# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1433288'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 F3 Fe N3 O'
_chemical_formula_sum            'C17 H16 F3 Fe N3 O'
_chemical_formula_weight         391.18
_chemical_melting_point          ?

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3579(2)
_cell_length_b                   8.72054(14)
_cell_length_c                   36.8998(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3333.04(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9099
_cell_measurement_temperature    183(1)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            22551
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.208
_diffrn_ambient_temperature      183(1)
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00  106.00   0.8000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8897   19.0000  -60.0000 225

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -55.40   0.8000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5147  178.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega  -72.00   57.60   0.8000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8897  -37.0000 -150.0000 162

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   67.00   0.8000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5147  178.0000  150.0000 40
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0275900000
_diffrn_orient_matrix_UB_12      -0.0176276000
_diffrn_orient_matrix_UB_13      0.0170942000
_diffrn_orient_matrix_UB_21      0.0082603000
_diffrn_orient_matrix_UB_22      0.0793440000
_diffrn_orient_matrix_UB_23      0.0035199000
_diffrn_orient_matrix_UB_31      -0.0621358000
_diffrn_orient_matrix_UB_32      0.0026740000
_diffrn_orient_matrix_UB_33      0.0080599000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2586
_reflns_number_total             3034

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL2014 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS97 (Sheldrick, 2008)'
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+3.5764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 3A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C14(H14)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1035(2) 0.5540(3) 0.35851(6) 0.0326(5) Uani 1 1 d . . . . .
C2 C 0.1823(3) 0.5641(3) 0.32736(7) 0.0429(6) Uani 1 1 d . . . . .
H2 H 0.2550 0.5047 0.3227 0.051 Uiso 1 1 calc R . . . .
C3 C 0.1320(3) 0.6798(3) 0.30448(8) 0.0480(7) Uani 1 1 d . . . . .
H3 H 0.1653 0.7089 0.2821 0.058 Uiso 1 1 calc R . . . .
C4 C 0.0236(3) 0.7429(3) 0.32144(8) 0.0460(7) Uani 1 1 d . . . . .
H4 H -0.0279 0.8210 0.3122 0.055 Uiso 1 1 calc R . . . .
C5 C 0.0058(2) 0.6676(3) 0.35495(7) 0.0379(6) Uani 1 1 d . . . . .
H5 H -0.0587 0.6886 0.3718 0.045 Uiso 1 1 calc R . . . .
C6 C -0.0490(5) 0.2879(5) 0.31170(11) 0.0862(12) Uani 1 1 d . . . . .
H6 H -0.0140 0.2117 0.3263 0.103 Uiso 1 1 calc R . . . .
C7 C -0.0017(4) 0.3345(4) 0.27857(11) 0.0788(11) Uani 1 1 d . . . . .
H7 H 0.0707 0.2944 0.2671 0.095 Uiso 1 1 calc R . . . .
C8 C -0.0796(4) 0.4507(4) 0.26511(9) 0.0739(10) Uani 1 1 d . . . . .
H8 H -0.0680 0.5013 0.2432 0.089 Uiso 1 1 calc R . . . .
C9 C -0.1776(4) 0.4790(5) 0.28982(13) 0.0887(12) Uani 1 1 d . . . . .
H9 H -0.2433 0.5511 0.2878 0.106 Uiso 1 1 calc R . . . .
C10 C -0.1567(5) 0.3736(6) 0.31932(12) 0.0935(13) Uani 1 1 d . . . . .
H10 H -0.2075 0.3652 0.3400 0.112 Uiso 1 1 calc R . . . .
C11 C 0.1242(3) 0.4530(3) 0.39060(7) 0.0407(6) Uani 1 1 d . . . . .
H11A H 0.0418 0.4264 0.4014 0.049 Uiso 1 1 calc R . . . .
H11B H 0.1667 0.3590 0.3832 0.049 Uiso 1 1 calc R . . . .
C12 C 0.3136(2) 0.4794(2) 0.43048(6) 0.0269(5) Uani 1 1 d . . . . .
C13 C 0.3859(2) 0.5895(2) 0.45378(6) 0.0257(5) Uani 1 1 d . . . . .
C14 C 0.3431(2) 0.6676(3) 0.48369(6) 0.0286(5) Uani 1 1 d . . . . .
H14 H 0.2605 0.6631 0.4935 0.034 Uiso 1 1 calc R . . . .
C15 C 0.5140(2) 0.6365(2) 0.45021(6) 0.0264(5) Uani 1 1 d . . . . .
C16 C 0.4419(3) 0.8488(3) 0.52842(6) 0.0368(6) Uani 1 1 d . . . . .
H16A H 0.4433 0.7856 0.5497 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.3656 0.9113 0.5286 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.5170 0.9134 0.5281 0.055 Uiso 1 1 calc GR . . . .
C17 C 0.6079(2) 0.5941(3) 0.42150(7) 0.0359(6) Uani 1 1 d . . . . .
F1 F 0.54879(17) 0.5627(2) 0.39035(4) 0.0561(5) Uani 1 1 d . . . . .
F2 F 0.67832(17) 0.47135(19) 0.42993(5) 0.0592(5) Uani 1 1 d . . . . .
F3 F 0.69170(15) 0.70592(18) 0.41451(5) 0.0543(5) Uani 1 1 d . . . . .
Fe1 Fe -0.00290(4) 0.51429(4) 0.31346(2) 0.03745(14) Uani 1 1 d . . . . .
N1 N 0.2043(2) 0.5339(2) 0.41713(6) 0.0337(5) Uani 1 1 d . . . . .
H1 H 0.191(2) 0.623(3) 0.4191(7) 0.033(7) Uiso 1 1 d . . . . .
N2 N 0.44165(19) 0.7517(2) 0.49619(5) 0.0293(4) Uani 1 1 d . . . . .
N3 N 0.54912(19) 0.7358(2) 0.47612(5) 0.0297(4) Uani 1 1 d . . . . .
O1 O 0.35539(17) 0.34946(18) 0.42505(5) 0.0404(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.413(4) . ?
C1 C5 1.422(3) . ?
C1 C11 1.492(3) . ?
C1 Fe1 2.024(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.415(4) . ?
C2 Fe1 2.033(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(4) . ?
C3 Fe1 2.037(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.412(4) . ?
C4 Fe1 2.034(3) . ?
C5 H5 0.9300 . ?
C5 Fe1 2.034(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(6) . ?
C6 C10 1.372(6) . ?
C6 Fe1 2.032(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(5) . ?
C7 Fe1 2.029(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(6) . ?
C8 Fe1 2.030(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.441(6) . ?
C9 Fe1 2.032(4) . ?
C10 H10 0.9300 . ?
C10 Fe1 2.022(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N1 1.464(3) . ?
C12 C13 1.491(3) . ?
C12 N1 1.323(3) . ?
C12 O1 1.229(3) . ?
C13 C14 1.371(3) . ?
C13 C15 1.395(3) . ?
C14 H14 0.9300 . ?
C14 N2 1.338(3) . ?
C15 C17 1.485(3) . ?
C15 N3 1.340(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 N2 1.460(3) . ?
C17 F1 1.331(3) . ?
C17 F2 1.332(3) . ?
C17 F3 1.331(3) . ?
N1 H1 0.79(3) . ?
N2 N3 1.344(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
C2 C1 C5 107.0(2) . . ?
C2 C1 C11 126.8(2) . . ?
C2 C1 Fe1 69.96(14) . . ?
C5 C1 C11 126.0(2) . . ?
C5 C1 Fe1 69.88(14) . . ?
C11 C1 Fe1 129.00(17) . . ?
C1 C2 H2 125.8 . . ?
C1 C2 C3 108.5(2) . . ?
C1 C2 Fe1 69.28(14) . . ?
C3 C2 H2 125.8 . . ?
C3 C2 Fe1 69.79(16) . . ?
Fe1 C2 H2 126.7 . . ?
C2 C3 H3 126.0 . . ?
C2 C3 Fe1 69.51(16) . . ?
C4 C3 C2 108.0(2) . . ?
C4 C3 H3 126.0 . . ?
C4 C3 Fe1 69.79(17) . . ?
Fe1 C3 H3 126.3 . . ?
C3 C4 H4 125.8 . . ?
C3 C4 C5 108.3(2) . . ?
C3 C4 Fe1 70.02(16) . . ?
C5 C4 H4 125.8 . . ?
C5 C4 Fe1 69.72(15) . . ?
Fe1 C4 H4 126.0 . . ?
C1 C5 H5 125.9 . . ?
C1 C5 Fe1 69.11(14) . . ?
C4 C5 C1 108.2(2) . . ?
C4 C5 H5 125.9 . . ?
C4 C5 Fe1 69.66(15) . . ?
Fe1 C5 H5 126.9 . . ?
C7 C6 H6 126.0 . . ?
C7 C6 Fe1 70.1(2) . . ?
C10 C6 H6 126.0 . . ?
C10 C6 C7 108.1(4) . . ?
C10 C6 Fe1 69.8(2) . . ?
Fe1 C6 H6 125.7 . . ?
C6 C7 H7 125.5 . . ?
C6 C7 C8 109.0(4) . . ?
C6 C7 Fe1 70.3(2) . . ?
C8 C7 H7 125.5 . . ?
C8 C7 Fe1 70.0(2) . . ?
Fe1 C7 H7 125.8 . . ?
C7 C8 H8 125.7 . . ?
C7 C8 Fe1 69.97(19) . . ?
C9 C8 C7 108.7(4) . . ?
C9 C8 H8 125.7 . . ?
C9 C8 Fe1 70.12(19) . . ?
Fe1 C8 H8 125.8 . . ?
C8 C9 H9 127.1 . . ?
C8 C9 C10 105.9(4) . . ?
C8 C9 Fe1 70.0(2) . . ?
C10 C9 H9 127.1 . . ?
C10 C9 Fe1 68.8(2) . . ?
Fe1 C9 H9 125.7 . . ?
C6 C10 C9 108.3(4) . . ?
C6 C10 H10 125.8 . . ?
C6 C10 Fe1 70.6(2) . . ?
C9 C10 H10 125.8 . . ?
C9 C10 Fe1 69.6(2) . . ?
Fe1 C10 H10 125.6 . . ?
C1 C11 H11A 109.9 . . ?
C1 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N1 C11 C1 109.1(2) . . ?
N1 C11 H11A 109.9 . . ?
N1 C11 H11B 109.9 . . ?
N1 C12 C13 114.41(19) . . ?
O1 C12 C13 120.7(2) . . ?
O1 C12 N1 124.9(2) . . ?
C14 C13 C12 128.5(2) . . ?
C14 C13 C15 103.7(2) . . ?
C15 C13 C12 127.8(2) . . ?
C13 C14 H14 126.2 . . ?
N2 C14 C13 107.6(2) . . ?
N2 C14 H14 126.2 . . ?
C13 C15 C17 128.1(2) . . ?
N3 C15 C13 112.4(2) . . ?
N3 C15 C17 119.5(2) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
F1 C17 C15 111.5(2) . . ?
F1 C17 F2 106.8(2) . . ?
F2 C17 C15 113.1(2) . . ?
F3 C17 C15 112.5(2) . . ?
F3 C17 F1 106.5(2) . . ?
F3 C17 F2 106.1(2) . . ?
C1 Fe1 C2 40.76(10) . . ?
C1 Fe1 C3 68.82(10) . . ?
C1 Fe1 C4 68.88(10) . . ?
C1 Fe1 C5 41.01(10) . . ?
C1 Fe1 C6 108.69(13) . . ?
C1 Fe1 C7 130.55(13) . . ?
C1 Fe1 C8 168.95(15) . . ?
C1 Fe1 C9 149.67(16) . . ?
C2 Fe1 C3 40.70(11) . . ?
C2 Fe1 C4 68.07(12) . . ?
C2 Fe1 C5 68.16(11) . . ?
C4 Fe1 C3 40.19(12) . . ?
C4 Fe1 C5 40.62(11) . . ?
C5 Fe1 C3 68.06(12) . . ?
C6 Fe1 C2 115.94(17) . . ?
C6 Fe1 C3 147.65(19) . . ?
C6 Fe1 C4 171.33(18) . . ?
C6 Fe1 C5 132.28(15) . . ?
C6 Fe1 C9 68.28(18) . . ?
C7 Fe1 C2 108.64(15) . . ?
C7 Fe1 C3 116.13(16) . . ?
C7 Fe1 C4 148.07(15) . . ?
C7 Fe1 C5 170.09(14) . . ?
C7 Fe1 C6 39.68(17) . . ?
C7 Fe1 C8 39.98(14) . . ?
C7 Fe1 C9 67.41(17) . . ?
C8 Fe1 C2 130.50(16) . . ?
C8 Fe1 C3 108.61(14) . . ?
C8 Fe1 C4 116.60(13) . . ?
C8 Fe1 C5 149.10(13) . . ?
C8 Fe1 C6 67.35(15) . . ?
C8 Fe1 C9 39.91(17) . . ?
C9 Fe1 C2 168.81(17) . . ?
C9 Fe1 C3 130.44(16) . . ?
C9 Fe1 C4 109.33(15) . . ?
C9 Fe1 C5 117.52(15) . . ?
C10 Fe1 C1 116.41(14) . . ?
C10 Fe1 C2 147.79(18) . . ?
C10 Fe1 C3 171.14(19) . . ?
C10 Fe1 C4 133.27(19) . . ?
C10 Fe1 C5 110.66(16) . . ?
C10 Fe1 C6 39.56(18) . . ?
C10 Fe1 C7 66.66(19) . . ?
C10 Fe1 C8 67.68(17) . . ?
C10 Fe1 C9 41.64(18) . . ?
C11 N1 H1 115.8(19) . . ?
C12 N1 C11 124.1(2) . . ?
C12 N1 H1 117.9(19) . . ?
C14 N2 C16 126.9(2) . . ?
C14 N2 N3 112.65(19) . . ?
N3 N2 C16 120.5(2) . . ?
C15 N3 N2 103.60(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.79(3) 2.05(3) 2.836(3) 177(3) 7_665

