# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_0179A-1
_database_code_depnum_ccdc_archive 'CCDC 1518351'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H44 Fe2 N2 O8'
_chemical_formula_sum            'C48 H44 Fe2 N2 O8'
_chemical_formula_weight         888.55

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                   10.0781(4)
_cell_length_b                   12.2736(5)
_cell_length_c                   18.5840(8)
_cell_angle_alpha                74.2212(19)
_cell_angle_beta                 75.854(2)
_cell_angle_gamma                70.4236(19)
_cell_volume                     2054.25(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    134289
_cell_measurement_theta_min      2.176
_cell_measurement_theta_max      35.754

_exptl_crystal_description       platy
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   0.689
_exptl_transmission_factor_max   0.747
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.765
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            134289
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         35.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             18791
_reflns_number_gt                12638
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0569P)²+0.5550P] 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         18791
_refine_ls_number_parameters     545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.48585(2) 0.96539(2) 0.09047(2) 0.01791(5) Uani 1 1 d . . . . .
N1 N 0.44304(14) 0.81287(11) 0.15890(7) 0.0197(2) Uani 1 1 d . . . . .
O1 O 0.44522(12) 1.02887(10) 0.17926(6) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.48243(12) 0.90243(9) -0.00191(6) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.68253(12) 0.88146(10) 0.09313(6) 0.0237(2) Uani 1 1 d . . . . .
O4 O 0.25426(13) 1.04278(11) 0.09238(7) 0.0257(2) Uani 1 1 d . . . . .
C1 C 0.37522(17) 0.80413(14) 0.22771(9) 0.0214(3) Uani 1 1 d . . . . .
H1A H 0.3621 0.7293 0.2537 0.026 Uiso 1 1 calc R U . . .
C2 C 0.31745(16) 0.89950(14) 0.26849(8) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.22493(18) 0.88062(15) 0.33829(9) 0.0259(3) Uani 1 1 d . . . . .
H3A H 0.1996 0.8087 0.3551 0.031 Uiso 1 1 calc R U . . .
C4 C 0.17078(19) 0.96462(17) 0.38240(10) 0.0295(3) Uani 1 1 d . . . . .
H4A H 0.1068 0.9518 0.4286 0.035 Uiso 1 1 calc R U . . .
C5 C 0.21109(19) 1.06895(16) 0.35839(10) 0.0290(3) Uani 1 1 d . . . . .
H5A H 0.1750 1.1267 0.3889 0.035 Uiso 1 1 calc R U . . .
C6 C 0.30277(18) 1.08922(14) 0.29077(9) 0.0242(3) Uani 1 1 d . . . . .
H6A H 0.3294 1.1605 0.2758 0.029 Uiso 1 1 calc R U . . .
C7 C 0.35737(16) 1.00617(14) 0.24374(8) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.43463(16) 0.81093(13) -0.00169(8) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.37148(17) 0.81383(14) -0.06139(9) 0.0225(3) Uani 1 1 d . . . . .
H9A H 0.3602 0.8808 -0.1021 0.027 Uiso 1 1 calc R U . . .
C10 C 0.32488(18) 0.71949(16) -0.06176(10) 0.0259(3) Uani 1 1 d . . . . .
H10A H 0.2833 0.7219 -0.1031 0.031 Uiso 1 1 calc R U . . .
C11 C 0.33866(19) 0.62195(15) -0.00217(10) 0.0274(3) Uani 1 1 d . . . . .
H11A H 0.3085 0.5568 -0.0029 0.033 Uiso 1 1 calc R U . . .
C12 C 0.39694(19) 0.62038(15) 0.05861(10) 0.0262(3) Uani 1 1 d . . . . .
H12A H 0.4036 0.5547 0.1002 0.031 Uiso 1 1 calc R U . . .
C13 C 0.44597(17) 0.71333(13) 0.05988(9) 0.0212(3) Uani 1 1 d . . . . .
C14 C 0.51047(18) 0.70531(13) 0.12768(9) 0.0226(3) Uani 1 1 d . . . . .
H14A H 0.4885 0.6377 0.1679 0.027 Uiso 1 1 calc R U . . .
C15 C 0.67342(18) 0.68022(14) 0.11009(9) 0.0242(3) Uani 1 1 d . . . . .
C16 C 0.7522(2) 0.56305(16) 0.10856(10) 0.0319(4) Uani 1 1 d . . . . .
H16A H 0.7028 0.5055 0.1184 0.038 Uiso 1 1 calc R U . . .
C17 C 0.9001(2) 0.52776(19) 0.09313(11) 0.0397(5) Uani 1 1 d . . . . .
H17A H 0.9511 0.4479 0.0907 0.048 Uiso 1 1 calc R U . . .
C18 C 0.9724(2) 0.6110(2) 0.08125(10) 0.0396(5) Uani 1 1 d . . . . .
H18A H 1.0739 0.5878 0.0718 0.048 Uiso 1 1 calc R U . . .
C19 C 0.89705(19) 0.72822(18) 0.08309(9) 0.0313(4) Uani 1 1 d . . . . .
H19A H 0.9482 0.7839 0.0758 0.038 Uiso 1 1 calc R U . . .
C20 C 0.74657(18) 0.76642(15) 0.09557(8) 0.0242(3) Uani 1 1 d . . . . .
C21 C 0.1762(2) 1.15992(16) 0.10705(11) 0.0334(4) Uani 1 1 d . . . . .
H21A H 0.1771 1.2209 0.0596 0.040 Uiso 1 1 calc R U . . .
H21B H 0.2176 1.1792 0.1435 0.040 Uiso 1 1 calc R U . . .
C22 C 0.0289(3) 1.1516(4) 0.1397(3) 0.0965(14) Uani 1 1 d . . . . .
H22A H 0.0140 1.1385 0.1957 0.116 Uiso 1 1 calc R U . . .
H22B H -0.0418 1.2262 0.1208 0.116 Uiso 1 1 calc R U . . .
C23 C 0.0103(3) 1.0550(3) 0.1178(2) 0.0677(9) Uani 1 1 d . . . . .
H23A H -0.0588 1.0846 0.0822 0.081 Uiso 1 1 calc R U . . .
H23B H -0.0259 1.0013 0.1629 0.081 Uiso 1 1 calc R U . . .
C24 C 0.15486(19) 0.99101(18) 0.08007(12) 0.0333(4) Uani 1 1 d . . . . .
H24A H 0.1790 0.9054 0.1029 0.040 Uiso 1 1 calc R U . . .
H24B H 0.1566 1.0017 0.0251 0.040 Uiso 1 1 calc R U . . .
Fe2 Fe 0.99211(2) 0.61511(2) 0.43396(2) 0.01662(5) Uani 1 1 d . . . . .
N2 N 0.96959(14) 0.62653(11) 0.32427(7) 0.0186(2) Uani 1 1 d . . . . .
O5 O 0.94602(12) 0.78287(9) 0.41451(6) 0.0203(2) Uani 1 1 d . . . . .
O6 O 1.19195(12) 0.58474(10) 0.39541(6) 0.0232(2) Uani 1 1 d . . . . .
O7 O 1.00577(12) 0.55937(9) 0.54494(6) 0.0185(2) Uani 1 1 d . . . . .
O8 O 0.75568(12) 0.65251(10) 0.46687(7) 0.0237(2) Uani 1 1 d . . . . .
C25 C 0.90405(17) 0.72125(13) 0.28162(8) 0.0205(3) Uani 1 1 d . . . . .
H25A H 0.9014 0.7170 0.2317 0.025 Uiso 1 1 calc R U . . .
C26 C 0.83399(16) 0.83379(13) 0.30407(8) 0.0197(3) Uani 1 1 d . . . . .
C27 C 0.85878(16) 0.86029(13) 0.36870(8) 0.0185(3) Uani 1 1 d . . . . .
C28 C 0.78866(18) 0.97361(14) 0.38411(9) 0.0241(3) Uani 1 1 d . . . . .
H28A H 0.8046 0.9931 0.4268 0.029 Uiso 1 1 calc R U . . .
C29 C 0.69668(18) 1.05734(14) 0.33812(10) 0.0254(3) Uani 1 1 d . . . . .
H29A H 0.6494 1.1330 0.3500 0.030 Uiso 1 1 calc R U . . .
C30 C 0.67266(18) 1.03179(14) 0.27453(9) 0.0247(3) Uani 1 1 d . . . . .
H30A H 0.6095 1.0897 0.2432 0.030 Uiso 1 1 calc R U . . .
C31 C 0.74166(18) 0.92151(14) 0.25759(9) 0.0238(3) Uani 1 1 d . . . . .
H31A H 0.7266 0.9045 0.2138 0.029 Uiso 1 1 calc R U . . .
C32 C 1.26815(17) 0.52201(14) 0.34291(9) 0.0230(3) Uani 1 1 d . . . . .
C33 C 1.41850(18) 0.48943(16) 0.33525(10) 0.0298(4) Uani 1 1 d . . . . .
H33A H 1.4604 0.5162 0.3652 0.036 Uiso 1 1 calc R U . . .
C34 C 1.5062(2) 0.41913(17) 0.28484(12) 0.0375(5) Uani 1 1 d . . . . .
H34A H 1.6071 0.3972 0.2811 0.045 Uiso 1 1 calc R U . . .
C35 C 1.4469(2) 0.38082(17) 0.23987(12) 0.0384(5) Uani 1 1 d . . . . .
H35A H 1.5063 0.3311 0.2062 0.046 Uiso 1 1 calc R U . . .
