178.4(3) . . . . ?
N4 C15 C16 N6 175.5(2) . . . . ?
C14 C15 C16 N6 -2.9(4) . . . . ?
N5 C19 C20 C21 -176.6(2) . . . . ?
C19 C20 C21 C22 -178.4(3) . . . . ?
N6 C23 C24 C25 -173.7(3) . . . . ?
C23 C24 C25 C26 174.5(3) . . . . ?
C5 C6 N1 C2 -1.2(4) . . . . ?
C7 C6 N1 C2 178.0(2) . . . . ?
C5 C6 N1 FE1 172.7(2) . . . . ?
C7 C6 N1 FE1 -8.1(3) . . . . ?
C3 C2 N1 C6 0.8(4) . . . . ?
C1 C2 N1 C6 178.3(2) . . . . ?
C3 C2 N1 FE1 -173.2(2) . . . . ?
C1 C2 N1 FE1 4.3(3) . . . . ?
C9 C8 N2 C17 81.9(3) . . . . ?
C9 C8 N2 C7 -156.9(2) . . . . ?
C9 C8 N2 FE1 -41.1(3) . . . . ?
C6 C7 N2 C17 -159.2(2) . . . . ?
C6 C7 N2 C8 78.7(3) . . . . ?
C6 C7 N2 FE1 -35.4(3) . . . . ?
C11 C10 N3 C18 -159.6(2) . . . . ?
C11 C10 N3 C9 78.4(3) . . . . ?
C11 C10 N3 FE1 -34.5(3) . . . . ?
C8 C9 N3 C18 78.5(3) . . . . ?
C8 C9 N3 C10 -160.8(2) . . . . ?
C8 C9 N3 FE1 -45.0(2) . . . . ?
C12 C11 N4 C15 -0.6(4) . . . . ?
C10 C11 N4 C15 176.5(2) . . . . ?
C12 C11 N4 FE1 177.71(19) . . . . ?
C10 C11 N4 FE1 -5.2(3) . . . . ?
C14 C15 N4 C11 -1.0(4) . . . . ?
C16 C15 N4 C11 -179.4(2) . . . . ?
C14 C15 N4 FE1 -179.3(2) . . . . ?
C16 C15 N4 FE1 2.2(3) . . . . ?
O1 C1 N5 C19 3.3(4) . . . . ?
C2 C1 N5 C19 -178.0(2) . . . . ?
C20 C19 N5 C1 178.1(3) . . . . ?
O2 C16 N6 C23 -0.2(4) . . . . ?
C15 C16 N6 C23 -178.9(2) . . . . ?
C24 C23 N6 C16 -91.9(3) . . . . ?
N5 C1 O1 FE1 -174.9(2) . . . . ?
C2 C1 O1 FE1 6.4(3) . . . . ?
N6 C16 O2 FE1 -175.9(2) . . . . ?
C15 C16 O2 FE1 2.8(3) . . . . ?

_refine_diff_density_max         1.147
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.090

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

data_[Fe(II)(mepOH)Cl]Cl
_database_code_depnum_ccdc_archive 'CCDC 1880896'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 Cl2 Fe N5 O'
_chemical_formula_weight         468.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.5537(6)
_cell_length_b                   11.6440(6)
_cell_length_c                   17.9699(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.349(2)
_cell_angle_gamma                90
_cell_volume                     2172.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9818
_cell_measurement_theta_min      2.447
_cell_measurement_theta_max      28.796