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
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 Fe1 -58.64(18) . . . . ?
C1 C11 N1 C12 -124.9(3) . . . . ?
C2 C1 C5 C4 1.5(3) . . . . ?
C2 C1 C5 Fe1 60.40(17) . . . . ?
C2 C1 C11 N1 89.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 Fe1 -59.2(2) . . . . ?
C3 C4 C5 C1 -1.1(3) . . . . ?
C3 C4 C5 Fe1 -59.6(2) . . . . ?
C5 C1 C2 C3 -1.4(3) . . . . ?
C5 C1 C2 Fe1 -60.35(17) . . . . ?
C5 C1 C11 N1 -85.3(3) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 Fe1 59.7(3) . . . . ?
C7 C6 C10 C9 -0.3(4) . . . . ?
C7 C6 C10 Fe1 -59.8(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C7 C8 C9 Fe1 59.6(2) . . . . ?
C8 C9 C10 C6 0.3(4) . . . . ?
C8 C9 C10 Fe1 60.5(2) . . . . ?
C10 C6 C7 C8 0.2(4) . . . . ?
C10 C6 C7 Fe1 59.7(3) . . . . ?
C11 C1 C2 C3 -176.7(2) . . . . ?
C11 C1 C2 Fe1 124.3(2) . . . . ?
C11 C1 C5 C4 176.9(2) . . . . ?
C11 C1 C5 Fe1 -124.2(2) . . . . ?
C12 C13 C14 N2 179.2(2) . . . . ?
C12 C13 C15 C17 3.0(4) . . . . ?
C12 C13 C15 N3 -179.3(2) . . . . ?
C13 C12 N1 C11 173.3(2) . . . . ?
C13 C14 N2 C16 -177.5(2) . . . . ?
C13 C14 N2 N3 0.6(3) . . . . ?
C13 C15 C17 F1 28.7(3) . . . . ?
C13 C15 C17 F2 -91.6(3) . . . . ?
C13 C15 C17 F3 148.2(2) . . . . ?
C13 C15 N3 N2 -0.1(2) . . . . ?
C14 C13 C15 C17 -177.3(2) . . . . ?
C14 C13 C15 N3 0.5(3) . . . . ?
C14 N2 N3 C15 -0.3(2) . . . . ?
C15 C13 C14 N2 -0.6(2) . . . . ?
C16 N2 N3 C15 178.0(2) . . . . ?
C17 C15 N3 N2 177.8(2) . . . . ?
Fe1 C1 C2 C3 58.95(19) . . . . ?
Fe1 C1 C5 C4 -58.88(18) . . . . ?
Fe1 C1 C11 N1 -177.60(18) . . . . ?
Fe1 C2 C3 C4 59.4(2) . . . . ?
Fe1 C3 C4 C5 59.42(19) . . . . ?
Fe1 C4 C5 C1 58.54(17) . . . . ?
Fe1 C6 C7 C8 -59.5(2) . . . . ?
Fe1 C6 C10 C9 59.5(2) . . . . ?
Fe1 C7 C8 C9 -59.7(2) . . . . ?
Fe1 C8 C9 C10 -59.8(2) . . . . ?
Fe1 C9 C10 C6 -60.2(3) . . . . ?
N1 C12 C13 C14 54.6(3) . . . . ?
N1 C12 C13 C15 -125.7(2) . . . . ?
N3 C15 C17 F1 -148.9(2) . . . . ?
N3 C15 C17 F2 90.8(3) . . . . ?
N3 C15 C17 F3 -29.4(3) . . . . ?
O1 C12 C13 C14 -125.0(3) . . . . ?
O1 C12 C13 C15 54.8(3) . . . . ?
O1 C12 N1 C11 -7.2(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0304 0.0000 0.0000 0.9992 0.0171 0.0035 0.0081
0 0 -1 0.0284 -0.0000 -0.0000 -0.9992 -0.0171 -0.0035 -0.0081
1 0 -1 0.0391 0.9991 -0.0001 -0.9988 0.0105 0.0047 -0.0701
-1 0 1 0.0361 -0.9991 0.0001 0.9988 -0.0105 -0.0047 0.0701
0 1 1 0.1605 0.0001 0.9993 0.9996 -0.0005 0.0828 0.0107
0 -1 0 0.1652 -0.0000 -0.9993 -0.0004 0.0176 -0.0793 -0.0027
-1 0 -4 0.0329 -0.9993 -0.0000 -3.9971 -0.0959 -0.0223 0.0299
1 0 4 0.0339 0.9993 0.0000 3.9971 0.0959 0.0223 -0.0299
0 1 -3 0.1461 -0.0000 0.9992 -2.9971 -0.0688 0.0687 -0.0215