C36 C 1.2998(2) 0.41618(15) 0.24476(10) 0.0310(4) Uani 1 1 d . . . . .
H36A H 1.2598 0.3916 0.2128 0.037 Uiso 1 1 calc R U . . .
C37 C 1.20798(18) 0.48667(13) 0.29490(9) 0.0231(3) Uani 1 1 d . . . . .
C38 C 1.04829(18) 0.52060(13) 0.29269(8) 0.0214(3) Uani 1 1 d . . . . .
C39 C 1.01881(17) 0.57912(13) 0.66742(8) 0.0198(3) Uani 1 1 d . . . . .
C40 C 1.05783(18) 0.63728(14) 0.71023(9) 0.0243(3) Uani 1 1 d . . . . .
H40A H 1.0410 0.6144 0.7640 0.029 Uiso 1 1 calc R U . . .
C41 C 1.12061(19) 0.72765(15) 0.67617(10) 0.0256(3) Uani 1 1 d . . . . .
H41A H 1.1440 0.7678 0.7062 0.031 Uiso 1 1 calc R U . . .
C42 C 1.14877(18) 0.75862(15) 0.59757(10) 0.0239(3) Uani 1 1 d . . . . .
H42A H 1.1938 0.8192 0.5737 0.029 Uiso 1 1 calc R U . . .
C43 C 1.11176(16) 0.70192(13) 0.55361(9) 0.0204(3) Uani 1 1 d . . . . .
H43A H 1.1322 0.7234 0.4999 0.024 Uiso 1 1 calc R U . . .
C44 C 1.04454(16) 0.61341(13) 0.58799(8) 0.0181(3) Uani 1 1 d . . . . .
C45 C 0.66856(19) 0.73852(15) 0.51243(10) 0.0281(3) Uani 1 1 d . . . . .
H45A H 0.7144 0.8009 0.5067 0.034 Uiso 1 1 calc R U . . .
H45B H 0.6517 0.7002 0.5667 0.034 Uiso 1 1 calc R U . . .
C46 C 0.5298(2) 0.7893(2) 0.48064(19) 0.0591(7) Uani 1 1 d . . . . .
H46A H 0.4479 0.8142 0.5206 0.071 Uiso 1 1 calc R U . . .
H46B H 0.5342 0.8585 0.4386 0.071 Uiso 1 1 calc R U . . .
C47 C 0.5156(3) 0.6930(2) 0.4532(2) 0.0634(8) Uani 1 1 d . . . . .
H47A H 0.4840 0.7233 0.4032 0.076 Uiso 1 1 calc R U . . .
H47B H 0.4446 0.6565 0.4893 0.076 Uiso 1 1 calc R U . . .
C48 C 0.66132(18) 0.60364(17) 0.44662(11) 0.0298(4) Uani 1 1 d . . . . .
H48A H 0.6580 0.5272 0.4814 0.036 Uiso 1 1 calc R U . . .
H48B H 0.6947 0.5905 0.3941 0.036 Uiso 1 1 calc R U . . .
H38 H 1.034(2) 0.5374(16) 0.2389(11) 0.019(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O3 1.9091(12) . ?
Fe1 O1 1.9111(11) . ?
Fe1 O2 2.0203(10) 2_675 ?
Fe1 N1 2.0702(13) . ?
Fe1 O2 2.0770(11) . ?
Fe1 O4 2.2007(12) . ?
N1 C1 1.289(2) . ?
N1 C14 1.471(2) . ?
O1 C7 1.3275(18) . ?
O2 C8 1.3611(18) . ?
O2 Fe1 2.0202(10) 2_675 ?
O3 C20 1.334(2) . ?
O4 C24 1.441(2) . ?
O4 C21 1.453(2) . ?
C1 C2 1.447(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.413(2) . ?
C2 C7 1.422(2) . ?
C3 C4 1.377(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.407(2) . ?
C6 H6A 0.9500 . ?
C8 C9 1.395(2) . ?
C8 C13 1.409(2) . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.394(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.520(2) . ?
C14 C15 1.534(2) . ?
C14 H14A 1.0000 . ?
C15 C16 1.395(2) . ?
C15 C20 1.416(2) . ?
C16 C17 1.384(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.409(2) . ?
C19 H19A 0.9500 . ?
C21 C22 1.486(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.434(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.505(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
Fe2 O5 1.9032(11) . ?
Fe2 O6 1.9092(11) . ?
Fe2 O7 2.0122(10) . ?
Fe2 O7 2.0633(11) 2_766 ?
Fe2 N2 2.0678(12) . ?
Fe2 O8 2.2293(12) . ?
N2 C25 1.2870(19) . ?
N2 C38 1.4698(19) . ?
O5 C27 1.3292(17) . ?
O6 C32 1.334(2) . ?
O7 C44 1.3593(17) . ?
O7 Fe2 2.0633(11) 2_766 ?
O8 C48 1.444(2) . ?
O8 C45 1.450(2) . ?
C25 C26 1.448(2) . ?
C25 H25A 0.9500 . ?
C26 C31 1.410(2) . ?
C26 C27 1.423(2) . ?
C27 C28 1.405(2) . ?
C28 C29 1.385(2) . ?
C28 H28A 0.9500 . ?
C29 C30 1.395(2) . ?
C29 H29A 0.9500 . ?
C30 C31 1.382(2) . ?
C30 H30A 0.9500 . ?
C31 H31A 0.9500 . ?
C32 C33 1.413(2) . ?
C32 C37 1.415(2) . ?
C33 C34 1.388(3) . ?
C33 H33A 0.9500 . ?
C34 C35 1.387(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.386(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.398(2) . ?
C36 H36A 0.9500 . ?
C37 C38 1.529(2) . ?
C38 C39 1.524(2) 2_766 ?
C38 H38 1.000(19) . ?
C39 C40 1.395(2) . ?
C39 C44 1.404(2) . ?
C39 C38 1.523(2) 2_766 ?
C40 C41 1.387(2) . ?
C40 H40A 0.9500 . ?
C41 C42 1.388(2) . ?
C41 H41A 0.9500 . ?
C42 C43 1.387(2) . ?
C42 H42A 0.9500 . ?
C43 C44 1.397(2) . ?
C43 H43A 0.9500 . ?
C45 C46 1.521(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.468(3) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.510(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?

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
O3 Fe1 O1 98.37(5) . . ?
O3 Fe1 O2 96.88(5) . 2_675 ?
O1 Fe1 O2 105.77(5) . 2_675 ?
O3 Fe1 N1 86.07(5) . . ?
O1 Fe1 N1 88.71(5) . . ?
O2 Fe1 N1 164.55(5) 2_675 . ?
O3 Fe1 O2 93.18(5) . . ?
O1 Fe1 O2 167.56(5) . . ?
O2 Fe1 O2 77.23(5) 2_675 . ?
N1 Fe1 O2 87.49(5) . . ?
O3 Fe1 O4 173.56(5) . . ?
O1 Fe1 O4 83.13(5) . . ?
O2 Fe1 O4 88.69(5) 2_675 . ?
N1 Fe1 O4 87.71(5) . . ?
O2 Fe1 O4 84.89(4) . . ?
C1 N1 C14 119.02(13) . . ?
C1 N1 Fe1 125.01(11) . . ?
C14 N1 Fe1 115.60(9) . . ?
C7 O1 Fe1 128.56(10) . . ?
C8 O2 Fe1 127.30(9) . 2_675 ?
C8 O2 Fe1 128.01(9) . . ?
Fe1 O2 Fe1 102.78(5) 2_675 . ?
C20 O3 Fe1 128.14(11) . . ?
C24 O4 C21 108.44(14) . . ?
C24 O4 Fe1 128.19(10) . . ?
C21 O4 Fe1 123.37(11) . . ?
N1 C1 C2 125.04(14) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C3 C2 C7 119.60(15) . . ?
C3 C2 C1 117.44(14) . . ?
C7 C2 C1 122.82(14) . . ?
C4 C3 C2 121.13(16) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 119.24(16) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 120.89(16) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 121.15(15) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
O1 C7 C6 119.33(14) . . ?
O1 C7 C2 122.68(14) . . ?
C6 C7 C2 117.97(14) . . ?
O2 C8 C9 120.54(13) . . ?
O2 C8 C13 120.04(13) . . ?
C9 C8 C13 119.41(14) . . ?
C10 C9 C8 120.51(15) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C11 C10 C9 120.36(15) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 119.35(15) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C13 121.33(16) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C12 C13 C8 118.97(15) . . ?
C12 C13 C14 118.68(14) . . ?
C8 C13 C14 122.35(14) . . ?
N1 C14 C13 110.67(13) . . ?
N1 C14 C15 110.62(13) . . ?
C13 C14 C15 113.29(13) . . ?
N1 C14 H14A 107.3 . . ?
C13 C14 H14A 107.3 . . ?
C15 C14 H14A 107.3 . . ?
C16 C15 C20 119.14(16) . . ?
C16 C15 C14 116.03(16) . . ?
C20 C15 C14 124.82(14) . . ?
C17 C16 C15 122.3(2) . . ?
C17 C16 H16A 118.9 . . ?
C15 C16 H16A 118.9 . . ?
C16 C17 C18 118.84(18) . . ?
C16 C17 H17A 120.6 . . ?
C18 C17 H17A 120.6 . . ?
C17 C18 C19 120.29(18) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C20 121.51(19) . . ?
C18 C19 H19A 119.2 . . ?
C20 C19 H19A 119.2 . . ?
O3 C20 C19 117.74(16) . . ?
