# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1521743'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 Fe N7, C H4 O'
_chemical_formula_sum            'C18 H27 Fe N7 O'
_chemical_formula_weight         413.31

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.8410(17)
_cell_length_b                   11.5544(18)
_cell_length_c                   15.814(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.199(5)
_cell_angle_gamma                90
_cell_volume                     1975.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    82(2)
_cell_measurement_reflns_used    2345
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      24.31

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.786
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6666
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      82(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12140
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.884
_diffrn_reflns_theta_max         25.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3624
_reflns_number_gt                2675
_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    'Bruker APEX2, intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were 
assigned to 
ideal positions and refined isotropically using a riding model, 
except for those 
on nitrogen atoms which were localized on the difference 
Fourier map, and refined 
using DFIX constraints. 
The shape of the thermal ellipsoid of C18 atom suggest some disorder in
the molecule of methanol, and was refined using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+2.2619P] 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         3624
_refine_ls_number_parameters     254
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.039
_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 0.25108(5) 0.76816(5) 0.51051(3) 0.0141(2) Uani 1 1 d . . . . .
N2 N 0.3631(3) 0.7055(3) 0.40316(19) 0.0156(7) Uani 1 1 d . . . . .
N5 N 0.1327(3) 0.7047(3) 0.6120(2) 0.0170(7) Uani 1 1 d . . . . .
N1 N 0.2364(3) 0.5826(3) 0.50078(18) 0.0164(7) Uani 1 1 d . . . . .
N3 N 0.3565(3) 0.9253(3) 0.45816(19) 0.0176(7) Uani 1 1 d D . . . .
N4 N 0.1859(3) 0.9284(3) 0.5845(2) 0.0186(8) Uani 1 1 d D . . . .
N7 N 0.5027(3) 0.7813(3) 0.6438(2) 0.0248(8) Uani 1 1 d . . . . .
O1 O 0.7588(4) 0.8300(3) 0.7003(3) 0.0587(11) Uani 1 1 d . U . . .
H1 H 0.6835 0.8371 0.6844 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3771(4) 0.5972(3) 0.3920(2) 0.0168(9) Uani 1 1 d . . . . .
C1 C 0.1618(4) 0.5245(3) 0.5507(2) 0.0175(9) Uani 1 1 d . . . . .
C17 C 0.4136(4) 0.7652(3) 0.6008(2) 0.0174(9) Uani 1 1 d . . . . .
C14 C 0.1051(4) 0.5972(3) 0.6145(2) 0.0194(9) Uani 1 1 d . . . . .
C5 C 0.2989(4) 0.5231(3) 0.4438(2) 0.0180(9) Uani 1 1 d . . . . .
C4 C 0.2868(4) 0.4039(3) 0.4344(2) 0.0220(9) Uani 1 1 d . . . . .
H4 H 0.3341 0.3629 0.3960 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2701(4) 1.0268(3) 0.5743(2) 0.0186(9) Uani 1 1 d . . . . .
H11A H 0.3482 1.0151 0.6098 0.022 Uiso 1 1 calc R U . . .
H11B H 0.2314 1.0994 0.5924 0.022 Uiso 1 1 calc R U . . .
N6 N 0.0080(4) 0.8523(4) 0.3884(3) 0.0405(11) Uani 1 1 d . . . . .
C2 C 0.1419(4) 0.4052(3) 0.5415(2) 0.0220(9) Uani 1 1 d . . . . .
H2 H 0.0865 0.3660 0.5756 0.026 Uiso 1 1 calc R U . . .
C10 C 0.2965(4) 1.0345(3) 0.4814(2) 0.0192(9) Uani 1 1 d . . . . .
H10A H 0.2184 1.0457 0.4458 0.023 Uiso 1 1 calc R U . . .
H10B H 0.3517 1.1010 0.4723 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4313(4) 0.7918(3) 0.3569(2) 0.0197(9) Uani 1 1 d . . . . .
H8A H 0.4293 0.7709 0.2961 0.024 Uiso 1 1 calc R U . . .
H8B H 0.5187 0.7944 0.3798 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1718(4) 0.8942(3) 0.6729(2) 0.0210(9) Uani 1 1 d . . . . .
H12B H 0.1350 0.9585 0.7039 0.025 Uiso 1 1 calc R U . . .
H12A H 0.2536 0.8756 0.7017 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3712(4) 0.9089(3) 0.3670(2) 0.0206(9) Uani 1 1 d . . . . .
H9B H 0.4239 0.9709 0.3457 0.025 Uiso 1 1 calc R U . . .
H9A H 0.2896 0.9115 0.3346 0.025 Uiso 1 1 calc R U . . .
C16 C 0.0930(4) 0.8126(4) 0.4248(2) 0.0204(9) Uani 1 1 d . . . . .
C13 C 0.0882(4) 0.7889(3) 0.6722(3) 0.0227(10) Uani 1 1 d . . . . .
H13A H 0.0901 0.7545 0.7296 0.027 Uiso 1 1 calc R U . . .
H13B H 0.0019 0.8114 0.6548 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2038(4) 0.3461(4) 0.4825(3) 0.0258(10) Uani 1 1 d . . . . .
H3 H 0.1901 0.2655 0.4745 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4636(4) 0.5402(4) 0.3349(3) 0.0295(11) Uani 1 1 d . . . . .
H7A H 0.5010 0.5992 0.3003 0.044 Uiso 1 1 calc R U . . .
H7B H 0.4176 0.4848 0.2978 0.044 Uiso 1 1 calc R U . . .
H7C H 0.5288 0.4995 0.3693 0.044 Uiso 1 1 calc R U . . .
C15 C 0.0258(4) 0.5409(4) 0.6772(3) 0.0297(11) Uani 1 1 d . . . . .
H15A H 0.0785 0.4976 0.7191 0.045 Uiso 1 1 calc R U . . .
H15B H -0.0329 0.4878 0.6472 0.045 Uiso 1 1 calc R U . . .
H15C H -0.0198 0.6006 0.7060 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7731(5) 0.7426(6) 0.7653(3) 0.068(2) Uani 1 1 d . U . . .
H18A H 0.8580 0.7443 0.7913 0.101 Uiso 1 1 calc R U . . .
H18B H 0.7560 0.6662 0.7401 0.101 Uiso 1 1 calc R U . . .
H18C H 0.7151 0.7577 0.8087 0.101 Uiso 1 1 calc R U . . .
H4N H 0.110(3) 0.951(5) 0.555(3) 0.081 Uiso 1 1 d D U . . .
H3N H 0.434(3) 0.921(5) 0.493(3) 0.081 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 N1 2.154(3) . ?
Fe1 C16 2.168(4) . ?
Fe1 C17 2.185(4) . ?
Fe1 N5 2.250(3) . ?
Fe1 N2 2.276(3) . ?
Fe1 N4 2.327(3) . ?
Fe1 N3 2.330(3) . ?
N2 C6 1.275(5) . ?
N2 C8 1.469(5) . ?
N5 C14 1.279(5) . ?
N5 C13 1.468(5) . ?
N1 C1 1.349(5) . ?
N1 C5 1.354(5) . ?
N3 C9 1.474(5) . ?
N3 C10 1.478(5) . ?
N3 H3N 0.97(2) . ?
N4 C12 1.471(5) . ?
N4 C11 1.475(5) . ?
N4 H4N 0.96(2) . ?
N7 C17 1.155(5) . ?
O1 C18 1.441(6) . ?
O1 H1 0.8400 . ?
C6 C5 1.491(5) . ?
C6 C7 1.501(5) . ?
C1 C2 1.402(6) . ?
C1 C14 1.480(5) . ?
C14 C15 1.507(5) . ?
C5 C4 1.391(5) . ?
C4 C3 1.391(6) . ?
C4 H4 0.9500 . ?
C11 C10 1.520(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N6 C16 1.145(6) . ?
C2 C3 1.371(6) . ?
C2 H2 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 C9 1.515(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C12 C13 1.518(6) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 Fe1 C16 98.06(14) . . ?
N1 Fe1 C17 94.76(13) . . ?
C16 Fe1 C17 167.17(15) . . ?
N1 Fe1 N5 71.54(11) . . ?
C16 Fe1 N5 93.28(14) . . ?
C17 Fe1 N5 90.21(13) . . ?
N1 Fe1 N2 70.79(11) . . ?
C16 Fe1 N2 92.83(13) . . ?
C17 Fe1 N2 91.93(13) . . ?
N5 Fe1 N2 142.32(12) . . ?
N1 Fe1 N4 143.50(11) . . ?
C16 Fe1 N4 82.59(14) . . ?
C17 Fe1 N4 86.77(13) . . ?
N5 Fe1 N4 71.99(11) . . ?
N2 Fe1 N4 145.69(11) . . ?
N1 Fe1 N3 141.79(11) . . ?
C16 Fe1 N3 88.81(14) . . ?
C17 Fe1 N3 81.44(13) . . ?
