# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_e3408
_database_code_depnum_ccdc_archive 'CCDC 1550164'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C14 H20 N4 O0.60),C14 H20 N4, 2(C6 Fe N6), 7(H2 O)'
_chemical_formula_sum            'C54 H74 Fe2 N24 O8'
_chemical_formula_weight         1299.07

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

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

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

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

_cell_length_a                   7.0769(8)
_cell_length_b                   12.5517(14)
_cell_length_c                   17.9244(18)
_cell_angle_alpha                82.908(5)
_cell_angle_beta                 87.892(5)
_cell_angle_gamma                84.717(5)
_cell_volume                     1572.8(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             682
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.533
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17456
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.641
_diffrn_reflns_theta_max         28.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             7323
_reflns_number_gt                5044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0922P)²+8.6579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7323
_refine_ls_number_parameters     441
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2351
_refine_ls_wR_factor_gt          0.2133
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1979(7) 0.4210(4) 0.5962(3) 0.0177(9) Uani 1 1 d . . . . .
N1 N 0.2072(6) 0.4216(3) 0.6683(2) 0.0208(9) Uani 1 1 d . . . . .
H1 H 0.3070 0.4461 0.6861 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0583(8) 0.3834(5) 0.7217(3) 0.0287(12) Uani 1 1 d . . . . .
H2A H -0.0293 0.4452 0.7340 0.034 Uiso 1 1 calc R U . . .
H2B H 0.1165 0.3479 0.7688 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0507(9) 0.3043(5) 0.6873(3) 0.0369(15) Uani 1 1 d D . . . .
H3 H -0.1685 0.2936 0.7189 0.044 Uiso 1 1 calc R U . . .
O1 O 0.035(2) 0.2147(11) 0.6841(11) 0.053(4) Uani 0.3 1 d D . P . .
H1A H 0.0844 0.1924 0.7258 0.080 Uiso 0.3 1 calc DR U P . .
C4 C -0.1105(8) 0.3499(6) 0.6103(3) 0.0358(15) Uani 1 1 d . . . . .
H4A H -0.1690 0.2947 0.5861 0.043 Uiso 1 1 calc R U . . .
H4B H -0.2061 0.4121 0.6132 0.043 Uiso 1 1 calc R U . . .
N2 N 0.0557(6) 0.3849(4) 0.5649(2) 0.0239(9) Uani 1 1 d . . . . .
H2C H 0.0594 0.3816 0.5161 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3543(6) 0.4615(4) 0.5466(3) 0.0173(9) Uani 1 1 d . . . . .
C6 C 0.4317(7) 0.4023(4) 0.4907(3) 0.0188(10) Uani 1 1 d . . . . .
H6 H 0.3847 0.3355 0.4845 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4218(7) 0.5595(4) 0.5563(3) 0.0189(10) Uani 1 1 d . . . . .
H7 H 0.3685 0.6000 0.5946 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2904(7) 0.0478(4) 0.5939(3) 0.0223(11) Uani 1 1 d . . . . .
N3 N 0.2763(6) 0.0220(3) 0.6671(2) 0.0231(9) Uani 1 1 d . . . . .
H3A H 0.1741 -0.0073 0.6860 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4232(8) 0.0399(5) 0.7186(3) 0.0304(13) Uani 1 1 d . . . . .
H9A H 0.4969 -0.0295 0.7350 0.036 Uiso 1 1 calc R U . . .
H9B H 0.3627 0.0680 0.7637 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5525(12) 0.1175(9) 0.6813(4) 0.079(4) Uani 1 1 d D . . . .
H10 H 0.6703 0.1161 0.7106 0.095 Uiso 1 1 calc R U . . .
O2 O 0.460(2) 0.2191(10) 0.6723(10) 0.046(4) Uani 0.3 1 d . . P . .
H2 H 0.4386 0.2406 0.7146 0.068 Uiso 0.3 1 calc R U P . .
C11 C 0.5962(11) 0.1142(9) 0.6058(4) 0.074(3) Uani 1 1 d D . . . .
H11A H 0.6984 0.0559 0.6006 0.089 Uiso 1 1 calc R U . . .
H11B H 0.6454 0.1832 0.5847 0.089 Uiso 1 1 calc R U . . .
N4 N 0.4341(7) 0.0957(4) 0.5622(3) 0.0380(13) Uani 1 1 d D . . . .
H4 H 0.4335 0.1173 0.5136 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1388(6) 0.0232(4) 0.5460(3) 0.0182(10) Uani 1 1 d . . . . .
C13 C 0.0736(6) -0.0790(4) 0.5559(3) 0.0187(10) Uani 1 1 d . . . . .
H13 H 0.1239 -0.1325 0.5940 0.022 Uiso 1 1 calc R U . . .
C14 C 0.0664(6) 0.1016(4) 0.4907(3) 0.0191(10) Uani 1 1 d . . . . .
H14 H 0.1126 0.1709 0.4846 0.023 Uiso 1 1 calc R U . . .
C15 C 0.1625(7) 0.6447(4) 1.0032(3) 0.0269(12) Uani 1 1 d . . . . .
N5 N 0.0298(7) 0.6243(4) 1.0556(3) 0.0394(13) Uani 1 1 d . . . . .
H5 H 0.0440 0.5642 1.0866 0.047 Uiso 1 1 calc R U . . .
C16 C -0.1394(9) 0.6981(6) 1.0639(4) 0.0440(16) Uani 1 1 d . . . . .
H16A H -0.1126 0.7529 1.0964 0.053 Uiso 1 1 calc R U . . .
H16B H -0.2440 0.6578 1.0878 0.053 Uiso 1 1 calc R U . . .
C17 C -0.1961(10) 0.7517(6) 0.9882(4) 0.0465(17) Uani 1 1 d . . . . .
H17A H -0.3020 0.8076 0.9937 0.056 Uiso 1 1 calc R U . . .
H17B H -0.2411 0.6979 0.9585 0.056 Uiso 1 1 calc R U . . .
C18 C -0.0269(9) 0.8041(5) 0.9458(4) 0.0356(14) Uani 1 1 d . . . . .
H18A H -0.0558 0.8220 0.8918 0.043 Uiso 1 1 calc R U . . .
H18B H -0.0071 0.8718 0.9663 0.043 Uiso 1 1 calc R U . . .
N6 N 0.1452(7) 0.7308(4) 0.9539(3) 0.0323(11) Uani 1 1 d . . . . .
H6A H 0.2431 0.7453 0.9239 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3354(7) 0.5694(4) 1.0007(3) 0.0261(11) Uani 1 1 d . . . . .
C20 C 0.4176(8) 0.5240(5) 1.0681(3) 0.0288(12) Uani 1 1 d . . . . .
H20 H 0.3614 0.5404 1.1147 0.035 Uiso 1 1 calc R U . . .
C21 C 0.4193(7) 0.5448(4) 0.9332(3) 0.0258(11) Uani 1 1 d . . . . .
H21 H 0.3637 0.5758 0.8872 0.031 Uiso 1 1 calc R U . . .
Fe1 Fe 0.73684(9) 0.70992(5) 0.72919(4) 0.01393(19) Uani 1 1 d . . . . .
C22 C 0.8979(7) 0.6285(4) 0.8054(3) 0.0191(10) Uani 1 1 d . . . . .
N7 N 0.9870(7) 0.5766(4) 0.8505(3) 0.0288(10) Uani 1 1 d . . . . .
C23 C 0.6030(7) 0.5805(4) 0.7322(3) 0.0191(10) Uani 1 1 d . . . . .
N8 N 0.5302(7) 0.5022(4) 0.7364(3) 0.0309(11) Uani 1 1 d . . . . .
C24 C 0.8961(6) 0.6616(4) 0.6478(3) 0.0161(9) Uani 1 1 d . . . . .
N9 N 0.9773(6) 0.6360(3) 0.5947(2) 0.0231(9) Uani 1 1 d . . . . .
C25 C 0.5863(6) 0.7870(4) 0.6480(3) 0.0168(9) Uani 1 1 d . . . . .
N10 N 0.5119(6) 0.8300(3) 0.5953(2) 0.0238(9) Uani 1 1 d . . . . .
C26 C 0.8736(7) 0.8367(4) 0.7329(3) 0.0209(10) Uani 1 1 d . . . . .
N11 N 0.9524(7) 0.9112(4) 0.7378(3) 0.0312(11) Uani 1 1 d . . . . .
C27 C 0.5606(7) 0.7636(4) 0.8046(3) 0.0214(11) Uani 1 1 d . . . . .
N12 N 0.4576(7) 0.7978(4) 0.8483(3) 0.0320(11) Uani 1 1 d . . . . .
O1W O 0.3334(7) 0.9819(4) 0.9188(3) 0.0502(12) Uani 1 1 d D . . . .
H1WA H 0.438(6) 0.964(5) 0.942(4) 0.068 Uiso 1 1 d D U . . .
H1WB H 0.257(8) 1.035(4) 0.924(4) 0.068 Uiso 1 1 d D U . . .
O2W O -0.0079(8) 0.0691(4) 0.8415(3) 0.0549(13) Uani 1 1 d D . . . .
H2WA H -0.049(10) 0.119(5) 0.811(3) 0.063 Uiso 1 1 d D U . . .
H2WB H 0.084(7) 0.025(4) 0.847(4) 0.063 Uiso 1 1 d D U . . .
O3W O 0.6518(8) 0.1052(5) 0.9244(3) 0.0651(16) Uani 1 1 d D . . . .
H3WA H 0.623(10) 0.059(5) 0.959(3) 0.076 Uiso 1 1 d D U . . .
H3WB H 0.733(10) 0.105(6) 0.889(3) 0.076 Uiso 1 1 d D U . . .
O4W O 0.4902(11) 0.2777(6) 0.8077(5) 0.0316(18) Uani 0.5 1 d D . P . .
H4WA H 0.459(18) 0.314(12) 0.841(6) 0.063 Uiso 0.5 1 d D U P . .
H4WB H 0.582(12) 0.246(12) 0.789(8) 0.063 Uiso 0.5 1 d D U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.299(6) . ?
C1 N2 1.311(6) . ?
C1 C5 1.480(6) . ?
N1 C2 1.470(6) . ?
N1 H1 0.8800 . ?
C2 C3 1.512(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.235(13) . ?
C3 C4 1.489(9) . ?
C3 H3 1.0000 . ?
O1 H1A 0.8400 . ?
C4 N2 1.474(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N2 H2C 0.8800 . ?
C5 C6 1.388(7) . ?
C5 C7 1.392(6) . ?
C6 C7 1.394(6) 2_666 ?
C6 H6 0.9500 . ?
C7 C6 1.394(6) 2_666 ?
C7 H7 0.9500 . ?
C8 N4 1.305(6) . ?
C8 N3 1.315(6) . ?
C8 C12 1.475(6) . ?
N3 C9 1.465(6) . ?
N3 H3A 0.8800 . ?
C9 C10 1.481(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2 1.373(16) . ?
C10 C11 1.381(10) . ?
C10 H10 1.0000 . ?
O2 H2 0.8400 . ?
C11 N4 1.463(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N4 H4 0.8800 . ?
C12 C14 1.385(6) . ?
C12 C13 1.391(6) . ?
C13 C14 1.390(6) 2_556 ?
C13 H13 0.9500 . ?
C14 C13 1.390(6) 2_556 ?
C14 H14 0.9500 . ?
C15 N6 1.308(7) . ?
C15 N5 1.323(7) . ?
C15 C19 1.478(8) . ?
N5 C16 1.459(8) . ?
N5 H5 0.8800 . ?
C16 C17 1.490(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.548(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N6 1.458(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N6 H6A 0.8800 . ?
C19 C21 1.384(8) . ?
C19 C20 1.394(7) . ?
C20 C21 1.378(8) 2_667 ?
C20 H20 0.9500 . ?
C21 C20 1.378(8) 2_667 ?
C21 H21 0.9500 . ?
Fe1 C24 1.933(5) . ?
Fe1 C22 1.940(5) . ?
Fe1 C25 1.941(5) . ?
Fe1 C27 1.945(6) . ?
Fe1 C26 1.946(5) . ?
Fe1 C23 1.949(5) . ?
C22 N7 1.143(6) . ?
C23 N8 1.144(6) . ?
C24 N9 1.158(7) . ?
C25 N10 1.149(6) . ?
C26 N11 1.145(6) . ?
C27 N12 1.146(7) . ?
O1W H1WA 0.866(19) . ?
O1W H1WB 0.832(19) . ?
O2W H2WA 0.827(19) . ?
O2W H2WB 0.817(19) . ?
O3W H3WA 0.832(19) . ?
O3W H3WB 0.85(2) . ?
O4W H4WA 0.81(2) . ?
O4W H4WB 0.81(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 122.7(4) . . ?
N1 C1 C5 119.2(4) . . ?
N2 C1 C5 118.2(4) . . ?
C1 N1 C2 122.9(4) . . ?
C1 N1 H1 118.5 . . ?
C2 N1 H1 118.5 . . ?
N1 C2 C3 109.6(4) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 C4 108.7(10) . . ?
O1 C3 C2 114.9(10) . . ?
C4 C3 C2 110.3(5) . . ?
O1 C3 H3 107.6 . . ?
C4 C3 H3 107.6 . . ?
C2 C3 H3 107.6 . . ?
C3 O1 H1A 109.5 . . ?
N2 C4 C3 109.8(5) . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C1 N2 C4 121.0(4) . . ?
C1 N2 H2C 119.5 . . ?
C4 N2 H2C 119.5 . . ?
C6 C5 C7 120.5(4) . . ?
C6 C5 C1 120.0(4) . . ?
C7 C5 C1 119.5(4) . . ?
C5 C6 C7 120.2(4) . 2_666 ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 2_666 . ?
C5 C7 C6 119.4(5) . 2_666 ?
C5 C7 H7 120.3 . . ?
C6 C7 H7 120.3 2_666 . ?
N4 C8 N3 121.8(4) . . ?
N4 C8 C12 118.9(4) . . ?
N3 C8 C12 119.3(4) . . ?
C8 N3 C9 123.0(4) . . ?
C8 N3 H3A 118.5 . . ?
C9 N3 H3A 118.5 . . ?
N3 C9 C10 110.6(5) . . ?
N3 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 C11 95.5(10) . . ?
O2 C10 C9 109.7(11) . . ?
C11 C10 C9 117.9(7) . . ?
O2 C10 H10 110.9 . . ?
C11 C10 H10 110.9 . . ?
C9 C10 H10 110.9 . . ?
C10 O2 H2 109.5 . . ?
C10 C11 N4 113.4(6) . . ?
C10 C11 H11A 108.9 . . ?
N4 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
N4 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C8 N4 C11 121.4(5) . . ?
C8 N4 H4 119.3 . . ?
C11 N4 H4 119.3 . . ?
C14 C12 C13 120.9(4) . . ?
C14 C12 C8 119.3(4) . . ?
C13 C12 C8 119.7(4) . . ?
C14 C13 C12 118.9(4) 2_556 . ?
C14 C13 H13 120.5 2_556 . ?
C12 C13 H13 120.5 . . ?
C12 C14 C13 120.1(4) . 2_556 ?
C12 C14 H14 119.9 . . ?
C13 C14 H14 119.9 2_556 . ?
N6 C15 N5 121.5(5) . . ?
N6 C15 C19 119.1(5) . . ?
N5 C15 C19 119.4(5) . . ?
C15 N5 C16 122.3(5) . . ?
C15 N5 H5 118.9 . . ?
C16 N5 H5 118.9 . . ?
N5 C16 C17 109.0(6) . . ?
N5 C16 H16A 109.9 . . ?
C17 C16 H16A 109.9 . . ?
N5 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C16 C17 C18 110.8(5) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N6 C18 C17 110.4(5) . . ?
N6 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N6 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C15 N6 C18 123.8(5) . . ?
C15 N6 H6A 118.1 . . ?
C18 N6 H6A 118.1 . . ?
C21 C19 C20 119.4(5) . . ?
C21 C19 C15 121.7(5) . . ?
C20 C19 C15 118.9(5) . . ?
C21 C20 C19 119.7(5) 2_667 . ?
C21 C20 H20 120.1 2_667 . ?
C19 C20 H20 120.1 . . ?
C20 C21 C19 120.9(5) 2_667 . ?
C20 C21 H21 119.6 2_667 . ?
C19 C21 H21 119.6 . . ?
C24 Fe1 C22 92.8(2) . . ?
C24 Fe1 C25 83.5(2) . . ?
C22 Fe1 C25 176.2(2) . . ?
C24 Fe1 C27 175.1(2) . . ?
C22 Fe1 C27 92.1(2) . . ?
C25 Fe1 C27 91.7(2) . . ?
C24 Fe1 C26 93.1(2) . . ?
C22 Fe1 C26 90.6(2) . . ?
C25 Fe1 C26 89.9(2) . . ?
C27 Fe1 C26 87.7(2) . . ?
C24 Fe1 C23 89.0(2) . . ?
C22 Fe1 C23 86.29(19) . . ?
C25 Fe1 C23 93.30(19) . . ?
C27 Fe1 C23 90.5(2) . . ?
C26 Fe1 C23 176.4(2) . . ?
N7 C22 Fe1 176.6(4) . . ?
N8 C23 Fe1 176.8(4) . . ?
N9 C24 Fe1 173.5(4) . . ?
N10 C25 Fe1 173.3(5) . . ?
N11 C26 Fe1 177.6(5) . . ?
N12 C27 Fe1 178.3(4) . . ?
H1WA O1W H1WB 127(4) . . ?
H2WA O2W H2WB 140(5) . . ?
H3WA O3W H3WB 133(5) . . ?
H4WA O4W H4WB 142(7) . . ?

