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

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

data_aak_4165_2_100k
_database_code_depnum_ccdc_archive 'CCDC 2215980'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_date             2022-05-25T12:22:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H24 Fe N2 O6'
_chemical_formula_sum            'C24 H24 Fe N2 O6'
_chemical_formula_weight         492.3
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_Int_Tables_number      144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   10.1118(12)
_cell_length_b                   10.1118(12)
_cell_length_c                   18.832(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1667.6(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    904
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      17.64
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       cube
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2012/1 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  0.656
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.958

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.07633
_diffrn_orient_matrix_ub_12      0.018028
_diffrn_orient_matrix_ub_13      0.025484
_diffrn_orient_matrix_ub_21      -0.082495
_diffrn_orient_matrix_ub_22      -0.075116
_diffrn_orient_matrix_ub_23      -0.031897
_diffrn_orient_matrix_ub_31      -0.020208
_diffrn_orient_matrix_ub_32      -0.0841
_diffrn_orient_matrix_ub_33      0.033952
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1547
_diffrn_reflns_number            4188
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.081
_diffrn_reflns_theta_max         25.548
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_coverage         0.992
_reflns_number_total             4158
_reflns_number_gt                2781
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2014/7
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0122P)²+0.5902P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4158
_refine_ls_number_parameters     279
_refine_ls_number_restraints     163
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.102

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.718(2) 0.149(2) 0.9365(8) 0.010(4) Uani 1 1 d . U . . .
C2 C 0.630(2) 0.230(2) 0.9363(9) 0.013(5) Uani 1 1 d . U . . .
C3 C 0.662(2) 0.347(3) 0.9849(11) 0.013(3) Uani 1 1 d . U . . .
C4 C 0.5874(10) 0.4418(9) 0.9793(4) 0.012(3) Uani 1 1 d G U . . .
C5 C 0.4341(10) 0.3722(7) 0.9605(5) 0.020(4) Uani 1 1 d G U . . .
H5 H 0.376 0.2644 0.9555 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3660(8) 0.4604(10) 0.9491(5) 0.025(3) Uani 1 1 d G U . . .
H6 H 0.2612 0.4129 0.9362 0.03 Uiso 1 1 calc R U . . .
C7 C 0.4511(11) 0.6182(10) 0.9564(5) 0.029(4) Uani 1 1 d G U . . .
H7 H 0.4046 0.6785 0.9486 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6044(10) 0.6878(7) 0.9752(5) 0.025(4) Uani 1 1 d G U . . .
H8 H 0.6626 0.7956 0.9802 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6725(8) 0.5995(10) 0.9867(4) 0.016(4) Uani 1 1 d G U . . .
H9 H 0.7773 0.6471 0.9995 0.019 Uiso 1 1 calc R U . . .
C10 C 0.776(2) 0.376(2) 1.0359(9) 0.008(4) Uani 1 1 d . U . . .
C11 C 0.858(2) 0.295(2) 1.0368(10) 0.012(4) Uani 1 1 d . U . . .
C12 C 0.834(2) 0.183(2) 0.9871(11) 0.009(3) Uani 1 1 d . U . . .
C13 C 0.9208(14) 0.1002(14) 0.9847(7) 0.017(3) Uani 1 1 d G U . . .
C14 C 0.9402(12) 0.0400(13) 1.0476(5) 0.023(4) Uani 1 1 d G U . . .
H14 H 0.8952 0.049 1.0903 0.028 Uiso 1 1 calc R U . . .
C15 C 1.0254(12) -0.0334(11) 1.0481(5) 0.028(4) Uani 1 1 d G U . . .
H15 H 1.0386 -0.0746 1.0911 0.033 Uiso 1 1 calc R U . . .
C16 C 1.0911(12) -0.0466(13) 0.9857(7) 0.025(4) Uani 1 1 d G U . . .
H16 H 1.1494 -0.0968 0.986 0.029 Uiso 1 1 calc R U . . .
C17 C 1.0717(11) 0.0136(11) 0.9227(5) 0.021(4) Uani 1 1 d G U . . .
H17 H 1.1167 0.0046 0.8801 0.026 Uiso 1 1 calc R U . . .
C18 C 0.9866(13) 0.0870(12) 0.9223(5) 0.018(4) Uani 1 1 d G U . . .
H18 H 0.9733 0.1282 0.8793 0.021 Uiso 1 1 calc R U . . .
N1 N 0.1046(14) -0.3747(14) 0.8655(6) 0.017(3) Uani 1 1 d D . . . .
C19 C 0.2169(16) -0.2484(16) 0.8363(8) 0.019(4) Uani 1 1 d D U . . .
H19 H 0.2202 -0.2381 0.786 0.022 Uiso 1 1 calc R U . . .
C20 C 0.0861(18) -0.3968(17) 0.9412(6) 0.022(4) Uani 1 1 d D U . . .
H20A H 0.1748 -0.3141 0.9653 0.033 Uiso 1 1 calc R U . . .
H20B H 0.0775 -0.4949 0.9536 0.033 Uiso 1 1 calc R U . . .
H20C H -0.0066 -0.3966 0.9561 0.033 Uiso 1 1 calc R U . . .
C21 C -0.0088(15) -0.4971(15) 0.8209(6) 0.033(3) Uani 1 1 d D U . . .
H21A H 0.0222 -0.4753 0.771 0.05 Uiso 1 1 calc R U . . .
H21B H -0.1083 -0.504 0.8272 0.05 Uiso 1 1 calc R U . . .
H21C H -0.0165 -0.5942 0.8345 0.05 Uiso 1 1 calc R U . . .
N2 N 0.5830(15) -0.3470(15) 0.7770(7) 0.024(4) Uani 1 1 d D . . . .
C22 C 0.5975(16) -0.2168(15) 0.7990(8) 0.016(4) Uani 1 1 d D U . . .
H22 H 0.6722 -0.1622 0.8344 0.019 Uiso 1 1 calc R U . . .
C23 C 0.6878(15) -0.3984(17) 0.7996(8) 0.031(4) Uani 1 1 d D U . . .
H23A H 0.7604 -0.3261 0.8342 0.047 Uiso 1 1 calc R U . . .
H23B H 0.7437 -0.4042 0.7583 0.047 Uiso 1 1 calc R U . . .
H23C H 0.6299 -0.4996 0.8215 0.047 Uiso 1 1 calc R U . . .
C24 C 0.4613(17) -0.4454(16) 0.7294(8) 0.029(4) Uani 1 1 d D U . . .
H24A H 0.3832 -0.4152 0.7289 0.044 Uiso 1 1 calc R U . . .
H24B H 0.4158 -0.5514 0.7456 0.044 Uiso 1 1 calc R U . . .
H24C H 0.5025 -0.4365 0.6814 0.044 Uiso 1 1 calc R U . . .
O1 O 0.6739(14) 0.0432(15) 0.8875(6) 0.014(3) Uani 1 1 d . . . . .
O2 O 0.5276(17) 0.1861(16) 0.8872(6) 0.014(3) Uani 1 1 d . U . . .
O3 O 0.8195(15) 0.4835(16) 1.0848(6) 0.015(3) Uani 1 1 d . . . . .
O4 O 0.9628(14) 0.3339(15) 1.0853(5) 0.012(3) Uani 1 1 d . U . . .
O5 O 0.3170(14) -0.1440(14) 0.8723(6) 0.018(3) Uani 1 1 d . . . . .
O6 O 0.5206(15) -0.1595(13) 0.7770(5) 0.016(3) Uani 1 1 d . . . . .
Fe1 Fe 0.5164(4) 0.02763(15) 0.82068(15) 0.0133(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.31(2) . ?
C1 C12 1.41(2) . ?
C1 C2 1.48(2) . ?
C2 O2 1.29(2) . ?
C2 C3 1.39(3) . ?
C3 C10 1.42(3) . ?
C3 C4 1.493(11) . ?
C4 C5 1.39 . ?
C4 C9 1.39 . ?
C5 C6 1.39 . ?
C5 H5 0.95 . ?
C6 C7 1.39 . ?
C6 H6 0.95 . ?
C7 C8 1.39 . ?
C7 H7 0.95 . ?
C8 C9 1.39 . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C10 O3 1.32(2) . ?
C10 C11 1.42(2) . ?
C11 O4 1.30(2) . ?
C11 C12 1.40(2) . ?
C12 C13 1.489(10) . ?
C13 C14 1.39 . ?
C13 C18 1.39 . ?
C14 C15 1.39 . ?
C14 H14 0.95 . ?
C15 C16 1.39 . ?
C15 H15 0.95 . ?
C16 C17 1.39 . ?
C16 H16 0.95 . ?
C17 C18 1.39 . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
N1 C19 1.332(13) . ?
N1 C20 1.441(14) . ?
N1 C21 1.461(15) . ?
C19 O5 1.237(17) . ?
C19 H19 0.95 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
N2 C22 1.317(14) . ?
N2 C24 1.444(15) . ?
N2 C23 1.458(15) . ?
C22 O6 1.251(17) . ?
C22 H22 0.95 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
O1 Fe1 1.973(12) . ?
O2 Fe1 1.992(12) . ?
O3 Fe1 2.002(12) 2_655 ?
O4 Fe1 1.997(12) 2_655 ?
O5 Fe1 2.127(12) . ?
O6 Fe1 2.083(11) . ?
Fe1 O4 1.997(12) 3_664 ?
Fe1 O3 2.002(12) 3_664 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C12 124.8(16) . . ?
O1 C1 C2 113.7(16) . . ?
C12 C1 C2 121.5(17) . . ?
O2 C2 C3 125.0(17) . . ?
O2 C2 C1 114.0(18) . . ?
C3 C2 C1 120.9(17) . . ?
C2 C3 C10 116.3(9) . . ?
C2 C3 C4 121.1(16) . . ?
C10 C3 C4 122.4(16) . . ?
C5 C4 C9 120 . . ?
C5 C4 C3 119.1(12) . . ?
C9 C4 C3 120.7(12) . . ?
C4 C5 C6 120 . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C7 C6 C5 120 . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C6 C7 C8 120 . . ?
C6 C7 H7 120 . . ?
C8 C7 H7 120 . . ?
C9 C8 C7 120 . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C8 C9 C4 120 . . ?
C8 C9 H9 120 . . ?
C4 C9 H9 120 . . ?
O3 C10 C3 122.9(16) . . ?
O3 C10 C11 114.6(18) . . ?
C3 C10 C11 122.5(17) . . ?
O4 C11 C12 120.0(16) . . ?
O4 C11 C10 117.2(18) . . ?
C12 C11 C10 122.8(18) . . ?
C11 C12 C1 115.8(9) . . ?
C11 C12 C13 124.3(17) . . ?
C1 C12 C13 119.8(16) . . ?
C14 C13 C18 120 . . ?
C14 C13 C12 118.3(12) . . ?
C18 C13 C12 121.7(12) . . ?
C15 C14 C13 120 . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C16 C15 C14 120 . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
C15 C16 C17 120 . . ?
C15 C16 H16 120 . . ?
C17 C16 H16 120 . . ?
C18 C17 C16 120 . . ?
C18 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
C17 C18 C13 120 . . ?
C17 C18 H18 120 . . ?
C13 C18 H18 120 . . ?
C19 N1 C20 122.7(12) . . ?
C19 N1 C21 120.4(11) . . ?
C20 N1 C21 116.8(10) . . ?
O5 C19 N1 122.2(14) . . ?
O5 C19 H19 118.9 . . ?
N1 C19 H19 118.9 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 N2 C24 121.0(13) . . ?
C22 N2 C23 121.8(13) . . ?
C24 N2 C23 117.1(12) . . ?
O6 C22 N2 125.1(15) . . ?
O6 C22 H22 117.4 . . ?
N2 C22 H22 117.4 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 O1 Fe1 116.2(11) . . ?
C2 O2 Fe1 116.4(13) . . ?
C10 O3 Fe1 114.1(12) . 2_655 ?
C11 O4 Fe1 113.7(12) . 2_655 ?
C19 O5 Fe1 118.9(9) . . ?
C22 O6 Fe1 126.1(10) . . ?
O1 Fe1 O2 79.4(5) . . ?
O1 Fe1 O4 173.6(4) . 3_664 ?
O2 Fe1 O4 96.7(5) . 3_664 ?
O1 Fe1 O3 95.3(5) . 3_664 ?
O2 Fe1 O3 93.9(3) . 3_664 ?
O4 Fe1 O3 79.8(5) 3_664 3_664 ?
O1 Fe1 O6 86.7(5) . . ?
O2 Fe1 O6 163.8(4) . . ?
O4 Fe1 O6 97.9(5) 3_664 . ?
O3 Fe1 O6 95.7(5) 3_664 . ?
O1 Fe1 O5 99.9(5) . . ?
O2 Fe1 O5 91.1(5) . . ?
O4 Fe1 O5 85.1(5) 3_664 . ?
O3 Fe1 O5 164.6(5) 3_664 . ?
O6 Fe1 O5 83.1(4) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2215981'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_date             2022-01-18T15:25:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H28 Fe N2 O6'
_chemical_formula_sum            'C26 H28 Fe N2 O6'
_chemical_formula_weight         520.35