O3 C20 C15 124.41(15) . . ?
C19 C20 C15 117.85(16) . . ?
O4 C21 C22 103.74(19) . . ?
O4 C21 H21A 111.0 . . ?
C22 C21 H21A 111.0 . . ?
O4 C21 H21B 111.0 . . ?
C22 C21 H21B 111.0 . . ?
H21A C21 H21B 109.0 . . ?
C23 C22 C21 108.7(2) . . ?
C23 C22 H22A 109.9 . . ?
C21 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
C21 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C22 C23 C24 106.6(2) . . ?
C22 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
C22 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
O4 C24 C23 105.67(18) . . ?
O4 C24 H24A 110.6 . . ?
C23 C24 H24A 110.6 . . ?
O4 C24 H24B 110.6 . . ?
C23 C24 H24B 110.6 . . ?
H24A C24 H24B 108.7 . . ?
O5 Fe2 O6 97.24(5) . . ?
O5 Fe2 O7 105.77(4) . . ?
O6 Fe2 O7 97.61(5) . . ?
O5 Fe2 O7 167.21(5) . 2_766 ?
O6 Fe2 O7 94.67(5) . 2_766 ?
O7 Fe2 O7 77.15(4) . 2_766 ?
O5 Fe2 N2 89.29(5) . . ?
O6 Fe2 N2 85.79(5) . . ?
O7 Fe2 N2 163.91(5) . . ?
O7 Fe2 N2 86.92(4) 2_766 . ?
O5 Fe2 O8 82.50(5) . . ?
O6 Fe2 O8 174.13(5) . . ?
O7 Fe2 O8 88.09(4) . . ?
O7 Fe2 O8 85.18(4) 2_766 . ?
N2 Fe2 O8 88.34(5) . . ?
C25 N2 C38 119.71(13) . . ?
C25 N2 Fe2 124.50(10) . . ?
C38 N2 Fe2 115.45(9) . . ?
C27 O5 Fe2 127.00(9) . . ?
C32 O6 Fe2 127.52(10) . . ?
C44 O7 Fe2 126.79(9) . . ?
C44 O7 Fe2 128.02(9) . 2_766 ?
Fe2 O7 Fe2 102.85(4) . 2_766 ?
C48 O8 C45 107.76(13) . . ?
C48 O8 Fe2 128.94(10) . . ?
C45 O8 Fe2 123.26(10) . . ?
N2 C25 C26 124.84(14) . . ?
N2 C25 H25A 117.6 . . ?
C26 C25 H25A 117.6 . . ?
C31 C26 C27 119.31(14) . . ?
C31 C26 C25 117.75(14) . . ?
C27 C26 C25 122.90(13) . . ?
O5 C27 C28 118.87(13) . . ?
O5 C27 C26 122.80(13) . . ?
C28 C27 C26 118.33(13) . . ?
C29 C28 C27 121.06(15) . . ?
C29 C28 H28A 119.5 . . ?
C27 C28 H28A 119.5 . . ?
C28 C29 C30 120.74(15) . . ?
C28 C29 H29A 119.6 . . ?
C30 C29 H29A 119.6 . . ?
C31 C30 C29 119.34(14) . . ?
C31 C30 H30A 120.3 . . ?
C29 C30 H30A 120.3 . . ?
C30 C31 C26 121.20(15) . . ?
C30 C31 H31A 119.4 . . ?
C26 C31 H31A 119.4 . . ?
O6 C32 C33 117.30(16) . . ?
O6 C32 C37 124.24(14) . . ?
C33 C32 C37 118.46(16) . . ?
C34 C33 C32 121.31(19) . . ?
C34 C33 H33A 119.3 . . ?
C32 C33 H33A 119.3 . . ?
C35 C34 C33 120.11(18) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C36 C35 C34 119.03(18) . . ?
C36 C35 H35A 120.5 . . ?
C34 C35 H35A 120.5 . . ?
C35 C36 C37 122.51(19) . . ?
C35 C36 H36A 118.7 . . ?
C37 C36 H36A 118.7 . . ?
C36 C37 C32 118.48(16) . . ?
C36 C37 C38 116.51(16) . . ?
C32 C37 C38 125.02(14) . . ?
N2 C38 C39 109.92(12) . 2_766 ?
N2 C38 C37 111.15(13) . . ?
C39 C38 C37 113.43(13) 2_766 . ?
N2 C38 H38 108.6(11) . . ?
C39 C38 H38 104.1(11) 2_766 . ?
C37 C38 H38 109.3(11) . . ?
C40 C39 C44 118.72(14) . . ?
C40 C39 C38 119.71(13) . 2_766 ?
C44 C39 C38 121.56(13) . 2_766 ?
C41 C40 C39 121.58(15) . . ?
C41 C40 H40A 119.2 . . ?
C39 C40 H40A 119.2 . . ?
C40 C41 C42 119.10(14) . . ?
C40 C41 H41A 120.5 . . ?
C42 C41 H41A 120.5 . . ?
C43 C42 C41 120.53(15) . . ?
C43 C42 H42A 119.7 . . ?
C41 C42 H42A 119.7 . . ?
C42 C43 C44 120.33(14) . . ?
C42 C43 H43A 119.8 . . ?
C44 C43 H43A 119.8 . . ?
O7 C44 C43 120.35(13) . . ?
O7 C44 C39 119.95(13) . . ?
C43 C44 C39 119.70(13) . . ?
O8 C45 C46 103.61(15) . . ?
O8 C45 H45A 111.0 . . ?
C46 C45 H45A 111.0 . . ?
O8 C45 H45B 111.0 . . ?
C46 C45 H45B 111.0 . . ?
H45A C45 H45B 109.0 . . ?
C47 C46 C45 105.25(18) . . ?
C47 C46 H46A 110.7 . . ?
C45 C46 H46A 110.7 . . ?
C47 C46 H46B 110.7 . . ?
C45 C46 H46B 110.7 . . ?
H46A C46 H46B 108.8 . . ?
C46 C47 C48 106.54(18) . . ?
C46 C47 H47A 110.4 . . ?
C48 C47 H47A 110.4 . . ?
C46 C47 H47B 110.4 . . ?
C48 C47 H47B 110.4 . . ?
H47A C47 H47B 108.6 . . ?
O8 C48 C47 106.34(16) . . ?
O8 C48 H48A 110.5 . . ?
C47 C48 H48A 110.5 . . ?
O8 C48 H48B 110.5 . . ?
C47 C48 H48B 110.5 . . ?
H48A C48 H48B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C1 C2 172.87(14) . . . . ?
Fe1 N1 C1 C2 0.2(2) . . . . ?
N1 C1 C2 C3 169.10(16) . . . . ?
N1 C1 C2 C7 -15.2(2) . . . . ?
C7 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 C4 176.86(16) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
Fe1 O1 C7 C6 -157.25(12) . . . . ?
Fe1 O1 C7 C2 24.0(2) . . . . ?
C5 C6 C7 O1 -179.95(15) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C3 C2 C7 O1 179.15(14) . . . . ?
C1 C2 C7 O1 3.5(2) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C1 C2 C7 C6 -175.28(15) . . . . ?
Fe1 O2 C8 C9 -14.4(2) 2_675 . . . ?
Fe1 O2 C8 C9 147.05(12) . . . . ?
Fe1 O2 C8 C13 166.92(11) 2_675 . . . ?
Fe1 O2 C8 C13 -31.6(2) . . . . ?
O2 C8 C9 C10 178.91(14) . . . . ?
C13 C8 C9 C10 -2.4(2) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C11 C12 C13 C14 -179.18(16) . . . . ?
O2 C8 C13 C12 -179.66(14) . . . . ?
C9 C8 C13 C12 1.7(2) . . . . ?
O2 C8 C13 C14 0.1(2) . . . . ?
C9 C8 C13 C14 -178.63(15) . . . . ?
C1 N1 C14 C13 118.43(15) . . . . ?
Fe1 N1 C14 C13 -68.19(14) . . . . ?
C1 N1 C14 C15 -115.17(15) . . . . ?
Fe1 N1 C14 C15 58.21(14) . . . . ?
C12 C13 C14 N1 -128.58(15) . . . . ?
C8 C13 C14 N1 51.7(2) . . . . ?
C12 C13 C14 C15 106.52(17) . . . . ?
C8 C13 C14 C15 -73.20(19) . . . . ?
N1 C14 C15 C16 156.18(14) . . . . ?
C13 C14 C15 C16 -78.90(17) . . . . ?
N1 C14 C15 C20 -23.9(2) . . . . ?
C13 C14 C15 C20 100.98(17) . . . . ?
C20 C15 C16 C17 -0.2(2) . . . . ?
C14 C15 C16 C17 179.73(15) . . . . ?
C15 C16 C17 C18 2.2(3) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
Fe1 O3 C20 C19 168.51(11) . . . . ?
Fe1 O3 C20 C15 -11.7(2) . . . . ?
C18 C19 C20 O3 -177.07(15) . . . . ?
C18 C19 C20 C15 3.1(2) . . . . ?
C16 C15 C20 O3 177.76(15) . . . . ?
C14 C15 C20 O3 -2.1(2) . . . . ?
C16 C15 C20 C19 -2.4(2) . . . . ?
C14 C15 C20 C19 177.69(14) . . . . ?
C24 O4 C21 C22 27.0(2) . . . . ?
Fe1 O4 C21 C22 -153.1(2) . . . . ?
O4 C21 C22 C23 -21.3(4) . . . . ?