_refine_diff_density_max         1.426
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.131

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e3305
_database_code_depnum_ccdc_archive 'CCDC 1550166'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C14 H20 N4 O1.6), C14 H20 N4 O1.8, 2(C6 Fe N6), 8(H2 O)'
_chemical_formula_sum            'C54 H76 Fe2 N24 O13'
_chemical_formula_weight         1381.08

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

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

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

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

_cell_length_a                   7.1019(3)
_cell_length_b                   22.0731(10)
_cell_length_c                   20.6168(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.0750(10)
_cell_angle_gamma                90
_cell_volume                     3229.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    22000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.529
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21745
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             5689
_reflns_number_gt                5113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+8.6705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5689
_refine_ls_number_parameters     456
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.79493(5) 0.28361(2) 0.09899(2) 0.01370(14) Uani 1 1 d . . . A 1
C1 C 0.9317(4) 0.34676(14) 0.05484(14) 0.0170(6) Uani 1 1 d . . . A 1
N1 N 0.9990(4) 0.38407(12) 0.02433(12) 0.0223(6) Uani 1 1 d . . . A 1
C2 C 0.6418(4) 0.28193(13) 0.01927(15) 0.0177(6) Uani 1 1 d . . . A 1
N2 N 0.5609(4) 0.28372(13) -0.03022(13) 0.0244(6) Uani 1 1 d . . . A 1
C3 C 0.9466(4) 0.29017(13) 0.17925(14) 0.0168(6) Uani 1 1 d . . . A 1
N3 N 1.0249(4) 0.29688(12) 0.22870(12) 0.0223(6) Uani 1 1 d . . . A 1
C4 C 0.6472(4) 0.21957(14) 0.13634(14) 0.0195(6) Uani 1 1 d . . . A 1
N4 N 0.5616(4) 0.18034(13) 0.15732(14) 0.0304(7) Uani 1 1 d D . . A 1
C5 C 0.6364(4) 0.34459(14) 0.13698(14) 0.0183(6) Uani 1 1 d . . . A 1
N5 N 0.5486(4) 0.38072(13) 0.16205(13) 0.0284(6) Uani 1 1 d . . . A 1
C6 C 0.9557(4) 0.22122(14) 0.06447(14) 0.0208(7) Uani 1 1 d . . . A 1
N6 N 1.0467(4) 0.18283(14) 0.04465(14) 0.0332(7) Uani 1 1 d . . . A 1
C7 C 0.1340(4) 0.67372(13) 0.59982(14) 0.0176(6) Uani 1 1 d . . . B 1
N7 N 0.1355(4) 0.65603(12) 0.53915(12) 0.0197(5) Uani 1 1 d . . . B 1
H7 H 0.2329 0.6654 0.5159 0.024 Uiso 1 1 calc R U . B 1
C8 C -0.0203(5) 0.62105(16) 0.50853(16) 0.0286(8) Uani 1 1 d D . . B 1
C9 C -0.1062(6) 0.58227(19) 0.55968(19) 0.0342(11) Uani 0.886(8) 1 d D . P B 1
O1 O 0.0385(5) 0.54012(16) 0.58124(19) 0.0462(9) Uani 0.8 1 d . . P . .
H1A H -0.0086 0.5137 0.6051 0.069 Uiso 0.8 1 calc R U P B 1
C9' C -0.204(3) 0.6330(14) 0.5466(8) 0.0342(11) Uani 0.114(8) 1 d D . P B 2
C10 C -0.1656(5) 0.62225(18) 0.61604(18) 0.0355(9) Uani 1 1 d D . . . .
N8 N -0.0049(4) 0.66021(13) 0.63776(13) 0.0241(6) Uani 1 1 d . . . . .
H8 H -0.0017 0.6744 0.6777 0.029 Uiso 1 1 calc R U . B 1
C11 C 0.2958(4) 0.70951(13) 0.62643(14) 0.0171(6) Uani 1 1 d . . . . .
C12 C 0.3716(4) 0.69638(14) 0.68797(14) 0.0177(6) Uani 1 1 d . . . . .
H12 H 0.3178 0.6652 0.7132 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5252(4) 0.72864(14) 0.71258(14) 0.0180(6) Uani 1 1 d . . . . .
H13 H 0.5776 0.7196 0.7545 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6024(4) 0.77437(13) 0.67562(14) 0.0169(6) Uani 1 1 d . . . . .
C15 C 0.5265(4) 0.78787(13) 0.61387(14) 0.0178(6) Uani 1 1 d . . . . .
H15 H 0.5804 0.8190 0.5887 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3725(4) 0.75564(14) 0.58954(14) 0.0178(6) Uani 1 1 d . . . . .
H16 H 0.3193 0.7649 0.5478 0.021 Uiso 1 1 calc R U . . .
C17 C 0.7696(4) 0.80829(13) 0.70123(14) 0.0169(6) Uani 1 1 d . . . . .
N9 N 0.7702(3) 0.82988(11) 0.76027(12) 0.0183(5) Uani 1 1 d . . . . .
H9 H 0.6701 0.8243 0.7835 0.022 Uiso 1 1 calc R U . . .
C18 C 0.9306(4) 0.86286(15) 0.78922(15) 0.0236(7) Uani 1 1 d . . . . .
H18A H 1.0125 0.8346 0.8147 0.028 Uiso 1 1 calc R U . C 1
H18B H 0.8853 0.8944 0.8190 0.028 Uiso 1 1 calc R U . C 1
C19 C 1.0407(5) 0.89172(16) 0.73688(17) 0.0308(8) Uani 1 1 d . . . D 1
H19 H 1.1603 0.9088 0.7563 0.037 Uiso 1 1 calc R U . D 1
O2 O 0.9371(4) 0.93865(12) 0.70464(14) 0.0267(6) Uani 0.8 1 d . . P . .
H2A H 0.9478 0.9708 0.7262 0.040 Uiso 0.8 1 calc R U P D 1
C20 C 1.0867(5) 0.84514(17) 0.68717(17) 0.0313(8) Uani 1 1 d . . . . .
H20A H 1.1485 0.8648 0.6504 0.038 Uiso 1 1 calc R U . D 1
H20B H 1.1749 0.8149 0.7065 0.038 Uiso 1 1 calc R U . D 1
N10 N 0.9136(4) 0.81508(13) 0.66393(13) 0.0242(6) Uani 1 1 d . . . . .
H10 H 0.9060 0.8012 0.6239 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3026(4) 0.99204(13) 0.41205(13) 0.0157(6) Uani 1 1 d . . . . .
N11 N 0.4519(3) 1.02625(12) 0.42303(12) 0.0207(6) Uani 1 1 d . . . . .
H11 H 0.4528 1.0523 0.4553 0.025 Uiso 1 1 calc R U . . .
C22 C 0.6164(5) 1.02184(17) 0.38271(17) 0.0292(8) Uani 1 1 d . . . . .
H22A H 0.7049 0.9912 0.4011 0.035 Uiso 1 1 calc R U . . .
H22B H 0.6825 1.0613 0.3821 0.035 Uiso 1 1 calc R U . . .
C23 C 0.5552(5) 1.00427(15) 0.31512(16) 0.0267(7) Uani 1 1 d . . . . .
H23 H 0.6702 0.9958 0.2900 0.032 Uiso 1 1 calc R U . . .
O3 O 0.4593(4) 1.05362(13) 0.28585(14) 0.0347(6) Uani 0.9 1 d . . P . .
H3A H 0.3440 1.0454 0.2815 0.052 Uiso 0.9 1 calc R U P . .
C24 C 0.4387(4) 0.94725(15) 0.31682(15) 0.0221(7) Uani 1 1 d . . . . .
H24A H 0.3828 0.9388 0.2731 0.027 Uiso 1 1 calc R U . . .
H24B H 0.5198 0.9125 0.3299 0.027 Uiso 1 1 calc R U . . .
N12 N 0.2890(3) 0.95472(11) 0.36309(11) 0.0168(5) Uani 1 1 d . . . . .
H12A H 0.1855 0.9331 0.3576 0.020 Uiso 1 1 calc R U . . .
C25 C 0.1451(4) 0.99626(13) 0.45750(13) 0.0155(6) Uani 1 1 d . . . . .
C26 C 0.0661(4) 0.94326(14) 0.48137(14) 0.0170(6) Uani 1 1 d . . . . .
H26 H 0.1118 0.9048 0.4686 0.020 Uiso 1 1 calc R U . . .
C27 C 0.0797(4) 1.05263(13) 0.47602(14) 0.0167(6) Uani 1 1 d . . . . .
H27 H 0.1348 1.0884 0.4595 0.020 Uiso 1 1 calc R U . . .
O1W O 0.4775(5) 0.45868(15) 0.27111(16) 0.0574(9) Uani 1 1 d D . . . .
H1C H 0.529(8) 0.438(3) 0.2416(19) 0.094 Uiso 1 1 d D U . . .
H1D H 0.518(7) 0.465(3) 0.3091(13) 0.094 Uiso 1 1 d D U . . .
O2W O 0.4522(6) 0.05600(13) 0.15193(14) 0.0584(9) Uani 1 1 d D . . . .
H2C H 0.449(11) 0.040(3) 0.1888(17) 0.130 Uiso 1 1 d D U . . .
H2D H 0.493(10) 0.0936(12) 0.147(3) 0.130 Uiso 1 1 d D U . . .
O3W O 0.5882(10) 0.4611(3) 0.3984(2) 0.1390(13) Uani 1 1 d D . . . .
H3D H 0.514(7) 0.489(2) 0.4002(15) 0.140 Uiso 1 1 d D U . . .
H3C H 0.699(3) 0.460(3) 0.3805(17) 0.09(2) Uiso 1 1 d D . . . .
O4W O 0.3889(10) 0.5542(2) 0.4416(5) 0.150(3) Uani 1 1 d D . . . .
H4C H 0.495(5) 0.556(3) 0.460(3) 0.199 Uiso 1 1 d D U . . .
H4D H 0.299(5) 0.578(2) 0.441(3) 0.199 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C4 1.937(3) . ?
Fe1 C2 1.938(3) . ?
Fe1 C5 1.938(3) . ?
Fe1 C6 1.941(3) . ?
Fe1 C1 1.944(3) . ?
Fe1 C3 1.947(3) . ?
C1 N1 1.151(4) . ?
C2 N2 1.153(4) . ?
C3 N3 1.153(4) . ?
C4 N4 1.151(4) . ?
C5 N5 1.147(4) . ?
C6 N6 1.149(4) . ?
C7 N7 1.311(4) . ?
C7 N8 1.315(4) . ?
C7 C11 1.483(4) . ?
N7 C8 1.472(4) . ?
N7 H7 0.8800 . ?
C8 C9 1.505(5) . ?
C8 C9' 1.571(18) . ?
C9 O1 1.444(6) . ?
C9 C10 1.531(5) . ?
O1 H1A 0.8400 . ?
C9' C10 1.468(17) . ?
C10 N8 1.473(4) . ?
N8 H8 0.8800 . ?
C11 C12 1.391(4) . ?
C11 C16 1.394(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(4) . ?
C14 C17 1.485(4) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N9 1.307(4) . ?
C17 N10 1.311(4) . ?
N9 C18 1.461(4) . ?
N9 H9 0.8800 . ?
C18 C19 1.497(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.421(4) . ?
C19 C20 1.496(5) . ?
C19 H19 1.0000 . ?
O2 H2A 0.8400 . ?
C20 N10 1.462(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N10 H10 0.8800 . ?
C21 N12 1.304(4) . ?
C21 N11 1.315(4) . ?
C21 C25 1.488(4) . ?
N11 C22 1.462(4) . ?
N11 H11 0.8800 . ?
C22 C23 1.496(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O3 1.409(4) . ?
C23 C24 1.507(5) . ?
C23 H23 1.0000 . ?
O3 H3A 0.8400 . ?
C24 N12 1.463(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N12 H12A 0.8800 . ?
C25 C27 1.387(4) . ?
C25 C26 1.395(4) . ?
C26 C27 1.385(4) 3_576 ?
C26 H26 0.9500 . ?
C27 C26 1.385(4) 3_576 ?
C27 H27 0.9500 . ?
O1W H1C 0.851(19) . ?
O1W H1D 0.838(18) . ?
O2W H2C 0.842(19) . ?
O2W H2D 0.885(15) . ?
O3W H3D 0.804(19) . ?
O3W H3C 0.881(19) . ?
O4W H4C 0.831(10) . ?
O4W H4D 0.825(10) . ?

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
C4 Fe1 C2 91.59(12) . . ?
C4 Fe1 C5 90.87(13) . . ?
C2 Fe1 C5 92.27(12) . . ?
C4 Fe1 C6 87.84(13) . . ?
C2 Fe1 C6 89.71(13) . . ?
C5 Fe1 C6 177.66(12) . . ?
C4 Fe1 C1 175.30(12) . . ?
C2 Fe1 C1 83.75(12) . . ?
C5 Fe1 C1 89.93(13) . . ?
C6 Fe1 C1 91.52(12) . . ?
C4 Fe1 C3 90.43(12) . . ?
C2 Fe1 C3 176.80(12) . . ?
C5 Fe1 C3 85.22(12) . . ?
C6 Fe1 C3 92.84(12) . . ?
C1 Fe1 C3 94.25(12) . . ?
N1 C1 Fe1 173.5(2) . . ?
N2 C2 Fe1 174.8(3) . . ?
N3 C3 Fe1 174.4(3) . . ?
N4 C4 Fe1 178.0(3) . . ?
N5 C5 Fe1 176.6(3) . . ?
N6 C6 Fe1 177.7(3) . . ?
N7 C7 N8 122.2(3) . . ?
N7 C7 C11 118.6(3) . . ?
N8 C7 C11 119.2(3) . . ?
C7 N7 C8 122.2(3) . . ?
C7 N7 H7 118.9 . . ?
C8 N7 H7 118.9 . . ?
N7 C8 C9 108.4(3) . . ?
O1 C9 C8 106.3(3) . . ?
O1 C9 C10 110.5(3) . . ?
C8 C9 C10 109.5(3) . . ?
C9 O1 H1A 109.5 . . ?
C10 C9' C8 109.3(13) . . ?
C9' C10 N8 108.7(11) . . ?
N8 C10 C9 109.1(3) . . ?
C7 N8 C10 122.5(3) . . ?
C7 N8 H8 118.7 . . ?
C10 N8 H8 118.7 . . ?
C12 C11 C16 120.3(3) . . ?
C12 C11 C7 119.7(3) . . ?
C16 C11 C7 120.0(3) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 C17 119.9(3) . . ?
C15 C14 C17 119.6(3) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N9 C17 N10 121.9(3) . . ?
N9 C17 C14 119.4(3) . . ?
N10 C17 C14 118.7(3) . . ?
C17 N9 C18 122.6(3) . . ?
C17 N9 H9 118.7 . . ?
C18 N9 H9 118.7 . . ?
N9 C18 C19 109.7(3) . . ?
N9 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
N9 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O2 C19 C20 107.6(3) . . ?
O2 C19 C18 111.8(3) . . ?
C20 C19 C18 109.5(3) . . ?
O2 C19 H19 109.3 . . ?
C20 C19 H19 109.3 . . ?
C18 C19 H19 109.3 . . ?
C19 O2 H2A 109.5 . . ?
N10 C20 C19 109.5(3) . . ?
N10 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
N10 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C17 N10 C20 121.6(3) . . ?
C17 N10 H10 119.2 . . ?
C20 N10 H10 119.2 . . ?
N12 C21 N11 122.2(3) . . ?
N12 C21 C25 119.4(3) . . ?
N11 C21 C25 118.4(3) . . ?
C21 N11 C22 121.4(3) . . ?
C21 N11 H11 119.3 . . ?
C22 N11 H11 119.3 . . ?
N11 C22 C23 109.6(3) . . ?
N11 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
N11 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O3 C23 C22 108.6(3) . . ?
O3 C23 C24 113.5(3) . . ?
C22 C23 C24 109.6(3) . . ?
O3 C23 H23 108.4 . . ?
C22 C23 H23 108.4 . . ?
C24 C23 H23 108.4 . . ?
C23 O3 H3A 109.5 . . ?
N12 C24 C23 109.5(3) . . ?
N12 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
N12 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
C21 N12 C24 122.7(2) . . ?
C21 N12 H12A 118.6 . . ?
C24 N12 H12A 118.6 . . ?
C27 C25 C26 120.8(3) . . ?
C27 C25 C21 119.8(3) . . ?
C26 C25 C21 119.4(3) . . ?
C27 C26 C25 119.2(3) 3_576 . ?
C27 C26 H26 120.4 3_576 . ?
C25 C26 H26 120.4 . . ?
C26 C27 C25 119.9(3) 3_576 . ?
C26 C27 H27 120.0 3_576 . ?
C25 C27 H27 120.0 . . ?
H1C O1W H1D 128(4) . . ?
H2C O2W H2D 122(3) . . ?
H3D O3W H3C 130(4) . . ?
H4C O4W H4D 132(3) . . ?

