# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_H-3
_database_code_depnum_ccdc_archive 'CCDC 1480595'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-10-03 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         'C19 H16 Fe O2'
_chemical_formula_sum            'C19 H16 Fe O2'
_chemical_formula_weight         332.17

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'
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                   10.8724(3)
_cell_length_b                   11.7198(4)
_cell_length_c                   11.7222(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.078(3)
_cell_angle_gamma                90
_cell_volume                     1448.81(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5685
_cell_measurement_theta_min      3.8560
_cell_measurement_theta_max      28.5480

_exptl_crystal_description       block
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.045
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_T_min  0.95345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            12564
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.413
_diffrn_reflns_theta_max         29.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3534
_reflns_number_gt                2989
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0232P)²+0.8529P] 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         3534
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Fe Fe 0.11361(2) 0.33559(2) 0.16886(2) 0.01966(8) Uani 1 1 d . . . . .
O1 O 0.26552(13) 0.53209(12) 0.61266(11) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.34395(15) 0.50126(13) 0.83074(13) 0.0362(3) Uani 1 1 d . . . . .
H2A H 0.303(3) 0.529(3) 0.766(3) 0.072(9) Uiso 1 1 d . . . . .
C1 C 0.04306(18) 0.17473(17) 0.12586(19) 0.0327(4) Uani 1 1 d . . . . .
H1 H 0.0729 0.1211 0.0780 0.039 Uiso 1 1 calc R U . . .
C2 C 0.0870(2) 0.18582(18) 0.24838(19) 0.0379(5) Uani 1 1 d . . . . .
H2 H 0.1516 0.1412 0.2977 0.045 Uiso 1 1 calc R U . . .
C3 C 0.0182(2) 0.2749(2) 0.28536(19) 0.0455(6) Uani 1 1 d . . . . .
H3 H 0.0283 0.3009 0.3639 0.055 Uiso 1 1 calc R U . . .
C4 C -0.06929(19) 0.31905(19) 0.1835(2) 0.0409(5) Uani 1 1 d . . . . .
H4 H -0.1279 0.3795 0.1820 0.049 Uiso 1 1 calc R U . . .
C5 C -0.05243(17) 0.25635(18) 0.08608(18) 0.0330(5) Uani 1 1 d . . . . .
H5 H -0.0979 0.2674 0.0067 0.040 Uiso 1 1 calc R U . . .
C6 C 0.15269(16) 0.50533(15) 0.16036(15) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.0971 0.5663 0.1664 0.027 Uiso 1 1 calc R U . . .
C7 C 0.16239(16) 0.45131(16) 0.05518(15) 0.0238(4) Uani 1 1 d . . . . .
H7 H 0.1147 0.4699 -0.0218 0.029 Uiso 1 1 calc R U . . .
C8 C 0.25603(16) 0.36419(16) 0.08437(15) 0.0233(4) Uani 1 1 d . . . . .
H8 H 0.2814 0.3146 0.0302 0.028 Uiso 1 1 calc R U . . .
C9 C 0.30495(15) 0.36418(15) 0.20815(15) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.3686 0.3146 0.2513 0.026 Uiso 1 1 calc R U . . .
C10 C 0.24135(15) 0.45223(15) 0.25662(15) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.25421(16) 0.47816(15) 0.37946(15) 0.0223(4) Uani 1 1 d . . . . .
H11 H 0.1961 0.5313 0.3981 0.027 Uiso 1 1 calc R U . . .
C12 C 0.34123(16) 0.43346(15) 0.46919(15) 0.0229(4) Uani 1 1 d . . . . .
H12 H 0.4021 0.3816 0.4534 0.027 Uiso 1 1 calc R U . . .
C13 C 0.34441(16) 0.46294(15) 0.59122(15) 0.0225(4) Uani 1 1 d . . . . .
C14 C 0.43778(16) 0.40895(15) 0.68866(15) 0.0213(4) Uani 1 1 d . . . . .
C15 C 0.53294(16) 0.33470(15) 0.67110(16) 0.0237(4) Uani 1 1 d . . . . .
H15 H 0.5396 0.3196 0.5932 0.028 Uiso 1 1 calc R U . . .
C16 C 0.61678(17) 0.28322(17) 0.76383(17) 0.0287(4) Uani 1 1 d . . . . .
H16 H 0.6809 0.2339 0.7499 0.034 Uiso 1 1 calc R U . . .
C17 C 0.60672(17) 0.30409(17) 0.87834(17) 0.0302(4) Uani 1 1 d . . . . .
H17 H 0.6638 0.2679 0.9424 0.036 Uiso 1 1 calc R U . . .
C18 C 0.51540(18) 0.37624(16) 0.89962(16) 0.0291(4) Uani 1 1 d . . . . .
H18 H 0.5092 0.3896 0.9780 0.035 Uiso 1 1 calc R U . . .
C19 C 0.43159(17) 0.43001(15) 0.80576(16) 0.0251(4) Uani 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
Fe C3 2.0332(19) . ?
Fe C10 2.0399(17) . ?
Fe C2 2.041(2) . ?