C21 C22 C23 C24 8.0(4) . . . . ?
C21 O4 C24 C23 -22.5(2) . . . . ?
Fe1 O4 C24 C23 157.53(16) . . . . ?
C22 C23 C24 O4 8.6(4) . . . . ?
C38 N2 C25 C26 -174.19(15) . . . . ?
Fe2 N2 C25 C26 -1.1(2) . . . . ?
N2 C25 C26 C31 -166.68(16) . . . . ?
N2 C25 C26 C27 15.8(2) . . . . ?
Fe2 O5 C27 C28 152.61(12) . . . . ?
Fe2 O5 C27 C26 -27.9(2) . . . . ?
C31 C26 C27 O5 -178.94(14) . . . . ?
C25 C26 C27 O5 -1.4(2) . . . . ?
C31 C26 C27 C28 0.5(2) . . . . ?
C25 C26 C27 C28 178.01(15) . . . . ?
O5 C27 C28 C29 -179.96(15) . . . . ?
C26 C27 C28 C29 0.6(2) . . . . ?
C27 C28 C29 C30 -0.9(3) . . . . ?
C28 C29 C30 C31 0.0(3) . . . . ?
C29 C30 C31 C26 1.1(3) . . . . ?
C27 C26 C31 C30 -1.3(2) . . . . ?
C25 C26 C31 C30 -178.96(15) . . . . ?
Fe2 O6 C32 C33 -166.33(11) . . . . ?
Fe2 O6 C32 C37 13.7(2) . . . . ?
O6 C32 C33 C34 176.70(15) . . . . ?
C37 C32 C33 C34 -3.4(2) . . . . ?
C32 C33 C34 C35 1.0(3) . . . . ?
C33 C34 C35 C36 1.6(3) . . . . ?
C34 C35 C36 C37 -1.8(3) . . . . ?
C35 C36 C37 C32 -0.7(2) . . . . ?
C35 C36 C37 C38 178.79(15) . . . . ?
O6 C32 C37 C36 -176.92(14) . . . . ?
C33 C32 C37 C36 3.2(2) . . . . ?
O6 C32 C37 C38 3.7(2) . . . . ?
C33 C32 C37 C38 -176.25(14) . . . . ?
C25 N2 C38 C39 -116.55(15) . . . 2_766 ?
Fe2 N2 C38 C39 69.72(14) . . . 2_766 ?
C25 N2 C38 C37 117.02(15) . . . . ?
Fe2 N2 C38 C37 -56.70(14) . . . . ?
C36 C37 C38 N2 -158.58(13) . . . . ?
C32 C37 C38 N2 20.8(2) . . . . ?
C36 C37 C38 C39 76.96(17) . . . 2_766 ?
C32 C37 C38 C39 -103.62(17) . . . 2_766 ?
C44 C39 C40 C41 0.2(2) . . . . ?
C38 C39 C40 C41 179.30(15) 2_766 . . . ?
C39 C40 C41 C42 -1.8(3) . . . . ?
C40 C41 C42 C43 1.5(3) . . . . ?
C41 C42 C43 C44 0.5(2) . . . . ?
Fe2 O7 C44 C43 -15.12(19) . . . . ?
Fe2 O7 C44 C43 144.45(12) 2_766 . . . ?
Fe2 O7 C44 C39 165.77(11) . . . . ?
Fe2 O7 C44 C39 -34.65(19) 2_766 . . . ?
C42 C43 C44 O7 178.74(14) . . . . ?
C42 C43 C44 C39 -2.2(2) . . . . ?
C40 C39 C44 O7 -179.08(14) . . . . ?
C38 C39 C44 O7 1.8(2) 2_766 . . . ?
C40 C39 C44 C43 1.8(2) . . . . ?
C38 C39 C44 C43 -177.31(14) 2_766 . . . ?
C48 O8 C45 C46 -32.4(2) . . . . ?
Fe2 O8 C45 C46 145.54(15) . . . . ?
O8 C45 C46 C47 30.1(3) . . . . ?
C45 C46 C47 C48 -16.9(3) . . . . ?
C45 O8 C48 C47 22.2(2) . . . . ?
Fe2 O8 C48 C47 -155.57(17) . . . . ?
C46 C47 C48 O8 -2.5(3) . . . . ?

_refine_diff_density_max         0.942
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_N0137A-1
_database_code_depnum_ccdc_archive 'CCDC 1518349'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35

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'

_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                   15.0129(9)
_cell_length_b                   6.7964(4)
_cell_length_c                   16.6082(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.3358(19)
_cell_angle_gamma                90
_cell_volume                     1617.62(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    49967
_cell_measurement_theta_min      3.215
_cell_measurement_theta_max      27.999

_exptl_crystal_description       platy
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.713
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49967
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3893
_reflns_number_gt                3131
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0666P)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         3893
_refine_ls_number_parameters     226
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.380
_refine_ls_restrained_S_all      1.369
_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
N1 N 0.20678(7) 0.76245(15) 0.05821(6) 0.0182(2) Uani 1 1 d . U . . .
O1 O 0.19896(6) 0.51422(13) 0.17542(5) 0.0229(2) Uani 1 1 d . U . . .
O2 O 0.22875(6) 1.17140(14) 0.10678(6) 0.0254(2) Uani 1 1 d . U . . .
O3 O 0.24197(7) 0.93913(13) -0.15767(6) 0.0264(2) Uani 1 1 d . U . . .
C1 C 0.11757(9) 0.77464(18) 0.04052(8) 0.0225(3) Uani 1 1 d . U . . .
H1A H 0.0853 0.8570 -0.0051 0.027 Uiso 1 1 calc R U . . .
C2 C 0.06411(9) 0.67193(19) 0.08524(8) 0.0234(3) Uani 1 1 d . U . . .
C3 C 0.10797(9) 0.54216(19) 0.15193(8) 0.0236(3) Uani 1 1 d . U . . .
C4 C 0.05046(11) 0.4434(2) 0.19290(10) 0.0370(4) Uani 1 1 d . U . . .
H4A H 0.0776 0.3543 0.2375 0.044 Uiso 1 1 calc R U . . .
C5 C -0.04420(11) 0.4757(3) 0.16857(11) 0.0446(4) Uani 1 1 d . U . . .
H5A H -0.0814 0.4084 0.1971 0.054 Uiso 1 1 calc R U . . .
C6 C -0.08700(11) 0.6039(2) 0.10357(11) 0.0405(4) Uani 1 1 d . U . . .
H6A H -0.1525 0.6253 0.0883 0.049 Uiso 1 1 calc R U . . .
C7 C -0.03377(10) 0.6995(2) 0.06155(10) 0.0335(3) Uani 1 1 d . U . . .
H7A H -0.0628 0.7851 0.0161 0.040 Uiso 1 1 calc R U . . .
C8 C 0.26317(8) 0.86523(18) 0.01159(7) 0.0185(3) Uani 1 1 d . U . . .
H8A H 0.2221 0.9649 -0.0260 0.022 Uiso 1 1 calc R U . . .
C9 C 0.34251(9) 0.97492(18) 0.07321(7) 0.0195(3) Uani 1 1 d . U . . .
C10 C 0.32088(9) 1.13200(18) 0.11889(7) 0.0204(3) Uani 1 1 d . U . . .
C11 C 0.39134(10) 1.24357(19) 0.17259(8) 0.0245(3) Uani 1 1 d . U . . .
H11A H 0.3761 1.3492 0.2036 0.029 Uiso 1 1 calc R U . . .
C12 C 0.48407(10) 1.2006(2) 0.18098(8) 0.0293(3) Uani 1 1 d . U . . .
H12A H 0.5322 1.2772 0.2177 0.035 Uiso 1 1 calc R U . . .
C13 C 0.50670(9) 1.0472(2) 0.13618(8) 0.0290(3) Uani 1 1 d . U . . .
H13A H 0.5702 1.0185 0.1420 0.035 Uiso 1 1 calc R U . . .
C14 C 0.43633(9) 0.9348(2) 0.08264(8) 0.0240(3) Uani 1 1 d . U . . .
H14A H 0.4522 0.8293 0.0520 0.029 Uiso 1 1 calc R U . . .
C15 C 0.29192(8) 0.71711(18) -0.04416(7) 0.0189(3) Uani 1 1 d . U . . .
C16 C 0.27487(8) 0.75701(17) -0.13005(7) 0.0191(3) Uani 1 1 d . U . . .
C17 C 0.29227(10) 0.6126(2) -0.18324(8) 0.0261(3) Uani 1 1 d . U . . .
H17A H 0.2785 0.6374 -0.2420 0.031 Uiso 1 1 calc R U . . .
C18 C 0.32956(11) 0.4337(2) -0.15033(9) 0.0319(3) Uani 1 1 d . U . . .
H18A H 0.3408 0.3355 -0.1869 0.038 Uiso 1 1 calc R U . . .
C19 C 0.35078(10) 0.3956(2) -0.06462(9) 0.0312(3) Uani 1 1 d . U . . .
H19A H 0.3783 0.2740 -0.0420 0.037 Uiso 1 1 calc R U . . .
C20 C 0.33130(10) 0.53729(19) -0.01261(8) 0.0258(3) Uani 1 1 d . U . . .
H20A H 0.3451 0.5112 0.0460 0.031 Uiso 1 1 calc R U . . .
H2 H 0.2228(10) 1.283(2) 0.1359(10) 0.031 Uiso 1 1 d . U . . .
H3 H 0.2302(10) 0.953(2) -0.2157(10) 0.031 Uiso 1 1 d . U . . .