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1433289'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_2                   
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: The SQUEEZE program calculated 478 electrons in the cell
 ie. about 60 electrons per asymmetric unit. We propose to allocate
these electrons to one CHCl3 molecule (58e) per asymmetric unit.
The corresponding atoms were included in the formula which causes
some A alerts.
# Solvent Accessible Volume =    1174.4
# Electrons Found in S.A.V. =     477.6
;

# end Validation Reply Form

_audit_creation_date             2015-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F3 Fe N3 O, C H Cl3'
_chemical_formula_sum            'C23 H19 Cl3 F3 Fe N3 O'
_chemical_formula_weight         572.61
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   10.6241(2)
_cell_length_b                   15.1983(4)
_cell_length_c                   29.6784(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.352(2)
_cell_angle_gamma                90
_cell_volume                     4792.03(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9351
_cell_measurement_temperature    183(1)
_cell_measurement_theta_max      76.0
_cell_measurement_theta_min      3.0

_exptl_absorpt_coefficient_mu    8.534
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_correction_T_min  0.291
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16614
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         2.978
_diffrn_ambient_temperature      183(1)
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865   37.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865  125.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865   37.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega -117.00  -15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865  -37.0000   90.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega   84.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790   45.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -30.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   99.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -45.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -30.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   99.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -45.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega   33.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -77.0000   60.0000 113

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   99.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -45.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790  -30.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 13 omega   84.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790   45.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
 14 omega -115.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865  -57.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 15 omega -115.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865  -57.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
 16 omega -115.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8865  -57.0000   30.0000 104

#__ type_ start__ end____ width___ exp.time_
 17 omega   81.00  125.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8790   30.0000   30.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0294515000
_diffrn_orient_matrix_UB_12      -0.0550113000
_diffrn_orient_matrix_UB_13      0.0422513000
_diffrn_orient_matrix_UB_21      0.1419883000
_diffrn_orient_matrix_UB_22      -0.0116960000
_diffrn_orient_matrix_UB_23      0.0089913000
_diffrn_orient_matrix_UB_31      0.0003540000
_diffrn_orient_matrix_UB_32      0.0843568000
_diffrn_orient_matrix_UB_33      0.0287634000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3805
_reflns_number_total             4393

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS97 (Sheldrick, 2008)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+3.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.024 0.500 0.000 585 239 ' '
2 -0.018 0.000 0.500 585 239 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL rr2711_a.res in I2/a
CELL   10.6241   15.1983   29.6784     90.00     90.35     90.00
SPGR I2/a
# Solvent Accessible Volume =    1174.4
# Electrons Found in S.A.V. =     477.6
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.898 0.582 0.032 !      10.99 eA-3
C102 0.573 0.984 0.375 !       9.46 eA-3
C103 0.737 0.452 0.075 !       3.74 eA-3
C104 0.877 0.128 0.420 !       2.51 eA-3
C105 0.109 0.985 0.434 !       2.34 eA-3
C106 0.870 1.001 0.409 !       2.15 eA-3
C107 1.003 0.034 0.418 !       1.94 eA-3
Q108 0.682 0.966 0.211 !       0.86 eA-3
Q109 0.311 0.046 0.302 !       0.82 eA-3
Q110 0.291 0.126 0.273 !       0.81 eA-3
Q111 0.060 0.821 0.303 !       0.77 eA-3
C112 0.750 0.406 0.002 !       0.72 eA-3
Q113 0.084 0.913 0.243 !       0.65 eA-3
Q114 0.327 0.173 0.322 !       0.63 eA-3
Q115 0.440 0.390 0.323 !       0.61 eA-3
Q116 0.187 0.828 0.287 !       0.61 eA-3
Q117 0.085 0.517 0.290 !       0.60 eA-3
Q118 1.005 0.220 0.336 !       0.59 eA-3
Q119 0.097 0.156 0.070 !       0.59 eA-3
Q120 0.722 0.253 0.162 !       0.59 eA-3
Q121 0.595 0.261 0.441 !       0.58 eA-3
Q122 0.902 0.623 0.438 !       0.58 eA-3
Q123 0.060 0.072 0.124 !       0.57 eA-3
Q124 0.290 0.800 0.309 !       0.55 eA-3
Q125 0.992 0.189 0.017 !       0.55 eA-3
Q126 0.316 0.573 0.243 !       0.52 eA-3
Q127 0.984 0.535 0.442 !       0.51 eA-3
Q128 0.642 0.986 0.053 !       0.50 eA-3
;