Fe C6 2.0417(18) . ?
Fe C9 2.0460(16) . ?
Fe C4 2.0464(19) . ?
Fe C1 2.0515(19) . ?
Fe C5 2.0520(18) . ?
Fe C8 2.0584(17) . ?
Fe C7 2.0592(17) . ?
O1 C13 1.249(2) . ?
O2 C19 1.352(2) . ?
O2 H2A 0.85(3) . ?
C1 C2 1.405(3) . ?
C1 C5 1.405(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.413(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.430(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.413(2) . ?
C6 C10 1.435(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.434(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.445(2) . ?
C11 C12 1.339(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.464(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.474(2) . ?
C14 C15 1.405(2) . ?
C14 C19 1.412(2) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(3) . ?
C18 H18 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
C3 Fe C10 106.95(8) . . ?
C3 Fe C2 40.58(9) . . ?
C10 Fe C2 120.05(8) . . ?
C3 Fe C6 121.30(9) . . ?
C10 Fe C6 41.18(6) . . ?
C2 Fe C6 156.16(8) . . ?
C3 Fe C9 124.25(9) . . ?
C10 Fe C9 41.10(7) . . ?
C2 Fe C9 106.70(8) . . ?
C6 Fe C9 68.85(7) . . ?
C3 Fe C4 41.03(9) . . ?
C10 Fe C4 125.27(8) . . ?
C2 Fe C4 68.38(9) . . ?
C6 Fe C4 108.33(8) . . ?
C9 Fe C4 162.21(9) . . ?
C3 Fe C1 67.82(9) . . ?
C10 Fe C1 155.20(7) . . ?
C2 Fe C1 40.16(8) . . ?
C6 Fe C1 162.41(8) . . ?
C9 Fe C1 120.31(8) . . ?
C4 Fe C1 67.71(8) . . ?
C3 Fe C5 68.02(9) . . ?
C10 Fe C5 162.66(8) . . ?
C2 Fe C5 67.71(8) . . ?
C6 Fe C5 125.98(8) . . ?
C9 Fe C5 155.50(8) . . ?
C4 Fe C5 40.17(8) . . ?
C1 Fe C5 40.06(8) . . ?
C3 Fe C8 161.14(9) . . ?
C10 Fe C8 68.53(7) . . ?
C2 Fe C8 124.51(8) . . ?
C6 Fe C8 68.16(7) . . ?
C9 Fe C8 40.44(7) . . ?
C4 Fe C8 156.34(9) . . ?
C1 Fe C8 108.15(8) . . ?
C5 Fe C8 121.63(8) . . ?
C3 Fe C7 156.72(9) . . ?
C10 Fe C7 68.53(7) . . ?
C2 Fe C7 161.71(9) . . ?
C6 Fe C7 40.29(7) . . ?
C9 Fe C7 68.28(7) . . ?
C4 Fe C7 121.69(8) . . ?
C1 Fe C7 125.87(8) . . ?
C5 Fe C7 109.11(8) . . ?
C8 Fe C7 40.45(7) . . ?
C19 O2 H2A 107(2) . . ?
C2 C1 C5 108.44(19) . . ?
C2 C1 Fe 69.51(11) . . ?
C5 C1 Fe 69.99(11) . . ?
C2 C1 H1 125.8 . . ?
C5 C1 H1 125.8 . . ?
Fe C1 H1 126.3 . . ?
C1 C2 C3 107.96(19) . . ?
C1 C2 Fe 70.33(11) . . ?
C3 C2 Fe 69.43(12) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
Fe C2 H2 125.8 . . ?
C2 C3 C4 107.79(19) . . ?
C2 C3 Fe 69.99(11) . . ?
C4 C3 Fe 69.98(11) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Fe C3 H3 125.5 . . ?
C5 C4 C3 107.29(19) . . ?
C5 C4 Fe 70.13(11) . . ?
C3 C4 Fe 68.99(11) . . ?
C5 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
Fe C4 H4 126.1 . . ?
C1 C5 C4 108.52(19) . . ?
C1 C5 Fe 69.95(11) . . ?
C4 C5 Fe 69.70(11) . . ?
C1 C5 H5 125.7 . . ?
C4 C5 H5 125.7 . . ?
Fe C5 H5 126.2 . . ?
C7 C6 C10 108.26(15) . . ?
C7 C6 Fe 70.52(10) . . ?
C10 C6 Fe 69.34(10) . . ?
C7 C6 H6 125.9 . . ?
C10 C6 H6 125.9 . . ?
Fe C6 H6 125.9 . . ?
C6 C7 C8 108.21(15) . . ?
C6 C7 Fe 69.19(10) . . ?
C8 C7 Fe 69.75(10) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
Fe C7 H7 126.7 . . ?
C9 C8 C7 108.31(15) . . ?
C9 C8 Fe 69.31(9) . . ?
C7 C8 Fe 69.80(9) . . ?
C9 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
Fe C8 H8 126.6 . . ?
C8 C9 C10 107.95(15) . . ?
C8 C9 Fe 70.25(10) . . ?
C10 C9 Fe 69.22(9) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe C9 H9 126.1 . . ?
C9 C10 C6 107.26(15) . . ?
C9 C10 C11 127.38(15) . . ?
C6 C10 C11 125.16(16) . . ?
C9 C10 Fe 69.68(10) . . ?
C6 C10 Fe 69.48(10) . . ?
C11 C10 Fe 122.18(12) . . ?
C12 C11 C10 125.40(17) . . ?
C12 C11 H11 117.3 . . ?
C10 C11 H11 117.3 . . ?
C11 C12 C13 121.31(16) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
O1 C13 C12 119.70(16) . . ?
O1 C13 C14 120.00(16) . . ?
C12 C13 C14 120.28(15) . . ?
C15 C14 C19 117.49(16) . . ?
C15 C14 C13 123.06(16) . . ?
C19 C14 C13 119.44(16) . . ?
C16 C15 C14 121.71(17) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 119.43(18) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.83(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.81(18) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
O2 C19 C18 117.87(17) . . ?
O2 C19 C14 121.42(16) . . ?
C18 C19 C14 120.70(17) . . ?