N5 Fe1 N3 145.89(11) . . ?
N2 Fe1 N3 71.36(11) . . ?
N4 Fe1 N3 74.55(11) . . ?
C6 N2 C8 121.9(3) . . ?
C6 N2 Fe1 119.4(3) . . ?
C8 N2 Fe1 118.1(2) . . ?
C14 N5 C13 122.3(3) . . ?
C14 N5 Fe1 119.1(3) . . ?
C13 N5 Fe1 118.6(2) . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Fe1 119.8(2) . . ?
C5 N1 Fe1 121.0(2) . . ?
C9 N3 C10 115.7(3) . . ?
C9 N3 Fe1 109.8(2) . . ?
C10 N3 Fe1 109.9(2) . . ?
C9 N3 H3N 113(4) . . ?
C10 N3 H3N 106(4) . . ?
Fe1 N3 H3N 101(4) . . ?
C12 N4 C11 114.8(3) . . ?
C12 N4 Fe1 108.7(2) . . ?
C11 N4 Fe1 110.2(2) . . ?
C12 N4 H4N 113(4) . . ?
C11 N4 H4N 105(4) . . ?
Fe1 N4 H4N 105(4) . . ?
C18 O1 H1 109.5 . . ?
N2 C6 C5 114.2(3) . . ?
N2 C6 C7 126.9(4) . . ?
C5 C6 C7 118.9(3) . . ?
N1 C1 C2 121.6(4) . . ?
N1 C1 C14 114.4(3) . . ?
C2 C1 C14 124.0(4) . . ?
N7 C17 Fe1 169.0(3) . . ?
N5 C14 C1 114.8(3) . . ?
N5 C14 C15 125.9(4) . . ?
C1 C14 C15 119.3(4) . . ?
N1 C5 C4 121.8(4) . . ?
N1 C5 C6 114.0(3) . . ?
C4 C5 C6 124.2(4) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N4 C11 C10 108.2(3) . . ?
N4 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
N4 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N3 C10 C11 107.9(3) . . ?
N3 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
N3 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
N2 C8 C9 108.5(3) . . ?
N2 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N2 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N4 C12 C13 108.2(3) . . ?
N4 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
N4 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
H12B C12 H12A 108.4 . . ?
N3 C9 C8 107.2(3) . . ?
N3 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
N3 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
H9B C9 H9A 108.5 . . ?
N6 C16 Fe1 168.2(4) . . ?
N5 C13 C12 108.2(3) . . ?
N5 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
N5 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         1.067
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1521746'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C17 H23 Fe N7), 2(C H4 O)'
_chemical_formula_sum            'C36 H54 Fe2 N14 O2'
_chemical_formula_weight         826.63

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.8084(4)
_cell_length_b                   23.0976(11)
_cell_length_c                   15.5032(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.329(2)
_cell_angle_gamma                90
_cell_volume                     3859.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    82(2)
_cell_measurement_reflns_used    3865
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.26

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.805
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      82(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32296
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.585
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7896
_reflns_number_gt                5514
_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    'Bruker APEX2, intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to 
ideal positions and refined isotropically using a riding model, excpet for those 
on nitrogen atoms which were localized on the difference Fourier map, and refined 
using DFIX constraints. The crystal structure contains two crystallographically disordered 
methanol molecules (one bearing O3 and C19A, and one bearing O2 and C19B atoms)
which was refined over two positions using EADP and EXYZ constraints. Hydrogen atoms on these 
disordered solvent molecules were not introduced but are taken into account in the coumpound formula.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+7.3405P] 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         7896
_refine_ls_number_parameters     505
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.003
_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 0.52569(4) 0.24928(2) 0.25514(3) 0.01052(14) Uani 1 1 d . . . . .
N1 N 0.5083(2) 0.16960(13) 0.26226(18) 0.0107(6) Uani 1 1 d . . . . .
N5 N 0.4094(3) 0.24356(13) 0.35176(19) 0.0142(6) Uani 1 1 d . . . . .
N6 N 0.3000(3) 0.25302(15) 0.1199(2) 0.0219(7) Uani 1 1 d . . . . .
N7 N 0.7340(3) 0.26584(13) 0.4029(2) 0.0146(7) Uani 1 1 d . . . . .
N4 N 0.3018(3) 0.35593(14) 0.2873(2) 0.0174(7) Uani 1 1 d D . . . .
N2 N 0.6373(3) 0.22606(13) 0.17209(18) 0.0112(6) Uani 1 1 d . . . . .
N3 N 0.5688(3) 0.33320(13) 0.21177(19) 0.0112(6) Uani 1 1 d D . . . .
C13 C 0.3810(3) 0.29097(16) 0.4111(2) 0.0176(8) Uani 1 1 d . . . . .
H13A H 0.4561 0.3130 0.4258 0.021 Uiso 1 1 calc R U . . .
H13B H 0.3542 0.2745 0.4641 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4655(3) 0.05277(16) 0.2572(2) 0.0175(8) Uani 1 1 d . . . . .
H3 H 0.4501 0.0132 0.2551 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5544(3) 0.07628(16) 0.2069(2) 0.0172(8) Uani 1 1 d . . . . .
H4 H 0.6003 0.0528 0.1725 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3996(3) 0.08765(16) 0.3105(2) 0.0154(8) Uani 1 1 d . . . . .
H2 H 0.3407 0.0717 0.3443 0.018 Uiso 1 1 calc R U . . .
C9 C 0.6172(3) 0.32407(15) 0.1253(2) 0.0127(7) Uani 1 1 d . . . . .
H9A H 0.6624 0.3582 0.1091 0.015 Uiso 1 1 calc R U . . .
H9B H 0.5484 0.3182 0.0823 0.015 Uiso 1 1 calc R U . . .
C7 C 0.7374(4) 0.14593(16) 0.0961(3) 0.0197(9) Uani 1 1 d . . . . .
H7A H 0.7217 0.1637 0.0403 0.030 Uiso 1 1 calc R U . . .
H7B H 0.7231 0.1050 0.0911 0.030 Uiso 1 1 calc R U . . .
H7C H 0.8220 0.1528 0.1171 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6585(3) 0.25863(15) 0.3472(2) 0.0126(7) Uani 1 1 d . . . . .
C10 C 0.4806(3) 0.38270(16) 0.2054(2) 0.0155(8) Uani 1 1 d . . . . .
H10A H 0.4195 0.3760 0.1573 0.019 Uiso 1 1 calc R U . . .
H10B H 0.5258 0.4176 0.1929 0.019 Uiso 1 1 calc R U . . .
C11 C 0.4140(3) 0.39212(16) 0.2866(2) 0.0160(8) Uani 1 1 d . . . . .
H11A H 0.4697 0.3829 0.3367 0.019 Uiso 1 1 calc R U . . .
H11B H 0.3910 0.4326 0.2904 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5728(3) 0.13581(15) 0.2094(2) 0.0113(7) Uani 1 1 d . . . . .
C6 C 0.6521(3) 0.17137(16) 0.1580(2) 0.0130(8) Uani 1 1 d . . . . .
C14 C 0.3702(3) 0.19155(17) 0.3660(2) 0.0143(8) Uani 1 1 d . . . . .
C8 C 0.7020(3) 0.27194(15) 0.1275(2) 0.0134(8) Uani 1 1 d . . . . .
H8A H 0.7171 0.2599 0.0693 0.016 Uiso 1 1 calc R U . . .
H8B H 0.7809 0.2809 0.1587 0.016 Uiso 1 1 calc R U . . .
C15 C 0.2846(4) 0.17313(19) 0.4327(3) 0.0248(9) Uani 1 1 d . . . . .
H15A H 0.3325 0.1597 0.4834 0.037 Uiso 1 1 calc R U . . .
H15B H 0.2319 0.1425 0.4098 0.037 Uiso 1 1 calc R U . . .
H15C H 0.2345 0.2054 0.4475 0.037 Uiso 1 1 calc R U . . .
C1 C 0.4232(3) 0.14660(15) 0.3124(2) 0.0102(7) Uani 1 1 d . . . . .
C12 C 0.2803(4) 0.33185(17) 0.3724(3) 0.0214(9) Uani 1 1 d . . . . .
H12A H 0.2021 0.3111 0.3676 0.026 Uiso 1 1 calc R U . . .
H12B H 0.2718 0.3637 0.4123 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3856(3) 0.25133(16) 0.1691(2) 0.0142(8) Uani 1 1 d . . . . .
Fe1B Fe -0.02255(5) 0.00144(2) 0.26158(3) 0.01114(14) Uani 1 1 d . . . . .
N4B N 0.1958(3) -0.10493(13) 0.2207(2) 0.0149(7) Uani 1 1 d D . . . .
N3B N -0.0704(3) -0.08348(13) 0.29689(19) 0.0121(6) Uani 1 1 d D . . . .
N2B N -0.1368(3) 0.02264(13) 0.34345(19) 0.0125(6) Uani 1 1 d . . . . .