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42172(19) 0.42329(14) 0.37519(7) 0.0285(4) Uani 1 1 d . . . . .
C2 C 0.3221(2) 0.43340(16) 0.40657(8) 0.0352(5) Uani 1 1 d . . . . .
H2 H 0.2381 0.4133 0.4025 0.042 Uiso 1 1 calc R . . . .
C3 C 0.3692(2) 0.47853(16) 0.44480(8) 0.0390(5) Uani 1 1 d . . . . .
H3 H 0.3224 0.4944 0.4707 0.047 Uiso 1 1 calc R . . . .
C4 C 0.4994(2) 0.49595(16) 0.43753(8) 0.0366(5) Uani 1 1 d . . . . .
H4 H 0.5547 0.5254 0.4578 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5316(2) 0.46156(14) 0.39474(7) 0.0314(5) Uani 1 1 d . . . . .
H5 H 0.6126 0.4637 0.3814 0.038 Uiso 1 1 calc R . . . .
C6 C 0.5080(3) 0.23449(17) 0.42334(9) 0.0456(6) Uani 1 1 d . . . . .
H6 H 0.5154 0.2074 0.3946 0.055 Uiso 1 1 calc R . . . .
C7 C 0.3963(3) 0.24155(18) 0.44914(10) 0.0507(6) Uani 1 1 d . . . . .
H7 H 0.3155 0.2203 0.4406 0.061 Uiso 1 1 calc R . . . .
C8 C 0.4265(3) 0.28594(19) 0.48978(9) 0.0532(7) Uani 1 1 d . . . . .
H8 H 0.3698 0.2994 0.5134 0.064 Uiso 1 1 calc R . . . .
C9 C 0.5557(3) 0.30650(19) 0.48882(9) 0.0493(6) Uani 1 1 d . . . . .
H9 H 0.6012 0.3365 0.5118 0.059 Uiso 1 1 calc R . . . .
C10 C 0.6062(3) 0.27508(18) 0.44812(9) 0.0465(6) Uani 1 1 d . . . . .
H10 H 0.6914 0.2802 0.4389 0.056 Uiso 1 1 calc R . . . .
C11 C 0.4095(2) 0.38761(14) 0.32810(7) 0.0313(5) Uani 1 1 d . . . . .
H11A H 0.4887 0.3578 0.3196 0.038 Uiso 1 1 calc R . . . .
H11B H 0.3409 0.3435 0.3271 0.038 Uiso 1 1 calc R . . . .
C12 C 0.47306(19) 0.50758(13) 0.27742(7) 0.0269(4) Uani 1 1 d . . . . .
C13 C 0.42928(19) 0.57665(13) 0.24578(7) 0.0276(4) Uani 1 1 d . . . . .
C14 C 0.4992(2) 0.62654(14) 0.21463(8) 0.0308(4) Uani 1 1 d . . . . .
C15 C 0.30787(19) 0.60642(14) 0.23976(7) 0.0272(4) Uani 1 1 d . . . . .
H15 H 0.2356 0.5868 0.2555 0.033 Uiso 1 1 calc R . . . .
C16 C 0.6365(2) 0.62441(17) 0.20450(9) 0.0434(6) Uani 1 1 d . . . . .
C17 C 0.20713(19) 0.71658(14) 0.18832(8) 0.0303(4) Uani 1 1 d . . . . .
C18 C 0.2303(2) 0.78482(15) 0.15861(8) 0.0349(5) Uani 1 1 d . . . . .
H18 H 0.3142 0.7999 0.1509 0.042 Uiso 1 1 calc R . . . .
C19 C 0.1298(2) 0.83086(17) 0.14025(9) 0.0418(5) Uani 1 1 d . . . . .
H19 H 0.1448 0.8772 0.1195 0.050 Uiso 1 1 calc R . . . .
C20 C 0.0083(2) 0.80976(19) 0.15197(11) 0.0509(7) Uani 1 1 d . . . . .
H20 H -0.0604 0.8412 0.1391 0.061 Uiso 1 1 calc R . . . .
C21 C -0.0138(2) 0.7432(2) 0.18233(11) 0.0556(7) Uani 1 1 d . . . . .
H21 H -0.0977 0.7297 0.1908 0.067 Uiso 1 1 calc R . . . .
C22 C 0.0852(2) 0.69558(17) 0.20069(10) 0.0457(6) Uani 1 1 d . . . . .
H22 H 0.0698 0.6493 0.2214 0.055 Uiso 1 1 calc R . . . .
F1 F 0.70666(14) 0.65617(13) 0.23859(7) 0.0633(5) Uani 1 1 d . . . . .
F2 F 0.67845(14) 0.54354(11) 0.19659(6) 0.0585(5) Uani 1 1 d . . . . .
F3 F 0.66443(13) 0.67259(12) 0.16821(6) 0.0575(5) Uani 1 1 d . . . . .
Fe1 Fe 0.46462(3) 0.36365(2) 0.43538(2) 0.02894(11) Uani 1 1 d . . . . .
N1 N 0.38228(18) 0.45820(12) 0.29583(6) 0.0301(4) Uani 1 1 d . . . . .
H1 H 0.308(3) 0.4675(17) 0.2896(9) 0.035(7) Uiso 1 1 d . . . . .
N2 N 0.31060(15) 0.66855(12) 0.20736(6) 0.0277(4) Uani 1 1 d . . . . .
N3 N 0.42832(16) 0.68209(12) 0.19124(6) 0.0320(4) Uani 1 1 d . . . . .
O1 O 0.58592(14) 0.49627(10) 0.28564(5) 0.0345(3) 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 C2 1.423(3) . ?
C1 C5 1.425(3) . ?
C1 C11 1.504(3) . ?
C1 Fe1 2.052(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(3) . ?
C2 Fe1 2.033(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.426(3) . ?
C3 Fe1 2.039(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.417(3) . ?
C4 Fe1 2.045(2) . ?
C5 H5 0.9500 . ?
C5 Fe1 2.046(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.420(4) . ?
C6 C10 1.415(4) . ?
C6 Fe1 2.048(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.417(4) . ?
C7 Fe1 2.035(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.408(4) . ?
C8 Fe1 2.043(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.408(4) . ?
C9 Fe1 2.046(2) . ?
C10 H10 0.9500 . ?
C10 Fe1 2.052(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N1 1.466(3) . ?
C12 C13 1.481(3) . ?
C12 N1 1.341(3) . ?
C12 O1 1.234(3) . ?
C13 C14 1.410(3) . ?
C13 C15 1.378(3) . ?
C14 C16 1.491(3) . ?
C14 N3 1.325(3) . ?
C15 H15 0.9500 . ?
C15 N2 1.348(3) . ?
C16 F1 1.343(3) . ?
C16 F2 1.329(3) . ?
C16 F3 1.337(3) . ?
C17 C18 1.384(3) . ?
C17 C22 1.385(3) . ?
C17 N2 1.433(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(4) . ?
C22 H22 0.9500 . ?
N1 H1 0.82(3) . ?
N2 N3 1.357(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
C2 C1 C5 107.49(19) . . ?
C2 C1 C11 125.9(2) . . ?
C2 C1 Fe1 68.90(12) . . ?
C5 C1 C11 126.28(19) . . ?
C5 C1 Fe1 69.43(12) . . ?
C11 C1 Fe1 131.85(15) . . ?
C1 C2 H2 125.8 . . ?
C1 C2 Fe1 70.34(12) . . ?
C3 C2 C1 108.4(2) . . ?
C3 C2 H2 125.8 . . ?
C3 C2 Fe1 69.91(13) . . ?
Fe1 C2 H2 125.6 . . ?
C2 C3 H3 126.1 . . ?
C2 C3 C4 107.9(2) . . ?
C2 C3 Fe1 69.43(13) . . ?
C4 C3 H3 126.1 . . ?
C4 C3 Fe1 69.80(14) . . ?
Fe1 C3 H3 126.3 . . ?
C3 C4 H4 126.0 . . ?
C3 C4 Fe1 69.34(14) . . ?
C5 C4 C3 107.9(2) . . ?
C5 C4 H4 126.0 . . ?
C5 C4 Fe1 69.77(13) . . ?
Fe1 C4 H4 126.4 . . ?
C1 C5 H5 125.9 . . ?
C1 C5 Fe1 69.88(12) . . ?
C4 C5 C1 108.26(19) . . ?
C4 C5 H5 125.9 . . ?
C4 C5 Fe1 69.70(13) . . ?
Fe1 C5 H5 126.1 . . ?
C7 C6 H6 126.2 . . ?
C7 C6 Fe1 69.14(15) . . ?
C10 C6 H6 126.2 . . ?
C10 C6 C7 107.6(2) . . ?
C10 C6 Fe1 69.97(15) . . ?
Fe1 C6 H6 126.3 . . ?
C6 C7 H7 126.0 . . ?
C6 C7 Fe1 70.16(15) . . ?
C8 C7 C6 108.0(3) . . ?
C8 C7 H7 126.0 . . ?
C8 C7 Fe1 69.97(16) . . ?
Fe1 C7 H7 125.5 . . ?
C7 C8 H8 126.1 . . ?
C7 C8 Fe1 69.36(15) . . ?
C9 C8 C7 107.7(2) . . ?
C9 C8 H8 126.1 . . ?
C9 C8 Fe1 69.99(15) . . ?
Fe1 C8 H8 126.1 . . ?
C8 C9 H9 125.7 . . ?
C8 C9 C10 108.6(3) . . ?
C8 C9 Fe1 69.73(15) . . ?
C10 C9 H9 125.7 . . ?
C10 C9 Fe1 70.13(14) . . ?
Fe1 C9 H9 126.0 . . ?
C6 C10 H10 126.0 . . ?
C6 C10 Fe1 69.67(15) . . ?
C9 C10 C6 108.0(3) . . ?
C9 C10 H10 126.0 . . ?
C9 C10 Fe1 69.67(15) . . ?
Fe1 C10 H10 126.3 . . ?
C1 C11 H11A 109.4 . . ?
C1 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C11 C1 111.03(17) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
N1 C12 C13 115.54(18) . . ?
O1 C12 C13 121.65(19) . . ?
O1 C12 N1 122.80(19) . . ?
C14 C13 C12 129.19(19) . . ?
C15 C13 C12 127.23(19) . . ?
C15 C13 C14 103.58(18) . . ?
C13 C14 C16 129.8(2) . . ?
N3 C14 C13 112.72(19) . . ?
N3 C14 C16 117.49(19) . . ?
C13 C15 H15 126.3 . . ?
N2 C15 C13 107.35(18) . . ?
N2 C15 H15 126.3 . . ?
F1 C16 C14 112.3(2) . . ?
F2 C16 C14 112.7(2) . . ?
F2 C16 F1 106.3(2) . . ?
F2 C16 F3 106.7(2) . . ?
F3 C16 C14 111.89(19) . . ?
F3 C16 F1 106.6(2) . . ?
C18 C17 C22 120.8(2) . . ?
C18 C17 N2 119.62(19) . . ?
C22 C17 N2 119.6(2) . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 118.9(2) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C2 Fe1 C1 40.76(9) . . ?
C2 Fe1 C3 40.66(10) . . ?
C2 Fe1 C4 68.54(9) . . ?
C2 Fe1 C5 68.52(9) . . ?
C2 Fe1 C6 126.46(11) . . ?
C2 Fe1 C7 107.12(11) . . ?
C2 Fe1 C8 118.89(11) . . ?
C2 Fe1 C9 153.49(11) . . ?
C2 Fe1 C10 164.36(10) . . ?
C3 Fe1 C1 68.48(9) . . ?
C3 Fe1 C4 40.86(10) . . ?
C3 Fe1 C5 68.48(9) . . ?
C3 Fe1 C6 163.16(11) . . ?
C3 Fe1 C8 106.59(11) . . ?
C3 Fe1 C9 119.36(11) . . ?
C3 Fe1 C10 154.28(11) . . ?
C4 Fe1 C1 68.40(9) . . ?
C4 Fe1 C5 40.53(9) . . ?
C4 Fe1 C6 155.07(11) . . ?
C4 Fe1 C9 107.99(11) . . ?
C4 Fe1 C10 120.47(11) . . ?
C5 Fe1 C1 40.69(8) . . ?
C5 Fe1 C6 120.98(10) . . ?
C5 Fe1 C9 126.94(11) . . ?
C5 Fe1 C10 109.17(10) . . ?
C6 Fe1 C1 108.69(10) . . ?
C6 Fe1 C10 40.36(11) . . ?
C7 Fe1 C1 120.00(10) . . ?
C7 Fe1 C3 125.11(11) . . ?
C7 Fe1 C4 162.71(11) . . ?
C7 Fe1 C5 155.14(11) . . ?
C7 Fe1 C6 40.71(12) . . ?
C7 Fe1 C8 40.67(12) . . ?
C7 Fe1 C9 67.97(12) . . ?
C7 Fe1 C10 68.09(12) . . ?
C8 Fe1 C1 154.08(11) . . ?
C8 Fe1 C4 125.48(11) . . ?
C8 Fe1 C5 163.27(11) . . ?
C8 Fe1 C6 68.27(11) . . ?
C8 Fe1 C9 40.28(12) . . ?
C8 Fe1 C10 67.90(12) . . ?
C9 Fe1 C1 164.52(10) . . ?
C9 Fe1 C6 67.83(11) . . ?
C9 Fe1 C10 40.20(11) . . ?
C10 Fe1 C1 127.50(10) . . ?
C11 N1 H1 117.2(19) . . ?
C12 N1 C11 122.45(18) . . ?
C12 N1 H1 120.3(19) . . ?
C15 N2 C17 128.19(17) . . ?
C15 N2 N3 112.43(17) . . ?
N3 N2 C17 119.35(17) . . ?
C14 N3 N2 103.92(17) . . ?