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P -3'
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_Int_Tables_number      147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   18.2429(14)
_cell_length_b                   18.2429(14)
_cell_length_c                   7.8233(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2254.8(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9776
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      21.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       shard
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.15
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2012/1 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.715
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.958

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.052056
_diffrn_orient_matrix_ub_12      -0.002742
_diffrn_orient_matrix_ub_13      0.028047
_diffrn_orient_matrix_ub_21      -0.029774
_diffrn_orient_matrix_ub_22      -0.06117
_diffrn_orient_matrix_ub_23      -0.032792
_diffrn_orient_matrix_ub_31      0.020249
_diffrn_orient_matrix_ub_32      0.016032
_diffrn_orient_matrix_ub_33      -0.12032
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.05
_diffrn_reflns_number            3780
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.289
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             3780
_reflns_number_gt                2352
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.7117P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.51168(14) -0.03418(14) 0.6517(3) 0.0379(5) Uani 1 1 d . . . . .
C2 C 0.48828(14) 0.03427(14) 0.6521(3) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.47730(15) 0.06710(14) 0.5000(3) 0.0373(5) Uani 1 1 d . . . . .
C4 C 0.4551(3) 0.1360(2) 0.4931(5) 0.0467(6) Uani 0.498(5) 1 d G . P A 1
C5 C 0.5108(2) 0.2148(2) 0.4237(6) 0.0640(18) Uani 0.498(5) 1 d G . P A 1
H5 H 0.5619 0.2246 0.3746 0.077 Uiso 0.498(5) 1 calc R U P A 1
C6 C 0.4908(3) 0.2790(2) 0.4269(7) 0.092(3) Uani 0.498(5) 1 d G . P A 1
H6 H 0.5285 0.3322 0.3799 0.111 Uiso 0.498(5) 1 calc R U P A 1
C7 C 0.4152(4) 0.2645(3) 0.4995(7) 0.0956(13) Uani 0.498(5) 1 d G . P A 1
H7 H 0.4017 0.3079 0.5016 0.115 Uiso 0.498(5) 1 calc R U P A 1
C8 C 0.3594(3) 0.1857(3) 0.5689(7) 0.093(3) Uani 0.498(5) 1 d G . P A 1
H8 H 0.3083 0.1759 0.618 0.111 Uiso 0.498(5) 1 calc R U P A 1
C9 C 0.3794(3) 0.1215(3) 0.5657(6) 0.0701(19) Uani 0.498(5) 1 d G . P A 1
H9 H 0.3417 0.0682 0.6127 0.084 Uiso 0.498(5) 1 calc R U P A 1
C4B C 0.4549(3) 0.1355(2) 0.5075(5) 0.0467(6) Uani 0.502(5) 1 d G . P A 2
C5B C 0.5107(2) 0.2142(2) 0.5771(6) 0.0674(19) Uani 0.502(5) 1 d G . P A 2
H5B H 0.5618 0.224 0.6263 0.081 Uiso 0.502(5) 1 calc R U P A 2
C6B C 0.4908(3) 0.2785(2) 0.5737(7) 0.094(3) Uani 0.502(5) 1 d G . P A 2
H6B H 0.5285 0.3318 0.6208 0.112 Uiso 0.502(5) 1 calc R U P A 2
C7B C 0.4153(4) 0.2641(3) 0.5009(7) 0.0956(13) Uani 0.502(5) 1 d G . P A 2
H7B H 0.4019 0.3076 0.4986 0.115 Uiso 0.502(5) 1 calc R U P A 2
C8B C 0.3595(3) 0.1854(3) 0.4313(7) 0.094(3) Uani 0.502(5) 1 d G . P A 2
H8B H 0.3084 0.1757 0.382 0.112 Uiso 0.502(5) 1 calc R U P A 2
C9B C 0.3794(3) 0.1211(3) 0.4347(6) 0.0712(19) Uani 0.502(5) 1 d G . P A 2
H9B H 0.3417 0.0679 0.3876 0.085 Uiso 0.502(5) 1 calc R U P A 2
O1 O 0.47933(12) 0.05848(11) 0.79965(19) 0.0539(5) Uani 1 1 d . . . . .
O2 O 0.52061(13) -0.05852(11) 0.7997(2) 0.0543(5) Uani 1 1 d . . . . .
Fe1 Fe 0.5 0 1 0.04256(17) Uani 1 2 d S . P . .
C10 C 0.2629(8) -0.2688(7) 1.0568(15) 0.079(3) Uani 0.308(2) 1 d G . P B 1
H10A H 0.2108 -0.3229 1.0592 0.118 Uiso 0.308(2) 1 calc R U P B 1
H10B H 0.3015 -0.2709 0.9743 0.118 Uiso 0.308(2) 1 calc R U P B 1
H10C H 0.2887 -0.2564 1.1692 0.118 Uiso 0.308(2) 1 calc R U P B 1
C11 C 0.1540(7) -0.2319(9) 0.9750(19) 0.076(2) Uani 0.308(2) 1 d G . P B 1
H11A H 0.1225 -0.2926 0.9927 0.114 Uiso 0.308(2) 1 calc R U P B 1
H11B H 0.1336 -0.2048 1.0533 0.114 Uiso 0.308(2) 1 calc R U P B 1
H11C H 0.1462 -0.2192 0.8583 0.114 Uiso 0.308(2) 1 calc R U P B 1
N1 N 0.2436(7) -0.2003(6) 1.0063(10) 0.0661(13) Uani 0.308(2) 1 d G . P B 1
C12 C 0.3050(8) -0.1220(6) 0.9950(11) 0.0653(12) Uani 0.308(2) 1 d G . P B 1
C13 C 0.2779(13) -0.0569(8) 0.942(2) 0.107(6) Uani 0.308(2) 1 d G . P B 1
H13A H 0.2171 -0.0859 0.9252 0.16 Uiso 0.308(2) 1 calc R U P B 1
H13B H 0.2935 -0.0148 1.0313 0.16 Uiso 0.308(2) 1 calc R U P B 1
H13C H 0.3061 -0.0294 0.8365 0.16 Uiso 0.308(2) 1 calc R U P B 1
O3 O 0.3807(7) -0.1041(8) 1.0266(15) 0.051(2) Uani 0.308(2) 1 d G . P B 1
C10B C 0.2397(17) -0.0659(13) 0.913(4) 0.174(14) Uani 0.192(2) 1 d G . P B 2
H10D H 0.1837 -0.0764 0.8832 0.261 Uiso 0.192(2) 1 calc R U P B 2
H10E H 0.2626 -0.0247 1.0049 0.261 Uiso 0.192(2) 1 calc R U P B 2
H10F H 0.2765 -0.0441 0.814 0.261 Uiso 0.192(2) 1 calc R U P B 2
C11B C 0.1462(12) -0.2155(14) 0.962(3) 0.076(2) Uani 0.192(2) 1 d G . P B 2
H11D H 0.1118 -0.1923 0.9216 0.114 Uiso 0.192(2) 1 calc R U P B 2
H11E H 0.1411 -0.259 0.8838 0.114 Uiso 0.192(2) 1 calc R U P B 2
H11F H 0.127 -0.2399 1.0748 0.114 Uiso 0.192(2) 1 calc R U P B 2
N1B N 0.2342(12) -0.1486(10) 0.971(2) 0.069(4) Uani 0.192(2) 1 d G . P B 2
C12B C 0.3054(12) -0.1435(10) 1.016(2) 0.0653(12) Uani 0.192(2) 1 d G . P B 2
C13B C 0.3050(16) -0.2238(13) 1.076(3) 0.138(9) Uani 0.192(2) 1 d G . P B 2
H13D H 0.2476 -0.2714 1.0726 0.206 Uiso 0.192(2) 1 calc R U P B 2
H13E H 0.3407 -0.2351 1.001 0.206 Uiso 0.192(2) 1 calc R U P B 2
H13F H 0.3265 -0.2158 1.1918 0.206 Uiso 0.192(2) 1 calc R U P B 2
O3B O 0.3712(12) -0.0699(12) 1.005(4) 0.090(3) Uani 0.192(2) 1 d G . P B 2
C10C C 0.2629(8) -0.2678(7) 0.9418(14) 0.079(3) Uani 0.308(2) 1 d G . P B 3
H10G H 0.2107 -0.3218 0.9388 0.118 Uiso 0.308(2) 1 calc R U P B 3
H10H H 0.2889 -0.2552 0.8294 0.118 Uiso 0.308(2) 1 calc R U P B 3
H10I H 0.3014 -0.2703 1.0239 0.118 Uiso 0.308(2) 1 calc R U P B 3
C11C C 0.1542(7) -0.2331(10) 1.0237(19) 0.076(2) Uani 0.308(2) 1 d G . P B 3
H11G H 0.1242 -0.2937 1.0043 0.114 Uiso 0.308(2) 1 calc R U P B 3
H11H H 0.1455 -0.2217 1.1408 0.114 Uiso 0.308(2) 1 calc R U P B 3
H11I H 0.133 -0.2065 0.9463 0.114 Uiso 0.308(2) 1 calc R U P B 3
N1C N 0.2440(7) -0.1993(6) 0.9935(10) 0.0661(13) Uani 0.308(2) 1 d G . P B 3
C12C C 0.3055(8) -0.1211(6) 1.0057(11) 0.0653(12) Uani 0.308(2) 1 d G . P B 3
C13C C 0.2794(13) -0.0556(8) 1.0598(19) 0.107(6) Uani 0.308(2) 1 d G . P B 3
H13G H 0.2186 -0.0841 1.077 0.16 Uiso 0.308(2) 1 calc R U P B 3
H13H H 0.3079 -0.0284 1.1654 0.16 Uiso 0.308(2) 1 calc R U P B 3
H13I H 0.2953 -0.0132 0.9709 0.16 Uiso 0.308(2) 1 calc R U P B 3
O3C O 0.3806(7) -0.1055(8) 0.9727(15) 0.051(2) Uani 0.308(2) 1 d G . P B 3
C10D C 0.2323(17) -0.0709(13) 1.082(4) 0.174(14) Uani 0.192(2) 1 d G . P B 4
H10J H 0.1747 -0.0854 1.1096 0.261 Uiso 0.192(2) 1 calc R U P B 4
H10K H 0.2678 -0.0473 1.1824 0.261 Uiso 0.192(2) 1 calc R U P B 4
H10L H 0.2536 -0.0295 0.9906 0.261 Uiso 0.192(2) 1 calc R U P B 4
C11D C 0.1472(12) -0.2212(13) 1.032(3) 0.076(2) Uani 0.192(2) 1 d G . P B 4
H11J H 0.1097 -0.2012 1.0707 0.114 Uiso 0.192(2) 1 calc R U P B 4
H11K H 0.13 -0.2459 0.9193 0.114 Uiso 0.192(2) 1 calc R U P B 4
H11L H 0.1443 -0.2635 1.1112 0.114 Uiso 0.192(2) 1 calc R U P B 4
N1D N 0.2336(12) -0.1504(10) 1.025(2) 0.069(4) Uani 0.192(2) 1 d G . P B 4
C12D C 0.3065(12) -0.1418(10) 0.984(2) 0.0653(12) Uani 0.192(2) 1 d G . P B 4
C13D C 0.3096(16) -0.2209(13) 0.926(3) 0.138(9) Uani 0.192(2) 1 d G . P B 4
H13J H 0.253 -0.2697 0.9289 0.206 Uiso 0.192(2) 1 calc R U P B 4
H13K H 0.3316 -0.2126 0.8105 0.206 Uiso 0.192(2) 1 calc R U P B 4
H13L H 0.3461 -0.2302 1.0023 0.206 Uiso 0.192(2) 1 calc R U P B 4
O3D O 0.3709(12) -0.0674(11) 0.994(4) 0.090(3) Uani 0.192(2) 1 d G . P B 4