N5B N 0.0934(3) 0.00971(13) 0.16434(19) 0.0134(6) Uani 1 1 d . . . . .
N6B N 0.2027(3) -0.00840(15) 0.3980(2) 0.0230(8) Uani 1 1 d . . . . .
N7B N -0.2267(3) -0.00819(13) 0.1102(2) 0.0158(7) Uani 1 1 d . . . . .
N1B N -0.0049(2) 0.08112(13) 0.25818(18) 0.0104(6) Uani 1 1 d . . . . .
C16B C 0.1176(4) -0.00435(16) 0.3491(2) 0.0161(8) Uani 1 1 d . . . . .
C4B C 0.1008(3) 0.16483(15) 0.2121(2) 0.0150(8) Uani 1 1 d . . . . .
H4B H 0.1597 0.1817 0.1793 0.018 Uiso 1 1 calc R U . . .
C2B C -0.0552(3) 0.17337(16) 0.3157(2) 0.0160(8) Uani 1 1 d . . . . .
H2B H -0.1013 0.1961 0.3510 0.019 Uiso 1 1 calc R U . . .
C3B C 0.0323(3) 0.19819(16) 0.2659(2) 0.0175(8) Uani 1 1 d . . . . .
H3B H 0.0454 0.2380 0.2686 0.021 Uiso 1 1 calc R U . . .
C12B C -0.1232(3) -0.07721(15) 0.3823(2) 0.0147(8) Uani 1 1 d . . . . .
H12C H -0.0565 -0.0734 0.4274 0.018 Uiso 1 1 calc R U . . .
H12D H -0.1708 -0.1115 0.3943 0.018 Uiso 1 1 calc R U . . .
C8B C 0.1185(3) -0.03624(16) 0.1018(2) 0.0162(8) Uani 1 1 d . . . . .
H8B1 H 0.1449 -0.0187 0.0494 0.019 Uiso 1 1 calc R U . . .
H8B2 H 0.0426 -0.0576 0.0867 0.019 Uiso 1 1 calc R U . . .
C6B C 0.1306(3) 0.06241(16) 0.1519(2) 0.0136(8) Uani 1 1 d . . . . .
C17B C -0.1530(3) -0.00433(15) 0.1683(2) 0.0135(7) Uani 1 1 d . . . . .
C11B C 0.0160(3) -0.13364(15) 0.3015(2) 0.0143(8) Uani 1 1 d . . . . .
H11C H -0.0303 -0.1686 0.3118 0.017 Uiso 1 1 calc R U . . .
H11D H 0.0770 -0.1283 0.3500 0.017 Uiso 1 1 calc R U . . .
C14B C -0.1527(3) 0.07712(15) 0.3595(2) 0.0118(7) Uani 1 1 d . . . . .
C1B C -0.0723(3) 0.11352(15) 0.3112(2) 0.0114(7) Uani 1 1 d . . . . .
C5B C 0.0788(3) 0.10555(15) 0.2087(2) 0.0117(7) Uani 1 1 d . . . . .
C7B C 0.2106(4) 0.08268(17) 0.0832(3) 0.0207(9) Uani 1 1 d . . . . .
H7B1 H 0.2592 0.0509 0.0646 0.031 Uiso 1 1 calc R U . . .
H7B2 H 0.2648 0.1128 0.1061 0.031 Uiso 1 1 calc R U . . .
H7B3 H 0.1592 0.0973 0.0349 0.031 Uiso 1 1 calc R U . . .
C15B C -0.2424(3) 0.10086(16) 0.4198(2) 0.0161(8) Uani 1 1 d . . . . .
H15D H -0.3249 0.0884 0.4012 0.024 Uiso 1 1 calc R U . . .
H15E H -0.2388 0.1424 0.4194 0.024 Uiso 1 1 calc R U . . .
H15F H -0.2208 0.0870 0.4773 0.024 Uiso 1 1 calc R U . . .
C13B C -0.2065(3) -0.02409(15) 0.3820(2) 0.0152(8) Uani 1 1 d . . . . .
H13C H -0.2840 -0.0312 0.3479 0.018 Uiso 1 1 calc R U . . .
H13D H -0.2248 -0.0141 0.4404 0.018 Uiso 1 1 calc R U . . .
C10B C 0.0826(3) -0.14120(15) 0.2197(2) 0.0162(8) Uani 1 1 d . . . . .
H10C H 0.1053 -0.1816 0.2137 0.019 Uiso 1 1 calc R U . . .
H10D H 0.0270 -0.1308 0.1701 0.019 Uiso 1 1 calc R U . . .
C18 C 1.0055(4) 0.2470(2) 0.5263(3) 0.0280(10) Uani 1 1 d . . . . .
H18A H 1.0919 0.2454 0.5456 0.042 Uiso 1 1 calc R U . . .
H18B H 0.9791 0.2099 0.5039 0.042 Uiso 1 1 calc R U . . .
H18C H 0.9580 0.2570 0.5740 0.042 Uiso 1 1 calc R U . . .
O1 O 0.9869(3) 0.28910(14) 0.4608(2) 0.0341(8) Uani 1 1 d . . . . .
H1 H 0.9126 0.2915 0.4458 0.051 Uiso 1 1 calc R U . . .
O1C O 0.5188(5) 0.4768(2) 0.0362(4) 0.0746(19) Uani 0.5 1 d . . P A 1
O1B O 0.5265(8) 0.4788(2) 0.4797(4) 0.107(3) Uani 0.5 1 d . . P B 1
C18C C 0.5188(5) 0.4768(2) 0.0362(4) 0.0746(19) Uani 0.5 1 d . . P C 2
C18B C 0.5265(8) 0.4788(2) 0.4797(4) 0.107(3) Uani 0.5 1 d . . P D 2
C9B C 0.2184(4) -0.07814(16) 0.1382(2) 0.0187(8) Uani 1 1 d . . . . .
H9B1 H 0.2274 -0.1086 0.0960 0.022 Uiso 1 1 calc R U . . .
H9B2 H 0.2967 -0.0575 0.1450 0.022 Uiso 1 1 calc R U . . .
H3NB H -0.141(3) -0.0931(17) 0.257(2) 0.022 Uiso 1 1 d D U . . .
H3N H 0.642(3) 0.3476(17) 0.245(2) 0.022 Uiso 1 1 d D U . . .
H4NB H 0.184(4) -0.0738(13) 0.260(2) 0.022 Uiso 1 1 d D U . . .
H4N H 0.317(4) 0.3221(12) 0.253(2) 0.022 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 N1 1.854(3) . ?
Fe1 N2 1.906(3) . ?
Fe1 C16 1.941(4) . ?
Fe1 C17 1.958(4) . ?
Fe1 N5 2.031(3) . ?
Fe1 N3 2.115(3) . ?
N1 C1 1.357(4) . ?
N1 C5 1.361(4) . ?
N5 C14 1.298(5) . ?
N5 C13 1.478(5) . ?
N6 C16 1.155(5) . ?
N7 C17 1.155(5) . ?
N4 C12 1.465(5) . ?
N4 C11 1.474(5) . ?
N4 H4N 0.963(19) . ?
N2 C6 1.294(5) . ?
N2 C8 1.471(4) . ?
N3 C10 1.487(4) . ?
N3 C9 1.491(4) . ?
N3 H3N 0.966(19) . ?
C13 C12 1.530(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 C2 1.388(5) . ?
C3 C4 1.393(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C2 C1 1.385(5) . ?
C2 H2 0.9300 . ?
C9 C8 1.512(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C6 1.500(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 C11 1.512(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 C6 1.465(5) . ?
C14 C1 1.473(5) . ?
C14 C15 1.500(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
Fe1B N1B 1.851(3) . ?
Fe1B N2B 1.901(3) . ?
Fe1B C17B 1.947(4) . ?
Fe1B C16B 1.961(4) . ?
Fe1B N5B 2.041(3) . ?
Fe1B N3B 2.111(3) . ?
N4B C9B 1.458(5) . ?
N4B C10B 1.481(5) . ?
N4B H4NB 0.953(19) . ?
N3B C11B 1.487(4) . ?
N3B C12B 1.487(4) . ?
N3B H3NB 0.963(18) . ?
N2B C14B 1.297(5) . ?
N2B C13B 1.469(4) . ?
N5B C6B 1.301(5) . ?
N5B C8B 1.476(5) . ?
N6B C16B 1.151(5) . ?
N7B C17B 1.159(5) . ?
N1B C5B 1.353(4) . ?
N1B C1B 1.363(4) . ?
C4B C3B 1.389(5) . ?
C4B C5B 1.390(5) . ?
C4B H4B 0.9300 . ?
C2B C3B 1.389(5) . ?
C2B C1B 1.396(5) . ?
C2B H2B 0.9300 . ?
C3B H3B 0.9300 . ?
C12B C13B 1.521(5) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C8B C9B 1.526(5) . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C6B C5B 1.468(5) . ?