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
C5 C1 C2 C3 0.1(2) . . . . ?
Fe C1 C2 C3 59.46(14) . . . . ?
C5 C1 C2 Fe -59.36(13) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
Fe C2 C3 C4 60.03(14) . . . . ?
C1 C2 C3 Fe -60.03(13) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
Fe C3 C4 C5 59.94(14) . . . . ?
C2 C3 C4 Fe -60.04(14) . . . . ?
C2 C1 C5 C4 -0.2(2) . . . . ?
Fe C1 C5 C4 -59.23(14) . . . . ?
C2 C1 C5 Fe 59.06(13) . . . . ?
C3 C4 C5 C1 0.2(2) . . . . ?
Fe C4 C5 C1 59.38(13) . . . . ?
C3 C4 C5 Fe -59.22(13) . . . . ?
C10 C6 C7 C8 0.27(19) . . . . ?
Fe C6 C7 C8 -59.01(12) . . . . ?
C10 C6 C7 Fe 59.28(12) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
Fe C7 C8 C9 -58.78(12) . . . . ?
C6 C7 C8 Fe 58.66(12) . . . . ?
C7 C8 C9 C10 -0.08(19) . . . . ?
Fe C8 C9 C10 -59.17(11) . . . . ?
C7 C8 C9 Fe 59.09(12) . . . . ?
C8 C9 C10 C6 0.25(19) . . . . ?
Fe C9 C10 C6 -59.57(11) . . . . ?
C8 C9 C10 C11 175.39(16) . . . . ?
Fe C9 C10 C11 115.58(17) . . . . ?
C8 C9 C10 Fe 59.81(12) . . . . ?
C7 C6 C10 C9 -0.32(19) . . . . ?
Fe C6 C10 C9 59.70(11) . . . . ?
C7 C6 C10 C11 -175.60(16) . . . . ?
Fe C6 C10 C11 -115.59(17) . . . . ?
C7 C6 C10 Fe -60.01(12) . . . . ?
C9 C10 C11 C12 9.5(3) . . . . ?
C6 C10 C11 C12 -176.15(17) . . . . ?
Fe C10 C11 C12 97.48(19) . . . . ?
C10 C11 C12 C13 -178.33(16) . . . . ?
C11 C12 C13 O1 -0.8(3) . . . . ?
C11 C12 C13 C14 177.45(16) . . . . ?
O1 C13 C14 C15 -176.88(16) . . . . ?
C12 C13 C14 C15 4.9(3) . . . . ?
O1 C13 C14 C19 4.3(2) . . . . ?
C12 C13 C14 C19 -173.92(16) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C13 C14 C15 C16 -178.27(16) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 O2 -179.35(17) . . . . ?
C17 C18 C19 C14 1.5(3) . . . . ?
C15 C14 C19 O2 179.26(16) . . . . ?
C13 C14 C19 O2 -1.9(3) . . . . ?
C15 C14 C19 C18 -1.6(2) . . . . ?
C13 C14 C19 C18 177.26(16) . . . . ?

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
O2 H2A O1 0.85(3) 1.75(3) 2.5164(19) 151(3) .

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_H-2
_database_code_depnum_ccdc_archive 'CCDC 1480596'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-10-03 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         'C19 H16 Fe O2'
_chemical_formula_sum            'C19 H16 Fe O2'
_chemical_formula_weight         332.17

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'
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                   11.1055(4)
_cell_length_b                   11.4922(3)
_cell_length_c                   11.4191(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.713(3)
_cell_angle_gamma                90
_cell_volume                     1440.56(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6919
_cell_measurement_theta_min      3.9700
_cell_measurement_theta_max      28.1950