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.960
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
Final wR2(int)= 0.0928. The ratio of minimum to maximun
transmission is 0.6022.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40442
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         28.831
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5640
_reflns_number_gt                4705
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'USCF Chimera 1.10.1 and Ortep3'
_computing_publication_material  'WinGX CIF routines'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+7.2943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5640
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5433(3) 0.4121(3) 0.90894(18) 0.0187(6) Uani 1 1 d . . . . .
H1A H 0.524279 0.380947 0.956976 0.022 Uiso 1 1 calc R U . . .
H1B H 0.561726 0.495182 0.916068 0.022 Uiso 1 1 calc R U . . .
C2 C 0.6602(3) 0.3516(3) 0.88909(17) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.7820(3) 0.3656(3) 0.93221(18) 0.0200(6) Uani 1 1 d . . . . .
H3 H 0.794893 0.411925 0.976455 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8844(3) 0.3102(3) 0.9090(2) 0.0225(7) Uani 1 1 d . . . . .
H4 H 0.969148 0.318439 0.937154 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8626(3) 0.2423(3) 0.8442(2) 0.0215(6) Uani 1 1 d . . . . .
H5 H 0.931597 0.202793 0.828049 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7379(3) 0.2334(3) 0.80352(18) 0.0168(6) Uani 1 1 d . . . . .
C7 C 0.7051(3) 0.1726(3) 0.72817(19) 0.0205(6) Uani 1 1 d . . . . .
H7A H 0.728129 0.222611 0.688070 0.025 Uiso 1 1 calc R U . . .
H7B H 0.756833 0.101404 0.729777 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5400(3) 0.0392(3) 0.75175(18) 0.0204(6) Uani 1 1 d . . . . .
H8A H 0.596061 0.038840 0.802225 0.024 Uiso 1 1 calc R U . . .
H8B H 0.559319 -0.030406 0.724214 0.024 Uiso 1 1 calc R U . . .
C9 C 0.3991(3) 0.0376(3) 0.76084(18) 0.0198(6) Uani 1 1 d . . . . .
H9A H 0.343109 0.037285 0.710340 0.024 Uiso 1 1 calc R U . . .
H9B H 0.381501 -0.033256 0.787711 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4128(3) 0.1225(3) 0.88629(17) 0.0195(6) Uani 1 1 d . . . . .
H10A H 0.365061 0.058685 0.903600 0.029 Uiso 1 1 calc R U . . .
H10B H 0.397274 0.192729 0.913372 0.029 Uiso 1 1 calc R U . . .
H10C H 0.505138 0.104880 0.896341 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5303(4) 0.1248(3) 0.62655(18) 0.0226(7) Uani 1 1 d . . . . .
H11A H 0.534597 0.197905 0.600100 0.034 Uiso 1 1 calc R U . . .
H11B H 0.442292 0.094546 0.614889 0.034 Uiso 1 1 calc R U . . .
H11C H 0.589712 0.069707 0.610001 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2276(3) 0.1602(3) 0.79052(18) 0.0189(6) Uani 1 1 d . . . . .
H12A H 0.206392 0.215635 0.828222 0.023 Uiso 1 1 calc R U . . .
H12B H 0.182182 0.087310 0.796535 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1830(3) 0.2067(3) 0.71211(18) 0.0182(6) Uani 1 1 d . . . . .
C14 C 0.0575(3) 0.1865(3) 0.6734(2) 0.0234(7) Uani 1 1 d . . . . .
H14 H -0.000286 0.140229 0.695261 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0193(3) 0.2353(3) 0.6024(2) 0.0273(8) Uani 1 1 d . . . . .
H15 H -0.065764 0.224444 0.575230 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1079(4) 0.3005(3) 0.5718(2) 0.0256(7) Uani 1 1 d . . . . .
H16 H 0.084371 0.334795 0.523306 0.031 Uiso 1 1 calc R U . . .
C17 C 0.2305(3) 0.3146(3) 0.61308(18) 0.0205(6) Uani 1 1 d . . . . .
H17 H 0.291178 0.357313 0.591165 0.025 Uiso 1 1 calc R U . . .
C18 C 0.3907(4) 0.6145(3) 0.5079(2) 0.0257(7) Uani 1 1 d . . . . .
H18A H 0.435439 0.582359 0.555913 0.039 Uiso 1 1 calc R U . . .
H18B H 0.349529 0.687087 0.517484 0.039 Uiso 1 1 calc R U . . .
H18C H 0.452921 0.628297 0.474433 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2935(4) 0.5341(4) 0.4722(2) 0.0293(8) Uani 1 1 d . . . . .
N1 N 0.6391(2) 0.2870(2) 0.82684(14) 0.0144(5) Uani 1 1 d . . . . .
N2 N 0.5670(3) 0.1433(2) 0.70930(15) 0.0175(5) Uani 1 1 d . . . . .
N3 N 0.3692(3) 0.1397(2) 0.80415(14) 0.0159(5) Uani 1 1 d . . . . .
N4 N 0.2682(3) 0.2709(2) 0.68268(15) 0.0170(5) Uani 1 1 d . . . . .
N5 N 0.2188(4) 0.4699(4) 0.4450(2) 0.0490(11) Uani 1 1 d . . . . .
O1 O 0.4343(2) 0.3962(2) 0.85003(13) 0.0183(5) Uani 1 1 d . . . . .
CL1 Cl 0.52311(8) 0.43969(7) 0.67786(4) 0.02045(18) Uani 1 1 d . . . . .
CL2 Cl 0.22879(8) 0.39173(7) 0.94196(5) 0.0252(2) Uani 1 1 d . . . . .
FE1 Fe 0.45902(4) 0.29037(4) 0.75244(2) 0.01332(14) Uani 1 1 d . . . . .