C6B C7B 1.497(5) . ?
C11B C10B 1.515(5) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C14B C1B 1.457(5) . ?
C14B C15B 1.500(5) . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C18 O1 1.410(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1 H1 0.8200 . ?
O1C O1C 1.583(12) 3_665 ?
O1B O1B 1.320(10) 3_666 ?
C18C C18C 1.583(12) 3_665 ?
C18B C18B 1.320(10) 3_666 ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?

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 Fe1 N2 80.38(12) . . ?
N1 Fe1 C16 89.31(14) . . ?
N2 Fe1 C16 92.47(13) . . ?
N1 Fe1 C17 97.93(13) . . ?
N2 Fe1 C17 93.28(13) . . ?
C16 Fe1 C17 171.41(16) . . ?
N1 Fe1 N5 79.66(12) . . ?
N2 Fe1 N5 159.72(13) . . ?
C16 Fe1 N5 90.82(13) . . ?
C17 Fe1 N5 85.97(13) . . ?
N1 Fe1 N3 162.61(12) . . ?
N2 Fe1 N3 82.96(12) . . ?
C16 Fe1 N3 86.45(13) . . ?
C17 Fe1 N3 87.93(13) . . ?
N5 Fe1 N3 117.22(12) . . ?
C1 N1 C5 121.4(3) . . ?
C1 N1 Fe1 119.9(2) . . ?
C5 N1 Fe1 118.3(2) . . ?
C14 N5 C13 119.6(3) . . ?
C14 N5 Fe1 114.5(2) . . ?
C13 N5 Fe1 125.5(2) . . ?
C12 N4 C11 114.1(3) . . ?
C12 N4 H4N 103(2) . . ?
C11 N4 H4N 107(2) . . ?
C6 N2 C8 123.7(3) . . ?
C6 N2 Fe1 118.8(2) . . ?
C8 N2 Fe1 117.5(2) . . ?
C10 N3 C9 108.4(3) . . ?
C10 N3 Fe1 124.8(2) . . ?
C9 N3 Fe1 104.9(2) . . ?
C10 N3 H3N 105(2) . . ?
C9 N3 H3N 101(2) . . ?
Fe1 N3 H3N 110(2) . . ?
N5 C13 C12 112.8(3) . . ?
N5 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
N5 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
N3 C9 C8 110.2(3) . . ?
N3 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N7 C17 Fe1 177.3(3) . . ?
N3 C10 C11 113.4(3) . . ?
N3 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N3 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N4 C11 C10 111.6(3) . . ?
N4 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N4 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C5 C4 120.4(3) . . ?
N1 C5 C6 110.7(3) . . ?
C4 C5 C6 128.9(3) . . ?
N2 C6 C5 111.7(3) . . ?
N2 C6 C7 125.5(3) . . ?
C5 C6 C7 122.8(3) . . ?
N5 C14 C1 114.2(3) . . ?
N5 C14 C15 127.3(3) . . ?
C1 C14 C15 118.4(3) . . ?
N2 C8 C9 106.0(3) . . ?
N2 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
N2 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C1 C2 120.3(3) . . ?
N1 C1 C14 110.9(3) . . ?
C2 C1 C14 128.8(3) . . ?
N4 C12 C13 115.6(3) . . ?
N4 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
N4 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
N6 C16 Fe1 177.9(3) . . ?
N1B Fe1B N2B 80.59(12) . . ?
N1B Fe1B C17B 96.75(14) . . ?
N2B Fe1B C17B 92.46(13) . . ?
N1B Fe1B C16B 90.66(14) . . ?
N2B Fe1B C16B 93.56(14) . . ?
C17B Fe1B C16B 171.13(16) . . ?
N1B Fe1B N5B 79.37(12) . . ?
N2B Fe1B N5B 159.28(13) . . ?
C17B Fe1B N5B 84.75(13) . . ?
C16B Fe1B N5B 91.86(13) . . ?
N1B Fe1B N3B 163.47(12) . . ?
N2B Fe1B N3B 83.21(12) . . ?
C17B Fe1B N3B 87.19(13) . . ?
C16B Fe1B N3B 87.06(13) . . ?
N5B Fe1B N3B 117.05(12) . . ?
C9B N4B C10B 115.1(3) . . ?
C9B N4B H4NB 106(2) . . ?
C10B N4B H4NB 107(2) . . ?
C11B N3B C12B 108.4(3) . . ?
C11B N3B Fe1B 124.8(2) . . ?
C12B N3B Fe1B 105.0(2) . . ?
C11B N3B H3NB 108(2) . . ?
C12B N3B H3NB 105(2) . . ?
Fe1B N3B H3NB 104(2) . . ?
C14B N2B C13B 123.7(3) . . ?
C14B N2B Fe1B 118.7(2) . . ?
C13B N2B Fe1B 117.5(2) . . ?
C6B N5B C8B 120.1(3) . . ?
C6B N5B Fe1B 114.2(2) . . ?
C8B N5B Fe1B 124.8(2) . . ?
C5B N1B C1B 121.6(3) . . ?
C5B N1B Fe1B 120.4(2) . . ?
C1B N1B Fe1B 117.9(2) . . ?
N6B C16B Fe1B 177.3(3) . . ?
C3B C4B C5B 118.1(3) . . ?
C3B C4B H4B 120.9 . . ?
C5B C4B H4B 120.9 . . ?
C3B C2B C1B 118.3(3) . . ?
C3B C2B H2B 120.8 . . ?
C1B C2B H2B 120.8 . . ?
C4B C3B C2B 121.4(3) . . ?
C4B C3B H3B 119.3 . . ?
C2B C3B H3B 119.3 . . ?
N3B C12B C13B 110.0(3) . . ?
N3B C12B H12C 109.7 . . ?
C13B C12B H12C 109.7 . . ?
N3B C12B H12D 109.7 . . ?
C13B C12B H12D 109.7 . . ?
H12C C12B H12D 108.2 . . ?
N5B C8B C9B 111.9(3) . . ?
N5B C8B H8B1 109.2 . . ?
C9B C8B H8B1 109.2 . . ?
N5B C8B H8B2 109.2 . . ?
C9B C8B H8B2 109.2 . . ?
H8B1 C8B H8B2 107.9 . . ?
N5B C6B C5B 114.2(3) . . ?
N5B C6B C7B 126.8(3) . . ?
C5B C6B C7B 118.8(3) . . ?
N7B C17B Fe1B 177.0(3) . . ?
N3B C11B C10B 112.7(3) . . ?
N3B C11B H11C 109.0 . . ?
C10B C11B H11C 109.0 . . ?
N3B C11B H11D 109.0 . . ?
C10B C11B H11D 109.0 . . ?
H11C C11B H11D 107.8 . . ?
N2B C14B C1B 111.6(3) . . ?
N2B C14B C15B 125.2(3) . . ?
C1B C14B C15B 123.2(3) . . ?
N1B C1B C2B 119.9(3) . . ?
N1B C1B C14B 111.1(3) . . ?
C2B C1B C14B 128.9(3) . . ?
N1B C5B C4B 120.6(3) . . ?
N1B C5B C6B 111.0(3) . . ?
C4B C5B C6B 128.3(3) . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N2B C13B C12B 105.8(3) . . ?
N2B C13B H13C 110.6 . . ?
C12B C13B H13C 110.6 . . ?
N2B C13B H13D 110.6 . . ?
C12B C13B H13D 110.6 . . ?
H13C C13B H13D 108.7 . . ?
N4B C10B C11B 111.7(3) . . ?
N4B C10B H10C 109.3 . . ?
C11B C10B H10C 109.3 . . ?
N4B C10B H10D 109.3 . . ?
C11B C10B H10D 109.3 . . ?
H10C C10B H10D 107.9 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C18 O1 H1 109.5 . . ?
N4B C9B C8B 115.6(3) . . ?
N4B C9B H9B1 108.4 . . ?
C8B C9B H9B1 108.4 . . ?
N4B C9B H9B2 108.4 . . ?
C8B C9B H9B2 108.4 . . ?
H9B1 C9B H9B2 107.4 . . ?

_refine_diff_density_max         1.292
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1521744'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C17 H23 Fe N7), 2(C H4 O)'
_chemical_formula_sum            'C36 H54 Fe2 N14 O2'
_chemical_formula_weight         826.63

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.8708(8)
_cell_length_b                   23.2716(18)
_cell_length_c                   15.6275(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.751(3)
_cell_angle_gamma                90
_cell_volume                     3939.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2582
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.92

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.789
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29945
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.573
_diffrn_reflns_theta_max         25.260
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7095
_reflns_number_gt                3782
_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    'Bruker APEX2, intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to 
ideal positions and refined isotropically using a riding model, excpet for those 
on nitrogen atoms which were localized on the difference Fourier map, and refined 
using DFIX constraints. The crystal structure contains two crystallographically disordered 
methanol molecules (one bearing O3 and C19A, and one bearing O2 and C19B atoms)
which was refined over two positions using EADP and EXYZ constraints. Hydrogen atoms on these 
disordered solvent molecules were not introduced but are taken into account in the compound formula.