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.051
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_T_min  0.86477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            18403
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.712
_diffrn_reflns_theta_max         29.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3540
_reflns_number_gt                2856
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0404P)²+0.9779P] 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         3540
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Fe Fe 0.12155(2) 0.66267(2) 0.18292(2) 0.02083(10) Uani 1 1 d . . . . .
O1 O 0.26859(14) 0.45946(13) 0.63161(13) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.67985(15) 0.74615(15) 0.95103(14) 0.0325(4) Uani 1 1 d . . . . .
H2A H 0.715(3) 0.810(3) 0.923(3) 0.083(12) Uiso 1 1 d . . . . .
C1 C -0.0471(2) 0.6852(2) 0.2306(3) 0.0416(6) Uani 1 1 d . . . . .
H1 H -0.1012 0.6249 0.2459 0.050 Uiso 1 1 calc R U . . .
C2 C -0.0422(2) 0.7391(2) 0.1190(2) 0.0329(5) Uani 1 1 d . . . . .
H2 H -0.0921 0.7210 0.0462 0.040 Uiso 1 1 calc R U . . .
C3 C 0.0501(2) 0.82410(18) 0.1362(2) 0.0298(5) Uani 1 1 d . . . . .
H3 H 0.0727 0.8740 0.0768 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1037(2) 0.8229(2) 0.2567(2) 0.0336(5) Uani 1 1 d . . . . .
H4 H 0.1688 0.8710 0.2920 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0439(2) 0.7384(2) 0.3148(2) 0.0394(6) Uani 1 1 d . . . . .
H5 H 0.0612 0.7196 0.3966 0.047 Uiso 1 1 calc R U . . .
C6 C 0.15329(19) 0.48818(18) 0.17144(18) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.0978 0.4277 0.1826 0.030 Uiso 1 1 calc R U . . .
C7 C 0.16474(19) 0.54264(18) 0.06190(19) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.1184 0.5248 -0.0129 0.032 Uiso 1 1 calc R U . . .
C8 C 0.25762(19) 0.62859(19) 0.08378(19) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.2842 0.6780 0.0260 0.031 Uiso 1 1 calc R U . . .
C9 C 0.30380(18) 0.62794(18) 0.20662(18) 0.0235(4) Uani 1 1 d . . . . .
H9 H 0.3663 0.6771 0.2453 0.028 Uiso 1 1 calc R U . . .
C10 C 0.24008(17) 0.54046(17) 0.26223(18) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.25131(19) 0.51495(18) 0.38839(18) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.1941 0.4622 0.4128 0.029 Uiso 1 1 calc R U . . .
C12 C 0.33550(19) 0.55960(18) 0.47285(18) 0.0247(4) Uani 1 1 d . . . . .
H12 H 0.3943 0.6118 0.4504 0.030 Uiso 1 1 calc R U . . .
C13 C 0.34035(18) 0.53092(17) 0.59898(18) 0.0233(4) Uani 1 1 d . . . . .
C14 C 0.43213(18) 0.58883(17) 0.68831(18) 0.0230(4) Uani 1 1 d . . . . .
C15 C 0.51931(18) 0.66641(17) 0.65757(18) 0.0238(4) Uani 1 1 d . . . . .
H15 H 0.5211 0.6830 0.5764 0.029 Uiso 1 1 calc R U . . .
C16 C 0.60326(19) 0.71972(18) 0.74357(19) 0.0257(4) Uani 1 1 d . . . . .
H16 H 0.6621 0.7719 0.7211 0.031 Uiso 1 1 calc R U . . .
C17 C 0.60080(19) 0.69642(18) 0.86271(19) 0.0263(4) Uani 1 1 d . . . . .
C18 C 0.5151(2) 0.61935(19) 0.89523(19) 0.0288(5) Uani 1 1 d . . . . .
H18 H 0.5132 0.6036 0.9766 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4323(2) 0.56553(18) 0.80888(19) 0.0268(4) Uani 1 1 d . . . . .
H19 H 0.3749 0.5121 0.8318 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C5 2.039(2) . ?
Fe C9 2.0403(19) . ?
Fe C10 2.0407(19) . ?
Fe C6 2.044(2) . ?
Fe C1 2.045(2) . ?
Fe C4 2.047(2) . ?
Fe C2 2.052(2) . ?
Fe C3 2.056(2) . ?
Fe C8 2.058(2) . ?
Fe C7 2.060(2) . ?
O1 C13 1.240(2) . ?
O2 C17 1.359(3) . ?
O2 H2A 0.92(4) . ?
C1 C5 1.424(4) . ?
C1 C2 1.425(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.408(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.421(3) . ?
C6 C10 1.436(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.423(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.432(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.457(3) . ?
C11 C12 1.340(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.470(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.486(3) . ?
C14 C15 1.400(3) . ?
C14 C19 1.402(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C5 Fe C9 120.48(10) . . ?
C5 Fe C10 106.39(9) . . ?
C9 Fe C10 41.09(8) . . ?
C5 Fe C6 124.20(9) . . ?
C9 Fe C6 68.86(8) . . ?
C10 Fe C6 41.17(8) . . ?
C5 Fe C1 40.80(11) . . ?
C9 Fe C1 156.90(10) . . ?
C10 Fe C1 121.62(9) . . ?
C6 Fe C1 108.35(9) . . ?
C5 Fe C4 40.03(10) . . ?
C9 Fe C4 106.10(9) . . ?
C10 Fe C4 122.18(9) . . ?
C6 Fe C4 159.62(9) . . ?
C1 Fe C4 68.10(10) . . ?
C5 Fe C2 68.23(10) . . ?
C9 Fe C2 159.88(9) . . ?
C10 Fe C2 158.43(9) . . ?
C6 Fe C2 123.33(9) . . ?
C1 Fe C2 40.72(10) . . ?
C4 Fe C2 68.01(9) . . ?
C5 Fe C3 67.48(9) . . ?
C9 Fe C3 123.16(9) . . ?
C10 Fe C3 159.02(9) . . ?
C6 Fe C3 158.79(9) . . ?
C1 Fe C3 67.79(9) . . ?
C4 Fe C3 40.32(9) . . ?
C2 Fe C3 40.10(9) . . ?
C5 Fe C8 156.17(10) . . ?
C9 Fe C8 40.50(8) . . ?
C10 Fe C8 68.61(8) . . ?
C6 Fe C8 68.28(9) . . ?
C1 Fe C8 161.61(11) . . ?
C4 Fe C8 121.50(9) . . ?
C2 Fe C8 124.81(9) . . ?
C3 Fe C8 108.40(9) . . ?
C5 Fe C7 161.48(10) . . ?
C9 Fe C7 68.34(8) . . ?
C10 Fe C7 68.70(8) . . ?
C6 Fe C7 40.53(8) . . ?
C1 Fe C7 125.37(10) . . ?
C4 Fe C7 157.73(9) . . ?
C2 Fe C7 109.39(9) . . ?
C3 Fe C7 123.38(9) . . ?
C8 Fe C7 40.42(8) . . ?
C17 O2 H2A 110(2) . . ?
C5 C1 C2 107.3(2) . . ?
C5 C1 Fe 69.39(13) . . ?
C2 C1 Fe 69.89(12) . . ?
C5 C1 H1 126.4 . . ?
C2 C1 H1 126.4 . . ?
Fe C1 H1 125.9 . . ?
C3 C2 C1 107.6(2) . . ?
C3 C2 Fe 70.12(12) . . ?
C1 C2 Fe 69.38(13) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe C2 H2 125.9 . . ?
C2 C3 C4 108.6(2) . . ?
C2 C3 Fe 69.78(12) . . ?
C4 C3 Fe 69.49(12) . . ?
C2 C3 H3 125.7 . . ?
C4 C3 H3 125.7 . . ?
Fe C3 H3 126.6 . . ?
C5 C4 C3 107.9(2) . . ?
C5 C4 Fe 69.70(13) . . ?
C3 C4 Fe 70.19(12) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe C4 H4 125.7 . . ?
C4 C5 C1 108.5(2) . . ?
C4 C5 Fe 70.27(13) . . ?
C1 C5 Fe 69.80(13) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.7 . . ?
Fe C5 H5 125.8 . . ?
C7 C6 C10 108.15(18) . . ?
C7 C6 Fe 70.35(12) . . ?
C10 C6 Fe 69.31(11) . . ?
C7 C6 H6 125.9 . . ?
C10 C6 H6 125.9 . . ?
Fe C6 H6 126.0 . . ?
C6 C7 C8 108.07(18) . . ?
C6 C7 Fe 69.12(12) . . ?
C8 C7 Fe 69.73(12) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
Fe C7 H7 126.8 . . ?
C9 C8 C7 108.29(18) . . ?
C9 C8 Fe 69.07(11) . . ?
C7 C8 Fe 69.85(11) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Fe C8 H8 126.8 . . ?
C8 C9 C10 108.26(18) . . ?
C8 C9 Fe 70.43(11) . . ?
C10 C9 Fe 69.47(11) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe C9 H9 125.8 . . ?
C9 C10 C6 107.23(18) . . ?
C9 C10 C11 127.28(19) . . ?
C6 C10 C11 125.26(19) . . ?
C9 C10 Fe 69.44(11) . . ?
C6 C10 Fe 69.53(11) . . ?
C11 C10 Fe 122.02(14) . . ?
C12 C11 C10 125.50(19) . . ?
C12 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
C11 C12 C13 122.50(19) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
O1 C13 C12 120.85(19) . . ?
O1 C13 C14 119.70(18) . . ?
C12 C13 C14 119.45(18) . . ?
C15 C14 C19 118.02(19) . . ?
C15 C14 C13 122.81(18) . . ?
C19 C14 C13 119.17(18) . . ?
C16 C15 C14 121.28(19) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
O2 C17 C16 122.6(2) . . ?
O2 C17 C18 117.45(19) . . ?
C16 C17 C18 119.9(2) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?

