# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_d19205_a
_database_code_depnum_ccdc_archive 'CCDC 1999811'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Fe N O3'
_chemical_formula_sum            'C21 H21 Fe N O3'
_chemical_formula_weight         391.24

# start Validation Reply Form
_vrf_PLAT420_d19205_a            
;
PROBLEM: D-H Without Acceptor       O1       --H1O      .     Please Check 
RESPONSE: O1--H1O is involved in a O--H...pi(arene) interaction.
(see Hydrogen Bond table) Cg is the centroid of the C4--C9 ring.
;
# end Validation Reply Form

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9439(4)
_cell_length_b                   8.6162(4)
_cell_length_c                   25.8718(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1770.83(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9538
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.07

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.872
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53341
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.574
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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             4097
_reflns_number_gt                3861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       APEX3
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0294P)²+0.2582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
; 
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.007(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4097
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0536
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.26436(3) 0.88211(3) 0.69474(2) 0.01783(8) Uani 1 1 d . . . . .
O1 O 0.64180(19) 0.5831(2) 0.51204(6) 0.0268(4) Uani 1 1 d . . . . .
H1O H 0.608(4) 0.673(4) 0.5137(12) 0.053(10) Uiso 1 1 d . . . . .
O2 O 0.77678(18) 0.64119(17) 0.62410(7) 0.0318(4) Uani 1 1 d . . . . .
O3 O 0.75501(16) 0.38191(15) 0.62551(5) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.2478(2) 0.6372(2) 0.58878(6) 0.0237(3) Uani 1 1 d . . . . .
H1N H 0.175(3) 0.699(3) 0.5989(9) 0.029(7) Uiso 1 1 d . . . . .
C1 C 0.4182(2) 0.6665(2) 0.60728(8) 0.0180(4) Uani 1 1 d . . . . .
H1A H 0.468426 0.754400 0.587275 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5184(2) 0.5180(2) 0.59661(8) 0.0175(4) Uani 1 1 d . . . . .
H2A H 0.459589 0.429570 0.613955 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5246(2) 0.4842(2) 0.53790(8) 0.0201(4) Uani 1 1 d . . . . .
H3A H 0.565265 0.375168 0.533542 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3501(2) 0.4928(2) 0.51489(8) 0.0185(4) Uani 1 1 d . . . . .
C5 C 0.3160(3) 0.4229(2) 0.46744(8) 0.0235(4) Uani 1 1 d . . . . .
H5A H 0.404337 0.372001 0.449415 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1568(3) 0.4261(3) 0.44602(9) 0.0263(5) Uani 1 1 d . . . . .
H6A H 0.136491 0.380455 0.413185 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0268(3) 0.4968(2) 0.47310(8) 0.0239(5) Uani 1 1 d . . . . .
H7A H -0.083934 0.496314 0.459204 0.029 Uiso 1 1 calc R U . . .
C8 C 0.0570(3) 0.5679(2) 0.52008(8) 0.0216(4) Uani 1 1 d . . . . .
H8A H -0.032678 0.616505 0.538173 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2200(2) 0.5685(2) 0.54116(7) 0.0191(4) Uani 1 1 d . . . . .
C10 C 0.6963(2) 0.5257(2) 0.61720(8) 0.0190(4) Uani 1 1 d . . . . .
C11 C 0.9288(2) 0.3714(3) 0.64155(8) 0.0281(5) Uani 1 1 d . . . . .
H11A H 0.956924 0.262826 0.648833 0.042 Uiso 1 1 calc R U . . .
H11B H 0.945653 0.433739 0.672799 0.042 Uiso 1 1 calc R U . . .
H11C H 1.001651 0.410433 0.613890 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4095(2) 0.7098(2) 0.66359(8) 0.0180(4) Uani 1 1 d . . . . .
C13 C 0.2947(2) 0.6465(2) 0.70038(8) 0.0210(4) Uani 1 1 d . . . . .
H13A H 0.206601 0.566482 0.693226 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3266(3) 0.7182(3) 0.74898(8) 0.0255(5) Uani 1 1 d . . . . .
H14A H 0.264784 0.697461 0.781928 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4601(3) 0.8256(3) 0.74231(9) 0.0263(5) Uani 1 1 d . . . . .
H15A H 0.508980 0.893500 0.769835 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5122(2) 0.8208(2) 0.68984(9) 0.0236(4) Uani 1 1 d . . . . .
H16A H 0.604143 0.884164 0.674011 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2494(3) 1.1095(2) 0.67309(10) 0.0329(5) Uani 1 1 d . . . . .
H17A H 0.346750 1.180099 0.666126 0.040 Uiso 1 1 calc R U . . .
C18 C 0.1694(3) 1.0871(3) 0.72156(10) 0.0325(6) Uani 1 1 d . . . . .