_refine_diff_density_max         1.383
_refine_diff_density_min         -1.390
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_e3312
_database_code_depnum_ccdc_archive 'CCDC 1550167'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C14 H20 N4 O1.40, 0.5(C14 H20 N4)., C6 Fe N6, 4(H2 O)'
_chemical_formula_sum            'C27 H38 Fe N12 O5.40'
_chemical_formula_weight         668.91

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

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

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

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

_cell_length_a                   7.06960(10)
_cell_length_b                   35.4378(7)
_cell_length_c                   12.7602(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.7890(10)
_cell_angle_gamma                90
_cell_volume                     3185.67(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    35000
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             1396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35778
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             8993
_reflns_number_gt                7691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+4.7266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8993
_refine_ls_number_parameters     450
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H2D H 0.991(6) 0.4218(10) 0.206(3) 0.085 Uiso 1 1 d D U . A 2
H2C H 1.002(7) 0.4008(12) 0.3135(18) 0.085 Uiso 1 1 d D U . B 2
O1W O 0.5031(4) 0.41532(8) 0.03527(18) 0.0606(7) Uani 1 1 d D . . C 2
Fe1 Fe 0.23134(4) 0.63526(2) 0.34307(2) 0.01247(8) Uani 1 1 d . . . D 2
C1 C 0.3918(3) 0.59611(6) 0.40854(15) 0.0173(4) Uani 1 1 d . . . D 2
N1 N 0.4808(3) 0.57297(5) 0.45317(15) 0.0245(4) Uani 1 1 d . . . D 2
C2 C 0.0638(3) 0.59757(6) 0.27446(16) 0.0199(4) Uani 1 1 d . . . D 2
N2 N -0.0327(3) 0.57528(6) 0.23202(16) 0.0323(5) Uani 1 1 d . . . D 2
C3 C 0.3713(3) 0.63438(5) 0.21853(16) 0.0180(4) Uani 1 1 d . . . D 2
N3 N 0.4513(3) 0.63276(6) 0.14377(16) 0.0282(4) Uani 1 1 d . . . D 2
C4 C 0.0809(3) 0.67736(5) 0.28468(14) 0.0157(4) Uani 1 1 d . . . D 2
N4 N 0.0067(3) 0.70470(5) 0.25373(14) 0.0202(3) Uani 1 1 d . . . D 2
C5 C 0.3888(3) 0.67514(5) 0.40775(15) 0.0162(4) Uani 1 1 d . . . D 2
N5 N 0.4686(3) 0.70092(5) 0.44368(14) 0.0215(4) Uani 1 1 d . . . D 2
C6 C 0.0945(3) 0.63312(5) 0.46866(16) 0.0173(4) Uani 1 1 d . . . D 2
N6 N 0.0199(3) 0.63029(5) 0.54500(16) 0.0263(4) Uani 1 1 d . . . D 2
C7 C 0.1850(3) 0.79983(5) 0.15822(14) 0.0146(3) Uani 1 1 d . . . E 2
N7 N 0.1939(3) 0.83614(5) 0.14004(13) 0.0172(3) Uani 1 1 d . . . E 2
H7 H 0.2946 0.8451 0.1124 0.021 Uiso 1 1 calc R U . E 2
C8 C 0.0433(3) 0.86242(6) 0.16372(19) 0.0235(4) Uani 1 1 d . . . E 2
H8A H -0.0437 0.8665 0.0998 0.028 Uiso 1 1 calc R U . E 2
H8B H 0.0998 0.8870 0.1857 0.028 Uiso 1 1 calc R U . E 2
C9 C -0.0663(4) 0.84682(7) 0.25030(19) 0.0286(5) Uani 1 1 d . . . E 2
H9A H -0.1827 0.8625 0.2552 0.034 Uiso 1 1 calc R U . E 2
O1 O 0.0353(4) 0.84680(9) 0.3462(2) 0.0410(7) Uani 0.7 1 d . . P E 2
H1 H 0.0379 0.8687 0.3713 0.062 Uiso 1 1 calc R U . E 2
C10 C -0.1265(4) 0.80672(7) 0.2242(2) 0.0315(5) Uani 1 1 d . . . E 2
H10A H -0.1865 0.7955 0.2842 0.038 Uiso 1 1 calc R U . E 2
H10B H -0.2206 0.8066 0.1622 0.038 Uiso 1 1 calc R U . E 2
N8 N 0.0406(3) 0.78449(5) 0.20166(14) 0.0203(4) Uani 1 1 d . . . E 2
H8 H 0.0445 0.7603 0.2176 0.024 Uiso 1 1 calc R U . E 2
C11 C 0.3409(3) 0.77517(5) 0.12879(14) 0.0144(3) Uani 1 1 d . . . E 2
C12 C 0.4083(3) 0.77909(5) 0.02986(14) 0.0155(4) Uani 1 1 d . . . E 2
H12 H 0.3550 0.7975 -0.0179 0.019 Uiso 1 1 calc R U . E 2
C13 C 0.5536(3) 0.75592(6) 0.00161(14) 0.0160(4) Uani 1 1 d . . . E 2
H13 H 0.6008 0.7585 -0.0656 0.019 Uiso 1 1 calc R U . E 2
C14 C 0.6303(3) 0.72879(5) 0.07174(14) 0.0146(3) Uani 1 1 d . . . E 2
C15 C 0.5624(3) 0.72469(5) 0.17060(15) 0.0156(4) Uani 1 1 d . . . E 2
H15 H 0.6149 0.7061 0.2180 0.019 Uiso 1 1 calc R U . E 2
C16 C 0.4177(3) 0.74796(5) 0.19918(14) 0.0157(4) Uani 1 1 d . . . E 2
H16 H 0.3710 0.7454 0.2665 0.019 Uiso 1 1 calc R U . E 2
C17 C 0.7884(3) 0.70481(5) 0.04158(14) 0.0154(3) Uani 1 1 d . . . E 2
N9 N 0.7802(3) 0.66816(5) 0.05512(13) 0.0175(3) Uani 1 1 d . . . E 2
H9 H 0.6796 0.6585 0.0814 0.021 Uiso 1 1 calc R U . E 2
C18 C 0.9319(3) 0.64274(6) 0.02823(18) 0.0231(4) Uani 1 1 d . . . E 2
H18A H 0.8765 0.6186 0.0016 0.028 Uiso 1 1 calc R U . E 2
H18B H 1.0174 0.6373 0.0919 0.028 Uiso 1 1 calc R U . E 2
C19 C 1.0435(4) 0.66047(7) -0.05452(18) 0.0270(5) Uani 1 1 d . . . E 2
H19 H 1.1599 0.6451 -0.0627 0.032 Uiso 1 1 calc R U . E 2
O2 O 0.9376(4) 0.66284(8) -0.15055(18) 0.0331(6) Uani 0.7 1 d . . P E 2
H2 H 0.9322 0.6415 -0.1793 0.050 Uiso 1 1 calc R U . E 2
C20 C 1.1010(3) 0.69986(7) -0.0215(2) 0.0267(5) Uani 1 1 d . . . E 2
H20A H 1.1929 0.6989 0.0413 0.032 Uiso 1 1 calc R U . E 2
H20B H 1.1630 0.7125 -0.0788 0.032 Uiso 1 1 calc R U . E 2
N10 N 0.9335(3) 0.72118(5) 0.00239(14) 0.0204(4) Uani 1 1 d . . . E 2
H10 H 0.9295 0.7456 -0.0097 0.025 Uiso 1 1 calc R U . E 2
C21 C 0.3359(3) 0.49878(6) 0.64270(17) 0.0218(4) Uani 1 1 d . . . F 2
N11 N 0.3461(3) 0.47499(5) 0.72170(14) 0.0227(4) Uani 1 1 d . . . F 2
H11 H 0.2464 0.4609 0.7311 0.027 Uiso 1 1 calc R U . F 2
C24 C 0.5161(4) 0.47069(7) 0.79530(19) 0.0306(5) Uani 1 1 d D . . F 2
C23 C 0.6270(7) 0.50584(14) 0.7982(3) 0.0254(9) Uani 0.5 1 d D . P F 2
H23A H 0.5653 0.5243 0.8427 0.030 Uiso 0.5 1 calc R U P F 2
H23B H 0.7547 0.5005 0.8329 0.030 Uiso 0.5 1 calc R U P F 2
C23A C 0.6858(8) 0.49196(15) 0.7506(5) 0.0368(12) Uani 0.5 1 d D . P F 2
H23C H 0.7792 0.4979 0.8104 0.044 Uiso 0.5 1 calc R U P F 2
H23D H 0.7481 0.4743 0.7043 0.044 Uiso 0.5 1 calc R U P F 2
C22 C 0.6495(5) 0.52325(14) 0.6976(3) 0.0803(17) Uani 1 1 d D . . F 2
N12 N 0.4744(3) 0.52216(7) 0.62801(18) 0.0401(6) Uani 1 1 d . . . F 2
H12A H 0.4617 0.5378 0.5743 0.048 Uiso 1 1 calc R U . F 2
C25 C 0.1631(3) 0.49921(6) 0.56893(16) 0.0191(4) Uani 1 1 d . . . F 2
C26 C 0.0796(3) 0.46552(6) 0.53319(17) 0.0203(4) Uani 1 1 d . . . F 2
H26 H 0.1341 0.4421 0.5556 0.024 Uiso 1 1 calc R U . F 2