H1 H 0.2330(10) 0.680(2) 0.0981(10) 0.031 Uiso 1 1 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
N1 C1 1.2854(16) . ?
N1 C8 1.4815(15) . ?
N1 H1 0.869(16) . ?
O1 C3 1.3179(15) . ?
O2 C10 1.3637(15) . ?
O2 H2 0.921(17) . ?
O3 C16 1.3607(15) . ?
O3 H3 0.932(16) . ?
C1 C2 1.4277(18) . ?
C1 H1A 0.9500 . ?
C2 C3 1.416(2) . ?
C2 C7 1.4158(19) . ?
C3 C4 1.4172(18) . ?
C4 C5 1.374(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.371(2) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.5151(17) . ?
C8 C15 1.5151(16) . ?
C8 H8A 1.0000 . ?
C9 C14 1.3968(17) . ?
C9 C10 1.4027(18) . ?
C10 C11 1.3883(18) . ?
C11 C12 1.3883(19) . ?
C11 H11A 0.9500 . ?
C12 C13 1.381(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3891(19) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C20 1.3904(18) . ?
C15 C16 1.3986(16) . ?
C16 C17 1.3961(17) . ?
C17 C18 1.382(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3818(19) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 124.67(11) . . ?
C1 N1 H1 114.9(10) . . ?
C8 N1 H1 120.2(10) . . ?
C10 O2 H2 109.8(9) . . ?
C16 O3 H3 112.2(10) . . ?
N1 C1 C2 123.95(12) . . ?
N1 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C3 C2 C7 120.15(12) . . ?
C3 C2 C1 120.61(11) . . ?
C7 C2 C1 119.23(13) . . ?
O1 C3 C2 121.39(11) . . ?
O1 C3 C4 121.05(13) . . ?
C2 C3 C4 117.56(13) . . ?
C5 C4 C3 120.52(15) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 121.85(15) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C7 C6 C5 119.25(14) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C6 C7 C2 120.65(15) . . ?
C6 C7 H7A 119.7 . . ?
C2 C7 H7A 119.7 . . ?
N1 C8 C9 109.62(9) . . ?
N1 C8 C15 108.50(9) . . ?
C9 C8 C15 115.46(10) . . ?
N1 C8 H8A 107.7 . . ?
C9 C8 H8A 107.7 . . ?
C15 C8 H8A 107.7 . . ?
C14 C9 C10 118.42(11) . . ?
C14 C9 C8 122.92(11) . . ?
C10 C9 C8 118.53(11) . . ?
O2 C10 C11 122.18(11) . . ?
O2 C10 C9 117.25(11) . . ?
C11 C10 C9 120.56(12) . . ?
C12 C11 C10 119.93(12) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 120.34(12) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 119.84(13) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C13 C14 C9 120.92(12) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
C20 C15 C16 118.87(11) . . ?
C20 C15 C8 121.35(11) . . ?
C16 C15 C8 119.71(11) . . ?
O3 C16 C17 122.93(11) . . ?
O3 C16 C15 117.26(10) . . ?
C17 C16 C15 119.81(11) . . ?
C18 C17 C16 119.90(12) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C19 120.82(12) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C20 C19 C18 118.99(12) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C19 C20 C15 121.49(12) . . ?
C19 C20 H20A 119.3 . . ?
C15 C20 H20A 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 178.90(11) . . . . ?
N1 C1 C2 C3 -2.09(18) . . . . ?
N1 C1 C2 C7 178.61(12) . . . . ?
C7 C2 C3 O1 -179.80(11) . . . . ?
C1 C2 C3 O1 0.91(18) . . . . ?
C7 C2 C3 C4 0.00(18) . . . . ?
C1 C2 C3 C4 -179.29(11) . . . . ?
O1 C3 C4 C5 179.14(12) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C2 -1.5(2) . . . . ?
C3 C2 C7 C6 1.09(19) . . . . ?
C1 C2 C7 C6 -179.61(12) . . . . ?
C1 N1 C8 C9 129.01(12) . . . . ?
C1 N1 C8 C15 -104.08(13) . . . . ?
N1 C8 C9 C14 118.81(12) . . . . ?
C15 C8 C9 C14 -4.07(16) . . . . ?
N1 C8 C9 C10 -65.39(14) . . . . ?
C15 C8 C9 C10 171.73(10) . . . . ?
C14 C9 C10 O2 178.24(10) . . . . ?
C8 C9 C10 O2 2.26(16) . . . . ?
C14 C9 C10 C11 -0.48(17) . . . . ?
C8 C9 C10 C11 -176.46(11) . . . . ?
O2 C10 C11 C12 -178.26(11) . . . . ?
C9 C10 C11 C12 0.39(18) . . . . ?
C10 C11 C12 C13 -0.05(19) . . . . ?
C11 C12 C13 C14 -0.19(19) . . . . ?
C12 C13 C14 C9 0.09(19) . . . . ?
C10 C9 C14 C13 0.23(18) . . . . ?
C8 C9 C14 C13 176.03(11) . . . . ?
N1 C8 C15 C20 -48.98(15) . . . . ?
C9 C8 C15 C20 74.49(15) . . . . ?
N1 C8 C15 C16 128.06(11) . . . . ?
C9 C8 C15 C16 -108.47(13) . . . . ?
C20 C15 C16 O3 -175.84(11) . . . . ?
C8 C15 C16 O3 7.05(17) . . . . ?
C20 C15 C16 C17 3.79(18) . . . . ?
C8 C15 C16 C17 -173.32(12) . . . . ?
O3 C16 C17 C18 177.15(12) . . . . ?
C15 C16 C17 C18 -2.5(2) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C18 C19 C20 2.1(2) . . . . ?
C18 C19 C20 C15 -0.7(2) . . . . ?
C16 C15 C20 C19 -2.3(2) . . . . ?
C8 C15 C20 C19 174.80(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.869(16) 1.889(16) 2.6048(13) 138.6(14) .
O3 H3 O1 0.932(16) 1.741(16) 2.6712(12) 175.1(14) 4_575
O2 H2 O1 0.921(17) 1.777(17) 2.6892(13) 170.3(15) 1_565

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_0194A-1
_database_code_depnum_ccdc_archive 'CCDC 1518350'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O5, C4 H8 O'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9282(6)
_cell_length_b                   11.5903(4)
_cell_length_c                   21.7086(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.6330(19)
_cell_angle_gamma                90
_cell_volume                     4496.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    81505
_cell_measurement_theta_min      2.258
_cell_measurement_theta_max      29.529

_exptl_crystal_description       platy
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   0.682
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81505
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         29.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6242
_reflns_number_gt                4082
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0748P)²+2.0751P] 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     SHELXL
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6242
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.13555(7) 0.15709(10) 0.10696(6) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.23299(6) 0.07769(9) 0.03376(5) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.18123(7) 0.34452(10) 0.04699(5) 0.0352(3) Uani 1 1 d . . . . .
O3 O -0.01394(7) 0.05012(11) 0.10097(6) 0.0430(3) Uani 1 1 d . . . . .
O5 O 0.28183(8) -0.25624(11) 0.25875(6) 0.0518(4) Uani 1 1 d . . . . .
O4 O 0.38243(9) -0.29081(13) 0.21258(7) 0.0648(5) Uani 1 1 d . . . . .
N2 N 0.32235(10) -0.23933(13) 0.21643(8) 0.0457(4) Uani 1 1 d . . . . .
C2 C 0.21672(8) -0.00312(12) 0.13234(7) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.23964(9) -0.08456(13) 0.17746(7) 0.0309(3) Uani 1 1 d . . . . .
H7A H 0.2141 -0.0905 0.2140 0.037 Uiso 1 1 calc R U . . .
C1 C 0.15683(8) 0.07397(12) 0.14370(7) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.1316 0.0632 0.1801 0.032 Uiso 1 1 calc R U . . .
C8 C 0.07520(8) 0.24003(13) 0.11776(7) 0.0279(3) Uani 1 1 d . . . . .
H8A H 0.0512 0.2139 0.1554 0.033 Uiso 1 1 calc R U . . .
C9 C 0.10741(8) 0.35883(13) 0.13123(7) 0.0279(3) Uani 1 1 d . . . . .
C15 C 0.01631(8) 0.23346(13) 0.06356(7) 0.0289(3) Uani 1 1 d . . . . .
C20 C 0.00343(8) 0.32140(14) 0.02036(7) 0.0319(3) Uani 1 1 d . . . . .
H20A H 0.0326 0.3898 0.0243 0.038 Uiso 1 1 calc R U . . .
C10 C 0.16100(8) 0.40748(13) 0.09570(7) 0.0292(3) Uani 1 1 d . . . . .
C6 C 0.29917(9) -0.15621(14) 0.16892(8) 0.0358(4) Uani 1 1 d . . . . .
C16 C -0.02765(9) 0.13341(14) 0.05732(8) 0.0340(4) Uani 1 1 d . . . . .
C4 C 0.31568(10) -0.07158(15) 0.07024(9) 0.0403(4) Uani 1 1 d . . . . .
H4A H 0.3419 -0.0684 0.0340 0.048 Uiso 1 1 calc R U . . .
C11 C 0.19120(9) 0.51589(14) 0.11096(8) 0.0376(4) Uani 1 1 d . . . . .
H11A H 0.2286 0.5482 0.0875 0.045 Uiso 1 1 calc R U . . .
C3 C 0.25414(8) 0.00497(13) 0.07605(7) 0.0296(3) Uani 1 1 d . . . . .