H18A H 0.200297 1.139095 0.754790 0.039 Uiso 1 1 calc R U . . .
C19 C 0.0378(3) 0.9792(3) 0.71448(9) 0.0285(5) Uani 1 1 d . . . . .
H19A H -0.039784 0.940630 0.742053 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0349(3) 0.9337(3) 0.66165(8) 0.0235(4) Uani 1 1 d . . . . .
H20A H -0.044741 0.857888 0.645535 0.028 Uiso 1 1 calc R U . . .
C21 C 0.1662(3) 1.0144(3) 0.63611(9) 0.0267(5) Uani 1 1 d . . . . .
H21A H 0.195483 1.005720 0.598628 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C17 2.041(2) . ?
Fe1 C15 2.042(2) . ?
Fe1 C16 2.042(2) . ?
Fe1 C18 2.042(2) . ?
Fe1 C12 2.0452(19) . ?
Fe1 C19 2.049(2) . ?
Fe1 C13 2.0494(19) . ?
Fe1 C14 2.051(2) . ?
Fe1 C21 2.051(2) . ?
Fe1 C20 2.062(2) . ?
O1 C3 1.428(3) . ?
O1 H1O 0.82(3) . ?
O2 C10 1.196(2) . ?
O3 C10 1.341(2) . ?
O3 C11 1.444(2) . ?
N1 C9 1.384(2) . ?
N1 C1 1.458(2) . ?
N1 H1N 0.83(3) . ?
C1 C12 1.505(3) . ?
C1 C2 1.533(3) . ?
C1 H1A 1.0000 . ?
C2 C10 1.512(3) . ?
C2 C3 1.547(3) . ?
C2 H2A 1.0000 . ?
C3 C4 1.511(3) . ?
C3 H3A 1.0000 . ?
C4 C5 1.394(3) . ?
C4 C9 1.398(3) . ?
C5 C6 1.381(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.389(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.405(3) . ?
C8 H8A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.426(3) . ?
C12 C16 1.428(3) . ?
C13 C14 1.424(3) . ?
C13 H13A 1.0000 . ?
C14 C15 1.418(3) . ?
C14 H14A 1.0000 . ?
C15 C16 1.420(3) . ?
C15 H15A 1.0000 . ?
C16 H16A 1.0000 . ?
C17 C18 1.419(4) . ?
C17 C21 1.423(3) . ?
C17 H17A 1.0000 . ?
C18 C19 1.410(3) . ?
C18 H18A 1.0000 . ?
C19 C20 1.422(3) . ?
C19 H19A 1.0000 . ?
C20 C21 1.417(3) . ?
C20 H20A 1.0000 . ?
C21 H21A 1.0000 . ?

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
C17 Fe1 C15 116.00(9) . . ?
C17 Fe1 C16 106.70(9) . . ?
C15 Fe1 C16 40.68(10) . . ?
C17 Fe1 C18 40.67(10) . . ?
C15 Fe1 C18 106.42(9) . . ?
C16 Fe1 C18 126.95(9) . . ?
C17 Fe1 C12 128.43(9) . . ?
C15 Fe1 C12 68.60(8) . . ?
C16 Fe1 C12 40.91(8) . . ?
C18 Fe1 C12 165.93(10) . . ?
C17 Fe1 C19 68.00(9) . . ?
C15 Fe1 C19 128.01(9) . . ?
C16 Fe1 C19 165.38(9) . . ?
C18 Fe1 C19 40.33(10) . . ?
C12 Fe1 C19 152.83(9) . . ?
C17 Fe1 C13 167.73(9) . . ?
C15 Fe1 C13 68.36(9) . . ?
C16 Fe1 C13 68.56(8) . . ?
C18 Fe1 C13 151.16(9) . . ?
C12 Fe1 C13 40.77(8) . . ?
C19 Fe1 C13 119.35(9) . . ?
C17 Fe1 C14 149.59(9) . . ?
C15 Fe1 C14 40.53(9) . . ?
C16 Fe1 C14 68.40(9) . . ?
C18 Fe1 C14 116.87(9) . . ?
C12 Fe1 C14 68.52(8) . . ?
C19 Fe1 C14 108.81(9) . . ?
C13 Fe1 C14 40.62(8) . . ?
C17 Fe1 C21 40.69(9) . . ?
C15 Fe1 C21 150.19(10) . . ?
C16 Fe1 C21 117.68(9) . . ?
C18 Fe1 C21 68.30(9) . . ?
C12 Fe1 C21 109.05(8) . . ?
C19 Fe1 C21 67.88(9) . . ?
C13 Fe1 C21 130.38(9) . . ?
C14 Fe1 C21 168.52(9) . . ?