C27 C 0.0834(3) 0.53373(6) 0.53530(17) 0.0205(4) Uani 1 1 d . . . F 2
H27 H 0.1410 0.5567 0.5594 0.025 Uiso 1 1 calc R U . F 2
H1C H 0.476(7) 0.4013(14) -0.018(3) 0.116 Uiso 1 1 d D U . G 2
H1D H 0.618(4) 0.4181(15) 0.062(4) 0.116 Uiso 1 1 d D U . H 2
O2W O 1.0281(4) 0.40424(8) 0.24875(19) 0.0567(6) Uani 1 1 d D . . I 2
O3W O 0.8426(4) 0.54080(9) 0.0340(2) 0.0718(8) Uani 1 1 d D . . J 2
H3C H 0.916(5) 0.5211(7) 0.027(4) 0.096 Uiso 1 1 d D U . K 2
H3D H 0.875(6) 0.5558(11) 0.088(3) 0.096 Uiso 1 1 d D U . L 2
O4W O 0.8466(5) 0.45687(10) 0.0994(3) 0.0855(10) Uani 1 1 d D . . M 2
H4C H 0.783(4) 0.4464(10) 0.147(2) 0.097 Uiso 1 1 d D U . N 2
H4D H 0.808(6) 0.4749(10) 0.058(3) 0.097 Uiso 1 1 d D U . O 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1W H1C 0.854(18) . ?
O1W H1D 0.857(18) . ?
Fe1 C1 1.937(2) . ?
Fe1 C5 1.940(2) . ?
Fe1 C3 1.941(2) . ?
Fe1 C6 1.941(2) . ?
Fe1 C2 1.944(2) . ?
Fe1 C4 1.944(2) . ?
C1 N1 1.154(3) . ?
C2 N2 1.149(3) . ?
C3 N3 1.150(3) . ?
C4 N4 1.155(3) . ?
C5 N5 1.149(3) . ?
C6 N6 1.150(3) . ?
C7 N7 1.310(2) . ?
C7 N8 1.319(3) . ?
C7 C11 1.479(3) . ?
N7 C8 1.465(3) . ?
N7 H7 0.8800 . ?
C8 C9 1.506(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.366(4) . ?
C9 C10 1.513(4) . ?
C9 H9A 1.0000 . ?
O1 H1 0.8400 . ?
C10 N8 1.468(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N8 H8 0.8800 . ?
C11 C12 1.393(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(3) . ?
C14 C17 1.480(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N9 1.312(2) . ?
C17 N10 1.313(3) . ?
N9 C18 1.463(3) . ?
N9 H9 0.8800 . ?
C18 C19 1.507(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.384(3) . ?
C19 C20 1.504(3) . ?
C19 H19 1.0000 . ?
O2 H2 0.8400 . ?
C20 N10 1.458(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N10 H10 0.8800 . ?
C21 N12 1.308(3) . ?
C21 N11 1.311(3) . ?
C21 C25 1.478(3) . ?
N11 C24 1.470(3) . ?
N11 H11 0.8800 . ?
C24 C23 1.471(5) . ?
C24 C23A 1.564(6) . ?
C23 C22 1.445(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23A C22 1.313(6) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C22 N12 1.463(3) . ?
N12 H12A 0.8800 . ?
C25 C26 1.392(3) . ?
C25 C27 1.399(3) . ?
C26 C27 1.387(3) 3_566 ?
C26 H26 0.9500 . ?
C27 C26 1.387(3) 3_566 ?
C27 H27 0.9500 . ?
O2W H2D 0.851(17) . ?
O2W H2C 0.871(18) . ?
O3W H3C 0.879(18) . ?
O3W H3D 0.880(18) . ?
O4W H4C 0.866(18) . ?
O4W H4D 0.858(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1C O1W H1D 121(3) . . ?
C1 Fe1 C5 92.50(8) . . ?
C1 Fe1 C3 91.23(8) . . ?
C5 Fe1 C3 92.66(8) . . ?
C1 Fe1 C6 86.00(8) . . ?
C5 Fe1 C6 89.14(8) . . ?
C3 Fe1 C6 176.76(8) . . ?
C1 Fe1 C2 90.86(9) . . ?
C5 Fe1 C2 176.63(9) . . ?
C3 Fe1 C2 87.33(9) . . ?
C6 Fe1 C2 91.03(9) . . ?
C1 Fe1 C4 175.52(8) . . ?
C5 Fe1 C4 83.12(8) . . ?
C3 Fe1 C4 89.92(8) . . ?
C6 Fe1 C4 92.97(8) . . ?
C2 Fe1 C4 93.51(9) . . ?
N1 C1 Fe1 175.59(18) . . ?
N2 C2 Fe1 178.4(2) . . ?
N3 C3 Fe1 177.75(19) . . ?
N4 C4 Fe1 173.02(18) . . ?
N5 C5 Fe1 173.81(18) . . ?
N6 C6 Fe1 176.27(19) . . ?
N7 C7 N8 121.99(18) . . ?
N7 C7 C11 119.16(17) . . ?
N8 C7 C11 118.85(17) . . ?
C7 N7 C8 122.77(18) . . ?
C7 N7 H7 118.6 . . ?
C8 N7 H7 118.6 . . ?
N7 C8 C9 110.19(17) . . ?
N7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O1 C9 C8 113.2(2) . . ?
O1 C9 C10 108.3(2) . . ?
C8 C9 C10 109.61(19) . . ?
O1 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C9 O1 H1 109.5 . . ?
N8 C10 C9 109.3(2) . . ?
N8 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N8 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C7 N8 C10 121.65(18) . . ?
C7 N8 H8 119.2 . . ?
C10 N8 H8 119.2 . . ?
C12 C11 C16 120.49(18) . . ?
C12 C11 C7 119.32(17) . . ?
C16 C11 C7 120.18(16) . . ?
C13 C12 C11 119.58(17) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.96(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.56(18) . . ?
C13 C14 C17 119.43(17) . . ?
C15 C14 C17 119.99(17) . . ?
C16 C15 C14 119.56(17) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 119.84(17) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N9 C17 N10 122.15(18) . . ?
N9 C17 C14 119.42(18) . . ?
N10 C17 C14 118.43(17) . . ?
C17 N9 C18 122.48(18) . . ?
C17 N9 H9 118.8 . . ?
C18 N9 H9 118.8 . . ?
N9 C18 C19 110.15(17) . . ?
N9 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
N9 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
O2 C19 C20 107.8(2) . . ?
O2 C19 C18 111.7(2) . . ?
C20 C19 C18 109.63(19) . . ?
O2 C19 H19 109.2 . . ?
C20 C19 H19 109.2 . . ?
C18 C19 H19 109.2 . . ?
C19 O2 H2 109.5 . . ?
N10 C20 C19 109.53(19) . . ?
N10 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
N10 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C17 N10 C20 121.63(18) . . ?
C17 N10 H10 119.2 . . ?
C20 N10 H10 119.2 . . ?
N12 C21 N11 121.6(2) . . ?
N12 C21 C25 119.37(19) . . ?
N11 C21 C25 119.08(19) . . ?
C21 N11 C24 123.2(2) . . ?
C21 N11 H11 118.4 . . ?
C24 N11 H11 118.4 . . ?
N11 C24 C23 109.5(2) . . ?
N11 C24 C23A 109.2(3) . . ?
C23 C24 C23A 34.7(3) . . ?
C22 C23 C24 115.9(4) . . ?
C22 C23 H23A 108.3 . . ?
C24 C23 H23A 108.3 . . ?
C22 C23 H23B 108.3 . . ?
C24 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
C22 C23A C24 118.2(4) . . ?
C22 C23A H23C 107.8 . . ?
C24 C23A H23C 107.8 . . ?
C22 C23A H23D 107.8 . . ?
C24 C23A H23D 107.8 . . ?
H23C C23A H23D 107.1 . . ?
C23A C22 C23 38.1(3) . . ?
C23A C22 N12 114.2(4) . . ?
C23 C22 N12 112.2(3) . . ?
C21 N12 C22 122.4(2) . . ?
C21 N12 H12A 118.8 . . ?
C22 N12 H12A 118.8 . . ?
C26 C25 C27 120.03(19) . . ?
C26 C25 C21 120.32(18) . . ?
C27 C25 C21 119.64(19) . . ?
C27 C26 C25 119.82(18) 3_566 . ?
C27 C26 H26 120.1 3_566 . ?
C25 C26 H26 120.1 . . ?
C26 C27 C25 120.15(19) 3_566 . ?
C26 C27 H27 119.9 3_566 . ?
C25 C27 H27 119.9 . . ?
H2D O2W H2C 129(3) . . ?
H3C O3W H3D 116(3) . . ?
H4C O4W H4D 126(3) . . ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_e3313
_database_code_depnum_ccdc_archive 'CCDC 1550165'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C14 H20 N4 O, 0.5(C14 H20 N4), C6 Fe N6, 4(H2 O)'
_chemical_formula_sum            'C27 H38 Fe N12 O5'
_chemical_formula_weight         666.54