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
C5 C1 C2 C3 -0.4(2) . . . . ?
Fe C1 C2 C3 -59.95(15) . . . . ?
C5 C1 C2 Fe 59.58(15) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
Fe C2 C3 C4 -58.81(15) . . . . ?
C1 C2 C3 Fe 59.49(15) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
Fe C3 C4 C5 -59.71(15) . . . . ?
C2 C3 C4 Fe 58.98(15) . . . . ?
C3 C4 C5 C1 0.5(3) . . . . ?
Fe C4 C5 C1 -59.53(16) . . . . ?
C3 C4 C5 Fe 60.02(15) . . . . ?
C2 C1 C5 C4 -0.1(3) . . . . ?
Fe C1 C5 C4 59.82(16) . . . . ?
C2 C1 C5 Fe -59.89(15) . . . . ?
C10 C6 C7 C8 -0.2(2) . . . . ?
Fe C6 C7 C8 59.03(14) . . . . ?
C10 C6 C7 Fe -59.21(14) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
Fe C7 C8 C9 58.53(14) . . . . ?
C6 C7 C8 Fe -58.65(14) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
Fe C8 C9 C10 59.39(14) . . . . ?
C7 C8 C9 Fe -59.01(14) . . . . ?
C8 C9 C10 C6 -0.5(2) . . . . ?
Fe C9 C10 C6 59.51(14) . . . . ?
C8 C9 C10 C11 -175.21(19) . . . . ?
Fe C9 C10 C11 -115.2(2) . . . . ?
C8 C9 C10 Fe -59.99(14) . . . . ?
C7 C6 C10 C9 0.4(2) . . . . ?
Fe C6 C10 C9 -59.45(13) . . . . ?
C7 C6 C10 C11 175.27(18) . . . . ?
Fe C6 C10 C11 115.41(19) . . . . ?
C7 C6 C10 Fe 59.86(14) . . . . ?
C9 C10 C11 C12 -9.3(3) . . . . ?
C6 C10 C11 C12 176.9(2) . . . . ?
Fe C10 C11 C12 -96.7(2) . . . . ?
C10 C11 C12 C13 179.21(18) . . . . ?
C11 C12 C13 O1 3.1(3) . . . . ?
C11 C12 C13 C14 -176.65(19) . . . . ?
O1 C13 C14 C15 177.13(18) . . . . ?
C12 C13 C14 C15 -3.1(3) . . . . ?
O1 C13 C14 C19 -2.9(3) . . . . ?
C12 C13 C14 C19 176.81(18) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C13 C14 C15 C16 179.50(18) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 O2 -179.63(18) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
O2 C17 C18 C19 -179.73(19) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C14 -1.0(3) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C13 C14 C19 C18 -178.85(19) . . . . ?