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O2 1.279(3) . ?
C1 C3 1.390(3) 4_656 ?
C1 C2 1.508(3) . ?
C2 O1 1.275(3) . ?
C2 C3 1.391(3) . ?
C3 C1 1.390(3) 4_656 ?
C3 C4B 1.495(3) . ?
C3 C4 1.502(3) . ?
C4 C5 1.39 . ?
C4 C9 1.39 . ?
C5 C6 1.39 . ?
C5 H5 0.94 . ?
C6 C7 1.39 . ?
C6 H6 0.94 . ?
C7 C8 1.39 . ?
C7 H7 0.94 . ?
C8 C9 1.39 . ?
C8 H8 0.94 . ?
C9 H9 0.94 . ?
C4B C5B 1.39 . ?
C4B C9B 1.39 . ?
C5B C6B 1.39 . ?
C5B H5B 0.94 . ?
C6B C7B 1.39 . ?
C6B H6B 0.94 . ?
C7B C8B 1.39 . ?
C7B H7B 0.94 . ?
C8B C9B 1.39 . ?
C8B H8B 0.94 . ?
C9B H9B 0.94 . ?
O1 Fe1 2.0345(16) . ?
O2 Fe1 2.0340(16) . ?
Fe1 O2 2.0340(16) 4_657 ?
Fe1 O1 2.0345(16) 4_657 ?
Fe1 O3B 2.038(19) 4_657 ?
Fe1 O3B 2.038(19) . ?
Fe1 O3D 2.04(2) 4_657 ?
Fe1 O3D 2.04(2) . ?
Fe1 O3 2.063(10) 4_657 ?
Fe1 O3 2.063(10) . ?
Fe1 O3C 2.074(10) 4_657 ?
Fe1 O3C 2.074(10) . ?
C10 N1 1.5089 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C10 H10C 0.97 . ?
C11 N1 1.4569 . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C11 H11C 0.97 . ?
N1 C12 1.3045 . ?
C12 O3 1.2739 . ?
C12 C13 1.5545 . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C13 H13C 0.97 . ?
C10B N1B 1.5299 . ?
C10B H10D 0.97 . ?
C10B H10E 0.97 . ?
C10B H10F 0.97 . ?
C11B N1B 1.4533 . ?
C11B H11D 0.97 . ?
C11B H11E 0.97 . ?
C11B H11F 0.97 . ?
N1B C12B 1.3028 . ?
C12B O3B 1.2801 . ?
C12B C13B 1.5361 . ?
C13B H13D 0.97 . ?
C13B H13E 0.97 . ?
C13B H13F 0.97 . ?
C10C N1C 1.5085 . ?
C10C H10G 0.97 . ?
C10C H10H 0.97 . ?
C10C H10I 0.97 . ?
C11C N1C 1.452 . ?
C11C H11G 0.97 . ?
C11C H11H 0.97 . ?
C11C H11I 0.97 . ?
N1C C12C 1.3039 . ?
C12C O3C 1.2798 . ?
C12C C13C 1.5513 . ?
C13C H13G 0.97 . ?
C13C H13H 0.97 . ?
C13C H13I 0.97 . ?
C10D N1D 1.5288 . ?
C10D H10J 0.97 . ?
C10D H10K 0.97 . ?
C10D H10L 0.97 . ?
C11D N1D 1.4557 . ?
C11D H11J 0.97 . ?
C11D H11K 0.97 . ?
C11D H11L 0.97 . ?
N1D C12D 1.3006 . ?
C12D O3D 1.2781 . ?
C12D C13D 1.5389 . ?
C13D H13J 0.97 . ?
C13D H13K 0.97 . ?
C13D H13L 0.97 . ?