H1 H 0.368(7) 0.399(6) 0.863(4) 0.07(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.429(4) . ?
C1 C2 1.518(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.333(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.345(4) . ?
C6 C7 1.512(4) . ?
C7 N2 1.476(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.487(4) . ?
C8 C9 1.525(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.486(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.479(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N2 1.484(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N3 1.490(4) . ?
C12 C13 1.504(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N4 1.348(4) . ?
C13 C14 1.401(5) . ?
C14 C15 1.389(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9500 . ?
C17 N4 1.343(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.450(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N5 1.132(5) . ?
N1 FE1 2.118(3) . ?
N2 FE1 2.269(3) . ?
N3 FE1 2.271(3) . ?
N4 FE1 2.185(3) . ?
O1 FE1 2.197(2) . ?
O1 H1 0.78(7) . ?
CL1 FE1 2.3669(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 110.2(2) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 122.3(3) . . ?
N1 C2 C1 116.0(3) . . ?
C3 C2 C1 121.7(3) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C5 121.0(3) . . ?
N1 C6 C7 115.5(3) . . ?
C5 C6 C7 123.3(3) . . ?
N2 C7 C6 111.8(3) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 C9 110.2(3) . . ?
N2 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 C8 110.4(3) . . ?
N3 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 110.3(2) . . ?
N3 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N3 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
N4 C13 C14 122.4(3) . . ?
N4 C13 C12 116.7(3) . . ?
C14 C13 C12 120.9(3) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
N4 C17 C16 123.2(3) . . ?
N4 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 C18 178.8(5) . . ?
C2 N1 C6 120.1(3) . . ?
C2 N1 FE1 121.0(2) . . ?
C6 N1 FE1 118.0(2) . . ?
C7 N2 C11 109.4(3) . . ?
C7 N2 C8 110.0(3) . . ?
C11 N2 C8 110.9(3) . . ?
C7 N2 FE1 106.45(19) . . ?
C11 N2 FE1 113.3(2) . . ?
C8 N2 FE1 106.61(18) . . ?
C10 N3 C9 111.0(2) . . ?
C10 N3 C12 108.0(2) . . ?
C9 N3 C12 110.1(2) . . ?
C10 N3 FE1 115.76(19) . . ?
C9 N3 FE1 105.09(18) . . ?
C12 N3 FE1 106.79(19) . . ?
C17 N4 C13 118.0(3) . . ?
C17 N4 FE1 125.7(2) . . ?
C13 N4 FE1 116.3(2) . . ?
C1 O1 FE1 117.95(18) . . ?
C1 O1 H1 115(5) . . ?
FE1 O1 H1 120(5) . . ?
N1 FE1 N4 172.02(10) . . ?
N1 FE1 O1 74.23(9) . . ?
N4 FE1 O1 106.66(9) . . ?
N1 FE1 N2 75.71(10) . . ?
N4 FE1 N2 101.16(10) . . ?
O1 FE1 N2 146.62(10) . . ?
N1 FE1 N3 96.92(10) . . ?
N4 FE1 N3 75.23(10) . . ?
O1 FE1 N3 89.35(9) . . ?
N2 FE1 N3 80.14(10) . . ?
N1 FE1 CL1 93.20(7) . . ?
N4 FE1 CL1 94.54(8) . . ?
O1 FE1 CL1 97.29(7) . . ?
N2 FE1 CL1 98.56(7) . . ?
N3 FE1 CL1 169.11(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -6.5(4) . . . . ?
O1 C1 C2 C3 171.8(3) . . . . ?
N1 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 -178.0(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 N1 -1.5(5) . . . . ?
C4 C5 C6 C7 173.4(3) . . . . ?
N1 C6 C7 N2 -23.2(4) . . . . ?
C5 C6 C7 N2 161.7(3) . . . . ?
N2 C8 C9 N3 -61.0(3) . . . . ?
N3 C12 C13 N4 -30.4(4) . . . . ?
N3 C12 C13 C14 151.5(3) . . . . ?
N4 C13 C14 C15 -0.6(5) . . . . ?
C12 C13 C14 C15 177.3(3) . . . . ?
C13 C14 C15 C16 1.3(5) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 N4 -1.9(5) . . . . ?
C3 C2 N1 C6 -0.5(5) . . . . ?
C1 C2 N1 C6 177.7(3) . . . . ?
C3 C2 N1 FE1 -169.4(2) . . . . ?
C1 C2 N1 FE1 8.9(4) . . . . ?
C5 C6 N1 C2 1.2(5) . . . . ?
C7 C6 N1 C2 -174.0(3) . . . . ?
C5 C6 N1 FE1 170.4(2) . . . . ?
C7 C6 N1 FE1 -4.8(4) . . . . ?
C6 C7 N2 C11 159.2(3) . . . . ?
C6 C7 N2 C8 -78.7(3) . . . . ?
C6 C7 N2 FE1 36.4(3) . . . . ?
C9 C8 N2 C7 155.4(3) . . . . ?
C9 C8 N2 C11 -83.4(3) . . . . ?
C9 C8 N2 FE1 40.4(3) . . . . ?
C8 C9 N3 C10 -80.1(3) . . . . ?
C8 C9 N3 C12 160.4(3) . . . . ?
C8 C9 N3 FE1 45.8(3) . . . . ?
C13 C12 N3 C10 166.0(3) . . . . ?
C13 C12 N3 C9 -72.7(3) . . . . ?
C13 C12 N3 FE1 40.9(3) . . . . ?
C16 C17 N4 C13 2.5(5) . . . . ?
C16 C17 N4 FE1 -179.3(3) . . . . ?
C14 C13 N4 C17 -1.2(5) . . . . ?
C12 C13 N4 C17 -179.3(3) . . . . ?
C14 C13 N4 FE1 -179.6(2) . . . . ?
C12 C13 N4 FE1 2.4(4) . . . . ?
C2 C1 O1 FE1 1.6(3) . . . . ?

_refine_diff_density_max         1.222
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.141