C19 C -0.05123(9) 0.31095(15) -0.02842(8) 0.0380(4) Uani 1 1 d . . . . .
H19A H -0.0592 0.3713 -0.0578 0.046 Uiso 1 1 calc R U . . .
C14 C 0.08330(10) 0.42186(15) 0.18050(8) 0.0382(4) Uani 1 1 d . . . . .
H14A H 0.0463 0.3899 0.2045 0.046 Uiso 1 1 calc R U . . .
C5 C 0.33773(10) -0.14897(15) 0.11535(9) 0.0427(4) Uani 1 1 d . . . . .
H5A H 0.3793 -0.1981 0.1105 0.051 Uiso 1 1 calc R U . . .
C17 C -0.08280(10) 0.12290(16) 0.00837(9) 0.0427(4) Uani 1 1 d . . . . .
H17A H -0.1124 0.0549 0.0041 0.051 Uiso 1 1 calc R U . . .
C12 C 0.16614(11) 0.57598(16) 0.16063(9) 0.0468(5) Uani 1 1 d . . . . .
H12A H 0.1865 0.6498 0.1710 0.056 Uiso 1 1 calc R U . . .
C18 C -0.09411(10) 0.21125(16) -0.03368(9) 0.0438(4) Uani 1 1 d . . . . .
H18A H -0.1318 0.2039 -0.0668 0.053 Uiso 1 1 calc R U . . .
C13 C 0.11200(12) 0.52997(17) 0.19525(9) 0.0491(5) Uani 1 1 d . . . . .
H13A H 0.0947 0.5722 0.2288 0.059 Uiso 1 1 calc R U . . .
O6 O 0.87173(7) 0.90904(11) 0.11100(6) 0.0435(3) Uani 1 1 d . . . . .
C21 C 0.86360(13) 0.90596(18) 0.17547(9) 0.0515(5) Uani 1 1 d . . . . .
H21A H 0.8100 0.9036 0.1834 0.062 Uiso 1 1 calc R U . . .
H21B H 0.8868 0.9749 0.1960 0.062 Uiso 1 1 calc R U . . .
C22 C 0.90224(19) 0.7995(3) 0.19851(12) 0.0849(9) Uani 1 1 d . . . . .
H22A H 0.9549 0.8162 0.2129 0.102 Uiso 1 1 calc R U . . .
H22B H 0.8769 0.7659 0.2332 0.102 Uiso 1 1 calc R U . . .
C24 C 0.87460(13) 0.79241(18) 0.09004(10) 0.0561(5) Uani 1 1 d . . . . .
H24A H 0.9110 0.7849 0.0583 0.067 Uiso 1 1 calc R U . . .
H24B H 0.8248 0.7676 0.0717 0.067 Uiso 1 1 calc R U . . .
C23 C 0.8983(2) 0.7201(2) 0.14535(13) 0.0955(10) Uani 1 1 d . . . . .
H23A H 0.8614 0.6581 0.1507 0.115 Uiso 1 1 calc R U . . .
H23B H 0.9477 0.6845 0.1408 0.115 Uiso 1 1 calc R U . . .
H1 H 0.1631(19) 0.165(3) 0.0694(16) 0.115 Uiso 1 1 d . U . . .
H2 H 0.211(2) 0.382(3) 0.0202(15) 0.115 Uiso 1 1 d . U . . .
H3 H -0.0544(19) -0.002(3) 0.1025(15) 0.115 Uiso 1 1 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
N1 C1 1.2885(19) . ?
N1 C8 1.4801(18) . ?
N1 H1 0.99(3) . ?
O1 C3 1.2808(19) . ?
O2 C10 1.3579(18) . ?
O2 H2 0.93(3) . ?
O3 C16 1.361(2) . ?
O3 H3 0.95(3) . ?
O5 N2 1.232(2) . ?
O4 N2 1.240(2) . ?
N2 C6 1.447(2) . ?
C2 C7 1.398(2) . ?
C2 C1 1.434(2) . ?
C2 C3 1.444(2) . ?
C7 C6 1.377(2) . ?
C7 H7A 0.9500 . ?
C1 H1A 0.9500 . ?
C8 C9 1.513(2) . ?
C8 C15 1.518(2) . ?
C8 H8A 1.0000 . ?
C9 C14 1.393(2) . ?
C9 C10 1.398(2) . ?
C15 C20 1.392(2) . ?
C15 C16 1.402(2) . ?
C20 C19 1.389(2) . ?
C20 H20A 0.9500 . ?
C10 C11 1.397(2) . ?
C6 C5 1.403(3) . ?
C16 C17 1.397(2) . ?
C4 C5 1.363(3) . ?
C4 C3 1.429(2) . ?
C4 H4A 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11A 0.9500 . ?
C19 C18 1.388(3) . ?
C19 H19A 0.9500 . ?
C14 C13 1.382(3) . ?
C14 H14A 0.9500 . ?
C5 H5A 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17A 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12A 0.9500 . ?
C18 H18A 0.9500 . ?
C13 H13A 0.9500 . ?
O6 C21 1.419(2) . ?
O6 C24 1.429(2) . ?
C21 C22 1.482(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.473(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 C23 1.497(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 124.84(13) . . ?
C1 N1 H1 116.0(19) . . ?
C8 N1 H1 119.2(19) . . ?
C10 O2 H2 116(2) . . ?
C16 O3 H3 112(2) . . ?
O5 N2 O4 122.78(16) . . ?
O5 N2 C6 118.98(15) . . ?
O4 N2 C6 118.24(17) . . ?
C7 C2 C1 118.83(13) . . ?
C7 C2 C3 120.44(13) . . ?
C1 C2 C3 120.71(13) . . ?
C6 C7 C2 120.02(15) . . ?
C6 C7 H7A 120.0 . . ?
C2 C7 H7A 120.0 . . ?
N1 C1 C2 123.23(13) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
N1 C8 C9 110.45(12) . . ?
N1 C8 C15 108.44(12) . . ?
C9 C8 C15 115.23(13) . . ?
N1 C8 H8A 107.5 . . ?
C9 C8 H8A 107.5 . . ?
C15 C8 H8A 107.5 . . ?
C14 C9 C10 118.81(15) . . ?
C14 C9 C8 119.25(14) . . ?
C10 C9 C8 121.94(13) . . ?
C20 C15 C16 118.63(14) . . ?
C20 C15 C8 123.56(14) . . ?
C16 C15 C8 117.81(14) . . ?
C19 C20 C15 121.22(15) . . ?
C19 C20 H20A 119.4 . . ?
C15 C20 H20A 119.4 . . ?
O2 C10 C11 123.03(15) . . ?
O2 C10 C9 116.83(13) . . ?
C11 C10 C9 120.14(15) . . ?
C7 C6 C5 120.99(15) . . ?
C7 C6 N2 119.12(16) . . ?
C5 C6 N2 119.89(15) . . ?
O3 C16 C17 123.00(15) . . ?
O3 C16 C15 116.78(15) . . ?
C17 C16 C15 120.21(16) . . ?
C5 C4 C3 121.77(16) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C12 C11 C10 119.44(17) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
O1 C3 C4 122.08(14) . . ?
O1 C3 C2 121.24(13) . . ?
C4 C3 C2 116.68(14) . . ?
C18 C19 C20 119.18(17) . . ?
C18 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
C13 C14 C9 121.37(17) . . ?
C13 C14 H14A 119.3 . . ?
C9 C14 H14A 119.3 . . ?
C4 C5 C6 120.09(15) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C18 C17 C16 119.81(17) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C13 C12 C11 120.96(17) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C17 C18 C19 120.94(17) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C12 C13 C14 119.25(17) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C21 O6 C24 107.43(15) . . ?
O6 C21 C22 105.75(17) . . ?
O6 C21 H21A 110.6 . . ?
C22 C21 H21A 110.6 . . ?
O6 C21 H21B 110.6 . . ?
C22 C21 H21B 110.6 . . ?
H21A C21 H21B 108.7 . . ?
C23 C22 C21 105.3(2) . . ?
C23 C22 H22A 110.7 . . ?
C21 C22 H22A 110.7 . . ?
C23 C22 H22B 110.7 . . ?
C21 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
O6 C24 C23 106.82(17) . . ?
O6 C24 H24A 110.4 . . ?
C23 C24 H24A 110.4 . . ?
O6 C24 H24B 110.4 . . ?
C23 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
C22 C23 C24 105.7(2) . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23B 110.6 . . ?
C24 C23 H23B 110.6 . . ?
H23A C23 H23B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C7 C6 -177.13(14) . . . . ?
C3 C2 C7 C6 1.3(2) . . . . ?
C8 N1 C1 C2 -178.53(13) . . . . ?
C7 C2 C1 N1 174.78(14) . . . . ?
C3 C2 C1 N1 -3.6(2) . . . . ?
C1 N1 C8 C9 110.73(16) . . . . ?
C1 N1 C8 C15 -122.13(15) . . . . ?
N1 C8 C9 C14 -134.01(15) . . . . ?
C15 C8 C9 C14 102.71(16) . . . . ?
N1 C8 C9 C10 45.84(19) . . . . ?
C15 C8 C9 C10 -77.44(17) . . . . ?
N1 C8 C15 C20 -110.57(15) . . . . ?
C9 C8 C15 C20 13.8(2) . . . . ?
N1 C8 C15 C16 69.96(16) . . . . ?
C9 C8 C15 C16 -165.70(13) . . . . ?
C16 C15 C20 C19 -0.5(2) . . . . ?