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
O2 C1 C3 123.5(2) . 4_656 ?
O2 C1 C2 115.05(18) . . ?
C3 C1 C2 121.43(18) 4_656 . ?
O1 C2 C3 123.7(2) . . ?
O1 C2 C1 115.26(18) . . ?
C3 C2 C1 121.07(18) . . ?
C1 C3 C2 117.5(2) 4_656 . ?
C1 C3 C4B 123.6(2) 4_656 . ?
C2 C3 C4B 118.9(2) . . ?
C1 C3 C4 119.3(2) 4_656 . ?
C2 C3 C4 123.2(2) . . ?
C5 C4 C9 120 . . ?
C5 C4 C3 121.0(3) . . ?
C9 C4 C3 118.9(3) . . ?
C6 C5 C4 120 . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C7 120 . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
C8 C7 C6 120 . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
C7 C8 C9 120 . . ?
C7 C8 H8 120 . . ?
C9 C8 H8 120 . . ?
C8 C9 C4 120 . . ?
C8 C9 H9 120 . . ?
C4 C9 H9 120 . . ?
C5B C4B C9B 120 . . ?
C5B C4B C3 120.9(3) . . ?
C9B C4B C3 119.0(3) . . ?
C4B C5B C6B 120 . . ?
C4B C5B H5B 120 . . ?
C6B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B H6B 120 . . ?
C7B C6B H6B 120 . . ?
C8B C7B C6B 120 . . ?
C8B C7B H7B 120 . . ?
C6B C7B H7B 120 . . ?
C9B C8B C7B 120 . . ?
C9B C8B H8B 120 . . ?
C7B C8B H8B 120 . . ?
C8B C9B C4B 120 . . ?
C8B C9B H9B 120 . . ?
C4B C9B H9B 120 . . ?
C2 O1 Fe1 115.24(14) . . ?
C1 O2 Fe1 115.21(14) . . ?
O2 Fe1 O2 180.00(11) . 4_657 ?
O2 Fe1 O1 79.23(7) . . ?
O2 Fe1 O1 100.77(7) 4_657 . ?
O2 Fe1 O1 100.77(7) . 4_657 ?
O2 Fe1 O1 79.23(7) 4_657 4_657 ?
O1 Fe1 O1 180 . 4_657 ?
O2 Fe1 O3B 82(2) . 4_657 ?
O2 Fe1 O3B 98(2) 4_657 4_657 ?
O1 Fe1 O3B 96.6(19) . 4_657 ?
O1 Fe1 O3B 83.4(19) 4_657 4_657 ?
O2 Fe1 O3B 98.3(8) . . ?
O2 Fe1 O3B 81.7(8) 4_657 . ?
O1 Fe1 O3B 83.4(8) . . ?
O1 Fe1 O3B 96.6(8) 4_657 . ?
O3B Fe1 O3B 180.0(16) 4_657 . ?
O2 Fe1 O3D 82.8(19) . 4_657 ?
O2 Fe1 O3D 97.2(19) 4_657 4_657 ?
O1 Fe1 O3D 99(2) . 4_657 ?
O1 Fe1 O3D 81(2) 4_657 4_657 ?
O2 Fe1 O3D 97.2(7) . . ?
O2 Fe1 O3D 82.8(7) 4_657 . ?
O1 Fe1 O3D 80.6(8) . . ?
O1 Fe1 O3D 99.4(8) 4_657 . ?
O3D Fe1 O3D 180.0(17) 4_657 . ?
O2 Fe1 O3 91.1(11) . 4_657 ?
O2 Fe1 O3 88.9(11) 4_657 4_657 ?
O1 Fe1 O3 80.0(10) . 4_657 ?
O1 Fe1 O3 100.0(10) 4_657 4_657 ?
O2 Fe1 O3 88.9(4) . . ?
O2 Fe1 O3 91.1(4) 4_657 . ?
O1 Fe1 O3 100.0(4) . . ?
O1 Fe1 O3 80.0(4) 4_657 . ?
O3 Fe1 O3 180.0(9) 4_657 . ?
O2 Fe1 O3C 100.5(10) . 4_657 ?
O2 Fe1 O3C 79.5(10) 4_657 4_657 ?
O1 Fe1 O3C 88.7(11) . 4_657 ?
O1 Fe1 O3C 91.3(11) 4_657 4_657 ?
O2 Fe1 O3C 79.5(4) . . ?
O2 Fe1 O3C 100.5(4) 4_657 . ?
O1 Fe1 O3C 91.3(4) . . ?
O1 Fe1 O3C 88.7(4) 4_657 . ?
O3C Fe1 O3C 180.0(9) 4_657 . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N1 C11 126.9 . . ?
C12 N1 C10 119.8 . . ?
C11 N1 C10 113.4 . . ?
O3 C12 N1 119.6 . . ?
O3 C12 C13 125 . . ?
N1 C12 C13 115.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 O3 Fe1 136.5(7) . . ?
N1B C10B H10D 109.5 . . ?
N1B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N1B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N1B C11B H11D 109.5 . . ?
N1B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N1B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C12B N1B C11B 135.8 . . ?
C12B N1B C10B 115.9 . . ?
C11B N1B C10B 108.3 . . ?
O3B C12B N1B 115.8 . . ?
O3B C12B C13B 125.2 . . ?
N1B C12B C13B 119 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C12B O3B Fe1 147.1(11) . . ?
N1C C10C H10G 109.5 . . ?
N1C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
N1C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
N1C C11C H11G 109.5 . . ?
N1C C11C H11H 109.5 . . ?
H11G C11C H11H 109.5 . . ?
N1C C11C H11I 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C12C N1C C11C 128.6 . . ?
C12C N1C C10C 119.8 . . ?
C11C N1C C10C 111.6 . . ?
O3C C12C N1C 118 . . ?
O3C C12C C13C 126.2 . . ?
N1C C12C C13C 115.8 . . ?
C12C C13C H13G 109.5 . . ?
C12C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
C12C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C12C O3C Fe1 134.2(7) . . ?
N1D C10D H10J 109.5 . . ?
N1D C10D H10K 109.5 . . ?
H10J C10D H10K 109.5 . . ?
N1D C10D H10L 109.5 . . ?
H10J C10D H10L 109.5 . . ?
H10K C10D H10L 109.5 . . ?
N1D C11D H11J 109.5 . . ?
N1D C11D H11K 109.5 . . ?
H11J C11D H11K 109.5 . . ?
N1D C11D H11L 109.5 . . ?
H11J C11D H11L 109.5 . . ?
H11K C11D H11L 109.5 . . ?
C12D N1D C11D 134.9 . . ?
C12D N1D C10D 117.3 . . ?
C11D N1D C10D 107.9 . . ?
O3D C12D N1D 117 . . ?
O3D C12D C13D 124.7 . . ?
N1D C12D C13D 118.3 . . ?
C12D C13D H13J 109.5 . . ?
C12D C13D H13K 109.5 . . ?
H13J C13D H13K 109.5 . . ?
C12D C13D H13L 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?
C12D O3D Fe1 144.3(11) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_AAK-4161-3_250K
_database_code_depnum_ccdc_archive 'CCDC 2215984'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_date             2022-07-12T12:37:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H28 Fe N2 O6'
_chemical_formula_sum            'C26 H28 Fe N2 O6'
_chemical_formula_weight         520.35

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9614(8)
_cell_length_b                   12.0601(12)
_cell_length_c                   13.2291(13)
_cell_angle_alpha                90.645(4)
_cell_angle_beta                 93.670(3)
_cell_angle_gamma                90.906(4)
_cell_volume                     1267.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    4005
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.03
_cell_measurement_wavelength     0.7288

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       piece
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_T_max  0.745
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.96