C17 Fe1 C20 68.17(9) . . ?
C15 Fe1 C20 167.07(9) . . ?
C16 Fe1 C20 151.89(9) . . ?
C18 Fe1 C20 68.17(9) . . ?
C12 Fe1 C20 119.41(8) . . ?
C19 Fe1 C20 40.47(9) . . ?
C13 Fe1 C20 110.30(9) . . ?
C14 Fe1 C20 130.19(9) . . ?
C21 Fe1 C20 40.30(9) . . ?
C3 O1 H1O 109(2) . . ?
C10 O3 C11 115.88(17) . . ?
C9 N1 C1 120.94(17) . . ?
C9 N1 H1N 116.4(18) . . ?
C1 N1 H1N 115.7(18) . . ?
N1 C1 C12 108.53(16) . . ?
N1 C1 C2 106.16(16) . . ?
C12 C1 C2 113.89(16) . . ?
N1 C1 H1A 109.4 . . ?
C12 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C10 C2 C1 112.66(16) . . ?
C10 C2 C3 108.93(16) . . ?
C1 C2 C3 110.50(16) . . ?
C10 C2 H2A 108.2 . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
O1 C3 C4 112.62(17) . . ?
O1 C3 C2 111.63(17) . . ?
C4 C3 C2 110.39(16) . . ?
O1 C3 H3A 107.3 . . ?
C4 C3 H3A 107.3 . . ?
C2 C3 H3A 107.3 . . ?
C5 C4 C9 119.08(18) . . ?
C5 C4 C3 120.28(18) . . ?
C9 C4 C3 120.63(18) . . ?
C6 C5 C4 121.52(19) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 119.17(19) . . ?
C5 C6 H6A 120.4 . . ?
C7 C6 H6A 120.4 . . ?
C8 C7 C6 120.56(19) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C7 C8 C9 120.23(19) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
N1 C9 C4 120.94(18) . . ?
N1 C9 C8 119.61(18) . . ?
C4 C9 C8 119.37(18) . . ?
O2 C10 O3 123.97(18) . . ?
O2 C10 C2 126.09(19) . . ?
O3 C10 C2 109.92(17) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C16 107.67(18) . . ?
C13 C12 C1 125.50(18) . . ?
C16 C12 C1 126.83(19) . . ?
C13 C12 Fe1 69.77(11) . . ?
C16 C12 Fe1 69.44(11) . . ?
C1 C12 Fe1 125.94(13) . . ?
C14 C13 C12 108.05(18) . . ?
C14 C13 Fe1 69.76(12) . . ?
C12 C13 Fe1 69.46(11) . . ?
C14 C13 H13A 126.0 . . ?
C12 C13 H13A 126.0 . . ?
Fe1 C13 H13A 126.0 . . ?
C15 C14 C13 107.99(19) . . ?
C15 C14 Fe1 69.39(12) . . ?
C13 C14 Fe1 69.61(11) . . ?
C15 C14 H14A 126.0 . . ?
C13 C14 H14A 126.0 . . ?
Fe1 C14 H14A 126.0 . . ?
C14 C15 C16 108.36(19) . . ?
C14 C15 Fe1 70.08(12) . . ?
C16 C15 Fe1 69.67(12) . . ?
C14 C15 H15A 125.8 . . ?
C16 C15 H15A 125.8 . . ?
Fe1 C15 H15A 125.8 . . ?
C15 C16 C12 107.94(19) . . ?
C15 C16 Fe1 69.66(12) . . ?
C12 C16 Fe1 69.65(11) . . ?
C15 C16 H16A 126.0 . . ?
C12 C16 H16A 126.0 . . ?
Fe1 C16 H16A 126.0 . . ?
C18 C17 C21 107.9(2) . . ?
C18 C17 Fe1 69.71(12) . . ?
C21 C17 Fe1 70.04(12) . . ?
C18 C17 H17A 126.0 . . ?
C21 C17 H17A 126.0 . . ?
Fe1 C17 H17A 126.0 . . ?
C19 C18 C17 107.9(2) . . ?
C19 C18 Fe1 70.10(13) . . ?
C17 C18 Fe1 69.62(12) . . ?
C19 C18 H18A 126.1 . . ?
C17 C18 H18A 126.1 . . ?
Fe1 C18 H18A 126.1 . . ?
C18 C19 C20 108.6(2) . . ?
C18 C19 Fe1 69.57(13) . . ?
C20 C19 Fe1 70.26(13) . . ?
C18 C19 H19A 125.7 . . ?
C20 C19 H19A 125.7 . . ?
Fe1 C19 H19A 125.7 . . ?
C21 C20 C19 107.5(2) . . ?
C21 C20 Fe1 69.43(12) . . ?
C19 C20 Fe1 69.26(13) . . ?