;
_vrf_PLAT973_shelx               
;
PROBLEM: Check Calcd Positive Residual Density on     Fe1       2.31 eA-3  
RESPONSE: The residual electron density observed next to Fe1 suggests a few percentage of the compound in its high-spin configuration, since it is localized in the same position where the Fe1 appears in the structure with a high-spin state. This can be explained taking into account that the structure was collected after gently increasing  the temperature of the crystal from 82 to 250 K, allowing the system to transit from a photo-induced high-spin state to a low-spin configuration. In this process, a few percentage of the compound could have been kept in its high-spin configuration. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1641P)²] 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         7095
_refine_ls_number_parameters     503
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2836
_refine_ls_wR_factor_gt          0.2340
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Fe1B Fe 0.01884(8) 0.00096(5) 0.23971(5) 0.0198(3) Uani 1 1 d . . . . .
N4B N -0.1956(5) -0.1055(2) 0.2773(4) 0.0325(14) Uani 1 1 d D . . . .
N6B N -0.2054(6) -0.0071(3) 0.1049(4) 0.0437(17) Uani 1 1 d . . . . .
N7B N 0.2263(5) -0.0092(3) 0.3865(4) 0.0370(15) Uani 1 1 d . . . . .
N1B N 0.0019(4) 0.0798(3) 0.2442(3) 0.0206(14) Uani 1 1 d . . . . .
N5B N -0.0947(5) 0.0084(2) 0.3354(3) 0.0272(13) Uani 1 1 d . . . . .
N2B N 0.1312(5) 0.0228(2) 0.1571(3) 0.0253(13) Uani 1 1 d . . . . .
N3B N 0.0674(5) -0.0830(2) 0.2035(3) 0.0261(12) Uani 1 1 d D . . . .
C1B C -0.0783(6) 0.1044(3) 0.2952(4) 0.0258(15) Uani 1 1 d . . . . .
C14B C -0.1294(6) 0.0609(3) 0.3498(4) 0.0279(16) Uani 1 1 d . . . . .
C6B C 0.1458(6) 0.0768(3) 0.1424(4) 0.0239(15) Uani 1 1 d . . . . .
C17B C 0.1506(6) -0.0046(3) 0.3309(4) 0.0215(14) Uani 1 1 d . . . . .
C16B C -0.1201(6) -0.0040(3) 0.1529(4) 0.0250(14) Uani 1 1 d . . . . .
C5B C 0.0681(6) 0.1121(3) 0.1923(4) 0.0249(15) Uani 1 1 d . . . . .
C9B C 0.1175(6) -0.0764(3) 0.1172(4) 0.0302(16) Uani 1 1 d . . . . .
H2B1 H 0.1651 -0.1102 0.1048 0.036 Uiso 1 1 calc R U . . .
H2B2 H 0.0497 -0.0729 0.0731 0.036 Uiso 1 1 calc R U . . .
C8B C 0.1981(6) -0.0240(3) 0.1167(4) 0.0364(18) Uani 1 1 d . . . . .
H1B1 H 0.2768 -0.0311 0.1489 0.044 Uiso 1 1 calc R U . . .
H1B2 H 0.2132 -0.0138 0.0583 0.044 Uiso 1 1 calc R U . . .
C10B C -0.0171(6) -0.1334(3) 0.1994(5) 0.0343(17) Uani 1 1 d . . . . .
H3B1 H 0.0302 -0.1678 0.1902 0.041 Uiso 1 1 calc R U . . .
H3B2 H -0.0776 -0.1289 0.1507 0.041 Uiso 1 1 calc R U . . .
C2B C -0.0985(7) 0.1628(3) 0.2935(5) 0.0372(19) Uani 1 1 d . . . . .
H2B H -0.1563 0.1795 0.3264 0.045 Uiso 1 1 calc R U . . .
C13B C -0.1199(6) -0.0380(3) 0.3967(4) 0.0335(17) Uani 1 1 d . . . . .
H6B1 H -0.1465 -0.0210 0.4488 0.040 Uiso 1 1 calc R U . . .
H6B2 H -0.0443 -0.0592 0.4118 0.040 Uiso 1 1 calc R U . . .
C3B C -0.0308(7) 0.1956(4) 0.2419(5) 0.0433(19) Uani 1 1 d . . . . .
H3B H -0.0422 0.2352 0.2410 0.052 Uiso 1 1 calc R U . . .
C4B C 0.0530(7) 0.1721(3) 0.1917(5) 0.0361(18) Uani 1 1 d . . . . .
H4B H 0.0991 0.1953 0.1579 0.043 Uiso 1 1 calc R U . . .
C15B C -0.2091(7) 0.0794(3) 0.4191(5) 0.046(2) Uani 1 1 d . . . . .
H8B1 H -0.2212 0.1203 0.4161 0.068 Uiso 1 1 calc R U . . .
H8B2 H -0.2875 0.0604 0.4112 0.068 Uiso 1 1 calc R U . . .
H8B3 H -0.1693 0.0695 0.4743 0.068 Uiso 1 1 calc R U . . .
C11B C -0.0831(7) -0.1408(3) 0.2790(5) 0.0346(17) Uani 1 1 d . . . . .
H4B1 H -0.1050 -0.1810 0.2849 0.042 Uiso 1 1 calc R U . . .
H4B2 H -0.0281 -0.1303 0.3286 0.042 Uiso 1 1 calc R U . . .
C12B C -0.2186(7) -0.0794(3) 0.3596(5) 0.0416(19) Uani 1 1 d . . . . .
H5B2 H -0.2274 -0.1099 0.4009 0.050 Uiso 1 1 calc R U . . .
H5B1 H -0.2965 -0.0589 0.3526 0.050 Uiso 1 1 calc R U . . .
C7B C 0.2333(7) 0.1007(3) 0.0807(5) 0.042(2) Uani 1 1 d . . . . .
H7B1 H 0.3159 0.0884 0.0979 0.063 Uiso 1 1 calc R U . . .
H7B2 H 0.2298 0.1419 0.0812 0.063 Uiso 1 1 calc R U . . .
H7B3 H 0.2096 0.0870 0.0238 0.063 Uiso 1 1 calc R U . . .
Fe1 Fe 0.47932(8) 0.24900(5) 0.25019(5) 0.0210(3) Uani 1 1 d . . . . .
N1 N 0.4951(4) 0.1705(2) 0.2422(3) 0.0183(13) Uani 1 1 d . . . . .
N6 N 0.7052(6) 0.2532(3) 0.3832(4) 0.0449(18) Uani 1 1 d . . . . .
N7 N 0.2719(5) 0.2626(3) 0.1035(4) 0.0380(16) Uani 1 1 d . . . . .
N5 N 0.5921(5) 0.2433(2) 0.1546(3) 0.0252(12) Uani 1 1 d . . . . .
N2 N 0.3693(5) 0.2267(2) 0.3327(3) 0.0244(13) Uani 1 1 d . . . . .
N3 N 0.4334(5) 0.3324(2) 0.2911(4) 0.0292(13) Uani 1 1 d D . . . .
N4 N 0.6970(5) 0.3561(3) 0.2180(4) 0.0344(14) Uani 1 1 d D . . . .
C16 C 0.6193(6) 0.2512(3) 0.3357(4) 0.0255(15) Uani 1 1 d . . . . .
C14 C 0.6292(6) 0.1911(3) 0.1387(4) 0.0250(15) Uani 1 1 d . . . . .
C6 C 0.3537(6) 0.1725(3) 0.3468(4) 0.0287(16) Uani 1 1 d . . . . .
C17 C 0.3473(6) 0.2571(3) 0.1588(4) 0.0235(15) Uani 1 1 d . . . . .
C1 C 0.5775(6) 0.1466(3) 0.1922(4) 0.0217(14) Uani 1 1 d . . . . .
C13 C 0.6198(6) 0.2907(3) 0.0955(4) 0.0329(17) Uani 1 1 d . . . . .
H13B H 0.5449 0.3124 0.0806 0.040 Uiso 1 1 calc R U . . .
H13A H 0.6467 0.2744 0.0430 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4290(6) 0.1373(3) 0.2942(4) 0.0243(15) Uani 1 1 d . . . . .
C8 C 0.3042(6) 0.2717(3) 0.3770(4) 0.0336(17) Uani 1 1 d . . . . .
H8A H 0.2910 0.2598 0.4350 0.040 Uiso 1 1 calc R U . . .
H8B H 0.2248 0.2798 0.3465 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5181(6) 0.3827(3) 0.2970(4) 0.0319(16) Uani 1 1 d . . . . .
H10A H 0.5789 0.3774 0.3454 0.038 Uiso 1 1 calc R U . . .