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'ALS-U Lawrence Berkeley National Laboratory'
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CCD
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'ALS-U Beamline 12.2.1'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_number            5177
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.582
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_full        25.93
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             5177
_reflns_number_gt                4479
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.40A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2014/7
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5177
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0037 0.0017 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.007 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0123 0.0065 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3621 0.8896 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.3429(2) -0.03232(14) -0.05096(12) 0.0297(3) Uani 1 1 d . . . . .
C2 C 0.3541(2) 0.03266(14) 0.04947(12) 0.0306(3) Uani 1 1 d . . . . .
C3 C 0.5108(2) 0.06097(14) 0.09754(12) 0.0307(3) Uani 1 1 d . . . . .
C4 C 0.5210(2) 0.12022(15) 0.19744(12) 0.0338(4) Uani 1 1 d . . . . .
C5 C 0.6056(3) 0.07455(18) 0.28127(15) 0.0478(5) Uani 1 1 d . . . . .
H5 H 0.6597 0.0063 0.2749 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6112(3) 0.1284(2) 0.37446(16) 0.0624(6) Uani 1 1 d . . . . .
H6 H 0.6684 0.0965 0.431 0.075 Uiso 1 1 calc R U . . .
C7 C 0.5331(3) 0.2289(2) 0.38442(17) 0.0627(6) Uani 1 1 d . . . . .
H7 H 0.5375 0.2656 0.4476 0.075 Uiso 1 1 calc R U . . .
C8 C 0.4495(3) 0.27501(19) 0.30244(18) 0.0575(6) Uani 1 1 d . . . . .
H8 H 0.3958 0.3433 0.3093 0.069 Uiso 1 1 calc R U . . .
C9 C 0.4434(3) 0.22128(17) 0.20903(16) 0.0451(4) Uani 1 1 d . . . . .
H9 H 0.386 0.2538 0.1529 0.054 Uiso 1 1 calc R U . . .
C10 C 0.0494(3) 0.2502(2) -0.26673(17) 0.0628(6) Uani 1 1 d . . . . .
H10A H 0.0937 0.3057 -0.3109 0.094 Uiso 1 1 calc R U . . .
H10B H -0.0528 0.2173 -0.2988 0.094 Uiso 1 1 calc R U . . .
H10C H 0.1322 0.193 -0.2543 0.094 Uiso 1 1 calc R U . . .
C11 C -0.0146(4) 0.42189(19) -0.1729(2) 0.0681(7) Uani 1 1 d . . . . .
H11A H -0.1173 0.4386 -0.1406 0.102 Uiso 1 1 calc R U . . .
H11B H -0.0239 0.4467 -0.2425 0.102 Uiso 1 1 calc R U . . .
H11C H 0.0798 0.4597 -0.1367 0.102 Uiso 1 1 calc R U . . .
C12 C -0.0037(3) 0.24028(18) -0.09140(15) 0.0505(5) Uani 1 1 d . . . . .
C13 C -0.0319(5) 0.2948(2) 0.00900(19) 0.0813(9) Uani 1 1 d . . . . .
H13A H -0.037 0.2385 0.0606 0.122 Uiso 1 1 calc R U . . .
H13B H -0.137 0.3345 0.0039 0.122 Uiso 1 1 calc R U . . .
H13C H 0.0602 0.3463 0.0271 0.122 Uiso 1 1 calc R U . . .
C14 C 0.3447(2) 0.53004(14) 0.44843(12) 0.0298(3) Uani 1 1 d . . . . .
C15 C 0.3536(2) 0.47970(13) 0.55466(12) 0.0294(3) Uani 1 1 d . . . . .
C16 C 0.5080(2) 0.44714(14) 0.60104(12) 0.0301(3) Uani 1 1 d . . . . .
C17 C 0.5145(2) 0.39153(16) 0.70084(13) 0.0368(4) Uani 1 1 d . . . . .
C18 C 0.5832(3) 0.28668(18) 0.71089(17) 0.0524(5) Uani 1 1 d . . . . .
H18 H 0.6291 0.2527 0.6548 0.063 Uiso 1 1 calc R U . . .
C19 C 0.5852(3) 0.2313(2) 0.8024(2) 0.0713(7) Uani 1 1 d . . . . .
H19 H 0.6311 0.1601 0.8079 0.086 Uiso 1 1 calc R U . . .
C20 C 0.5198(3) 0.2809(3) 0.88494(19) 0.0783(8) Uani 1 1 d . . . . .
H20 H 0.521 0.2437 0.947 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4530(3) 0.3844(3) 0.87665(17) 0.0723(7) Uani 1 1 d . . . . .
H21 H 0.4087 0.4181 0.9333 0.087 Uiso 1 1 calc R U . . .
C22 C 0.4499(3) 0.4403(2) 0.78499(14) 0.0517(5) Uani 1 1 d . . . . .
H22 H 0.4037 0.5115 0.7802 0.062 Uiso 1 1 calc R U . . .
C23 C 0.1578(4) 0.1335(2) 0.49291(19) 0.0750(7) Uani 1 1 d . . . . .
H23A H 0.1829 0.1998 0.5336 0.112 Uiso 1 1 calc R U . . .
H23B H 0.2613 0.0945 0.483 0.112 Uiso 1 1 calc R U . . .
H23C H 0.0815 0.0856 0.5273 0.112 Uiso 1 1 calc R U . . .
C24 C 0.0846(3) 0.0825(2) 0.31299(19) 0.0679(7) Uani 1 1 d . . . . .
H24A H -0.0162 0.0882 0.2683 0.102 Uiso 1 1 calc R U . . .
H24B H 0.0904 0.0086 0.341 0.102 Uiso 1 1 calc R U . . .
H24C H 0.1829 0.0966 0.2751 0.102 Uiso 1 1 calc R U . . .
C25 C 0.0182(3) 0.26510(18) 0.38478(15) 0.0470(5) Uani 1 1 d . . . . .
C26 C -0.0524(3) 0.3011(2) 0.28288(18) 0.0662(6) Uani 1 1 d . . . . .
H26A H -0.1211 0.3659 0.2908 0.099 Uiso 1 1 calc R U . . .
H26B H -0.1208 0.2414 0.2513 0.099 Uiso 1 1 calc R U . . .
H26C H 0.0392 0.3191 0.2406 0.099 Uiso 1 1 calc R U . . .
N1 N 0.0123(2) 0.30202(15) -0.17136(13) 0.0530(4) Uani 1 1 d . . . . .
N2 N 0.0798(2) 0.16422(15) 0.39535(13) 0.0520(4) Uani 1 1 d . . . . .
O1 O 0.19553(14) -0.05989(11) -0.08434(9) 0.0374(3) Uani 1 1 d . . . . .
O2 O 0.21505(14) 0.05725(11) 0.08410(9) 0.0398(3) Uani 1 1 d . . . . .
O3 O 0.0065(2) 0.13766(12) -0.09823(11) 0.0602(4) Uani 1 1 d . . . . .
O4 O 0.19828(15) 0.54705(11) 0.41034(9) 0.0399(3) Uani 1 1 d . . . . .
O5 O 0.21379(15) 0.47020(11) 0.59462(9) 0.0377(3) Uani 1 1 d . . . . .
O6 O 0.0199(2) 0.32903(13) 0.45888(12) 0.0583(4) Uani 1 1 d . . . . .
Fe1 Fe 0 0 0 0.03054(10) Uani 1 2 d S . P . .
Fe2 Fe 0 0.5 0.5 0.03339(10) Uani 1 2 d S . P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.265(2) . ?
C1 C3 1.398(2) 2_655 ?
C1 C2 1.532(2) . ?
C2 O2 1.263(2) . ?
C2 C3 1.399(2) . ?
C3 C1 1.398(2) 2_655 ?
C3 C4 1.492(2) . ?
C4 C5 1.384(3) . ?
C4 C9 1.387(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.94 . ?
C6 C7 1.380(4) . ?
C6 H6 0.94 . ?
C7 C8 1.364(4) . ?
C7 H7 0.94 . ?
C8 C9 1.387(3) . ?
C8 H8 0.94 . ?
C9 H9 0.94 . ?
C10 N1 1.451(3) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C10 H10C 0.97 . ?
C11 N1 1.465(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C11 H11C 0.97 . ?
C12 O3 1.244(3) . ?
C12 N1 1.312(3) . ?
C12 C13 1.506(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C13 H13C 0.97 . ?
C14 O4 1.261(2) . ?
C14 C16 1.404(2) 2_666 ?
C14 C15 1.535(2) . ?
C15 O5 1.266(2) . ?
C15 C16 1.402(2) . ?
C16 C14 1.404(2) 2_666 ?
C16 C17 1.486(2) . ?
C17 C22 1.385(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.389(3) . ?
C18 H18 0.94 . ?
C19 C20 1.374(4) . ?
C19 H19 0.94 . ?
C20 C21 1.367(4) . ?
C20 H20 0.94 . ?
C21 C22 1.393(3) . ?
C21 H21 0.94 . ?
C22 H22 0.94 . ?
C23 N2 1.451(3) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C23 H23C 0.97 . ?
C24 N2 1.464(3) . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?
C24 H24C 0.97 . ?
C25 O6 1.240(2) . ?
C25 N2 1.325(3) . ?
C25 C26 1.498(3) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C26 H26C 0.97 . ?
O1 Fe1 2.1046(12) . ?
O2 Fe1 2.0850(12) . ?
O3 Fe1 2.1218(14) . ?
O4 Fe2 2.1089(12) . ?
O5 Fe2 2.0856(12) . ?
O6 Fe2 2.1374(15) . ?
Fe1 O2 2.0850(12) 2 ?
Fe1 O1 2.1046(12) 2 ?
Fe1 O3 2.1218(14) 2 ?
Fe2 O5 2.0856(12) 2_566 ?
Fe2 O4 2.1089(12) 2_566 ?
Fe2 O6 2.1375(15) 2_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C3 124.31(15) . 2_655 ?
O1 C1 C2 115.24(14) . . ?
C3 C1 C2 120.41(14) 2_655 . ?
O2 C2 C3 123.83(15) . . ?
O2 C2 C1 115.67(14) . . ?
C3 C2 C1 120.50(14) . . ?
C1 C3 C2 119.06(15) 2_655 . ?
C1 C3 C4 120.68(15) 2_655 . ?
C2 C3 C4 120.26(15) . . ?
C5 C4 C9 118.39(17) . . ?
C5 C4 C3 120.76(16) . . ?
C9 C4 C3 120.84(16) . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C8 C7 C6 119.95(19) . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.8(2) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N1 120.2(2) . . ?
O3 C12 C13 120.3(2) . . ?
N1 C12 C13 119.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C16 123.90(16) . 2_666 ?
O4 C14 C15 115.27(14) . . ?
C16 C14 C15 120.83(14) 2_666 . ?
O5 C15 C16 124.21(15) . . ?
O5 C15 C14 115.16(14) . . ?
C16 C15 C14 120.63(14) . . ?
C15 C16 C14 118.34(15) . 2_666 ?
C15 C16 C17 120.41(15) . . ?
C14 C16 C17 121.24(15) 2_666 . ?
C22 C17 C18 118.29(17) . . ?
C22 C17 C16 121.72(17) . . ?
C18 C17 C16 119.97(17) . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120 . . ?
C19 C20 H20 120 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.3(2) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 N2 119.9(2) . . ?
O6 C25 C26 120.6(2) . . ?
N2 C25 C26 119.5(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C12 N1 C10 119.52(18) . . ?
C12 N1 C11 124.0(2) . . ?
C10 N1 C11 116.41(19) . . ?
C25 N2 C23 118.73(19) . . ?
C25 N2 C24 124.37(19) . . ?
C23 N2 C24 116.8(2) . . ?
C1 O1 Fe1 115.50(10) . . ?
C2 O2 Fe1 116.03(11) . . ?
C12 O3 Fe1 137.42(14) . . ?
C14 O4 Fe2 115.68(10) . . ?
C15 O5 Fe2 116.03(10) . . ?
C25 O6 Fe2 142.58(15) . . ?
O2 Fe1 O2 180 . 2 ?
O2 Fe1 O1 77.40(4) . . ?
O2 Fe1 O1 102.59(4) 2 . ?
O2 Fe1 O1 102.60(4) . 2 ?
O2 Fe1 O1 77.40(4) 2 2 ?
O1 Fe1 O1 180 . 2 ?
O2 Fe1 O3 88.33(6) . 2 ?
O2 Fe1 O3 91.67(6) 2 2 ?
O1 Fe1 O3 95.58(6) . 2 ?
O1 Fe1 O3 84.42(6) 2 2 ?
O2 Fe1 O3 91.67(6) . . ?
O2 Fe1 O3 88.33(6) 2 . ?
O1 Fe1 O3 84.42(6) . . ?
O1 Fe1 O3 95.58(6) 2 . ?
O3 Fe1 O3 180 2 . ?
O5 Fe2 O5 180 . 2_566 ?
O5 Fe2 O4 77.10(4) . . ?
O5 Fe2 O4 102.90(4) 2_566 . ?
O5 Fe2 O4 102.90(4) . 2_566 ?
O5 Fe2 O4 77.10(4) 2_566 2_566 ?
O4 Fe2 O4 180 . 2_566 ?
O5 Fe2 O6 84.08(6) . . ?
O5 Fe2 O6 95.92(6) 2_566 . ?
O4 Fe2 O6 92.31(6) . . ?
O4 Fe2 O6 87.69(6) 2_566 . ?
O5 Fe2 O6 95.92(6) . 2_566 ?
O5 Fe2 O6 84.08(6) 2_566 2_566 ?
O4 Fe2 O6 87.69(6) . 2_566 ?
O4 Fe2 O6 92.31(6) 2_566 2_566 ?
O6 Fe2 O6 180 . 2_566 ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
####################################################################### 
# 
# 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_AAK_4113_3
_database_code_depnum_ccdc_archive 'CCDC 2215982'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_date             2022-10-03T15:50:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H28 Fe N2 O6'
_chemical_formula_sum            'C26 H28 Fe N2 O6'
_chemical_formula_weight         520.35

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P -3'
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_Int_Tables_number      147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   18.0920(10)
_cell_length_b                   18.0920(10)
_cell_length_c                   7.8010(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2211.3(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6687
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      19.68
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2012/1 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.745
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.957