C21 C20 H20A 126.3 . . ?
C19 C20 H20A 126.3 . . ?
Fe1 C20 H20A 126.3 . . ?
C20 C21 C17 108.1(2) . . ?
C20 C21 Fe1 70.26(12) . . ?
C17 C21 Fe1 69.27(12) . . ?
C20 C21 H21A 125.9 . . ?
C17 C21 H21A 125.9 . . ?
Fe1 C21 H21A 125.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C12 -168.28(17) . . . . ?
C9 N1 C1 C2 -45.5(2) . . . . ?
N1 C1 C2 C10 -175.92(16) . . . . ?
C12 C1 C2 C10 -56.6(2) . . . . ?
N1 C1 C2 C3 62.0(2) . . . . ?
C12 C1 C2 C3 -178.66(17) . . . . ?
C10 C2 C3 O1 -47.8(2) . . . . ?
C1 C2 C3 O1 76.4(2) . . . . ?
C10 C2 C3 C4 -173.92(16) . . . . ?
C1 C2 C3 C4 -49.7(2) . . . . ?
O1 C3 C4 C5 73.8(2) . . . . ?
C2 C3 C4 C5 -160.70(18) . . . . ?
O1 C3 C4 C9 -107.2(2) . . . . ?
C2 C3 C4 C9 18.3(3) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C5 C6 178.62(19) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C5 C6 C7 C8 2.2(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C1 N1 C9 C4 15.1(3) . . . . ?
C1 N1 C9 C8 -168.13(18) . . . . ?
C5 C4 C9 N1 178.94(19) . . . . ?
C3 C4 C9 N1 -0.1(3) . . . . ?
C5 C4 C9 C8 2.2(3) . . . . ?
C3 C4 C9 C8 -176.82(18) . . . . ?
C7 C8 C9 N1 -178.60(19) . . . . ?
C7 C8 C9 C4 -1.8(3) . . . . ?
C11 O3 C10 O2 -2.8(3) . . . . ?
C11 O3 C10 C2 175.45(15) . . . . ?
C1 C2 C10 O2 -25.9(3) . . . . ?
C3 C2 C10 O2 97.1(2) . . . . ?
C1 C2 C10 O3 155.92(16) . . . . ?
C3 C2 C10 O3 -81.1(2) . . . . ?
N1 C1 C12 C13 35.9(3) . . . . ?
C2 C1 C12 C13 -82.1(2) . . . . ?
N1 C1 C12 C16 -143.72(19) . . . . ?
C2 C1 C12 C16 98.3(2) . . . . ?
N1 C1 C12 Fe1 -53.7(2) . . . . ?
C2 C1 C12 Fe1 -171.68(14) . . . . ?
C16 C12 C13 C14 0.0(2) . . . . ?
C1 C12 C13 C14 -179.66(18) . . . . ?
Fe1 C12 C13 C14 -59.29(14) . . . . ?
C16 C12 C13 Fe1 59.32(13) . . . . ?
C1 C12 C13 Fe1 -120.36(19) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
Fe1 C13 C14 C15 -58.96(15) . . . . ?
C12 C13 C14 Fe1 59.10(13) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
Fe1 C14 C15 C16 -59.36(14) . . . . ?
C13 C14 C15 Fe1 59.11(14) . . . . ?
C14 C15 C16 C12 0.3(2) . . . . ?
Fe1 C15 C16 C12 -59.35(13) . . . . ?
C14 C15 C16 Fe1 59.62(15) . . . . ?
C13 C12 C16 C15 -0.2(2) . . . . ?
C1 C12 C16 C15 179.50(18) . . . . ?
Fe1 C12 C16 C15 59.35(14) . . . . ?
C13 C12 C16 Fe1 -59.53(13) . . . . ?
C1 C12 C16 Fe1 120.15(19) . . . . ?
C21 C17 C18 C19 0.0(2) . . . . ?
Fe1 C17 C18 C19 -59.91(15) . . . . ?
C21 C17 C18 Fe1 59.87(14) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
Fe1 C18 C19 C20 -59.62(16) . . . . ?
C17 C18 C19 Fe1 59.61(14) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
Fe1 C19 C20 C21 -59.14(15) . . . . ?
C18 C19 C20 Fe1 59.20(16) . . . . ?
C19 C20 C21 C17 -0.1(2) . . . . ?
Fe1 C20 C21 C17 -59.12(14) . . . . ?
C19 C20 C21 Fe1 59.03(15) . . . . ?
C18 C17 C21 C20 0.1(2) . . . . ?
Fe1 C17 C21 C20 59.74(15) . . . . ?
C18 C17 C21 Fe1 -59.66(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O Cg 0.82(3) 2.93(3) 3.6495(12) 14893) 4_566 yes

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040