H10B H 0.4711 0.4170 0.3076 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3861(6) 0.3234(3) 0.3782(4) 0.0338(17) Uani 1 1 d . . . . .
H9B H 0.4552 0.3182 0.4209 0.041 Uiso 1 1 calc R U . . .
H9A H 0.3403 0.3570 0.3938 0.041 Uiso 1 1 calc R U . . .
C15 C 0.7135(7) 0.1728(3) 0.0714(5) 0.042(2) Uani 1 1 d . . . . .
H15A H 0.7250 0.1319 0.0741 0.063 Uiso 1 1 calc R U . . .
H15C H 0.6770 0.1832 0.0155 0.063 Uiso 1 1 calc R U . . .
H15B H 0.7919 0.1916 0.0819 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7187(7) 0.3310(3) 0.1342(5) 0.0415(19) Uani 1 1 d . . . . .
H12B H 0.7963 0.3102 0.1403 0.050 Uiso 1 1 calc R U . . .
H12A H 0.7282 0.3621 0.0940 0.050 Uiso 1 1 calc R U . . .
C3 C 0.5301(8) 0.0543(3) 0.2444(5) 0.0436(19) Uani 1 1 d . . . . .
H3 H 0.5424 0.0148 0.2455 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2704(8) 0.1480(3) 0.4087(5) 0.049(2) Uani 1 1 d . . . . .
H7C H 0.2750 0.1068 0.4074 0.074 Uiso 1 1 calc R U . . .
H7A H 0.2957 0.1614 0.4656 0.074 Uiso 1 1 calc R U . . .
H7B H 0.1871 0.1599 0.3930 0.074 Uiso 1 1 calc R U . . .
C4 C 0.4451(7) 0.0783(3) 0.2946(5) 0.0401(19) Uani 1 1 d . . . . .
H4 H 0.3991 0.0550 0.3283 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5840(6) 0.3913(3) 0.2165(5) 0.0340(17) Uani 1 1 d . . . . .
H11A H 0.5291 0.3811 0.1668 0.041 Uiso 1 1 calc R U . . .
H11B H 0.6056 0.4316 0.2114 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5971(7) 0.0879(3) 0.1927(5) 0.0383(19) Uani 1 1 d . . . . .
H2 H 0.6542 0.0715 0.1589 0.046 Uiso 1 1 calc R U . . .
C18 C 0.9927(16) 0.2402(7) 0.9725(9) 0.113(5) Uani 1 1 d . . . . .
O1 O 1.0048(12) 0.2820(6) 1.0243(9) 0.189(7) Uani 1 1 d . . . . .
O18D O 0.5103(17) -0.0224(6) 0.4792(9) 0.155(6) Uani 0.5 1 d . . P A 1
C18B C 0.507(5) 0.010(2) -0.005(3) 0.099(6) Uani 0.5 1 d . . P B 1
C18D C 0.5103(17) -0.0224(6) 0.4792(9) 0.155(6) Uani 0.5 1 d . . P C 2
O18B O 0.465(2) 0.0284(10) -0.0424(13) 0.099(6) Uani 0.5 1 d . . P D 2
H3BN H 0.135(7) -0.103(4) 0.238(6) 0.119 Uiso 1 1 d D U . . .
H3N H 0.362(7) 0.350(4) 0.257(6) 0.119 Uiso 1 1 d D U . . .
H4BN H -0.195(10) -0.068(2) 0.248(6) 0.119 Uiso 1 1 d D U . . .
H4N H 0.702(10) 0.318(2) 0.243(6) 0.119 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
Fe1B N1B 1.846(6) . ?
Fe1B N2B 1.917(5) . ?
Fe1B C17B 1.939(6) . ?
Fe1B C16B 1.948(7) . ?
Fe1B N5B 2.024(5) . ?
Fe1B N3B 2.112(5) . ?
N4B C12B 1.462(9) . ?
N4B C11B 1.473(9) . ?
N4B H4BN 0.98(2) . ?
N6B C16B 1.145(9) . ?
N7B C17B 1.152(8) . ?
N1B C5B 1.355(8) . ?
N1B C1B 1.356(8) . ?
N5B C14B 1.303(9) . ?
N5B C13B 1.484(8) . ?
N2B C6B 1.291(8) . ?
N2B C8B 1.479(8) . ?
N3B C10B 1.489(8) . ?
N3B C9B 1.503(8) . ?
N3B H3BN 0.99(2) . ?
C1B C2B 1.378(10) . ?
C1B C14B 1.462(10) . ?
C14B C15B 1.505(9) . ?
C6B C5B 1.451(9) . ?
C6B C7B 1.515(9) . ?
C5B C4B 1.407(9) . ?
C9B C8B 1.502(9) . ?
C9B H2B1 0.9700 . ?
C9B H2B2 0.9700 . ?
C8B H1B1 0.9700 . ?
C8B H1B2 0.9700 . ?
C10B C11B 1.496(9) . ?
C10B H3B1 0.9700 . ?
C10B H3B2 0.9700 . ?
C2B C3B 1.368(11) . ?
C2B H2B 0.9300 . ?
C13B C12B 1.519(9) . ?
C13B H6B1 0.9700 . ?
C13B H6B2 0.9700 . ?
C3B C4B 1.364(10) . ?
C3B H3B 0.9300 . ?
C4B H4B 0.9300 . ?
C15B H8B1 0.9600 . ?
C15B H8B2 0.9600 . ?
C15B H8B3 0.9600 . ?
C11B H4B1 0.9700 . ?
C11B H4B2 0.9700 . ?
C12B H5B2 0.9700 . ?
C12B H5B1 0.9700 . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
Fe1 N1 1.839(6) . ?
Fe1 N2 1.902(5) . ?
Fe1 C16 1.941(7) . ?
Fe1 C17 1.949(6) . ?
Fe1 N5 2.014(5) . ?
Fe1 N3 2.116(5) . ?
N1 C1 1.356(8) . ?
N1 C5 1.368(8) . ?
N6 C16 1.144(9) . ?
N7 C17 1.148(8) . ?
N5 C14 1.310(8) . ?
N5 C13 1.485(8) . ?
N2 C6 1.293(8) . ?
N2 C8 1.469(8) . ?
N3 C10 1.487(8) . ?
N3 C9 1.509(8) . ?
N3 H3N 1.00(2) . ?
N4 C12 1.470(9) . ?
N4 C11 1.475(9) . ?
N4 H4N 0.98(2) . ?
C14 C1 1.471(9) . ?
C14 C15 1.513(9) . ?
C6 C5 1.460(9) . ?
C6 C7 1.492(9) . ?
C1 C2 1.383(9) . ?
C13 C12 1.515(9) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C5 C4 1.386(10) . ?
C8 C9 1.497(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.512(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15C 0.9600 . ?
C15 H15B 0.9600 . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C3 C2 1.374(10) . ?
C3 C4 1.378(11) . ?
C3 H3 0.9300 . ?
C7 H7C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C4 H4 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2 0.9300 . ?
C18 O1 1.27(2) . ?
O18D O18D 1.26(2) 3_656 ?
C18B C18B 0.54(7) 3_655 ?
C18D C18D 1.26(2) 3_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1B Fe1B N2B 80.4(2) . . ?
N1B Fe1B C17B 96.2(2) . . ?
N2B Fe1B C17B 92.2(2) . . ?
N1B Fe1B C16B 90.7(2) . . ?
N2B Fe1B C16B 92.7(2) . . ?
C17B Fe1B C16B 172.1(3) . . ?
N1B Fe1B N5B 79.5(2) . . ?
N2B Fe1B N5B 159.4(3) . . ?
C17B Fe1B N5B 85.5(2) . . ?
C16B Fe1B N5B 92.0(2) . . ?
N1B Fe1B N3B 163.2(2) . . ?
N2B Fe1B N3B 82.9(2) . . ?
C17B Fe1B N3B 87.1(2) . . ?
C16B Fe1B N3B 87.5(2) . . ?
N5B Fe1B N3B 117.3(2) . . ?
C12B N4B C11B 114.7(6) . . ?
C12B N4B H4BN 93(6) . . ?
C11B N4B H4BN 118(6) . . ?
C5B N1B C1B 121.2(6) . . ?
C5B N1B Fe1B 117.9(4) . . ?
C1B N1B Fe1B 120.8(5) . . ?
C14B N5B C13B 120.0(6) . . ?
C14B N5B Fe1B 114.3(4) . . ?
C13B N5B Fe1B 124.8(5) . . ?
C6B N2B C8B 124.7(6) . . ?
C6B N2B Fe1B 118.2(5) . . ?
C8B N2B Fe1B 117.1(4) . . ?
C10B N3B C9B 108.0(5) . . ?
C10B N3B Fe1B 125.0(4) . . ?
C9B N3B Fe1B 105.3(4) . . ?
C10B N3B H3BN 95(6) . . ?
C9B N3B H3BN 103(6) . . ?
Fe1B N3B H3BN 118(6) . . ?