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.005458
_diffrn_orient_matrix_ub_12      -0.05318
_diffrn_orient_matrix_ub_13      -0.051208
_diffrn_orient_matrix_ub_21      -0.060302
_diffrn_orient_matrix_ub_22      -0.01901
_diffrn_orient_matrix_ub_23      -0.033111
_diffrn_orient_matrix_ub_31      0.020186
_diffrn_orient_matrix_ub_32      0.029733
_diffrn_orient_matrix_ub_33      -0.112758
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.045
_diffrn_reflns_number            17482
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.3
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             3030
_reflns_number_gt                2297
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+2.6193P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.51152(16) -0.03442(16) 0.6529(3) 0.0225(5) Uani 1 1 d . . . . .
C2 C 0.48864(16) 0.03483(16) 0.6528(3) 0.0222(5) Uani 1 1 d . . . . .
C3 C 0.47764(16) 0.06830(16) 0.5001(3) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.4553(3) 0.1375(2) 0.4976(6) 0.0287(6) Uani 0.499(4) 1 d G . P A 1
C5 C 0.5102(2) 0.2161(2) 0.4234(5) 0.0406(17) Uani 0.499(4) 1 d G . P A 1
H5 H 0.5616 0.2256 0.3708 0.049 Uiso 0.499(4) 1 calc R U P A 1
C6 C 0.4899(3) 0.2807(2) 0.4261(6) 0.058(2) Uani 0.499(4) 1 d G . P A 1
H6 H 0.5275 0.3344 0.3754 0.069 Uiso 0.499(4) 1 calc R U P A 1
C7 C 0.4147(4) 0.2668(3) 0.5031(7) 0.0614(12) Uani 0.499(4) 1 d G . P A 1
H7 H 0.4009 0.3109 0.5049 0.074 Uiso 0.499(4) 1 calc R U P A 1
C8 C 0.3598(3) 0.1881(3) 0.5773(6) 0.061(2) Uani 0.499(4) 1 d G . P A 1
H8 H 0.3084 0.1786 0.6299 0.073 Uiso 0.499(4) 1 calc R U P A 1
C9 C 0.3801(3) 0.1235(2) 0.5746(6) 0.0420(17) Uani 0.499(4) 1 d G . P A 1
H9 H 0.3425 0.0698 0.6253 0.05 Uiso 0.499(4) 1 calc R U P A 1
C4B C 0.4552(3) 0.1375(2) 0.5022(6) 0.0287(6) Uani 0.501(4) 1 d G . P A 2
C5B C 0.5100(2) 0.2161(2) 0.5765(5) 0.0401(17) Uani 0.501(4) 1 d G . P A 2
H5B H 0.5615 0.2257 0.629 0.048 Uiso 0.501(4) 1 calc R U P A 2
C6B C 0.4896(3) 0.2807(2) 0.5741(6) 0.058(2) Uani 0.501(4) 1 d G . P A 2
H6B H 0.5272 0.3344 0.6249 0.069 Uiso 0.501(4) 1 calc R U P A 2
C7B C 0.4144(4) 0.2667(3) 0.4973(7) 0.0614(12) Uani 0.501(4) 1 d G . P A 2
H7B H 0.4004 0.3108 0.4956 0.074 Uiso 0.501(4) 1 calc R U P A 2
C8B C 0.3595(3) 0.1881(3) 0.4230(6) 0.059(2) Uani 0.501(4) 1 d G . P A 2
H8B H 0.3081 0.1785 0.3705 0.071 Uiso 0.501(4) 1 calc R U P A 2
C9B C 0.3799(3) 0.1235(2) 0.4254(6) 0.0415(17) Uani 0.501(4) 1 d G . P A 2
H9B H 0.3424 0.0698 0.3746 0.05 Uiso 0.501(4) 1 calc R U P A 2
O1 O 0.48001(14) 0.05958(13) 0.8017(2) 0.0361(5) Uani 1 1 d . . . . .
O2 O 0.52008(14) -0.05952(13) 0.8018(2) 0.0360(5) Uani 1 1 d . . . . .
Fe1 Fe 0.5 0 1 0.02667(17) Uani 1 2 d S . P . .
C10 C 0.2604(6) -0.2685(5) 1.0597(12) 0.043(2) Uani 0.315(3) 1 d G . P B 1
H10A H 0.207 -0.3232 1.0684 0.065 Uiso 0.315(3) 1 calc R U P B 1
H10B H 0.2984 -0.2736 0.9771 0.065 Uiso 0.315(3) 1 calc R U P B 1
H10C H 0.2882 -0.2529 1.1722 0.065 Uiso 0.315(3) 1 calc R U P B 1
C11 C 0.1516(4) -0.2324(5) 0.973(2) 0.045(3) Uani 0.315(3) 1 d G . P B 1
H11A H 0.1192 -0.2936 0.9978 0.067 Uiso 0.315(3) 1 calc R U P B 1
H11B H 0.1323 -0.2021 1.0481 0.067 Uiso 0.315(3) 1 calc R U P B 1
H11C H 0.1424 -0.2228 0.8528 0.067 Uiso 0.315(3) 1 calc R U P B 1
N1 N 0.2414(4) -0.2009(4) 1.0008(9) 0.0398(12) Uani 0.315(3) 1 d G . P B 1
C12 C 0.3032(4) -0.1234(4) 0.9806(11) 0.0423(12) Uani 0.315(3) 1 d G . P B 1
C13 C 0.2764(6) -0.0591(4) 0.9195(16) 0.055(2) Uani 0.315(3) 1 d G . P B 1
H13A H 0.2143 -0.0885 0.9054 0.082 Uiso 0.315(3) 1 calc R U P B 1
H13B H 0.2939 -0.0136 1.0047 0.082 Uiso 0.315(3) 1 calc R U P B 1
H13C H 0.3039 -0.0344 0.8096 0.082 Uiso 0.315(3) 1 calc R U P B 1
O3 O 0.3790(4) -0.1055(6) 1.011(2) 0.0405(15) Uani 0.315(3) 1 d G . P B 1
C10B C 0.2306(11) -0.0706(10) 0.900(3) 0.092(7) Uani 0.185(3) 1 d G . P B 2
H10D H 0.1716 -0.0841 0.8806 0.139 Uiso 0.185(3) 1 calc R U P B 2
H10E H 0.2577 -0.0242 0.9838 0.139 Uiso 0.185(3) 1 calc R U P B 2
H10F H 0.2623 -0.0527 0.7916 0.139 Uiso 0.185(3) 1 calc R U P B 2
C11B C 0.1440(9) -0.2176(11) 0.980(3) 0.045(3) Uani 0.185(3) 1 d G . P B 2
H11D H 0.1054 -0.1973 0.9429 0.067 Uiso 0.185(3) 1 calc R U P B 2
H11E H 0.1359 -0.2651 0.9073 0.067 Uiso 0.185(3) 1 calc R U P B 2
H11F H 0.1313 -0.2369 1.0996 0.067 Uiso 0.185(3) 1 calc R U P B 2
N1B N 0.2311(9) -0.1490(8) 0.9675(18) 0.044(4) Uani 0.185(3) 1 d G . P B 2
C12B C 0.3053(9) -0.1400(9) 0.9987(14) 0.0423(12) Uani 0.185(3) 1 d G . P B 2
C13B C 0.3110(14) -0.2159(12) 1.067(3) 0.078(6) Uani 0.185(3) 1 d G . P B 2
H13D H 0.2534 -0.2652 1.0788 0.117 Uiso 0.185(3) 1 calc R U P B 2
H13E H 0.344 -0.2299 0.9868 0.117 Uiso 0.185(3) 1 calc R U P B 2
H13F H 0.3392 -0.2015 1.179 0.117 Uiso 0.185(3) 1 calc R U P B 2
O3B O 0.3686(9) -0.0664(10) 0.969(2) 0.033(4) Uani 0.185(3) 1 d G . P B 2
C10C C 0.2602(6) -0.2679(5) 0.9395(12) 0.043(2) Uani 0.315(3) 1 d G . P B 3
H10G H 0.207 -0.3227 0.93 0.065 Uiso 0.315(3) 1 calc R U P B 3
H10H H 0.2882 -0.2518 0.8272 0.065 Uiso 0.315(3) 1 calc R U P B 3
H10I H 0.2982 -0.2731 1.0221 0.065 Uiso 0.315(3) 1 calc R U P B 3
C11C C 0.1507(4) -0.2351(5) 1.026(2) 0.045(3) Uani 0.315(3) 1 d G . P B 3
H11G H 0.1202 -0.2962 0.9986 0.067 Uiso 0.315(3) 1 calc R U P B 3
H11H H 0.1403 -0.2269 1.1454 0.067 Uiso 0.315(3) 1 calc R U P B 3
H11I H 0.1303 -0.2056 0.9506 0.067 Uiso 0.315(3) 1 calc R U P B 3
N1C N 0.2408(4) -0.2008(4) 0.9992(9) 0.0398(12) Uani 0.315(3) 1 d G . P B 3
C12C C 0.3023(4) -0.1232(4) 1.0205(11) 0.0423(12) Uani 0.315(3) 1 d G . P B 3
C13C C 0.2757(6) -0.0591(5) 1.0823(16) 0.055(2) Uani 0.315(3) 1 d G . P B 3
H13G H 0.2136 -0.0884 1.0964 0.082 Uiso 0.315(3) 1 calc R U P B 3
H13H H 0.3033 -0.0346 1.1923 0.082 Uiso 0.315(3) 1 calc R U P B 3
H13I H 0.2933 -0.0133 0.9975 0.082 Uiso 0.315(3) 1 calc R U P B 3
O3C O 0.3778(4) -0.1069(6) 0.989(2) 0.0405(15) Uani 0.315(3) 1 d G . P B 3
C10D C 0.2271(12) -0.0736(10) 1.098(3) 0.092(7) Uani 0.185(3) 1 d G . P B 4
H10J H 0.1674 -0.0897 1.1175 0.139 Uiso 0.185(3) 1 calc R U P B 4
H10K H 0.2587 -0.054 1.2063 0.139 Uiso 0.185(3) 1 calc R U P B 4
H10L H 0.2524 -0.0276 1.0134 0.139 Uiso 0.185(3) 1 calc R U P B 4
C11D C 0.1453(9) -0.2213(10) 1.022(3) 0.045(3) Uani 0.185(3) 1 d G . P B 4
H11J H 0.1052 -0.2028 1.0584 0.067 Uiso 0.185(3) 1 calc R U P B 4
H11K H 0.1329 -0.2415 0.9029 0.067 Uiso 0.185(3) 1 calc R U P B 4
H11L H 0.1393 -0.2676 1.096 0.067 Uiso 0.185(3) 1 calc R U P B 4
N1D N 0.2315(9) -0.1503(8) 1.0328(17) 0.044(4) Uani 0.185(3) 1 d G . P B 4
C12D C 0.3061(9) -0.1397(9) 1.0010(14) 0.0423(12) Uani 0.185(3) 1 d G . P B 4
C13D C 0.3123(14) -0.2159(12) 0.935(3) 0.078(6) Uani 0.185(3) 1 d G . P B 4
H13J H 0.2548 -0.2658 0.9256 0.117 Uiso 0.185(3) 1 calc R U P B 4
H13K H 0.3397 -0.2024 0.8221 0.117 Uiso 0.185(3) 1 calc R U P B 4
H13L H 0.3462 -0.2286 1.0151 0.117 Uiso 0.185(3) 1 calc R U P B 4
O3D O 0.3695(9) -0.0659(10) 1.027(2) 0.033(4) Uani 0.185(3) 1 d G . P B 4



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O2 1.285(3) . ?
C1 C3 1.399(4) 4_656 ?
C1 C2 1.503(4) . ?
C2 O1 1.282(3) . ?
C2 C3 1.395(3) . ?
C3 C1 1.399(4) 4_656 ?
C3 C4 1.495(4) . ?
C3 C4B 1.498(4) . ?
C4 C5 1.39 . ?
C4 C9 1.39 . ?
C5 C6 1.39 . ?
C5 H5 0.95 . ?
C6 C7 1.39 . ?
C6 H6 0.95 . ?
C7 C8 1.39 . ?
C7 H7 0.95 . ?
C8 C9 1.39 . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C4B C5B 1.39 . ?
C4B C9B 1.39 . ?
C5B C6B 1.39 . ?
C5B H5B 0.95 . ?
C6B C7B 1.39 . ?
C6B H6B 0.95 . ?
C7B C8B 1.39 . ?
C7B H7B 0.95 . ?
C8B C9B 1.39 . ?
C8B H8B 0.95 . ?
C9B H9B 0.95 . ?
O1 Fe1 2.0189(18) . ?
O2 Fe1 2.0179(18) . ?
Fe1 O2 2.0179(18) 4_657 ?
Fe1 O1 2.0189(18) 4_657 ?
Fe1 O3D 2.056(14) 4_657 ?
Fe1 O3D 2.056(14) . ?
Fe1 O3 2.065(7) 4_657 ?
Fe1 O3 2.065(7) . ?
Fe1 O3B 2.073(14) . ?
Fe1 O3B 2.073(14) 4_657 ?
Fe1 O3C 2.088(7) 4_657 ?
Fe1 O3C 2.088(7) . ?
C10 N1 1.4972 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 N1 1.445 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
N1 C12 1.2938 . ?
C12 O3 1.2636 . ?
C12 C13 1.5424 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C10B N1B 1.5182 . ?
C10B H10D 0.98 . ?
C10B H10E 0.98 . ?
C10B H10F 0.98 . ?
C11B N1B 1.4413 . ?
C11B H11D 0.98 . ?
C11B H11E 0.98 . ?
C11B H11F 0.98 . ?
N1B C12B 1.2922 . ?
C12B O3B 1.2697 . ?
C12B C13B 1.5244 . ?
C13B H13D 0.98 . ?
C13B H13E 0.98 . ?
C13B H13F 0.98 . ?
C10C N1C 1.4968 . ?
C10C H10G 0.98 . ?
C10C H10H 0.98 . ?
C10C H10I 0.98 . ?
C11C N1C 1.4401 . ?
C11C H11G 0.98 . ?
C11C H11H 0.98 . ?
C11C H11I 0.98 . ?
N1C C12C 1.2933 . ?
C12C O3C 1.2695 . ?
C12C C13C 1.5392 . ?
C13C H13G 0.98 . ?
C13C H13H 0.98 . ?
C13C H13I 0.98 . ?
C10D N1D 1.5171 . ?
C10D H10J 0.98 . ?
C10D H10K 0.98 . ?
C10D H10L 0.98 . ?
C11D N1D 1.4437 . ?
C11D H11J 0.98 . ?
C11D H11K 0.98 . ?
C11D H11L 0.98 . ?
N1D C12D 1.2901 . ?
C12D O3D 1.2677 . ?
C12D C13D 1.527 . ?
C13D H13J 0.98 . ?
C13D H13K 0.98 . ?
C13D H13L 0.98 . ?