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
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 Fe1 -60.03(15) . . . . ?
C1 C11 N1 C12 84.6(2) . . . . ?
C2 C1 C5 C4 -0.8(2) . . . . ?
C2 C1 C5 Fe1 58.57(15) . . . . ?
C2 C1 C11 N1 89.5(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 Fe1 -59.19(17) . . . . ?
C3 C4 C5 C1 0.4(3) . . . . ?
C3 C4 C5 Fe1 -59.05(17) . . . . ?
C5 C1 C2 C3 0.9(3) . . . . ?
C5 C1 C2 Fe1 -58.91(15) . . . . ?
C5 C1 C11 N1 -83.3(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 Fe1 60.10(18) . . . . ?
C7 C6 C10 C9 0.2(3) . . . . ?
C7 C6 C10 Fe1 -59.09(18) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 Fe1 59.33(19) . . . . ?
C8 C9 C10 C6 0.0(3) . . . . ?
C8 C9 C10 Fe1 59.32(19) . . . . ?
C10 C6 C7 C8 -0.4(3) . . . . ?
C10 C6 C7 Fe1 59.61(18) . . . . ?
C11 C1 C2 C3 -173.1(2) . . . . ?
C11 C1 C2 Fe1 127.1(2) . . . . ?
C11 C1 C5 C4 173.2(2) . . . . ?
C11 C1 C5 Fe1 -127.5(2) . . . . ?
C12 C13 C14 C16 0.0(4) . . . . ?
C12 C13 C14 N3 179.2(2) . . . . ?
C12 C13 C15 N2 -179.2(2) . . . . ?
C13 C12 N1 C11 -179.43(18) . . . . ?
C13 C14 C16 F1 -69.3(3) . . . . ?
C13 C14 C16 F2 50.7(4) . . . . ?
C13 C14 C16 F3 170.9(2) . . . . ?
C13 C14 N3 N2 0.1(3) . . . . ?
C13 C15 N2 C17 177.7(2) . . . . ?
C13 C15 N2 N3 0.0(2) . . . . ?
C14 C13 C15 N2 0.1(2) . . . . ?
C15 C13 C14 C16 -179.3(2) . . . . ?
C15 C13 C14 N3 -0.2(3) . . . . ?
C15 N2 N3 C14 -0.1(2) . . . . ?
C16 C14 N3 N2 179.4(2) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C17 N2 N3 C14 -178.04(19) . . . . ?
C18 C17 C22 C21 1.0(4) . . . . ?
C18 C17 N2 C15 173.0(2) . . . . ?
C18 C17 N2 N3 -9.4(3) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
C20 C21 C22 C17 0.6(5) . . . . ?
C22 C17 C18 C19 -1.7(4) . . . . ?
C22 C17 N2 C15 -5.4(4) . . . . ?
C22 C17 N2 N3 172.2(2) . . . . ?
Fe1 C1 C2 C3 59.76(16) . . . . ?
Fe1 C1 C5 C4 -59.34(16) . . . . ?
Fe1 C1 C11 N1 -177.49(15) . . . . ?
Fe1 C2 C3 C4 59.42(17) . . . . ?
Fe1 C3 C4 C5 59.32(16) . . . . ?
Fe1 C4 C5 C1 59.45(15) . . . . ?
Fe1 C6 C7 C8 -59.98(19) . . . . ?
Fe1 C6 C10 C9 59.32(18) . . . . ?
Fe1 C7 C8 C9 -59.73(19) . . . . ?
Fe1 C8 C9 C10 -59.56(19) . . . . ?
Fe1 C9 C10 C6 -59.31(18) . . . . ?
N1 C12 C13 C14 -165.9(2) . . . . ?
N1 C12 C13 C15 13.2(3) . . . . ?
N2 C17 C18 C19 179.9(2) . . . . ?
N2 C17 C22 C21 179.4(3) . . . . ?
N3 C14 C16 F1 111.6(2) . . . . ?
N3 C14 C16 F2 -128.5(2) . . . . ?
N3 C14 C16 F3 -8.2(3) . . . . ?
O1 C12 C13 C14 13.3(3) . . . . ?
O1 C12 C13 C15 -167.5(2) . . . . ?
O1 C12 N1 C11 1.3(3) . . . . ?