C8 C15 C20 C19 180.00(14) . . . . ?
C14 C9 C10 O2 -178.05(14) . . . . ?
C8 C9 C10 O2 2.1(2) . . . . ?
C14 C9 C10 C11 2.0(2) . . . . ?
C8 C9 C10 C11 -177.84(14) . . . . ?
C2 C7 C6 C5 0.1(2) . . . . ?
C2 C7 C6 N2 179.53(14) . . . . ?
O5 N2 C6 C7 10.9(2) . . . . ?
O4 N2 C6 C7 -169.29(15) . . . . ?
O5 N2 C6 C5 -169.65(16) . . . . ?
O4 N2 C6 C5 10.2(2) . . . . ?
C20 C15 C16 O3 -179.17(14) . . . . ?
C8 C15 C16 O3 0.3(2) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C8 C15 C16 C17 179.85(14) . . . . ?
O2 C10 C11 C12 178.42(15) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
C5 C4 C3 O1 -179.80(16) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C7 C2 C3 O1 178.73(14) . . . . ?
C1 C2 C3 O1 -2.9(2) . . . . ?
C7 C2 C3 C4 -1.5(2) . . . . ?
C1 C2 C3 C4 176.87(14) . . . . ?
C15 C20 C19 C18 0.6(2) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C8 C9 C14 C13 178.91(16) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C7 C6 C5 C4 -1.1(3) . . . . ?
N2 C6 C5 C4 179.40(17) . . . . ?
O3 C16 C17 C18 179.25(16) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C20 C19 C18 C17 -0.5(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C9 C14 C13 C12 -0.5(3) . . . . ?
C24 O6 C21 C22 30.7(2) . . . . ?
O6 C21 C22 C23 -27.1(3) . . . . ?
C21 O6 C24 C23 -22.1(3) . . . . ?
C21 C22 C23 C24 13.5(4) . . . . ?
O6 C24 C23 C22 4.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O6 0.95(3) 1.70(3) 2.6448(17) 175(3) 1_445
O2 H2 O1 0.93(3) 1.67(3) 2.5859(15) 169(3) 7
N1 H1 O2 0.99(3) 2.16(3) 2.6939(17) 112(2) .
N1 H1 O1 0.99(3) 1.83(3) 2.6216(16) 134(3) .

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_0229A-1
_database_code_depnum_ccdc_archive 'CCDC 1518352'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H26 Fe2 N4 O10, 3(C6 H6)'
_chemical_formula_sum            'C58 H44 Fe2 N4 O10'
_chemical_formula_weight         1068.67

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                   8.6390(3)
_cell_length_b                   28.5416(10)
_cell_length_c                   10.0003(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.528(2)
_cell_angle_gamma                90
_cell_volume                     2438.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    39542
_cell_measurement_theta_min      2.179
_cell_measurement_theta_max      28.270

_exptl_crystal_description       platy
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   0.678
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.663
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39542
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6043
_reflns_number_gt                4088
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0490P)²+1.3335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6043
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Fe1 Fe 0.52461(4) 0.04420(2) 0.41104(4) 0.01854(11) Uani 1 1 d . . . . .
N1 N 0.5319(2) 0.11255(7) 0.4768(2) 0.0193(5) Uani 1 1 d . . . . .
N2 N 0.0808(3) 0.22884(9) 0.0861(3) 0.0406(7) Uani 1 1 d . . . . .
O1 O 0.3639(2) 0.06139(6) 0.27068(18) 0.0239(4) Uani 1 1 d . . . . .
O2 O 0.5178(2) 0.02572(6) 0.60065(17) 0.0199(4) Uani 1 1 d . . . . .
O3 O 0.7329(2) 0.04967(6) 0.39184(19) 0.0256(4) Uani 1 1 d . . . . .
O4 O -0.0213(3) 0.22734(8) -0.0138(3) 0.0527(7) Uani 1 1 d . . . . .
O5 O 0.1237(3) 0.26546(8) 0.1448(3) 0.0588(7) Uani 1 1 d . . . . .
C1 C 0.4599(3) 0.14809(9) 0.4173(3) 0.0224(6) Uani 1 1 d . . . . .
H1A H 0.4856 0.1783 0.4539 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3425(3) 0.14494(9) 0.2986(3) 0.0223(6) Uani 1 1 d . . . . .
C3 C 0.2976(3) 0.10186(9) 0.2319(3) 0.0211(5) Uani 1 1 d . . . . .
C4 C 0.1791(3) 0.10232(9) 0.1188(3) 0.0256(6) Uani 1 1 d . . . . .
H4A H 0.1473 0.0737 0.0748 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1087(3) 0.14330(10) 0.0710(3) 0.0292(6) Uani 1 1 d . . . . .
H5A H 0.0286 0.1432 -0.0052 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1567(3) 0.18530(9) 0.1363(3) 0.0293(6) Uani 1 1 d . . . . .
C7 C 0.2701(3) 0.18666(9) 0.2474(3) 0.0285(6) Uani 1 1 d . . . . .
H7A H 0.2999 0.2157 0.2898 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6470(3) 0.12026(9) 0.5989(3) 0.0212(6) Uani 1 1 d . . . . .
H8A H 0.6544 0.1548 0.6147 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5829(3) 0.09873(9) 0.7182(3) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.5204(3) 0.05332(8) 0.7138(2) 0.0185(5) Uani 1 1 d . . . . .
C11 C 0.4568(3) 0.03564(9) 0.8232(3) 0.0238(6) Uani 1 1 d . . . . .
H11A H 0.4132 0.0050 0.8188 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4567(3) 0.06252(10) 0.9390(3) 0.0283(6) Uani 1 1 d . . . . .
H12A H 0.4139 0.0501 1.0138 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5186(3) 0.10725(10) 0.9456(3) 0.0315(7) Uani 1 1 d . . . . .
H13A H 0.5194 0.1256 1.0249 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5800(3) 0.12514(9) 0.8348(3) 0.0259(6) Uani 1 1 d . . . . .
H14A H 0.6208 0.1561 0.8390 0.031 Uiso 1 1 calc R U . . .
C15 C 0.8106(3) 0.10296(9) 0.5807(3) 0.0211(5) Uani 1 1 d . . . . .
C16 C 0.8444(3) 0.07101(9) 0.4812(3) 0.0228(6) Uani 1 1 d . . . . .
C17 C 1.0008(3) 0.06062(10) 0.4712(3) 0.0287(6) Uani 1 1 d . . . . .
H17A H 1.0240 0.0398 0.4028 0.034 Uiso 1 1 calc R U . . .
C18 C 1.1220(3) 0.08028(11) 0.5594(3) 0.0331(7) Uani 1 1 d . . . . .
H18A H 1.2273 0.0725 0.5518 0.040 Uiso 1 1 calc R U . . .
C19 C 1.0907(3) 0.11115(10) 0.6586(3) 0.0327(7) Uani 1 1 d . . . . .
H19A H 1.1737 0.1243 0.7201 0.039 Uiso 1 1 calc R U . . .
C20 C 0.9363(3) 0.12260(10) 0.6670(3) 0.0272(6) Uani 1 1 d . . . . .
H20A H 0.9152 0.1445 0.7335 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7757(5) 0.17648(14) 0.2466(5) 0.0622(11) Uani 1 1 d . . . . .
H21A H 0.7671 0.1447 0.2186 0.075 Uiso 1 1 calc R U . . .
C22 C 0.8826(5) 0.18925(16) 0.3517(4) 0.0656(12) Uani 1 1 d . . . . .
H22A H 0.9508 0.1666 0.3983 0.079 Uiso 1 1 calc R U . . .
C23 C 0.8925(7) 0.2350(2) 0.3910(5) 0.0982(19) Uani 1 1 d . . . . .
H23A H 0.9654 0.2437 0.4676 0.118 Uiso 1 1 calc R U . . .
C24 C 0.8002(6) 0.26859(16) 0.3230(5) 0.0757(14) Uani 1 1 d . . . . .
H24A H 0.8117 0.3005 0.3495 0.091 Uiso 1 1 calc R U . . .
C25 C 0.6926(5) 0.25609(14) 0.2179(5) 0.0733(13) Uani 1 1 d . . . . .
H25A H 0.6266 0.2790 0.1701 0.088 Uiso 1 1 calc R U . . .
C26 C 0.6791(6) 0.20988(15) 0.1803(5) 0.0845(16) Uani 1 1 d . . . . .
H26A H 0.6016 0.2009 0.1072 0.101 Uiso 1 1 calc R U . . .
C27 C 0.8800(5) 0.02920(13) 0.9586(6) 0.0654(14) Uani 1 1 d . . . . .
H27 H 0.7954 0.0498 0.9290 0.078 Uiso 1 1 calc R U . . .
C28 C 0.9757(7) 0.01533(14) 0.8707(4) 0.0677(15) Uani 1 1 d . . . . .
H28A H 0.9585 0.0262 0.7799 0.081 Uiso 1 1 calc R U . . .
C29 C 1.0968(5) -0.01418(16) 0.9127(5) 0.0630(13) Uani 1 1 d . . . . .
H29 H 1.1645 -0.0241 0.8515 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O3 1.8446(18) . ?
Fe1 O1 1.8871(17) . ?
Fe1 O2 1.9774(17) . ?
Fe1 O2 2.0291(17) 3_656 ?
Fe1 N1 2.057(2) . ?
N1 C1 1.288(3) . ?
N1 C8 1.473(3) . ?
N2 O5 1.229(3) . ?
N2 O4 1.232(3) . ?