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
O2 C1 C3 123.3(2) . 4_656 ?
O2 C1 C2 115.3(2) . . ?
C3 C1 C2 121.5(2) 4_656 . ?
O1 C2 C3 123.6(2) . . ?
O1 C2 C1 115.0(2) . . ?
C3 C2 C1 121.4(2) . . ?
C2 C3 C1 117.2(2) . 4_656 ?
C2 C3 C4 122.1(3) . . ?
C1 C3 C4 120.8(3) 4_656 . ?
C2 C3 C4B 120.7(3) . . ?
C1 C3 C4B 122.1(3) 4_656 . ?
C5 C4 C9 120 . . ?
C5 C4 C3 120.5(3) . . ?
C9 C4 C3 119.5(3) . . ?
C6 C5 C4 120 . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C7 C6 C5 120 . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C6 C7 C8 120 . . ?
C6 C7 H7 120 . . ?
C8 C7 H7 120 . . ?
C7 C8 C9 120 . . ?
C7 C8 H8 120 . . ?
C9 C8 H8 120 . . ?
C8 C9 C4 120 . . ?
C8 C9 H9 120 . . ?
C4 C9 H9 120 . . ?
C5B C4B C9B 120 . . ?
C5B C4B C3 120.4(3) . . ?
C9B C4B C3 119.6(3) . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B H6B 120 . . ?
C7B C6B H6B 120 . . ?
C8B C7B C6B 120 . . ?
C8B C7B H7B 120 . . ?
C6B C7B H7B 120 . . ?
C7B C8B C9B 120 . . ?
C7B C8B H8B 120 . . ?
C9B C8B H8B 120 . . ?
C8B C9B C4B 120 . . ?
C8B C9B H9B 120 . . ?
C4B C9B H9B 120 . . ?
C2 O1 Fe1 114.96(16) . . ?
C1 O2 Fe1 114.75(17) . . ?
O2 Fe1 O2 180 4_657 . ?
O2 Fe1 O1 79.98(7) 4_657 4_657 ?
O2 Fe1 O1 100.02(7) . 4_657 ?
O2 Fe1 O1 100.02(7) 4_657 . ?
O2 Fe1 O1 79.98(7) . . ?
O1 Fe1 O1 180 4_657 . ?
O2 Fe1 O3D 103.3(13) 4_657 4_657 ?
O2 Fe1 O3D 76.7(13) . 4_657 ?
O1 Fe1 O3D 85.8(14) 4_657 4_657 ?
O1 Fe1 O3D 94.2(14) . 4_657 ?
O2 Fe1 O3D 76.7(5) 4_657 . ?
O2 Fe1 O3D 103.3(5) . . ?
O1 Fe1 O3D 94.2(5) 4_657 . ?
O1 Fe1 O3D 85.8(5) . . ?
O3D Fe1 O3D 180.0(14) 4_657 . ?
O2 Fe1 O3 85.9(12) 4_657 4_657 ?
O2 Fe1 O3 94.1(12) . 4_657 ?
O1 Fe1 O3 97.7(10) 4_657 4_657 ?
O1 Fe1 O3 82.3(10) . 4_657 ?
O2 Fe1 O3 94.1(4) 4_657 . ?
O2 Fe1 O3 85.9(4) . . ?
O1 Fe1 O3 82.3(4) 4_657 . ?
O1 Fe1 O3 97.7(4) . . ?
O3 Fe1 O3 180.0(11) 4_657 . ?
O2 Fe1 O3B 86.5(5) 4_657 . ?
O2 Fe1 O3B 93.5(5) . . ?
O1 Fe1 O3B 103.9(4) 4_657 . ?
O1 Fe1 O3B 76.1(4) . . ?
O2 Fe1 O3B 93.5(14) 4_657 4_657 ?
O2 Fe1 O3B 86.5(14) . 4_657 ?
O1 Fe1 O3B 76.1(13) 4_657 4_657 ?
O1 Fe1 O3B 103.9(13) . 4_657 ?
O3B Fe1 O3B 180.0(13) . 4_657 ?
O2 Fe1 O3C 82.2(10) 4_657 4_657 ?
O2 Fe1 O3C 97.8(10) . 4_657 ?
O1 Fe1 O3C 94.3(12) 4_657 4_657 ?
O1 Fe1 O3C 85.7(12) . 4_657 ?
O2 Fe1 O3C 97.8(4) 4_657 . ?
O2 Fe1 O3C 82.2(4) . . ?
O1 Fe1 O3C 85.7(4) 4_657 . ?
O1 Fe1 O3C 94.3(4) . . ?
O3C Fe1 O3C 180.0(11) 4_657 . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N1 C11 126.9 . . ?
C12 N1 C10 119.8 . . ?
C11 N1 C10 113.4 . . ?
O3 C12 N1 119.6 . . ?
O3 C12 C13 125.1 . . ?
N1 C12 C13 115.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 O3 Fe1 138.0(5) . . ?
N1B C10B H10D 109.5 . . ?
N1B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N1B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N1B C11B H11D 109.5 . . ?
N1B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N1B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C12B N1B C11B 135.7 . . ?
C12B N1B C10B 115.9 . . ?
C11B N1B C10B 108.3 . . ?
O3B C12B N1B 115.8 . . ?
O3B C12B C13B 125.2 . . ?
N1B C12B C13B 119 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C12B O3B Fe1 139.3(8) . . ?
N1C C10C H10G 109.5 . . ?
N1C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
N1C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
N1C C11C H11G 109.5 . . ?
N1C C11C H11H 109.5 . . ?
H11G C11C H11H 109.5 . . ?
N1C C11C H11I 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C12C N1C C11C 128.5 . . ?
C12C N1C C10C 119.8 . . ?
C11C N1C C10C 111.6 . . ?
O3C C12C N1C 117.9 . . ?
O3C C12C C13C 126.2 . . ?
N1C C12C C13C 115.8 . . ?
C12C C13C H13G 109.5 . . ?
C12C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
C12C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C12C O3C Fe1 136.5(5) . . ?
N1D C10D H10J 109.5 . . ?
N1D C10D H10K 109.5 . . ?
H10J C10D H10K 109.5 . . ?
N1D C10D H10L 109.5 . . ?
H10J C10D H10L 109.5 . . ?
H10K C10D H10L 109.5 . . ?
N1D C11D H11J 109.5 . . ?
N1D C11D H11K 109.5 . . ?
H11J C11D H11K 109.5 . . ?
N1D C11D H11L 109.5 . . ?
H11J C11D H11L 109.5 . . ?
H11K C11D H11L 109.5 . . ?
C12D N1D C11D 134.8 . . ?
C12D N1D C10D 117.3 . . ?
C11D N1D C10D 107.9 . . ?
O3D C12D N1D 117 . . ?
O3D C12D C13D 124.7 . . ?
N1D C12D C13D 118.3 . . ?
C12D C13D H13J 109.5 . . ?
C12D C13D H13K 109.5 . . ?
H13J C13D H13K 109.5 . . ?
C12D C13D H13L 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?
C12D O3D Fe1 140.0(9) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_aak_4165_2_250
_database_code_depnum_ccdc_archive 'CCDC 2215983'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_date             2022-05-25T11:48:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H24 Fe N2 O6'
_chemical_formula_sum            'C24 H24 Fe N2 O6'
_chemical_formula_weight         492.3
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_Int_Tables_number      144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   10.248(2)
_cell_length_b                   10.248(2)
_cell_length_c                   19.033(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1731.0(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    819
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      17.41
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       cube
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2012/1 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.664
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.014023
_diffrn_orient_matrix_ub_12      0.093285
_diffrn_orient_matrix_ub_13      0.023666
_diffrn_orient_matrix_ub_21      -0.073197
_diffrn_orient_matrix_ub_22      0.00397
_diffrn_orient_matrix_ub_23      -0.033444
_diffrn_orient_matrix_ub_31      -0.084511
_diffrn_orient_matrix_ub_32      -0.063078
_diffrn_orient_matrix_ub_33      0.032893
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1345
_diffrn_reflns_av_unetI/netI     0.2031
_diffrn_reflns_number            4290
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.07
_diffrn_reflns_theta_max         25.416
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         1
_reflns_number_total             4260
_reflns_number_gt                2167
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2014/7
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²+0.9342P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4260
_refine_ls_number_parameters     279
_refine_ls_number_restraints     163
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.095