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

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

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

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

_cell_length_a                   7.0846(5)
_cell_length_b                   35.531(2)
_cell_length_c                   12.6872(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.818(2)
_cell_angle_gamma                90
_cell_volume                     3182.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    16000
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16842
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             5524
_reflns_number_gt                4699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+6.2679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5524
_refine_ls_number_parameters     450
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1W O 0.5051(5) 0.41742(8) 0.0367(2) 0.0513(7) Uani 1 1 d D . . A 4
O3W O 1.0270(5) 0.40454(10) 0.2456(3) 0.0684(9) Uani 1 1 d D . . B 4
H3C H 0.982(6) 0.4254(10) 0.214(4) 0.097 Uiso 1 1 d D U . C 4
Fe1 Fe 0.22731(5) 0.63538(2) 0.34103(3) 0.01229(12) Uani 1 1 d . . . D 4
C1 C 0.3859(4) 0.67514(7) 0.4057(2) 0.0150(6) Uani 1 1 d . . . D 4
N1 N 0.4659(3) 0.70087(7) 0.4419(2) 0.0209(5) Uani 1 1 d . . . D 4
C2 C 0.3892(4) 0.59637(7) 0.4069(2) 0.0167(6) Uani 1 1 d . . . D 4
N2 N 0.4783(4) 0.57347(7) 0.4514(2) 0.0251(6) Uani 1 1 d . . . D 4
C3 C 0.0767(4) 0.67736(7) 0.2824(2) 0.0148(6) Uani 1 1 d . . . D 4
N3 N 0.0024(3) 0.70461(7) 0.25135(19) 0.0203(5) Uani 1 1 d . . . D 4
C4 C 0.0926(4) 0.63334(7) 0.4682(2) 0.0176(6) Uani 1 1 d . . . D 4
N4 N 0.0196(4) 0.63047(7) 0.5455(2) 0.0264(6) Uani 1 1 d . . . D 4
C5 C 0.3661(4) 0.63428(7) 0.2152(2) 0.0164(6) Uani 1 1 d . . . D 4
N5 N 0.4446(4) 0.63238(7) 0.1397(2) 0.0266(6) Uani 1 1 d . . . D 4
C6 C 0.0565(4) 0.59794(8) 0.2735(2) 0.0192(6) Uani 1 1 d . . . D 4
N6 N -0.0420(4) 0.57601(7) 0.2317(2) 0.0293(6) Uani 1 1 d . . . D 4
C7 C 0.6834(4) 0.70020(7) 0.6578(2) 0.0149(6) Uani 1 1 d . . . E 4
N7 N 0.6938(3) 0.66396(6) 0.64060(19) 0.0180(5) Uani 1 1 d . . . E 4
H7 H 0.7948 0.6550 0.6133 0.022 Uiso 1 1 calc R U . E 4
C8 C 0.5441(4) 0.63759(8) 0.6649(3) 0.0251(7) Uani 1 1 d . . . E 4
H8A H 0.6013 0.6132 0.6883 0.030 Uiso 1 1 calc R U . E 4
H8B H 0.4582 0.6330 0.6006 0.030 Uiso 1 1 calc R U . E 4
C9 C 0.4335(5) 0.65351(9) 0.7507(3) 0.0327(8) Uani 1 1 d . . . E 4
H9 H 0.3171 0.6379 0.7551 0.039 Uiso 1 1 calc R U . E 4
O1 O 0.5286(7) 0.65381(14) 0.8448(3) 0.0339(11) Uani 0.5 1 d . . P E 4
H1 H 0.5311 0.6320 0.8703 0.051 Uiso 1 1 calc R U . E 4
C10 C 0.3736(5) 0.69324(9) 0.7247(3) 0.0335(8) Uani 1 1 d . . . E 4
H10A H 0.2783 0.6933 0.6630 0.040 Uiso 1 1 calc R U . E 4
H10B H 0.3152 0.7045 0.7855 0.040 Uiso 1 1 calc R U . E 4
N8 N 0.5385(3) 0.71541(7) 0.70072(19) 0.0211(5) Uani 1 1 d . . . E 4
H8 H 0.5411 0.7396 0.7154 0.025 Uiso 1 1 calc R U . E 4
C11 C 0.8386(4) 0.72499(7) 0.6274(2) 0.0149(6) Uani 1 1 d . . . E 4
C12 C 0.9141(4) 0.75229(7) 0.6973(2) 0.0153(6) Uani 1 1 d . . . E 4
H12 H 0.8670 0.7550 0.7648 0.018 Uiso 1 1 calc R U . E 4
C13 C 1.0583(4) 0.77549(7) 0.6683(2) 0.0157(6) Uani 1 1 d . . . E 4
H13 H 1.1104 0.7942 0.7158 0.019 Uiso 1 1 calc R U . E 4
C14 C 1.1261(4) 0.77127(7) 0.5692(2) 0.0149(6) Uani 1 1 d . . . E 4
C15 C 1.0504(4) 0.74398(7) 0.4993(2) 0.0158(6) Uani 1 1 d . . . E 4
H15 H 1.0977 0.7412 0.4318 0.019 Uiso 1 1 calc R U . E 4
C16 C 0.9059(4) 0.72090(7) 0.5282(2) 0.0150(6) Uani 1 1 d . . . E 4
H16 H 0.8531 0.7024 0.4804 0.018 Uiso 1 1 calc R U . E 4
C17 C 1.2838(4) 0.79528(7) 0.5382(2) 0.0158(6) Uani 1 1 d . . . E 4
N9 N 1.4287(3) 0.77889(7) 0.4992(2) 0.0217(5) Uani 1 1 d . . . E 4
H9A H 1.4247 0.7545 0.4871 0.026 Uiso 1 1 calc R U . E 4
C18 C 1.5971(4) 0.80016(9) 0.4752(3) 0.0304(8) Uani 1 1 d . . . E 4
H18A H 1.6593 0.7875 0.4177 0.036 Uiso 1 1 calc R U . E 4
H18B H 1.6886 0.8012 0.5385 0.036 Uiso 1 1 calc R U . E 4
C19 C 1.5392(5) 0.83926(9) 0.4418(3) 0.0316(8) Uani 1 1 d . . . E 4
H19 H 1.6552 0.8547 0.4337 0.038 Uiso 1 1 calc R U . E 4
O2 O 1.4405(6) 0.83578(12) 0.3472(3) 0.0268(10) Uani 0.5 1 d . . P E 4
H2 H 1.4320 0.8569 0.3173 0.040 Uiso 1 1 calc R U . E 4
C20 C 1.4258(4) 0.85723(8) 0.5229(3) 0.0232(7) Uani 1 1 d . . . E 4
H20A H 1.5098 0.8632 0.5870 0.028 Uiso 1 1 calc R U . E 4
H20B H 1.3697 0.8810 0.4944 0.028 Uiso 1 1 calc R U . E 4
N10 N 1.2751(3) 0.83189(6) 0.55064(18) 0.0178(5) Uani 1 1 d . . . E 4
H10 H 1.1746 0.8416 0.5767 0.021 Uiso 1 1 calc R U . E 4
C21 C 0.6640(4) 0.49999(8) 0.3562(2) 0.0216(6) Uani 1 1 d . . . F 4
N11 N 0.5306(4) 0.47513(9) 0.3693(2) 0.0385(8) Uani 1 1 d . . . F 4
H11A H 0.5440 0.4599 0.4240 0.046 Uiso 1 1 calc R U . F 4
C22 C 0.3599(6) 0.47190(15) 0.2958(4) 0.0677(16) Uani 1 1 d . . . F 4
C23 C 0.3100(7) 0.50707(14) 0.2506(5) 0.0332(11) Uani 0.7 1 d . . P F 4
H23A H 0.2578 0.5231 0.3051 0.040 Uiso 0.7 1 calc R U P F 4
H23B H 0.2084 0.5032 0.1931 0.040 Uiso 0.7 1 calc R U P F 4
C23A C 0.3704(14) 0.4938(3) 0.2036(8) 0.018(2) Uani 0.3 1 d . . P F 4
H23C H 0.2387 0.5000 0.1769 0.021 Uiso 0.3 1 calc R U P F 4
H23D H 0.4219 0.4773 0.1500 0.021 Uiso 0.3 1 calc R U P F 4
C24 C 0.4766(5) 0.52838(9) 0.2050(3) 0.0299(7) Uani 1 1 d . . . F 4
N12 N 0.6486(3) 0.52414(7) 0.27796(19) 0.0215(5) Uani 1 1 d . . . F 4
H12A H 0.7463 0.5387 0.2684 0.026 Uiso 1 1 calc R U . F 4
C25 C 0.8362(4) 0.50022(8) 0.4306(2) 0.0201(6) Uani 1 1 d . . . F 4
C26 C 0.9191(4) 0.46625(8) 0.4643(2) 0.0209(6) Uani 1 1 d . . . F 4
H26 H 0.8637 0.4431 0.4401 0.025 Uiso 1 1 calc R U . F 4
C27 C 0.9176(4) 0.53396(8) 0.4668(2) 0.0210(6) Uani 1 1 d . . . F 4
H27 H 0.8614 0.5572 0.4443 0.025 Uiso 1 1 calc R U . F 4
H1C H 0.518(7) 0.4019(11) -0.011(3) 0.082 Uiso 1 1 d D U . G 4
H1D H 0.554(5) 0.4363(8) 0.059(4) 0.082 Uiso 1 1 d D U . H 4
O2W O 0.8361(4) 0.54076(9) 0.0344(2) 0.0570(8) Uani 1 1 d D . . I 4
H2C H 0.930(5) 0.5286(12) 0.011(3) 0.071 Uiso 1 1 d D U . J 4
H2D H 0.853(6) 0.5528(12) 0.094(2) 0.071 Uiso 1 1 d D U . K 4
H3D H 0.983(7) 0.3973(14) 0.306(3) 0.097 Uiso 1 1 d D U . L 4
O4W O 0.8454(5) 0.45931(10) 0.0941(3) 0.0740(10) Uani 1 1 d D . . M 4
H4C H 0.778(4) 0.4475(12) 0.139(3) 0.086 Uiso 1 1 d D U . N 4
H4D H 0.807(7) 0.4767(12) 0.052(4) 0.086 Uiso 1 1 d D U . O 4