N1B C1B C2B 120.9(7) . . ?
N1B C1B C14B 110.2(6) . . ?
C2B C1B C14B 128.8(7) . . ?
N5B C14B C1B 114.8(6) . . ?
N5B C14B C15B 125.8(7) . . ?
C1B C14B C15B 119.4(7) . . ?
N2B C6B C5B 111.7(6) . . ?
N2B C6B C7B 124.3(6) . . ?
C5B C6B C7B 124.0(6) . . ?
N7B C17B Fe1B 177.5(6) . . ?
N6B C16B Fe1B 176.8(6) . . ?
N1B C5B C4B 119.1(6) . . ?
N1B C5B C6B 111.7(6) . . ?
C4B C5B C6B 129.1(6) . . ?
C8B C9B N3B 110.0(5) . . ?
C8B C9B H2B1 109.7 . . ?
N3B C9B H2B1 109.7 . . ?
C8B C9B H2B2 109.7 . . ?
N3B C9B H2B2 109.7 . . ?
H2B1 C9B H2B2 108.2 . . ?
N2B C8B C9B 106.7(5) . . ?
N2B C8B H1B1 110.4 . . ?
C9B C8B H1B1 110.4 . . ?
N2B C8B H1B2 110.4 . . ?
C9B C8B H1B2 110.4 . . ?
H1B1 C8B H1B2 108.6 . . ?
N3B C10B C11B 113.1(6) . . ?
N3B C10B H3B1 109.0 . . ?
C11B C10B H3B1 109.0 . . ?
N3B C10B H3B2 109.0 . . ?
C11B C10B H3B2 109.0 . . ?
H3B1 C10B H3B2 107.8 . . ?
C3B C2B C1B 118.0(7) . . ?
C3B C2B H2B 121.0 . . ?
C1B C2B H2B 121.0 . . ?
N5B C13B C12B 112.2(6) . . ?
N5B C13B H6B1 109.2 . . ?
C12B C13B H6B1 109.2 . . ?
N5B C13B H6B2 109.2 . . ?
C12B C13B H6B2 109.2 . . ?
H6B1 C13B H6B2 107.9 . . ?
C4B C3B C2B 122.2(8) . . ?
C4B C3B H3B 118.9 . . ?
C2B C3B H3B 118.9 . . ?
C3B C4B C5B 118.5(7) . . ?
C3B C4B H4B 120.8 . . ?
C5B C4B H4B 120.8 . . ?
C14B C15B H8B1 109.5 . . ?
C14B C15B H8B2 109.5 . . ?
H8B1 C15B H8B2 109.5 . . ?
C14B C15B H8B3 109.5 . . ?
H8B1 C15B H8B3 109.5 . . ?
H8B2 C15B H8B3 109.5 . . ?
N4B C11B C10B 112.0(6) . . ?
N4B C11B H4B1 109.2 . . ?
C10B C11B H4B1 109.2 . . ?
N4B C11B H4B2 109.2 . . ?
C10B C11B H4B2 109.2 . . ?
H4B1 C11B H4B2 107.9 . . ?
N4B C12B C13B 115.6(6) . . ?
N4B C12B H5B2 108.4 . . ?
C13B C12B H5B2 108.4 . . ?
N4B C12B H5B1 108.4 . . ?
C13B C12B H5B1 108.4 . . ?
H5B2 C12B H5B1 107.4 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
N1 Fe1 N2 80.9(2) . . ?
N1 Fe1 C16 90.0(3) . . ?
N2 Fe1 C16 92.4(2) . . ?
N1 Fe1 C17 96.5(2) . . ?
N2 Fe1 C17 93.3(2) . . ?
C16 Fe1 C17 171.9(3) . . ?
N1 Fe1 N5 79.5(2) . . ?
N2 Fe1 N5 160.1(2) . . ?
C16 Fe1 N5 91.2(2) . . ?
C17 Fe1 N5 85.4(2) . . ?
N1 Fe1 N3 163.1(2) . . ?
N2 Fe1 N3 82.4(2) . . ?
C16 Fe1 N3 87.7(3) . . ?
C17 Fe1 N3 87.4(3) . . ?
N5 Fe1 N3 117.2(2) . . ?
C1 N1 C5 121.0(6) . . ?
C1 N1 Fe1 121.1(4) . . ?
C5 N1 Fe1 117.7(4) . . ?
C14 N5 C13 119.3(5) . . ?
C14 N5 Fe1 114.6(4) . . ?
C13 N5 Fe1 125.5(4) . . ?
C6 N2 C8 122.6(6) . . ?
C6 N2 Fe1 118.7(4) . . ?
C8 N2 Fe1 118.7(4) . . ?
C10 N3 C9 108.0(5) . . ?
C10 N3 Fe1 125.5(4) . . ?
C9 N3 Fe1 104.6(4) . . ?
C10 N3 H3N 99(6) . . ?
C9 N3 H3N 104(6) . . ?
Fe1 N3 H3N 114(6) . . ?
C12 N4 C11 113.7(6) . . ?
C12 N4 H4N 89(6) . . ?
C11 N4 H4N 122(6) . . ?
N6 C16 Fe1 176.8(6) . . ?
N5 C14 C1 114.1(6) . . ?
N5 C14 C15 127.3(6) . . ?
C1 C14 C15 118.6(6) . . ?
N2 C6 C5 111.3(6) . . ?
N2 C6 C7 125.4(6) . . ?
C5 C6 C7 123.3(6) . . ?
N7 C17 Fe1 178.1(6) . . ?
N1 C1 C2 120.8(6) . . ?
N1 C1 C14 109.8(6) . . ?
C2 C1 C14 129.3(6) . . ?
N5 C13 C12 112.6(6) . . ?
N5 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
N5 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
H13B C13 H13A 107.8 . . ?
N1 C5 C4 119.4(6) . . ?
N1 C5 C6 111.4(6) . . ?
C4 C5 C6 129.1(6) . . ?
N2 C8 C9 105.6(5) . . ?
N2 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
N2 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
N3 C10 C11 112.8(5) . . ?
N3 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N3 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C8 C9 N3 110.3(5) . . ?
C8 C9 H9B 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N3 C9 H9A 109.6 . . ?
H9B C9 H9A 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
N4 C12 C13 116.2(6) . . ?
N4 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
N4 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
H12B C12 H12A 107.4 . . ?
C2 C3 C4 121.2(8) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C6 C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N4 C11 C10 111.4(6) . . ?
N4 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N4 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C3 C2 C1 118.4(7) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?

_refine_diff_density_max         2.579
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.170

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1521745'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 Fe N7, C H4 O'
_chemical_formula_sum            'C18 H27 Fe N7 O'
_chemical_formula_weight         413.31

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.8196(19)
_cell_length_b                   11.5806(18)
_cell_length_c                   15.777(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.491(7)
_cell_angle_gamma                90
_cell_volume                     1970.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    82(2)
_cell_measurement_reflns_used    3834
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.32

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   0.6094
_shelx_estimated_absorpt_T_max   0.7452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6040
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      82(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23738
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_av_R_equivalents  0.1521
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         25.454
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3593
_reflns_number_gt                2271
_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    'Bruker APEX2, intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were 
assigned to 
ideal positions and refined isotropically using a riding model, 
except for those 
on nitrogen atoms which were localized on the difference 
Fourier map, and refined 
using DFIX constraints.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²] 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         3593
_refine_ls_number_parameters     254
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.009
_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 0.25155(6) 0.23271(5) 0.51384(4) 0.0129(2) Uani 1 1 d . . . . .
N1 N 0.2385(3) 0.4173(3) 0.50427(19) 0.0138(8) Uani 1 1 d . . . . .
N5 N 0.3640(4) 0.2941(3) 0.4065(2) 0.0154(9) Uani 1 1 d . . . . .
N2 N 0.1338(4) 0.2968(3) 0.6156(2) 0.0147(9) Uani 1 1 d . . . . .
O1 O 0.7599(4) 0.1676(3) 0.6989(2) 0.0319(9) Uani 1 1 d . . . . .
H1 H 0.6921 0.1769 0.6700 0.048 Uiso 1 1 calc R U . . .
N4 N 0.3558(4) 0.0741(3) 0.4616(2) 0.0170(9) Uani 1 1 d D . . . .
N3 N 0.1862(4) 0.0737(3) 0.5879(2) 0.0163(9) Uani 1 1 d D . . . .
N7 N 0.5075(4) 0.2157(3) 0.6456(2) 0.0261(10) Uani 1 1 d . . . . .
N6 N 0.0092(4) 0.1427(4) 0.3922(2) 0.0308(11) Uani 1 1 d . . . . .
C1 C 0.3007(4) 0.4766(4) 0.4473(2) 0.0150(10) Uani 1 1 d . . . . .
C6 C 0.1068(4) 0.4036(4) 0.6177(2) 0.0148(10) Uani 1 1 d . . . . .