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.725(3) 0.152(3) 0.9392(12) 0.025(7) Uani 1 1 d . U . . .
C2 C 0.631(3) 0.231(3) 0.9344(13) 0.032(8) Uani 1 1 d . U . . .
C3 C 0.665(3) 0.349(3) 0.9836(15) 0.022(4) Uani 1 1 d . U . . .
C4 C 0.5865(17) 0.4392(16) 0.9801(7) 0.032(5) Uani 1 1 d G U . . .
C5 C 0.4347(17) 0.3700(10) 0.9625(8) 0.049(6) Uani 1 1 d G U . . .
H5 H 0.378 0.2647 0.9578 0.059 Uiso 1 1 calc R U . . .
C6 C 0.3669(12) 0.4567(16) 0.9517(7) 0.054(6) Uani 1 1 d G U . . .
H6 H 0.2642 0.4099 0.9398 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4508(17) 0.6125(16) 0.9586(7) 0.066(7) Uani 1 1 d G U . . .
H7 H 0.4049 0.6711 0.9513 0.079 Uiso 1 1 calc R U . . .
C8 C 0.6026(16) 0.6816(10) 0.9762(7) 0.056(6) Uani 1 1 d G U . . .
H8 H 0.6593 0.7869 0.9808 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6705(12) 0.5949(16) 0.9869(7) 0.043(6) Uani 1 1 d G U . . .
H9 H 0.7731 0.6417 0.9988 0.052 Uiso 1 1 calc R U . . .
C10 C 0.773(3) 0.377(3) 1.0345(12) 0.021(7) Uani 1 1 d . U . . .
C11 C 0.860(3) 0.296(3) 1.0374(12) 0.022(6) Uani 1 1 d . U . . .
C12 C 0.828(3) 0.176(4) 0.9892(17) 0.030(4) Uani 1 1 d . U . . .
C13 C 0.918(2) 0.099(2) 0.9863(12) 0.030(4) Uani 1 1 d G U . . .
C14 C 0.9352(18) 0.0351(19) 1.0477(9) 0.045(7) Uani 1 1 d G U . . .
H14 H 0.8905 0.042 1.0896 0.054 Uiso 1 1 calc R U . . .
C15 C 1.018(2) -0.0386(18) 1.0470(9) 0.063(8) Uani 1 1 d G U . . .
H15 H 1.0293 -0.0816 1.0886 0.075 Uiso 1 1 calc R U . . .
C16 C 1.084(2) -0.049(2) 0.9850(12) 0.059(6) Uani 1 1 d G U . . .
H16 H 1.1399 -0.0987 0.9846 0.071 Uiso 1 1 calc R U . . .
C17 C 1.0671(18) 0.0148(19) 0.9236(9) 0.061(8) Uani 1 1 d G U . . .
H17 H 1.1117 0.0079 0.8817 0.074 Uiso 1 1 calc R U . . .
C18 C 0.984(2) 0.0886(19) 0.9242(9) 0.045(7) Uani 1 1 d G U . . .
H18 H 0.973 0.1316 0.8827 0.054 Uiso 1 1 calc R U . . .
N1 N 0.103(2) -0.376(2) 0.8646(10) 0.054(6) Uani 1 1 d D . . . .
C19 C 0.214(2) -0.251(2) 0.8384(11) 0.046(6) Uani 1 1 d D U . . .
H19 H 0.2175 -0.2397 0.7893 0.055 Uiso 1 1 calc R U . . .
C20 C 0.079(3) -0.399(2) 0.9395(8) 0.051(6) Uani 1 1 d D U . . .
H20A H 0.1519 -0.3089 0.9642 0.076 Uiso 1 1 calc R U . . .
H20B H 0.0908 -0.4834 0.9536 0.076 Uiso 1 1 calc R U . . .
H20C H -0.0221 -0.4202 0.9509 0.076 Uiso 1 1 calc R U . . .
C21 C -0.008(3) -0.500(3) 0.8210(9) 0.089(6) Uani 1 1 d D U . . .
H21A H 0.0248 -0.482 0.7723 0.134 Uiso 1 1 calc R U . . .
H21B H -0.1049 -0.5063 0.8251 0.134 Uiso 1 1 calc R U . . .
H21C H -0.0156 -0.5938 0.8366 0.134 Uiso 1 1 calc R U . . .
N2 N 0.578(3) -0.352(2) 0.7765(10) 0.058(8) Uani 1 1 d D . . . .
C22 C 0.601(3) -0.220(2) 0.7982(12) 0.043(6) Uani 1 1 d D U . . .
H22 H 0.6781 -0.1661 0.831 0.051 Uiso 1 1 calc R U . . .
C23 C 0.681(2) -0.405(3) 0.7990(12) 0.074(7) Uani 1 1 d D U . . .
H23A H 0.7607 -0.328 0.8275 0.111 Uiso 1 1 calc R U . . .
H23B H 0.7239 -0.4253 0.758 0.111 Uiso 1 1 calc R U . . .
H23C H 0.6253 -0.4964 0.8264 0.111 Uiso 1 1 calc R U . . .
C24 C 0.457(3) -0.446(2) 0.7288(14) 0.079(9) Uani 1 1 d D U . . .
H24A H 0.3614 -0.473 0.7503 0.119 Uiso 1 1 calc R U . . .
H24B H 0.4613 -0.5367 0.7186 0.119 Uiso 1 1 calc R U . . .
H24C H 0.4687 -0.3913 0.6855 0.119 Uiso 1 1 calc R U . . .
O1 O 0.677(2) 0.044(2) 0.8918(8) 0.038(6) Uani 1 1 d . . . . .
O2 O 0.531(2) 0.189(2) 0.8875(9) 0.034(5) Uani 1 1 d . U . . .
O3 O 0.812(2) 0.473(2) 1.0829(8) 0.033(5) Uani 1 1 d . . . . .
O4 O 0.961(2) 0.331(2) 1.0834(7) 0.032(5) Uani 1 1 d . U . . .
O5 O 0.309(2) -0.150(2) 0.8719(9) 0.041(6) Uani 1 1 d . . . . .
O6 O 0.523(2) -0.162(2) 0.7767(8) 0.044(6) Uani 1 1 d . . . . .
Fe1 Fe 0.5114(6) 0.01973(19) 0.8208(2) 0.0309(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.31(3) . ?
C1 C12 1.35(3) . ?
C1 C2 1.53(4) . ?
C2 O2 1.26(3) . ?
C2 C3 1.43(4) . ?
C3 C10 1.38(4) . ?
C3 C4 1.499(14) . ?
C4 C5 1.39 . ?
C4 C9 1.39 . ?
C5 C6 1.39 . ?
C5 H5 0.94 . ?
C6 C7 1.39 . ?
C6 H6 0.94 . ?
C7 C8 1.39 . ?
C7 H7 0.94 . ?
C8 C9 1.39 . ?
C8 H8 0.94 . ?
C9 H9 0.94 . ?
C10 O3 1.26(3) . ?
C10 C11 1.50(3) . ?
C11 O4 1.26(3) . ?
C11 C12 1.43(4) . ?
C12 C13 1.493(15) . ?
C13 C14 1.39 . ?
C13 C18 1.39 . ?
C14 C15 1.39 . ?
C14 H14 0.94 . ?
C15 C16 1.39 . ?
C15 H15 0.94 . ?
C16 C17 1.39 . ?
C16 H16 0.94 . ?
C17 C18 1.39 . ?
C17 H17 0.94 . ?
C18 H18 0.94 . ?
N1 C19 1.311(18) . ?
N1 C20 1.45(2) . ?
N1 C21 1.47(2) . ?
C19 O5 1.19(2) . ?
C19 H19 0.94 . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C20 H20C 0.97 . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C21 H21C 0.97 . ?
N2 C22 1.319(18) . ?
N2 C24 1.45(2) . ?
N2 C23 1.47(2) . ?
C22 O6 1.28(3) . ?
C22 H22 0.94 . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C23 H23C 0.97 . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?
C24 H24C 0.97 . ?
O1 Fe1 2.087(17) . ?
O2 Fe1 2.08(2) . ?
O3 Fe1 2.125(18) 2_655 ?
O4 Fe1 2.060(18) 2_655 ?
O5 Fe1 2.157(18) . ?
O6 Fe1 2.099(18) . ?
Fe1 O4 2.060(18) 3_664 ?
Fe1 O3 2.125(18) 3_664 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C12 125(3) . . ?
O1 C1 C2 110(2) . . ?
C12 C1 C2 126(2) . . ?
O2 C2 C3 124(3) . . ?
O2 C2 C1 119(3) . . ?
C3 C2 C1 117(2) . . ?
C10 C3 C2 117.6(12) . . ?
C10 C3 C4 121(2) . . ?
C2 C3 C4 121(2) . . ?
C5 C4 C9 120 . . ?
C5 C4 C3 120.5(18) . . ?
C9 C4 C3 119.2(18) . . ?
C6 C5 C4 120 . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C7 120 . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
C8 C7 C6 120 . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
C7 C8 C9 120 . . ?
C7 C8 H8 120 . . ?
C9 C8 H8 120 . . ?
C8 C9 C4 120 . . ?
C8 C9 H9 120 . . ?
C4 C9 H9 120 . . ?
O3 C10 C3 126(2) . . ?
O3 C10 C11 111(2) . . ?
C3 C10 C11 123(2) . . ?
O4 C11 C12 120(2) . . ?
O4 C11 C10 120(2) . . ?
C12 C11 C10 120(2) . . ?
C1 C12 C11 115.9(13) . . ?
C1 C12 C13 121(3) . . ?
C11 C12 C13 123(3) . . ?
C14 C13 C18 120 . . ?
C14 C13 C12 118.2(19) . . ?
C18 C13 C12 121.8(19) . . ?
C13 C14 C15 120 . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C16 C15 C14 120 . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
C17 C16 C15 120 . . ?
C17 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C16 C17 C18 120 . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C17 C18 C13 120 . . ?
C17 C18 H18 120 . . ?
C13 C18 H18 120 . . ?
C19 N1 C20 122(2) . . ?
C19 N1 C21 123.2(19) . . ?
C20 N1 C21 114.9(15) . . ?
O5 C19 N1 125(2) . . ?
O5 C19 H19 117.4 . . ?
N1 C19 H19 117.4 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 N2 C24 122(2) . . ?
C22 N2 C23 120(2) . . ?
C24 N2 C23 118.0(17) . . ?
O6 C22 N2 123(2) . . ?
O6 C22 H22 118.4 . . ?
N2 C22 H22 118.4 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 O1 Fe1 118.9(17) . . ?
C2 O2 Fe1 115.6(19) . . ?
C10 O3 Fe1 117.8(18) . 2_655 ?
C11 O4 Fe1 114.8(17) . 2_655 ?
C19 O5 Fe1 120.0(15) . . ?
C22 O6 Fe1 127.7(15) . . ?
O4 Fe1 O2 95.5(7) 3_664 . ?
O4 Fe1 O1 169.1(4) 3_664 . ?
O2 Fe1 O1 76.8(7) . . ?
O4 Fe1 O6 100.4(7) 3_664 . ?
O2 Fe1 O6 163.9(7) . . ?
O1 Fe1 O6 87.8(8) . . ?
O4 Fe1 O3 76.2(7) 3_664 3_664 ?
O2 Fe1 O3 89.1(4) . 3_664 ?
O1 Fe1 O3 95.8(8) . 3_664 ?
O6 Fe1 O3 97.2(7) . 3_664 ?
O4 Fe1 O5 86.3(7) 3_664 . ?
O2 Fe1 O5 92.9(7) . . ?
O1 Fe1 O5 101.6(7) . . ?
O6 Fe1 O5 85.6(5) . . ?
O3 Fe1 O5 162.5(7) 3_664 . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