_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
O1W H1C 0.827(18) . ?
O1W H1D 0.797(17) . ?
O3W H3C 0.890(18) . ?
O3W H3D 0.893(19) . ?
Fe1 C1 1.944(3) . ?
Fe1 C4 1.943(3) . ?
Fe1 C3 1.945(3) . ?
Fe1 C5 1.945(3) . ?
Fe1 C2 1.943(3) . ?
Fe1 C6 1.948(3) . ?
C1 N1 1.150(4) . ?
C2 N2 1.149(4) . ?
C3 N3 1.156(4) . ?
C4 N4 1.152(4) . ?
C5 N5 1.149(4) . ?
C6 N6 1.146(4) . ?
C7 N7 1.309(3) . ?
C7 N8 1.318(3) . ?
C7 C11 1.485(4) . ?
N7 C8 1.467(3) . ?
N7 H7 0.8800 . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.321(6) . ?
C9 C10 1.502(5) . ?
C9 H9 1.0000 . ?
O1 H1 0.8400 . ?
C10 N8 1.462(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N8 H8 0.8800 . ?
C11 C16 1.391(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C14 C17 1.485(4) . ?
C15 C16 1.385(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N9 1.313(4) . ?
C17 N10 1.312(3) . ?
N9 C18 1.466(4) . ?
N9 H9A 0.8800 . ?
C18 C19 1.499(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.343(5) . ?
C19 C20 1.500(4) . ?
C19 H19 1.0000 . ?
O2 H2 0.8400 . ?
C20 N10 1.462(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N10 H10 0.8800 . ?
C21 N12 1.310(4) . ?
C21 N11 1.314(4) . ?
C21 C25 1.478(4) . ?
N11 C22 1.468(5) . ?
N11 H11A 0.8800 . ?
C22 C23 1.408(7) . ?
C22 C23A 1.412(10) . ?
C23 C24 1.554(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23A C24 1.440(10) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C24 N12 1.474(4) . ?
N12 H12A 0.8800 . ?
C25 C27 1.392(4) . ?
C25 C26 1.394(4) . ?
C26 C27 1.390(4) 3_766 ?
C26 H26 0.9500 . ?
C27 C26 1.390(4) 3_766 ?
C27 H27 0.9500 . ?
O2W H2C 0.866(18) . ?
O2W H2D 0.864(18) . ?
O4W H4C 0.876(18) . ?
O4W H4D 0.843(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1C O1W H1D 139(4) . . ?
H3C O3W H3D 119(3) . . ?
C1 Fe1 C4 89.05(11) . . ?
C1 Fe1 C3 83.28(11) . . ?
C4 Fe1 C3 93.09(11) . . ?
C1 Fe1 C5 92.71(11) . . ?
C4 Fe1 C5 176.58(11) . . ?
C3 Fe1 C5 90.02(11) . . ?
C1 Fe1 C2 92.14(11) . . ?
C4 Fe1 C2 85.99(11) . . ?
C3 Fe1 C2 175.35(11) . . ?
C5 Fe1 C2 91.02(11) . . ?
C1 Fe1 C6 176.39(12) . . ?
C4 Fe1 C6 90.55(12) . . ?
C3 Fe1 C6 93.16(12) . . ?
C5 Fe1 C6 87.88(11) . . ?
C2 Fe1 C6 91.41(12) . . ?
N1 C1 Fe1 173.7(2) . . ?
N2 C2 Fe1 175.6(2) . . ?
N3 C3 Fe1 173.1(2) . . ?
N4 C4 Fe1 176.1(3) . . ?
N5 C5 Fe1 177.4(2) . . ?
N6 C6 Fe1 178.5(3) . . ?
N7 C7 N8 122.0(2) . . ?
N7 C7 C11 119.1(2) . . ?
N8 C7 C11 118.9(2) . . ?
C7 N7 C8 122.8(2) . . ?
C7 N7 H7 118.6 . . ?
C8 N7 H7 118.6 . . ?
N7 C8 C9 110.0(2) . . ?
N7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O1 C9 C10 107.7(3) . . ?
O1 C9 C8 113.6(4) . . ?
C10 C9 C8 110.5(3) . . ?
O1 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
C9 O1 H1 109.5 . . ?
N8 C10 C9 109.6(3) . . ?
N8 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N8 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C7 N8 C10 121.9(2) . . ?
C7 N8 H8 119.0 . . ?
C10 N8 H8 119.0 . . ?
C16 C11 C12 120.5(2) . . ?
C16 C11 C7 119.4(2) . . ?
C12 C11 C7 120.1(2) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 C17 119.3(2) . . ?
C13 C14 C17 120.2(2) . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 119.7(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N9 C17 N10 122.1(2) . . ?
N9 C17 C14 118.3(2) . . ?
N10 C17 C14 119.5(2) . . ?
C17 N9 C18 121.7(2) . . ?
C17 N9 H9A 119.2 . . ?
C18 N9 H9A 119.2 . . ?
N9 C18 C19 109.2(3) . . ?
N9 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
N9 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
O2 C19 C18 106.1(3) . . ?
O2 C19 C20 112.5(3) . . ?
C18 C19 C20 110.5(3) . . ?
O2 C19 H19 109.2 . . ?
C18 C19 H19 109.2 . . ?
C20 C19 H19 109.2 . . ?
C19 O2 H2 109.5 . . ?
N10 C20 C19 110.3(2) . . ?
N10 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
N10 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C17 N10 C20 122.6(2) . . ?
C17 N10 H10 118.7 . . ?
C20 N10 H10 118.7 . . ?
N12 C21 N11 121.4(3) . . ?
N12 C21 C25 119.5(3) . . ?
N11 C21 C25 119.2(3) . . ?
C21 N11 C22 122.4(3) . . ?
C21 N11 H11A 118.8 . . ?
C22 N11 H11A 118.8 . . ?
C23 C22 C23A 37.1(4) . . ?
C23 C22 N11 110.8(4) . . ?
C23A C22 N11 112.6(5) . . ?
C22 C23 C24 114.3(4) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C22 C23A C24 121.6(7) . . ?
C22 C23A H23C 106.9 . . ?
C24 C23A H23C 106.9 . . ?
C22 C23A H23D 106.9 . . ?
C24 C23A H23D 106.9 . . ?
H23C C23A H23D 106.7 . . ?
C23A C24 N12 108.9(4) . . ?
C23A C24 C23 34.6(4) . . ?
N12 C24 C23 109.3(3) . . ?
C21 N12 C24 123.7(3) . . ?
C21 N12 H12A 118.2 . . ?
C24 N12 H12A 118.2 . . ?
C27 C25 C26 119.5(3) . . ?
C27 C25 C21 120.8(3) . . ?
C26 C25 C21 119.7(3) . . ?
C25 C26 C27 120.3(3) . 3_766 ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 3_766 . ?
C25 C27 C26 120.2(3) . 3_766 ?
C25 C27 H27 119.9 . . ?
C26 C27 H27 119.9 3_766 . ?
H2C O2W H2D 119(3) . . ?
H4C O4W H4D 126(3) . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_e3326
_database_code_depnum_ccdc_archive 'CCDC 1550168'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C14 H20 N4 O1.60,0.5(C14 H20 N4 O0.60),C6 Fe N6,4(H2 O)'
_chemical_formula_sum            'C27 H38 Fe N12 O5.9'
_chemical_formula_weight         682.54

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

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

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

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

_cell_length_a                   7.08870(10)
_cell_length_b                   35.4699(7)
_cell_length_c                   12.8214(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.7200(10)
_cell_angle_gamma                90
_cell_volume                     3212.82(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    33000
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.530
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33286
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.964
_diffrn_reflns_theta_max         30.114
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9245
_reflns_number_gt                7663
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+3.9118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9245
_refine_ls_number_parameters     436
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.23678(3) 0.63520(2) 0.34528(2) 0.01252(7) Uani 1 1 d . . . . .
C1 C 0.3958(3) 0.59595(5) 0.41136(14) 0.0169(3) Uani 1 1 d . . . . .
N1 N 0.4828(3) 0.57261(5) 0.45582(14) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.3929(2) 0.67518(5) 0.40970(13) 0.0156(3) Uani 1 1 d . . . . .
N2 N 0.4728(2) 0.70111(5) 0.44516(13) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.0864(2) 0.67733(5) 0.28653(13) 0.0155(3) Uani 1 1 d . . . . .