_shelx_SHELXL_version_number     2014/7

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0114 0.0001 -0.0002 1.0006 0.0423 0.0090 0.0288
2 -2 -3 0.1015 1.9990 -2.0037 -3.0037 -0.0756 0.2803 -0.2547
1 1 1 0.1122 1.0007 0.9993 1.0041 -0.0420 0.1394 0.1135
1 -1 2 0.0965 0.9997 -1.0026 2.0001 0.1102 0.1717 -0.0267
0 -1 -1 0.0262 -0.0006 -1.0006 -1.0028 0.0127 0.0026 -0.1133
-1 0 0 0.1311 -1.0001 0.0013 -0.0012 0.0293 -0.1420 -0.0003
0 -1 -3 0.0322 -0.0007 -1.0002 -3.0040 -0.0719 -0.0154 -0.1708
0 1 1 0.0402 0.0006 1.0006 1.0028 -0.0127 -0.0026 0.1133
-1 0 -3 0.0929 -1.0003 0.0020 -3.0030 -0.0975 -0.1691 -0.0866
1 0 0 0.1311 1.0001 -0.0013 0.0012 -0.0293 0.1420 0.0003
0 2 -1 0.0487 0.0009 2.0019 -0.9961 -0.1522 -0.0322 0.1402
0 -2 1 0.0347 -0.0009 -2.0019 0.9961 0.1522 0.0322 -0.1402
0 0 -1 0.0374 -0.0001 0.0002 -1.0006 -0.0423 -0.0090 -0.0288

_olex2_submission_special_instructions 'No special instructions were received'

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1433290'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_date             2015-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 F3 Fe N3 O2'
_chemical_formula_sum            'C23 H20 F3 Fe N3 O2'
_chemical_formula_weight         483.27
_chemical_melting_point          ?

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

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

_cell_length_a                   9.4458(3)
_cell_length_b                   10.3520(4)
_cell_length_c                   11.0470(4)
_cell_angle_alpha                96.727(3)
_cell_angle_beta                 102.651(3)
_cell_angle_gamma                100.958(3)
_cell_volume                     1020.46(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10388
_cell_measurement_temperature    183(1)
_cell_measurement_theta_max      32.8
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.267
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      183(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   21.40   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8100  -99.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  2 omega  -55.00   46.60   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5912  -38.0000   90.0000 127

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   63.00   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5912  -99.0000 -120.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00  111.00   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5912  178.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   95.60   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5912   38.0000  -90.0000 127

#__ type_ start__ end____ width___ exp.time_
  6 omega  -13.00   99.00   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5912   77.0000    0.0000 140

#__ type_ start__ end____ width___ exp.time_
  7 omega  -96.00    6.40   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8100  -38.0000   60.0000 128

#__ type_ start__ end____ width___ exp.time_
  8 omega -108.00  -32.00   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8100  178.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
  9 omega  -46.00   55.60   0.8000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8100   38.0000    0.0000 127
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0788763000
_diffrn_orient_matrix_UB_12      0.0152323000
_diffrn_orient_matrix_UB_13      0.0190054000
_diffrn_orient_matrix_UB_21      0.0032030000
_diffrn_orient_matrix_UB_22      0.0155435000
_diffrn_orient_matrix_UB_23      -0.0603312000
_diffrn_orient_matrix_UB_31      -0.0001096000
_diffrn_orient_matrix_UB_32      0.0673400000
_diffrn_orient_matrix_UB_33      0.0212501000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5436
_reflns_number_total             6226