N2 C6 1.459(3) . ?
O1 C3 1.322(3) . ?
O2 C10 1.376(3) . ?
O2 Fe1 2.0290(17) 3_656 ?
O3 C16 1.357(3) . ?
C1 C2 1.445(4) . ?
C1 H1A 0.9500 . ?
C2 C7 1.406(4) . ?
C2 C3 1.425(4) . ?
C3 C4 1.408(4) . ?
C4 C5 1.371(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.398(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.368(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.518(4) . ?
C8 C15 1.533(4) . ?
C8 H8A 1.0000 . ?
C9 C14 1.392(4) . ?
C9 C10 1.402(3) . ?
C10 C11 1.390(4) . ?
C11 C12 1.390(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.394(4) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C20 1.400(4) . ?
C15 C16 1.412(4) . ?
C16 C17 1.401(4) . ?
C17 C18 1.384(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.383(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 C22 1.342(6) . ?
C21 C26 1.372(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.364(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.362(7) . ?
C23 H23A 0.9500 . ?
C24 C25 1.343(6) . ?
C24 H24A 0.9500 . ?
C25 C26 1.372(5) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 C29 1.343(6) 3_757 ?
C27 C28 1.352(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.360(6) . ?
C28 H28A 0.9500 . ?
C29 C27 1.343(6) 3_757 ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Fe1 O1 121.48(9) . . ?
O3 Fe1 O2 106.90(8) . . ?
O1 Fe1 O2 131.25(8) . . ?
O3 Fe1 O2 104.35(7) . 3_656 ?
O1 Fe1 O2 96.10(7) . 3_656 ?
O2 Fe1 O2 76.24(7) . 3_656 ?
O3 Fe1 N1 88.21(8) . . ?
O1 Fe1 N1 88.59(8) . . ?
O2 Fe1 N1 87.16(8) . . ?
O2 Fe1 N1 161.45(8) 3_656 . ?
C1 N1 C8 119.1(2) . . ?
C1 N1 Fe1 127.56(18) . . ?
C8 N1 Fe1 113.06(15) . . ?
O5 N2 O4 123.1(3) . . ?
O5 N2 C6 118.2(3) . . ?
O4 N2 C6 118.8(3) . . ?
C3 O1 Fe1 133.21(16) . . ?
C10 O2 Fe1 129.53(15) . . ?
C10 O2 Fe1 126.24(15) . 3_656 ?
Fe1 O2 Fe1 103.76(7) . 3_656 ?
C16 O3 Fe1 125.30(17) . . ?
N1 C1 C2 124.2(2) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C7 C2 C3 119.0(2) . . ?
C7 C2 C1 117.8(2) . . ?
C3 C2 C1 123.2(2) . . ?
O1 C3 C4 118.4(2) . . ?
O1 C3 C2 122.7(2) . . ?
C4 C3 C2 118.9(2) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 N2 119.1(3) . . ?
C5 C6 N2 118.8(3) . . ?
C6 C7 C2 119.9(3) . . ?
C6 C7 H7A 120.1 . . ?
C2 C7 H7A 120.1 . . ?
N1 C8 C9 108.1(2) . . ?
N1 C8 C15 112.0(2) . . ?
C9 C8 C15 114.4(2) . . ?
N1 C8 H8A 107.3 . . ?
C9 C8 H8A 107.3 . . ?
C15 C8 H8A 107.3 . . ?
C14 C9 C10 118.2(2) . . ?
C14 C9 C8 119.6(2) . . ?
C10 C9 C8 122.2(2) . . ?
O2 C10 C11 118.6(2) . . ?
O2 C10 C9 120.9(2) . . ?
C11 C10 C9 120.4(2) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C9 C14 C13 121.6(2) . . ?
C9 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C20 C15 C16 118.1(2) . . ?
C20 C15 C8 116.2(2) . . ?
C16 C15 C8 125.6(2) . . ?
O3 C16 C17 117.1(2) . . ?
O3 C16 C15 123.6(2) . . ?
C17 C16 C15 119.3(2) . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 119.0(3) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C19 C20 C15 122.2(3) . . ?
C19 C20 H20A 118.9 . . ?
C15 C20 H20A 118.9 . . ?
C22 C21 C26 119.3(4) . . ?
C22 C21 H21A 120.4 . . ?
C26 C21 H21A 120.4 . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C24 C23 C22 121.5(5) . . ?
C24 C23 H23A 119.2 . . ?
C22 C23 H23A 119.2 . . ?
C25 C24 C23 119.3(4) . . ?
C25 C24 H24A 120.3 . . ?
C23 C24 H24A 120.3 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25A 120.3 . . ?
C26 C25 H25A 120.3 . . ?
C21 C26 C25 120.9(4) . . ?
C21 C26 H26A 119.5 . . ?
C25 C26 H26A 119.5 . . ?
C29 C27 C28 120.7(4) 3_757 . ?
C29 C27 H27 119.7 3_757 . ?
C28 C27 H27 119.7 . . ?
C27 C28 C29 119.8(3) . . ?
C27 C28 H28A 120.1 . . ?
C29 C28 H28A 120.1 . . ?
C27 C29 C28 119.5(4) 3_757 . ?
C27 C29 H29 120.3 3_757 . ?
C28 C29 H29 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Fe1 O1 C3 -83.1(2) . . . . ?
O2 Fe1 O1 C3 88.9(2) . . . . ?
O2 Fe1 O1 C3 166.0(2) 3_656 . . . ?
N1 Fe1 O1 C3 4.0(2) . . . . ?
O1 Fe1 O3 C16 129.58(19) . . . . ?
O2 Fe1 O3 C16 -44.2(2) . . . . ?
O2 Fe1 O3 C16 -123.85(19) 3_656 . . . ?
N1 Fe1 O3 C16 42.3(2) . . . . ?
C8 N1 C1 C2 -178.7(2) . . . . ?
Fe1 N1 C1 C2 8.4(4) . . . . ?
N1 C1 C2 C7 178.0(3) . . . . ?
N1 C1 C2 C3 -2.1(4) . . . . ?
Fe1 O1 C3 C4 179.13(19) . . . . ?
Fe1 O1 C3 C2 0.0(4) . . . . ?
C7 C2 C3 O1 177.5(3) . . . . ?
C1 C2 C3 O1 -2.4(4) . . . . ?
C7 C2 C3 C4 -1.7(4) . . . . ?
C1 C2 C3 C4 178.4(3) . . . . ?
O1 C3 C4 C5 -178.1(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C4 C5 C6 N2 -179.5(3) . . . . ?
O5 N2 C6 C7 1.1(5) . . . . ?
O4 N2 C6 C7 -179.9(3) . . . . ?
O5 N2 C6 C5 179.7(3) . . . . ?
O4 N2 C6 C5 -1.3(4) . . . . ?
C5 C6 C7 C2 0.3(5) . . . . ?
N2 C6 C7 C2 178.8(3) . . . . ?
C3 C2 C7 C6 1.0(4) . . . . ?
C1 C2 C7 C6 -179.1(3) . . . . ?
C1 N1 C8 C9 112.9(3) . . . . ?
Fe1 N1 C8 C9 -73.2(2) . . . . ?
C1 N1 C8 C15 -120.2(3) . . . . ?
Fe1 N1 C8 C15 53.7(2) . . . . ?
N1 C8 C9 C14 -129.7(2) . . . . ?
C15 C8 C9 C14 104.7(3) . . . . ?
N1 C8 C9 C10 47.8(3) . . . . ?
C15 C8 C9 C10 -77.7(3) . . . . ?
Fe1 O2 C10 C11 155.94(18) . . . . ?
Fe1 O2 C10 C11 -14.9(3) 3_656 . . . ?
Fe1 O2 C10 C9 -22.8(3) . . . . ?
Fe1 O2 C10 C9 166.34(17) 3_656 . . . ?
C14 C9 C10 O2 179.1(2) . . . . ?
C8 C9 C10 O2 1.5(4) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C8 C9 C10 C11 -177.2(2) . . . . ?
O2 C10 C11 C12 -179.7(2) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C10 C9 C14 C13 0.7(4) . . . . ?
C8 C9 C14 C13 178.4(2) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
N1 C8 C15 C20 158.2(2) . . . . ?
C9 C8 C15 C20 -78.3(3) . . . . ?
N1 C8 C15 C16 -18.6(3) . . . . ?
C9 C8 C15 C16 104.8(3) . . . . ?
Fe1 O3 C16 C17 162.30(19) . . . . ?
Fe1 O3 C16 C15 -18.4(3) . . . . ?
C20 C15 C16 O3 180.0(2) . . . . ?
C8 C15 C16 O3 -3.3(4) . . . . ?
C20 C15 C16 C17 -0.8(4) . . . . ?
C8 C15 C16 C17 176.0(2) . . . . ?
O3 C16 C17 C18 -179.1(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C15 1.8(4) . . . . ?
C16 C15 C20 C19 -0.9(4) . . . . ?
C8 C15 C20 C19 -178.0(2) . . . . ?
C26 C21 C22 C23 0.4(7) . . . . ?
C21 C22 C23 C24 -2.5(8) . . . . ?
C22 C23 C24 C25 2.6(9) . . . . ?
C23 C24 C25 C26 -0.7(8) . . . . ?
C22 C21 C26 C25 1.5(8) . . . . ?
C24 C25 C26 C21 -1.3(8) . . . . ?
C29 C27 C28 C29 0.1(6) 3_757 . . . ?
C27 C28 C29 C27 -0.1(6) . . . 3_757 ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