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
O2 H2A O1 0.92(4) 1.84(4) 2.719(2) 160(4) 2_656

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_H-1
_database_code_depnum_ccdc_archive 'CCDC 1480597'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-10-03 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         'C19 H16 Fe O2'
_chemical_formula_sum            'C19 H16 Fe O2'
_chemical_formula_weight         332.17

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'
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                   11.7994(4)
_cell_length_b                   10.9413(3)
_cell_length_c                   11.2628(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.824(3)
_cell_angle_gamma                90
_cell_volume                     1428.17(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7414
_cell_measurement_theta_min      3.7200
_cell_measurement_theta_max      28.6850

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.060
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_T_min  0.83983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            18217
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.341
_diffrn_reflns_theta_max         29.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3529
_reflns_number_gt                3073
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0300P)²+0.7620P] 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         3529
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.12124(2) 0.66390(2) 0.17168(2) 0.01509(8) Uani 1 1 d . . . . .
O1 O 0.25973(11) 0.44956(11) 0.62838(11) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.67452(12) 0.77158(12) 0.70256(12) 0.0276(3) Uani 1 1 d . . . . .
H2A H 0.703(2) 0.824(2) 0.756(2) 0.049(8) Uiso 1 1 d . . . . .
C1 C -0.03747(16) 0.68664(17) 0.21715(19) 0.0272(4) Uani 1 1 d . . . . .
H1 H -0.0885 0.6232 0.2308 0.033 Uiso 1 1 calc R U . . .
C2 C 0.05026(16) 0.74042(17) 0.30512(16) 0.0260(4) Uani 1 1 d . . . . .
H2 H 0.0682 0.7189 0.3883 0.031 Uiso 1 1 calc R U . . .
C3 C 0.10659(16) 0.83158(15) 0.24811(16) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.1687 0.8817 0.2860 0.028 Uiso 1 1 calc R U . . .
C4 C 0.05360(16) 0.83449(15) 0.12445(16) 0.0233(4) Uani 1 1 d . . . . .
H4 H 0.0739 0.8873 0.0648 0.028 Uiso 1 1 calc R U . . .
C5 C -0.03507(16) 0.74488(16) 0.10490(17) 0.0251(4) Uani 1 1 d . . . . .
H5 H -0.0841 0.7270 0.0299 0.030 Uiso 1 1 calc R U . . .
C6 C 0.29361(14) 0.62455(15) 0.19954(15) 0.0177(3) Uani 1 1 d . . . . .
H6 H 0.3542 0.6748 0.2405 0.021 Uiso 1 1 calc R U . . .
C7 C 0.24774(15) 0.62662(15) 0.07390(15) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.2725 0.6785 0.0161 0.023 Uiso 1 1 calc R U . . .
C8 C 0.15816(15) 0.53765(15) 0.04893(15) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.1129 0.5201 -0.0282 0.023 Uiso 1 1 calc R U . . .
C9 C 0.14832(14) 0.47993(14) 0.15944(15) 0.0179(3) Uani 1 1 d . . . . .
H9 H 0.0953 0.4170 0.1691 0.022 Uiso 1 1 calc R U . . .
C10 C 0.23241(14) 0.53322(14) 0.25404(15) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.24367(14) 0.50487(14) 0.38136(15) 0.0178(3) Uani 1 1 d . . . . .
H11 H 0.1913 0.4473 0.4040 0.021 Uiso 1 1 calc R U . . .
C12 C 0.32275(15) 0.55406(15) 0.46972(15) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.3761 0.6116 0.4490 0.023 Uiso 1 1 calc R U . . .
C13 C 0.32940(14) 0.52181(14) 0.59731(15) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.42137(15) 0.57988(14) 0.68980(15) 0.0185(3) Uani 1 1 d . . . . .
C15 C 0.41782(16) 0.56667(15) 0.81268(16) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.3595 0.5181 0.8371 0.026 Uiso 1 1 calc R U . . .
C16 C 0.49978(16) 0.62486(16) 0.89884(16) 0.0240(4) Uani 1 1 d . . . . .
H16 H 0.4963 0.6166 0.9820 0.029 Uiso 1 1 calc R U . . .
C17 C 0.58660(16) 0.69481(16) 0.86539(16) 0.0231(4) Uani 1 1 d . . . . .
H17 H 0.6424 0.7339 0.9252 0.028 Uiso 1 1 calc R U . . .
C18 C 0.59125(14) 0.70729(15) 0.74330(16) 0.0206(3) Uani 1 1 d . . . . .
C19 C 0.50886(15) 0.64986(14) 0.65658(15) 0.0191(3) Uani 1 1 d . . . . .
H19 H 0.5124 0.6586 0.5734 0.023 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
Fe C2 2.0332(17) . ?
Fe C10 2.0417(16) . ?
Fe C6 2.0447(16) . ?