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS97 (Sheldrick, 2008)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.3799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.56141(2) 0.65683(2) 0.31571(2) 0.02550(7) Uani 1 1 d . . . . .
F1 F 1.01202(12) 1.36696(9) 0.07514(11) 0.0435(2) Uani 1 1 d . . . . .
F2 F 0.87823(15) 1.33092(10) 0.20598(11) 0.0505(3) Uani 1 1 d . . . . .
F3 F 0.79759(11) 1.23291(10) 0.01434(10) 0.0416(2) Uani 1 1 d . . . . .
O1 O 0.67877(13) 1.03926(11) 0.16430(12) 0.0382(3) Uani 1 1 d . . . . .
O2 O 1.03674(12) 0.83593(9) 0.17296(9) 0.0278(2) Uani 1 1 d . . . . .
N1 N 0.71030(14) 0.83990(12) 0.07913(12) 0.0289(2) Uani 1 1 d . . . . .
N2 N 1.16448(13) 1.05791(11) 0.18272(11) 0.0261(2) Uani 1 1 d . . . . .
N3 N 1.13581(13) 1.17756(11) 0.16309(11) 0.0267(2) Uani 1 1 d . . . . .
C1 C 0.53733(16) 0.65325(14) 0.12698(13) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.64589(17) 0.58134(15) 0.17431(15) 0.0324(3) Uani 1 1 d . . . . .
H2 H 0.7469 0.6001 0.1698 0.039 Uiso 1 1 calc R . . . .
C3 C 0.5775(2) 0.47654(15) 0.22949(16) 0.0372(3) Uani 1 1 d . . . . .
H3 H 0.6251 0.4142 0.2693 0.045 Uiso 1 1 calc R . . . .
C4 C 0.42563(19) 0.48158(15) 0.21464(15) 0.0357(3) Uani 1 1 d . . . . .
H4 H 0.3534 0.4228 0.2420 0.043 Uiso 1 1 calc R . . . .
C5 C 0.40087(16) 0.59027(15) 0.15162(14) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.3088 0.6166 0.1296 0.037 Uiso 1 1 calc R . . . .
C6 C 0.73053(19) 0.7923(2) 0.43840(18) 0.0477(5) Uani 1 1 d . . . . .
H6 H 0.8290 0.8179 0.4288 0.057 Uiso 1 1 calc R . . . .
C7 C 0.6771(2) 0.6866(2) 0.49944(17) 0.0503(5) Uani 1 1 d . . . . .
H7 H 0.7338 0.6292 0.5381 0.060 Uiso 1 1 calc R . . . .
C8 C 0.5257(2) 0.68178(18) 0.49267(16) 0.0408(4) Uani 1 1 d . . . . .
H8 H 0.4620 0.6202 0.5254 0.049 Uiso 1 1 calc R . . . .
C9 C 0.48500(18) 0.78451(16) 0.42864(15) 0.0334(3) Uani 1 1 d . . . . .
H9 H 0.3891 0.8042 0.4116 0.040 Uiso 1 1 calc R . . . .
C10 C 0.6102(2) 0.85315(16) 0.39404(15) 0.0362(3) Uani 1 1 d . . . . .
H10 H 0.6137 0.9263 0.3495 0.043 Uiso 1 1 calc R . . . .
C11 C 0.55611(16) 0.76853(15) 0.05660(14) 0.0311(3) Uani 1 1 d . . . . .
H11A H 0.5163 0.7349 -0.0346 0.037 Uiso 1 1 calc R . . . .
H11B H 0.4968 0.8315 0.0817 0.037 Uiso 1 1 calc R . . . .
C12 C 0.75805(15) 0.96988(13) 0.12973(12) 0.0250(3) Uani 1 1 d . . . . .
C13 C 0.91877(15) 1.02641(12) 0.14335(12) 0.0221(2) Uani 1 1 d . . . . .
C14 C 1.03746(15) 0.96630(12) 0.17024(12) 0.0231(2) Uani 1 1 d . . . . .
C15 C 0.98900(15) 1.15854(12) 0.13980(12) 0.0235(2) Uani 1 1 d . . . . .
C16 C 1.31764(17) 1.04135(17) 0.21707(16) 0.0360(3) Uani 1 1 d . . . . .
H16A H 1.3728 1.0803 0.1597 0.054 Uiso 1 1 calc GR . . . .
H16B H 1.3176 0.9461 0.2110 0.054 Uiso 1 1 calc GR . . . .
H16C H 1.3652 1.0865 0.3035 0.054 Uiso 1 1 calc GR . . . .
C17 C 0.91889(18) 1.27193(14) 0.10894(15) 0.0310(3) Uani 1 1 d . . . . .
C18 C 1.07116(14) 0.79240(13) 0.28904(13) 0.0237(2) Uani 1 1 d . . . . .
C19 C 1.06484(17) 0.65653(14) 0.27935(16) 0.0311(3) Uani 1 1 d . . . . .
H19 H 1.0401 0.6012 0.1994 0.037 Uiso 1 1 calc R . . . .
C20 C 1.09553(19) 0.60365(17) 0.38899(18) 0.0411(4) Uani 1 1 d . . . . .
H20 H 1.0911 0.5107 0.3843 0.049 Uiso 1 1 calc R . . . .
C21 C 1.13231(19) 0.6838(2) 0.50448(17) 0.0448(4) Uani 1 1 d . . . . .
H21 H 1.1532 0.6463 0.5791 0.054 Uiso 1 1 calc R . . . .
C22 C 1.13900(18) 0.81962(19) 0.51217(15) 0.0379(4) Uani 1 1 d . . . . .
H22 H 1.1648 0.8748 0.5922 0.045 Uiso 1 1 calc R . . . .
C23 C 1.10811(16) 0.87571(15) 0.40313(13) 0.0289(3) Uani 1 1 d . . . . .
H23 H 1.1125 0.9686 0.4076 0.035 Uiso 1 1 calc R . . . .
H1 H 0.770(2) 0.8020(19) 0.0519(19) 0.037(5) 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
Fe1 C1 2.0422(14) . ?
Fe1 C2 2.0455(16) . ?
Fe1 C3 2.0415(16) . ?
Fe1 C4 2.0485(15) . ?
Fe1 C5 2.0411(14) . ?
Fe1 C6 2.0273(17) . ?
Fe1 C7 2.0404(17) . ?
Fe1 C8 2.0508(17) . ?
Fe1 C9 2.0482(16) . ?
Fe1 C10 2.0369(16) . ?
F1 C17 1.3349(17) . ?
F2 C17 1.3363(18) . ?
F3 C17 1.3299(19) . ?
O1 C12 1.2199(18) . ?
O2 C14 1.3522(15) . ?
O2 C18 1.4006(15) . ?
N1 C11 1.4554(18) . ?
N1 C12 1.3450(18) . ?
N1 H1 0.83(2) . ?
N2 N3 1.3488(16) . ?
N2 C14 1.3499(17) . ?
N2 C16 1.4613(19) . ?
N3 C15 1.3251(18) . ?
C1 C2 1.423(2) . ?
C1 C5 1.4271(19) . ?
C1 C11 1.5025(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.424(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.419(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.420(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.421(3) . ?
C6 C10 1.424(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.407(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.411(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4871(19) . ?
C13 C14 1.3766(19) . ?
C13 C15 1.4112(17) . ?
C15 C17 1.4910(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.3868(19) . ?
C18 C23 1.376(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.373(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(2) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe1 C2 40.75(6) . . ?
C1 Fe1 C4 68.84(6) . . ?
C1 Fe1 C8 162.07(7) . . ?
C1 Fe1 C9 124.56(6) . . ?
C2 Fe1 C4 68.36(7) . . ?
C2 Fe1 C8 156.42(7) . . ?
C2 Fe1 C9 161.54(6) . . ?
C3 Fe1 C1 68.87(6) . . ?
C3 Fe1 C2 40.77(6) . . ?
C3 Fe1 C4 40.60(7) . . ?
C3 Fe1 C8 121.72(7) . . ?
C3 Fe1 C9 156.36(7) . . ?
C4 Fe1 C8 108.83(7) . . ?
C5 Fe1 C1 40.91(5) . . ?
C5 Fe1 C2 68.28(6) . . ?
C5 Fe1 C3 68.38(7) . . ?
C5 Fe1 C4 40.65(6) . . ?
C5 Fe1 C8 125.85(7) . . ?
C5 Fe1 C9 107.86(7) . . ?
C6 Fe1 C1 119.26(7) . . ?
C6 Fe1 C2 107.16(7) . . ?
C6 Fe1 C3 125.42(8) . . ?
C6 Fe1 C4 162.96(8) . . ?
C6 Fe1 C5 154.68(8) . . ?
C6 Fe1 C7 40.89(9) . . ?
C6 Fe1 C8 68.28(8) . . ?
C6 Fe1 C9 68.15(7) . . ?
C6 Fe1 C10 41.03(8) . . ?
C7 Fe1 C1 155.32(8) . . ?
C7 Fe1 C2 121.19(7) . . ?
C7 Fe1 C3 108.54(7) . . ?
C7 Fe1 C4 126.15(8) . . ?
C7 Fe1 C5 162.86(8) . . ?
C7 Fe1 C8 40.23(8) . . ?
C7 Fe1 C9 67.77(7) . . ?
C9 Fe1 C4 121.30(7) . . ?
C9 Fe1 C8 40.28(6) . . ?
C10 Fe1 C1 105.90(6) . . ?
C10 Fe1 C2 124.40(6) . . ?
C10 Fe1 C3 162.18(7) . . ?
C10 Fe1 C4 155.10(7) . . ?
C10 Fe1 C5 119.55(7) . . ?
C10 Fe1 C7 68.69(8) . . ?
C10 Fe1 C8 68.31(7) . . ?
C10 Fe1 C9 40.43(6) . . ?
C14 O2 C18 119.46(10) . . ?
C11 N1 H1 119.1(14) . . ?
C12 N1 C11 122.92(14) . . ?
C12 N1 H1 117.5(14) . . ?
N3 N2 C14 111.10(11) . . ?