N3 N 0.0125(2) 0.70461(5) 0.25545(13) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.0719(3) 0.59725(6) 0.27627(14) 0.0197(4) Uani 1 1 d . . . . .
N4 N -0.0223(3) 0.57474(6) 0.23331(15) 0.0321(4) Uani 1 1 d . . . . .
C5 C 0.0981(3) 0.63309(5) 0.46948(14) 0.0169(3) Uani 1 1 d . . . . .
N5 N 0.0223(3) 0.63052(5) 0.54546(14) 0.0263(4) Uani 1 1 d . . . . .
C6 C 0.3784(3) 0.63454(5) 0.22202(14) 0.0177(3) Uani 1 1 d . . . . .
N6 N 0.4585(3) 0.63312(5) 0.14738(15) 0.0278(4) Uani 1 1 d . . . . .
C7 C 0.6885(2) 0.70042(5) 0.65849(13) 0.0148(3) Uani 1 1 d . . . . .
N7 N 0.6968(2) 0.66416(4) 0.64023(12) 0.0160(3) Uani 1 1 d . . . . .
H7 H 0.7972 0.6551 0.6128 0.019 Uiso 1 1 calc R U . . .
C8 C 0.3774(3) 0.69392(6) 0.72363(19) 0.0276(4) Uani 1 1 d . . . . .
H8A H 0.2842 0.6941 0.6617 0.033 Uiso 1 1 calc R U . . .
H8B H 0.3172 0.7052 0.7832 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4359(3) 0.65381(6) 0.74981(16) 0.0257(4) Uani 1 1 d . . . . .
H9A H 0.3194 0.6383 0.7549 0.031 Uiso 1 1 calc R U . . .
O1 O 0.5407(3) 0.65373(7) 0.84718(14) 0.0344(5) Uani 0.8 1 d . . P . .
H1 H 0.5370 0.6321 0.8739 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5457(3) 0.63798(6) 0.66364(16) 0.0214(4) Uani 1 1 d . . . . .
H10A H 0.6014 0.6134 0.6857 0.026 Uiso 1 1 calc R U . . .
H10B H 0.4593 0.6339 0.6000 0.026 Uiso 1 1 calc R U . . .
N8 N 0.5445(2) 0.71595(5) 0.70171(13) 0.0193(3) Uani 1 1 d . . . . .
H8 H 0.5490 0.7401 0.7177 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8455(2) 0.72502(5) 0.62973(13) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.9132(2) 0.72123(5) 0.53088(13) 0.0151(3) Uani 1 1 d . . . . .
H12 H 0.8597 0.7030 0.4830 0.018 Uiso 1 1 calc R U . . .
C13 C 1.0589(2) 0.74431(5) 0.50312(13) 0.0157(3) Uani 1 1 d . . . . .
H13 H 1.1062 0.7418 0.4363 0.019 Uiso 1 1 calc R U . . .
C14 C 1.1358(2) 0.77126(5) 0.57362(13) 0.0142(3) Uani 1 1 d . . . . .
C15 C 1.0679(2) 0.77526(5) 0.67233(13) 0.0152(3) Uani 1 1 d . . . . .
H15 H 1.1206 0.7937 0.7200 0.018 Uiso 1 1 calc R U . . .
C16 C 0.9223(2) 0.75199(5) 0.70005(13) 0.0153(3) Uani 1 1 d . . . . .
H16 H 0.8751 0.7545 0.7670 0.018 Uiso 1 1 calc R U . . .
C17 C 1.2943(2) 0.79531(5) 0.54401(13) 0.0145(3) Uani 1 1 d . . . . .
N9 N 1.4387(2) 0.77896(5) 0.50435(13) 0.0192(3) Uani 1 1 d . . . . .
H9 H 1.4348 0.7545 0.4923 0.023 Uiso 1 1 calc R U . . .
C18 C 1.6059(3) 0.80039(6) 0.47983(17) 0.0246(4) Uani 1 1 d . . . . .
H18A H 1.6668 0.7879 0.4222 0.030 Uiso 1 1 calc R U . . .
H18B H 1.6985 0.8013 0.5419 0.030 Uiso 1 1 calc R U . . .
C19 C 1.5478(3) 0.83988(6) 0.44782(16) 0.0241(4) Uani 1 1 d . . . . .
H19 H 1.6640 0.8552 0.4397 0.029 Uiso 1 1 calc R U . . .
O2 O 1.4400(3) 0.83807(6) 0.35081(14) 0.0301(4) Uani 0.8 1 d . . P . .
H2 H 1.3257 0.8423 0.3596 0.045 Uiso 1 1 calc R U . . .
C20 C 1.4389(3) 0.85730(6) 0.53179(16) 0.0220(4) Uani 1 1 d . . . . .
H20A H 1.5255 0.8622 0.5949 0.026 Uiso 1 1 calc R U . . .
H20B H 1.3842 0.8817 0.5067 0.026 Uiso 1 1 calc R U . . .
N10 N 1.2868(2) 0.83188(4) 0.55836(12) 0.0167(3) Uani 1 1 d . . . . .
H10 H 1.1869 0.8415 0.5849 0.020 Uiso 1 1 calc R U . . .
C21 C 0.6651(3) 0.50244(6) 0.35745(15) 0.0201(4) Uani 1 1 d . . . . .
N11 N 0.6588(2) 0.52605(5) 0.27849(13) 0.0222(3) Uani 1 1 d . . . . .
H11 H 0.7596 0.5398 0.2696 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4905(3) 0.53063(7) 0.20382(18) 0.0305(5) Uani 1 1 d D . . . .
C23 C 0.3786(5) 0.49517(11) 0.1993(3) 0.0344(12) Uani 0.712(10) 1 d D . P A 1
H23 H 0.2558 0.4988 0.1563 0.041 Uiso 0.712(10) 1 calc R U P A 1
O3 O 0.497(2) 0.4702(3) 0.1492(9) 0.125(5) Uani 0.3 1 d . . P . .
H3A H 0.5149 0.4786 0.0896 0.187 Uiso 0.3 1 calc R U P A 1
C24 C 0.3456(4) 0.48038(11) 0.3046(2) 0.0589(10) Uani 1 1 d D . . . .
C23' C 0.3168(12) 0.5102(2) 0.2495(8) 0.035(3) Uani 0.288(10) 1 d D . P A 2
H23A H 0.2542 0.5288 0.2928 0.042 Uiso 0.288(10) 1 calc R U P A 2
H23B H 0.2252 0.5037 0.1898 0.042 Uiso 0.288(10) 1 calc R U P A 2
N12 N 0.5227(3) 0.48002(6) 0.37276(15) 0.0332(5) Uani 1 1 d . . . . .
H12A H 0.5336 0.4642 0.4258 0.040 Uiso 1 1 calc R U . . .
C25 C 0.8376(3) 0.50121(6) 0.43125(15) 0.0185(4) Uani 1 1 d . . . . .
C26 C 0.9143(3) 0.46659(5) 0.46425(15) 0.0188(4) Uani 1 1 d . . . . .
H26 H 0.8554 0.4438 0.4399 0.023 Uiso 1 1 calc R U . . .
C27 C 0.9231(3) 0.53468(5) 0.46732(15) 0.0187(4) Uani 1 1 d . . . . .
H27 H 0.8705 0.5583 0.4452 0.022 Uiso 1 1 calc R U . . .
O1W O 0.9717(3) 0.59564(6) 0.74921(16) 0.0528(5) Uani 1 1 d . . . . .
H1WA H 1.0047 0.6189 0.7767 0.079 Uiso 1 1 d R U . . .
H1WB H 1.0175 0.6021 0.6922 0.079 Uiso 1 1 d R U . . .
O2W O 0.5035(4) 0.58731(7) 0.96585(16) 0.0704(8) Uani 1 1 d . . . . .
H2WA H 0.5054 0.6025 1.0174 0.106 Uiso 1 1 d R U . . .
H2WB H 0.3866 0.5831 0.9498 0.106 Uiso 1 1 d R U . . .
O3W O 0.8417(5) 0.45491(10) 0.1041(3) 0.1025(11) Uani 1 1 d . . . . .
H3WB H 0.7670 0.4445 0.1456 0.154 Uiso 1 1 d R U . . .
H3WA H 0.9346 0.4623 0.1467 0.154 Uiso 1 1 d R U . . .
O4W O 0.8516(5) 0.54050(11) 0.0338(2) 0.1061(12) Uani 1 1 d . . . . .
H4WA H 0.9593 0.5329 0.0136 0.159 Uiso 1 1 d R U . . .
H4WB H 0.8851 0.5490 0.0957 0.159 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C5 1.9406(19) . ?
Fe1 C6 1.9410(19) . ?
Fe1 C2 1.9412(19) . ?
Fe1 C1 1.9413(19) . ?
Fe1 C4 1.947(2) . ?
Fe1 C3 1.9505(19) . ?
C1 N1 1.155(3) . ?
C2 N2 1.153(2) . ?
C3 N3 1.155(2) . ?
C4 N4 1.152(3) . ?
C5 N5 1.154(3) . ?
C6 N6 1.153(3) . ?
C7 N7 1.310(2) . ?
C7 N8 1.321(2) . ?
C7 C11 1.484(2) . ?
N7 C10 1.467(2) . ?
N7 H7 0.8800 . ?
C8 N8 1.465(3) . ?
C8 C9 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.399(3) . ?
C9 C10 1.511(3) . ?
C9 H9A 1.0000 . ?
O1 H1 0.8400 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N8 H8 0.8800 . ?
C11 C16 1.394(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(2) . ?
C14 C17 1.485(2) . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N10 1.312(2) . ?
C17 N9 1.315(2) . ?
N9 C18 1.464(2) . ?
N9 H9 0.8800 . ?
C18 C19 1.507(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.407(3) . ?
C19 C20 1.508(3) . ?
C19 H19 1.0000 . ?
O2 H2 0.8400 . ?
C20 N10 1.467(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N10 H10 0.8800 . ?
C21 N11 1.312(2) . ?
C21 N12 1.313(3) . ?
C21 C25 1.484(3) . ?
N11 C22 1.476(3) . ?
N11 H11 0.8800 . ?
C22 C23 1.486(4) . ?
C22 C23' 1.582(9) . ?
C23 O3 1.409(15) . ?
C23 C24 1.485(5) . ?
C23 H23 1.0000 . ?
O3 H3A 0.8400 . ?
C24 C23' 1.279(8) . ?
C24 N12 1.469(3) . ?
C23' H23A 0.9900 . ?
C23' H23B 0.9900 . ?
N12 H12A 0.8800 . ?
C25 C26 1.395(3) . ?
C25 C27 1.395(3) . ?
C26 C27 1.391(3) 3_766 ?
C26 H26 0.9500 . ?
C27 C26 1.390(3) 3_766 ?
C27 H27 0.9500 . ?
O1W H1WA 0.9210 . ?
O1W H1WB 0.8551 . ?
O2W H2WA 0.8522 . ?
O2W H2WB 0.8510 . ?
O3W H3WB 0.8640 . ?
O3W H3WA 0.8614 . ?
O4W H4WA 0.8687 . ?
O4W H4WB 0.8641 . ?