Fe C9 2.0468(16) . ?
Fe C1 2.0473(18) . ?
Fe C3 2.0476(16) . ?
Fe C7 2.0554(16) . ?
Fe C5 2.0570(18) . ?
Fe C8 2.0580(16) . ?
Fe C4 2.0601(17) . ?
O1 C13 1.237(2) . ?
O2 C18 1.357(2) . ?
O2 H2A 0.86(3) . ?
C1 C2 1.419(3) . ?
C1 C5 1.421(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.418(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.421(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.417(2) . ?
C6 C10 1.436(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.426(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.420(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.436(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.449(2) . ?
C11 C12 1.342(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.467(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.497(2) . ?
C14 C19 1.392(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(2) . ?
C19 H19 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
C2 Fe C10 105.73(7) . . ?
C2 Fe C6 120.61(7) . . ?
C10 Fe C6 41.16(6) . . ?
C2 Fe C9 123.08(7) . . ?
C10 Fe C9 41.13(6) . . ?
C6 Fe C9 68.89(7) . . ?
C2 Fe C1 40.70(8) . . ?
C10 Fe C1 120.75(7) . . ?
C6 Fe C1 156.55(8) . . ?
C9 Fe C1 107.34(7) . . ?
C2 Fe C3 40.65(7) . . ?
C10 Fe C3 122.29(7) . . ?
C6 Fe C3 106.51(7) . . ?
C9 Fe C3 159.39(7) . . ?
C1 Fe C3 68.44(7) . . ?
C2 Fe C7 156.81(8) . . ?
C10 Fe C7 68.60(7) . . ?
C6 Fe C7 40.44(7) . . ?
C9 Fe C7 68.32(7) . . ?
C1 Fe C7 161.55(8) . . ?
C3 Fe C7 122.02(7) . . ?
C2 Fe C5 68.12(7) . . ?
C10 Fe C5 157.40(7) . . ?
C6 Fe C5 160.83(7) . . ?
C9 Fe C5 122.65(7) . . ?
C1 Fe C5 40.51(8) . . ?
C3 Fe C5 68.11(7) . . ?
C7 Fe C5 125.53(7) . . ?
C2 Fe C8 160.30(7) . . ?
C10 Fe C8 68.66(6) . . ?
C6 Fe C8 68.40(7) . . ?
C9 Fe C8 40.47(6) . . ?
C1 Fe C8 124.65(7) . . ?
C3 Fe C8 158.29(7) . . ?
C7 Fe C8 40.56(7) . . ?
C5 Fe C8 109.38(7) . . ?
C2 Fe C4 67.94(7) . . ?
C10 Fe C4 159.47(7) . . ?
C6 Fe C4 123.81(7) . . ?
C9 Fe C4 158.66(7) . . ?
C1 Fe C4 68.05(7) . . ?
C3 Fe C4 40.32(7) . . ?
C7 Fe C4 109.06(7) . . ?
C5 Fe C4 40.37(7) . . ?
C8 Fe C4 123.73(7) . . ?
C18 O2 H2A 108.8(18) . . ?
C2 C1 C5 107.55(16) . . ?
C2 C1 Fe 69.12(10) . . ?
C5 C1 Fe 70.12(10) . . ?
C2 C1 H1 126.2 . . ?
C5 C1 H1 126.2 . . ?
Fe C1 H1 126.1 . . ?
C3 C2 C1 108.55(16) . . ?
C3 C2 Fe 70.22(10) . . ?
C1 C2 Fe 70.18(10) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe C2 H2 125.5 . . ?
C4 C3 C2 107.66(16) . . ?
C4 C3 Fe 70.31(9) . . ?
C2 C3 Fe 69.13(10) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
Fe C3 H3 126.0 . . ?
C3 C4 C5 108.26(16) . . ?
C3 C4 Fe 69.36(10) . . ?
C5 C4 Fe 69.70(10) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe C4 H4 126.6 . . ?
C4 C5 C1 107.98(16) . . ?
C4 C5 Fe 69.93(10) . . ?
C1 C5 Fe 69.38(10) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe C5 H5 126.3 . . ?
C7 C6 C10 108.03(14) . . ?
C7 C6 Fe 70.19(9) . . ?
C10 C6 Fe 69.31(9) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 H6 126.0 . . ?
Fe C6 H6 126.1 . . ?
C6 C7 C8 108.42(14) . . ?
C6 C7 Fe 69.37(9) . . ?
C8 C7 Fe 69.82(9) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 H7 125.8 . . ?
Fe C7 H7 126.6 . . ?
C9 C8 C7 108.09(15) . . ?
C9 C8 Fe 69.34(9) . . ?
C7 C8 Fe 69.62(9) . . ?
C9 C8 H8 126.0 . . ?
C7 C8 H8 126.0 . . ?
Fe C8 H8 126.6 . . ?
C8 C9 C10 108.11(14) . . ?
C8 C9 Fe 70.19(9) . . ?
C10 C9 Fe 69.24(9) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe C9 H9 126.2 . . ?
C9 C10 C6 107.35(14) . . ?
C9 C10 C11 124.72(15) . . ?
C6 C10 C11 127.73(15) . . ?
C9 C10 Fe 69.62(9) . . ?
C6 C10 Fe 69.53(9) . . ?
C11 C10 Fe 122.10(11) . . ?
C12 C11 C10 124.74(15) . . ?
C12 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C11 C12 C13 122.11(16) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
O1 C13 C12 120.95(15) . . ?
O1 C13 C14 120.50(15) . . ?
C12 C13 C14 118.54(15) . . ?
C19 C14 C15 118.94(16) . . ?
C19 C14 C13 121.58(15) . . ?
C15 C14 C13 119.45(15) . . ?
C16 C15 C14 119.81(17) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 121.08(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.36(16) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
O2 C18 C19 116.84(16) . . ?
O2 C18 C17 123.36(16) . . ?
C19 C18 C17 119.78(16) . . ?
C14 C19 C18 121.02(16) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?