N3 N2 C16 120.62(12) . . ?
C14 N2 C16 128.25(12) . . ?
C15 N3 N2 104.75(10) . . ?
C2 C1 Fe1 69.75(8) . . ?
C2 C1 C5 107.16(12) . . ?
C2 C1 C11 127.68(13) . . ?
C5 C1 Fe1 69.50(8) . . ?
C5 C1 C11 125.05(14) . . ?
C11 C1 Fe1 128.73(10) . . ?
Fe1 C2 H2 126.8 . . ?
C1 C2 Fe1 69.50(9) . . ?
C1 C2 H2 125.8 . . ?
C1 C2 C3 108.42(14) . . ?
C3 C2 Fe1 69.46(9) . . ?
C3 C2 H2 125.8 . . ?
Fe1 C3 H3 125.9 . . ?
C2 C3 Fe1 69.77(9) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 Fe1 69.96(9) . . ?
C4 C3 C2 108.01(14) . . ?
C4 C3 H3 126.0 . . ?
Fe1 C4 H4 126.6 . . ?
C3 C4 Fe1 69.43(9) . . ?
C3 C4 H4 126.1 . . ?
C3 C4 C5 107.80(13) . . ?
C5 C4 Fe1 69.40(8) . . ?
C5 C4 H4 126.1 . . ?
Fe1 C5 H5 126.3 . . ?
C1 C5 Fe1 69.58(8) . . ?
C1 C5 H5 125.7 . . ?
C4 C5 Fe1 69.95(9) . . ?
C4 C5 C1 108.60(14) . . ?
C4 C5 H5 125.7 . . ?
Fe1 C6 H6 125.6 . . ?
C7 C6 Fe1 70.05(10) . . ?
C7 C6 H6 126.1 . . ?
C7 C6 C10 107.89(16) . . ?
C10 C6 Fe1 69.85(9) . . ?
C10 C6 H6 126.1 . . ?
Fe1 C7 H7 126.3 . . ?
C6 C7 Fe1 69.06(10) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 Fe1 70.28(10) . . ?
C8 C7 C6 108.08(16) . . ?
C8 C7 H7 126.0 . . ?
Fe1 C8 H8 126.3 . . ?
C7 C8 Fe1 69.49(10) . . ?
C7 C8 H8 126.0 . . ?
C7 C8 C9 107.98(16) . . ?
C9 C8 Fe1 69.76(9) . . ?
C9 C8 H8 126.0 . . ?
Fe1 C9 H9 126.7 . . ?
C8 C9 Fe1 69.96(10) . . ?
C8 C9 H9 125.6 . . ?
C8 C9 C10 108.79(15) . . ?
C10 C9 Fe1 69.35(9) . . ?
C10 C9 H9 125.6 . . ?
Fe1 C10 H10 125.9 . . ?
C6 C10 Fe1 69.13(10) . . ?
C6 C10 H10 126.4 . . ?
C9 C10 Fe1 70.22(9) . . ?
C9 C10 C6 107.26(15) . . ?
C9 C10 H10 126.4 . . ?
N1 C11 C1 113.22(12) . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C1 C11 H11A 108.9 . . ?
C1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
O1 C12 N1 124.06(13) . . ?
O1 C12 C13 120.63(12) . . ?
N1 C12 C13 115.31(13) . . ?
C14 C13 C12 129.14(12) . . ?
C14 C13 C15 102.37(11) . . ?
C15 C13 C12 128.38(12) . . ?
O2 C14 C13 128.95(12) . . ?
N2 C14 O2 121.88(12) . . ?
N2 C14 C13 108.87(11) . . ?
N3 C15 C13 112.91(12) . . ?
N3 C15 C17 118.62(12) . . ?
C13 C15 C17 128.42(13) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 C17 F2 106.36(12) . . ?
F1 C17 C15 111.49(13) . . ?
F2 C17 C15 112.80(12) . . ?
F3 C17 F1 107.13(12) . . ?
F3 C17 F2 106.91(14) . . ?
F3 C17 C15 111.79(12) . . ?
C19 C18 O2 113.96(12) . . ?
C23 C18 O2 123.62(12) . . ?
C23 C18 C19 122.41(13) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.31(16) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.83(15) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.98(15) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.46(16) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 118.00(14) . . ?
C18 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 C1 C2 C3 58.71(11) . . . . ?
Fe1 C1 C5 C4 -59.26(11) . . . . ?
Fe1 C1 C11 N1 70.56(18) . . . . ?
Fe1 C2 C3 C4 59.75(12) . . . . ?
Fe1 C3 C4 C5 58.99(11) . . . . ?
Fe1 C4 C5 C1 59.03(10) . . . . ?
Fe1 C6 C7 C8 -59.68(13) . . . . ?
Fe1 C6 C10 C9 60.15(11) . . . . ?
Fe1 C7 C8 C9 -59.36(12) . . . . ?
Fe1 C8 C9 C10 -58.63(12) . . . . ?
Fe1 C9 C10 C6 -59.45(11) . . . . ?
O1 C12 C13 C14 144.90(15) . . . . ?
O1 C12 C13 C15 -30.6(2) . . . . ?
O2 C18 C19 C20 -179.33(14) . . . . ?
O2 C18 C23 C22 179.54(13) . . . . ?
N1 C12 C13 C14 -34.4(2) . . . . ?
N1 C12 C13 C15 150.12(14) . . . . ?
N2 N3 C15 C13 -0.16(15) . . . . ?
N2 N3 C15 C17 -177.77(12) . . . . ?
N3 N2 C14 O2 173.16(11) . . . . ?
N3 N2 C14 C13 -1.05(16) . . . . ?
N3 C15 C17 F1 17.45(19) . . . . ?
N3 C15 C17 F2 -102.14(16) . . . . ?
N3 C15 C17 F3 137.34(13) . . . . ?
C1 C2 C3 Fe1 -58.74(11) . . . . ?
C1 C2 C3 C4 1.01(18) . . . . ?
C2 C1 C5 Fe1 59.86(10) . . . . ?
C2 C1 C5 C4 0.60(17) . . . . ?
C2 C1 C11 N1 -22.8(2) . . . . ?
C2 C3 C4 Fe1 -59.62(11) . . . . ?
C2 C3 C4 C5 -0.63(19) . . . . ?
C3 C4 C5 Fe1 -59.01(11) . . . . ?
C3 C4 C5 C1 0.02(18) . . . . ?
C5 C1 C2 Fe1 -59.70(10) . . . . ?
C5 C1 C2 C3 -0.99(17) . . . . ?
C5 C1 C11 N1 161.38(14) . . . . ?
C6 C7 C8 Fe1 58.92(12) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C6 C10 Fe1 -59.97(12) . . . . ?
C7 C6 C10 C9 0.17(19) . . . . ?
C7 C8 C9 Fe1 59.19(12) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 Fe1 59.00(12) . . . . ?
C8 C9 C10 C6 -0.45(19) . . . . ?
C10 C6 C7 Fe1 59.84(12) . . . . ?
C10 C6 C7 C8 0.2(2) . . . . ?
C11 N1 C12 O1 1.9(2) . . . . ?
C11 N1 C12 C13 -178.84(12) . . . . ?
C11 C1 C2 Fe1 123.89(15) . . . . ?
C11 C1 C2 C3 -177.40(14) . . . . ?
C11 C1 C5 Fe1 -123.61(14) . . . . ?
C11 C1 C5 C4 177.13(14) . . . . ?
C12 N1 C11 C1 -119.60(16) . . . . ?
C12 C13 C14 O2 10.8(2) . . . . ?
C12 C13 C14 N2 -175.53(13) . . . . ?
C12 C13 C15 N3 175.99(12) . . . . ?
C12 C13 C15 C17 -6.7(2) . . . . ?
C13 C15 C17 F1 -159.74(14) . . . . ?
C13 C15 C17 F2 80.67(19) . . . . ?
C13 C15 C17 F3 -39.9(2) . . . . ?
C14 O2 C18 C19 179.24(12) . . . . ?
C14 O2 C18 C23 -0.8(2) . . . . ?
C14 N2 N3 C15 0.74(15) . . . . ?
C14 C13 C15 N3 -0.44(15) . . . . ?
C14 C13 C15 C17 176.89(13) . . . . ?
C15 C13 C14 O2 -172.81(13) . . . . ?
C15 C13 C14 N2 0.86(14) . . . . ?
C16 N2 N3 C15 -177.27(13) . . . . ?
C16 N2 C14 O2 -9.0(2) . . . . ?
C16 N2 C14 C13 176.77(14) . . . . ?
C18 O2 C14 N2 82.07(16) . . . . ?
C18 O2 C14 C13 -104.98(16) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C19 C18 C23 C22 -0.5(2) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C18 0.0(2) . . . . ?
C23 C18 C19 C20 0.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 3 0 0.0852 -4.0000 3.0000 -0.0000 -0.2698 0.0338 0.2025
4 -3 0 0.1212 4.0000 -3.0000 0.0000 0.2698 -0.0338 -0.2025
0 0 1 0.1572 -0.0000 0.0000 1.0000 0.0190 -0.0603 0.0213
-1 -4 -2 0.1141 -1.0000 -4.0000 -2.0000 -0.1778 0.0553 -0.3118
1 4 2 0.1141 1.0000 4.0000 2.0000 0.1778 -0.0553 0.3118
0 0 -1 0.1765 0.0000 -0.0000 -1.0000 -0.0190 0.0603 -0.0213
1 -3 -3 0.0932 1.0000 -3.0000 -3.0000 -0.0238 0.1376 -0.2659
3 -1 -3 0.1169 3.0000 -1.0000 -3.0000 0.1644 0.1751 -0.1314
-1 0 3 0.1132 -1.0000 0.0000 3.0000 -0.0219 -0.1842 0.0639
1 3 0 0.1359 1.0000 3.0000 -0.0000 0.1246 0.0498 0.2019
4 1 -1 0.1354 4.0000 1.0000 -1.0000 0.3117 0.0887 0.0457
-1 7 0 0.1312 -1.0000 7.0000 -0.0000 0.0277 0.1056 0.4715
2 -1 -3 0.1164 2.0000 -1.0000 -3.0000 0.0855 0.1719 -0.1313
-2 1 3 0.1164 -2.0000 1.0000 3.0000 -0.0855 -0.1719 0.1313

_olex2_date_sample_data_collection 2015-01-14

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