C14 C 0.3799(4) 0.4025(4) 0.3956(2) 0.0134(10) Uani 1 1 d . . . . .
C3 C 0.2034(5) 0.6536(4) 0.4837(3) 0.0213(11) Uani 1 1 d . . . . .
H3 H 0.1887 0.7338 0.4752 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1630(4) 0.4757(4) 0.5535(2) 0.0139(10) Uani 1 1 d . . . . .
C4 C 0.1419(4) 0.5941(4) 0.5428(2) 0.0183(11) Uani 1 1 d . . . . .
H4 H 0.0856 0.6331 0.5762 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4336(4) 0.2082(4) 0.3615(3) 0.0163(10) Uani 1 1 d . . . . .
H13A H 0.5204 0.2049 0.3863 0.020 Uiso 1 1 calc R U . . .
H13B H 0.4339 0.2291 0.3007 0.020 Uiso 1 1 calc R U . . .
C9 C 0.1724(5) 0.1076(4) 0.6760(2) 0.0184(11) Uani 1 1 d . . . . .
H9A H 0.2546 0.1257 0.7050 0.022 Uiso 1 1 calc R U . . .
H9B H 0.1355 0.0433 0.7069 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2683(4) -0.0256(4) 0.5771(3) 0.0186(11) Uani 1 1 d . . . . .
H10A H 0.2280 -0.0975 0.5947 0.022 Uiso 1 1 calc R U . . .
H10B H 0.3468 -0.0156 0.6129 0.022 Uiso 1 1 calc R U . . .
C16 C 0.0928(5) 0.1875(4) 0.4273(3) 0.0177(11) Uani 1 1 d . . . . .
C11 C 0.2945(4) -0.0332(4) 0.4842(2) 0.0164(10) Uani 1 1 d . . . . .
H11A H 0.3488 -0.1001 0.4751 0.020 Uiso 1 1 calc R U . . .
H11B H 0.2161 -0.0432 0.4482 0.020 Uiso 1 1 calc R U . . .
C8 C 0.0892(5) 0.2128(4) 0.6761(3) 0.0193(11) Uani 1 1 d . . . . .
H8A H 0.0024 0.1908 0.6589 0.023 Uiso 1 1 calc R U . . .
H8B H 0.0922 0.2468 0.7338 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2873(5) 0.5959(4) 0.4362(3) 0.0206(11) Uani 1 1 d . . . . .
H2 H 0.3341 0.6365 0.3974 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3708(5) 0.0913(4) 0.3706(2) 0.0172(10) Uani 1 1 d . . . . .
H12A H 0.2890 0.0903 0.3378 0.021 Uiso 1 1 calc R U . . .
H12B H 0.4226 0.0289 0.3490 0.021 Uiso 1 1 calc R U . . .
C7 C 0.0295(4) 0.4620(4) 0.6805(3) 0.0230(11) Uani 1 1 d . . . . .
H7A H -0.0124 0.4034 0.7128 0.034 Uiso 1 1 calc R U . . .
H7B H -0.0326 0.5114 0.6500 0.034 Uiso 1 1 calc R U . . .
H7C H 0.0831 0.5091 0.7197 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4679(4) 0.4575(4) 0.3393(3) 0.0217(11) Uani 1 1 d . . . . .
H15A H 0.4974 0.3994 0.3004 0.032 Uiso 1 1 calc R U . . .
H15B H 0.5386 0.4896 0.3741 0.032 Uiso 1 1 calc R U . . .
H15C H 0.4254 0.5195 0.3063 0.032 Uiso 1 1 calc R U . . .
C17 C 0.4165(5) 0.2346(4) 0.6037(3) 0.0175(10) Uani 1 1 d . . . . .
C18 C 0.7698(5) 0.2487(4) 0.7660(3) 0.0279(13) Uani 1 1 d . . . . .
H18A H 0.8560 0.2524 0.7901 0.042 Uiso 1 1 calc R U . . .
H18B H 0.7163 0.2251 0.8103 0.042 Uiso 1 1 calc R U . . .
H18C H 0.7440 0.3250 0.7443 0.042 Uiso 1 1 calc R U . . .
H4N H 0.436(2) 0.077(4) 0.492(2) 0.033 Uiso 1 1 d D U . . .
H3N H 0.110(3) 0.054(4) 0.555(2) 0.033 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 N1 2.147(4) . ?
Fe1 C16 2.173(5) . ?
Fe1 C17 2.191(5) . ?
Fe1 N2 2.252(3) . ?
Fe1 N5 2.275(3) . ?
Fe1 N3 2.320(4) . ?
Fe1 N4 2.339(4) . ?
N1 C1 1.352(5) . ?
N1 C5 1.352(5) . ?
N5 C14 1.280(5) . ?
N5 C13 1.464(5) . ?
N2 C6 1.272(5) . ?
N2 C8 1.470(5) . ?
O1 C18 1.414(5) . ?
O1 H1 0.8400 . ?
N4 C11 1.465(5) . ?
N4 C12 1.471(5) . ?
N4 H4N 0.956(19) . ?
N3 C9 1.464(5) . ?
N3 C10 1.471(5) . ?
N3 H3N 0.963(19) . ?
N7 C17 1.162(6) . ?
N6 C16 1.147(6) . ?
C1 C2 1.399(6) . ?
C1 C14 1.498(6) . ?
C6 C5 1.480(6) . ?
C6 C7 1.506(6) . ?
C14 C15 1.495(6) . ?
C3 C4 1.372(6) . ?
C3 C2 1.392(6) . ?
C3 H3 0.9500 . ?
C5 C4 1.398(6) . ?
C4 H4 0.9500 . ?
C13 C12 1.527(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C9 C8 1.515(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2 H2 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 Fe1 C16 98.71(15) . . ?
N1 Fe1 C17 94.65(15) . . ?
C16 Fe1 C17 166.64(17) . . ?
N1 Fe1 N2 71.60(12) . . ?
C16 Fe1 N2 93.69(14) . . ?
C17 Fe1 N2 90.73(14) . . ?
N1 Fe1 N5 70.88(12) . . ?
C16 Fe1 N5 92.84(14) . . ?
C17 Fe1 N5 91.30(14) . . ?
N2 Fe1 N5 142.47(13) . . ?
N1 Fe1 N3 143.57(12) . . ?
C16 Fe1 N3 82.43(15) . . ?
C17 Fe1 N3 86.98(15) . . ?
N2 Fe1 N3 71.99(12) . . ?
N5 Fe1 N3 145.54(12) . . ?
N1 Fe1 N4 142.00(12) . . ?
C16 Fe1 N4 88.19(15) . . ?
C17 Fe1 N4 81.09(14) . . ?
N2 Fe1 N4 145.60(12) . . ?
N5 Fe1 N4 71.49(12) . . ?
N3 Fe1 N4 74.25(12) . . ?
C1 N1 C5 118.9(4) . . ?
C1 N1 Fe1 121.3(3) . . ?
C5 N1 Fe1 119.8(3) . . ?
C14 N5 C13 121.5(3) . . ?
C14 N5 Fe1 119.4(3) . . ?
C13 N5 Fe1 118.2(3) . . ?
C6 N2 C8 122.6(3) . . ?
C6 N2 Fe1 118.9(3) . . ?
C8 N2 Fe1 118.5(3) . . ?
C18 O1 H1 109.5 . . ?
C11 N4 C12 116.0(3) . . ?
C11 N4 Fe1 109.9(2) . . ?
C12 N4 Fe1 109.3(3) . . ?
C11 N4 H4N 108(3) . . ?
C12 N4 H4N 109(3) . . ?
Fe1 N4 H4N 103(3) . . ?
C9 N3 C10 115.3(3) . . ?
C9 N3 Fe1 108.9(3) . . ?
C10 N3 Fe1 110.6(2) . . ?
C9 N3 H3N 115(3) . . ?
C10 N3 H3N 105(3) . . ?
Fe1 N3 H3N 101(3) . . ?
N1 C1 C2 122.1(4) . . ?
N1 C1 C14 114.0(4) . . ?
C2 C1 C14 123.8(4) . . ?
N2 C6 C5 115.1(4) . . ?
N2 C6 C7 126.5(4) . . ?
C5 C6 C7 118.4(4) . . ?
N5 C14 C15 126.5(4) . . ?
N5 C14 C1 113.6(4) . . ?
C15 C14 C1 119.9(4) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C6 114.2(4) . . ?
C4 C5 C6 124.4(4) . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N5 C13 C12 107.9(3) . . ?
N5 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
N5 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N3 C9 C8 108.7(3) . . ?
N3 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N3 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
N3 C10 C11 108.5(3) . . ?
N3 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
N3 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
N6 C16 Fe1 165.3(4) . . ?
N4 C11 C10 107.9(3) . . ?
N4 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
N4 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N2 C8 C9 107.9(3) . . ?
N2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
N4 C12 C13 107.2(3) . . ?
N4 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
N4 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 C17 Fe1 167.5(4) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.112