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
C5 C1 C2 C3 0.14(19) . . . . ?
Fe C1 C2 C3 59.98(12) . . . . ?
C5 C1 C2 Fe -59.84(12) . . . . ?
C1 C2 C3 C4 0.07(19) . . . . ?
Fe C2 C3 C4 60.02(12) . . . . ?
C1 C2 C3 Fe -59.95(12) . . . . ?
C2 C3 C4 C5 -0.25(19) . . . . ?
Fe C3 C4 C5 59.02(12) . . . . ?
C2 C3 C4 Fe -59.27(12) . . . . ?
C3 C4 C5 C1 0.33(19) . . . . ?
Fe C4 C5 C1 59.15(12) . . . . ?
C3 C4 C5 Fe -58.82(12) . . . . ?
C2 C1 C5 C4 -0.29(19) . . . . ?
Fe C1 C5 C4 -59.50(12) . . . . ?
C2 C1 C5 Fe 59.21(12) . . . . ?
C10 C6 C7 C8 0.12(18) . . . . ?
Fe C6 C7 C8 -59.08(11) . . . . ?
C10 C6 C7 Fe 59.19(11) . . . . ?
C6 C7 C8 C9 -0.05(18) . . . . ?
Fe C7 C8 C9 -58.85(11) . . . . ?
C6 C7 C8 Fe 58.80(11) . . . . ?
C7 C8 C9 C10 -0.03(18) . . . . ?
Fe C8 C9 C10 -59.06(11) . . . . ?
C7 C8 C9 Fe 59.03(11) . . . . ?
C8 C9 C10 C6 0.10(18) . . . . ?
Fe C9 C10 C6 -59.55(11) . . . . ?
C8 C9 C10 C11 175.26(15) . . . . ?
Fe C9 C10 C11 115.61(16) . . . . ?
C8 C9 C10 Fe 59.65(11) . . . . ?
C7 C6 C10 C9 -0.13(18) . . . . ?
Fe C6 C10 C9 59.61(11) . . . . ?
C7 C6 C10 C11 -175.10(15) . . . . ?
Fe C6 C10 C11 -115.36(16) . . . . ?
C7 C6 C10 Fe -59.74(11) . . . . ?
C9 C10 C11 C12 179.54(16) . . . . ?
C6 C10 C11 C12 -6.3(3) . . . . ?
Fe C10 C11 C12 -94.21(19) . . . . ?
C10 C11 C12 C13 179.76(15) . . . . ?
C11 C12 C13 O1 -1.8(2) . . . . ?
C11 C12 C13 C14 179.20(15) . . . . ?
O1 C13 C14 C19 172.29(15) . . . . ?
C12 C13 C14 C19 -8.7(2) . . . . ?
O1 C13 C14 C15 -9.6(2) . . . . ?
C12 C13 C14 C15 169.44(15) . . . . ?
C19 C14 C15 C16 1.1(2) . . . . ?
C13 C14 C15 C16 -177.07(15) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 O2 -178.46(16) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C15 C14 C19 C18 -0.7(2) . . . . ?
C13 C14 C19 C18 177.47(15) . . . . ?
O2 C18 C19 C14 178.75(14) . . . . ?
C17 C18 C19 C14 0.0(2) . . . . ?

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
O2 H2A O1 0.86(3) 1.89(3) 2.7321(18) 170(3) 2_656

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059