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
C5 Fe1 C6 177.02(8) . . ?
C5 Fe1 C2 89.35(8) . . ?
C6 Fe1 C2 92.30(8) . . ?
C5 Fe1 C1 85.96(8) . . ?
C6 Fe1 C1 91.49(8) . . ?
C2 Fe1 C1 92.74(8) . . ?
C5 Fe1 C4 91.18(8) . . ?
C6 Fe1 C4 87.31(8) . . ?
C2 Fe1 C4 176.79(8) . . ?
C1 Fe1 C4 90.46(8) . . ?
C5 Fe1 C3 92.79(8) . . ?
C6 Fe1 C3 89.86(8) . . ?
C2 Fe1 C3 83.04(7) . . ?
C1 Fe1 C3 175.62(8) . . ?
C4 Fe1 C3 93.76(8) . . ?
N1 C1 Fe1 175.62(17) . . ?
N2 C2 Fe1 173.88(16) . . ?
N3 C3 Fe1 173.03(16) . . ?
N4 C4 Fe1 178.11(19) . . ?
N5 C5 Fe1 176.49(18) . . ?
N6 C6 Fe1 177.57(18) . . ?
N7 C7 N8 122.15(17) . . ?
N7 C7 C11 119.16(16) . . ?
N8 C7 C11 118.70(17) . . ?
C7 N7 C10 122.75(16) . . ?
C7 N7 H7 118.6 . . ?
C10 N7 H7 118.6 . . ?
N8 C8 C9 109.46(17) . . ?
N8 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N8 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O1 C9 C10 112.59(19) . . ?
O1 C9 C8 108.4(2) . . ?
C10 C9 C8 109.62(17) . . ?
O1 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C9 O1 H1 109.5 . . ?
N7 C10 C9 110.06(16) . . ?
N7 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N7 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
C7 N8 C8 121.51(17) . . ?
C7 N8 H8 119.2 . . ?
C8 N8 H8 119.2 . . ?
C16 C11 C12 120.48(16) . . ?
C16 C11 C7 120.23(15) . . ?
C12 C11 C7 119.28(16) . . ?
C13 C12 C11 119.63(16) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.83(16) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.73(16) . . ?
C13 C14 C17 119.43(15) . . ?
C15 C14 C17 119.83(16) . . ?
C16 C15 C14 119.29(16) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 120.04(16) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N10 C17 N9 122.14(17) . . ?
N10 C17 C14 119.49(16) . . ?
N9 C17 C14 118.37(17) . . ?
C17 N9 C18 121.59(17) . . ?
C17 N9 H9 119.2 . . ?
C18 N9 H9 119.2 . . ?
N9 C18 C19 109.47(17) . . ?
N9 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
N9 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
O2 C19 C18 108.35(19) . . ?
O2 C19 C20 112.14(19) . . ?
C18 C19 C20 109.32(17) . . ?
O2 C19 H19 109.0 . . ?
C18 C19 H19 109.0 . . ?
C20 C19 H19 109.0 . . ?
C19 O2 H2 109.5 . . ?
N10 C20 C19 110.06(16) . . ?
N10 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
N10 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
C17 N10 C20 122.44(16) . . ?
C17 N10 H10 118.8 . . ?
C20 N10 H10 118.8 . . ?
N11 C21 N12 121.62(18) . . ?
N11 C21 C25 119.01(18) . . ?
N12 C21 C25 119.37(18) . . ?
C21 N11 C22 123.05(18) . . ?
C21 N11 H11 118.5 . . ?
C22 N11 H11 118.5 . . ?
N11 C22 C23 109.4(2) . . ?
N11 C22 C23' 108.7(3) . . ?
O3 C23 C24 109.7(6) . . ?
O3 C23 C22 102.3(6) . . ?
C24 C23 C22 112.8(3) . . ?
O3 C23 H23 110.6 . . ?
C24 C23 H23 110.6 . . ?
C22 C23 H23 110.6 . . ?
C23 O3 H3A 109.5 . . ?
C23' C24 N12 115.2(4) . . ?
N12 C24 C23 110.7(2) . . ?
C24 C23' C22 119.3(6) . . ?
C24 C23' H23A 107.5 . . ?
C22 C23' H23A 107.5 . . ?
C24 C23' H23B 107.5 . . ?
C22 C23' H23B 107.5 . . ?
H23A C23' H23B 107.0 . . ?
C21 N12 C24 122.41(19) . . ?
C21 N12 H12A 118.8 . . ?
C24 N12 H12A 118.8 . . ?
C26 C25 C27 120.06(17) . . ?
C26 C25 C21 119.98(17) . . ?
C27 C25 C21 119.96(17) . . ?
C27 C26 C25 120.15(17) 3_766 . ?
C27 C26 H26 119.9 3_766 . ?
C25 C26 H26 119.9 . . ?
C26 C27 C25 119.79(17) 3_766 . ?
C26 C27 H27 120.1 3_766 . ?
C25 C27 H27 120.1 . . ?
H1WA O1W H1WB 89.1 . . ?
H2WA O2W H2WB 104.6 . . ?
H3WB O3W H3WA 102.4 . . ?
H4WA O4W H4WB 101.4 . . ?

_refine_diff_density_max         0.736
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.073

_shelxl_version_number           2014-3

