# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_AP-FcNph
_database_code_depnum_ccdc_archive 'CCDC 1897600'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Fe'
_chemical_formula_sum            'C20 H16 Fe'
_chemical_formula_weight         312.18

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   20.2076(13)
_cell_length_b                   6.0150(4)
_cell_length_c                   22.725(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2762.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    114.7(7)
_cell_measurement_reflns_used    3010
_cell_measurement_theta_min      3.5030
_cell_measurement_theta_max      25.8550

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      114.7(7)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18663
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2411
_reflns_number_gt                1791
_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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0407P)²+0.0158P] 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         2411
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16035(13) 0.0747(4) 0.20935(12) 0.0193(6) Uani 1 1 d . . . . .
C2 C 0.18468(13) -0.0299(4) 0.15711(12) 0.0209(7) Uani 1 1 d . . . . .
H2 H 0.2002 -0.1751 0.1544 0.025 Uiso 1 1 calc R U . . .
C3 C 0.18111(13) 0.1248(4) 0.11017(13) 0.0237(7) Uani 1 1 d . . . . .
H3 H 0.1940 0.0993 0.0715 0.028 Uiso 1 1 calc R U . . .
C4 C 0.15432(13) 0.3250(5) 0.13274(12) 0.0224(7) Uani 1 1 d . . . . .
H4 H 0.1468 0.4543 0.1113 0.027 Uiso 1 1 calc R U . . .
C5 C 0.14100(12) 0.2958(4) 0.19306(12) 0.0193(6) Uani 1 1 d . . . . .
H5 H 0.1228 0.4017 0.2181 0.023 Uiso 1 1 calc R U . . .
C6 C 0.03228(14) -0.2044(5) 0.13050(16) 0.0375(9) Uani 1 1 d . . . . .
H6 H 0.0472 -0.3506 0.1316 0.045 Uiso 1 1 calc R U . . .
C7 C 0.03054(14) -0.0656(5) 0.08076(14) 0.0308(7) Uani 1 1 d . . . . .
H7 H 0.0445 -0.1035 0.0431 0.037 Uiso 1 1 calc R U . . .
C8 C 0.00424(13) 0.1392(5) 0.09786(14) 0.0263(7) Uani 1 1 d . . . . .
H8 H -0.0026 0.2608 0.0733 0.032 Uiso 1 1 calc R U . . .
C9 C -0.00996(13) 0.1307(5) 0.15790(13) 0.0286(7) Uani 1 1 d . . . . .
H9 H -0.0277 0.2455 0.1803 0.034 Uiso 1 1 calc R U . . .
C10 C 0.00722(14) -0.0813(5) 0.17860(15) 0.0339(8) Uani 1 1 d . . . . .
H10 H 0.0029 -0.1318 0.2171 0.041 Uiso 1 1 calc R U . . .
C11 C 0.15991(12) -0.0203(4) 0.26901(12) 0.0174(6) Uani 1 1 d . . . . .
C12 C 0.13710(12) 0.0980(4) 0.31657(12) 0.0188(6) Uani 1 1 d . . . . .
H12 H 0.1175 0.2360 0.3104 0.023 Uiso 1 1 calc R U . . .
C13 C 0.14258(12) 0.0155(4) 0.37487(12) 0.0195(6) Uani 1 1 d . . . . .
C14 C 0.12099(13) 0.1397(4) 0.42396(13) 0.0224(7) Uani 1 1 d . . . . .
H14 H 0.1016 0.2784 0.4184 0.027 Uiso 1 1 calc R U . . .
C15 C 0.12832(13) 0.0579(4) 0.47942(13) 0.0252(7) Uani 1 1 d . . . . .
H15 H 0.1134 0.1403 0.5114 0.030 Uiso 1 1 calc R U . . .
C16 C 0.15835(14) -0.1505(4) 0.48891(13) 0.0258(7) Uani 1 1 d . . . . .
H16 H 0.1638 -0.2034 0.5271 0.031 Uiso 1 1 calc R U . . .
C17 C 0.17937(13) -0.2747(4) 0.44250(13) 0.0239(7) Uani 1 1 d . . . . .
H17 H 0.1990 -0.4122 0.4492 0.029 Uiso 1 1 calc R U . . .
C18 C 0.17166(13) -0.1966(4) 0.38420(12) 0.0183(6) Uani 1 1 d . . . . .
C19 C 0.19316(13) -0.3188(4) 0.33445(13) 0.0211(7) Uani 1 1 d . . . . .
H19 H 0.2115 -0.4593 0.3396 0.025 Uiso 1 1 calc R U . . .
C20 C 0.18737(12) -0.2337(4) 0.27944(13) 0.0204(6) Uani 1 1 d . . . . .
H20 H 0.2018 -0.3177 0.2476 0.025 Uiso 1 1 calc R U . . .
Fe1 Fe 0.08872(2) 0.07097(6) 0.14466(2) 0.01795(14) 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
C1 C2 1.431(4) . ?
C1 C5 1.435(3) . ?
C1 C11 1.471(4) . ?
C1 Fe1 2.063(3) . ?
C2 C3 1.417(4) . ?
C2 Fe1 2.051(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.417(4) . ?
C3 Fe1 2.050(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(4) . ?
C4 Fe1 2.041(3) . ?
C4 H4 0.9300 . ?
C5 Fe1 2.038(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(4) . ?
C6 C10 1.414(4) . ?
C6 Fe1 2.037(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(4) . ?
C7 Fe1 2.041(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(4) . ?
C8 Fe1 2.053(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(4) . ?
C9 Fe1 2.048(3) . ?
C9 H9 0.9300 . ?
C10 Fe1 2.036(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 C20 1.418(3) . ?
C12 C13 1.419(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.412(4) . ?
C13 C18 1.420(4) . ?
C14 C15 1.361(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.409(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.414(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.417(4) . ?
C19 C20 1.356(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 C1 C5 106.7(2) . . ?
C2 C1 C11 126.6(2) . . ?
C5 C1 C11 126.6(2) . . ?
C2 C1 Fe1 69.20(15) . . ?
C5 C1 Fe1 68.59(15) . . ?
C11 C1 Fe1 130.40(19) . . ?
C3 C2 C1 108.6(2) . . ?
C3 C2 Fe1 69.76(15) . . ?
C1 C2 Fe1 70.10(15) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe1 C2 H2 126.0 . . ?
C4 C3 C2 107.8(2) . . ?
C4 C3 Fe1 69.39(15) . . ?
C2 C3 Fe1 69.82(15) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
Fe1 C3 H3 126.2 . . ?
C5 C4 C3 108.6(2) . . ?
C5 C4 Fe1 69.70(15) . . ?
C3 C4 Fe1 70.10(15) . . ?
C5 C4 H4 125.7 . . ?
C3 C4 H4 125.7 . . ?
Fe1 C4 H4 126.1 . . ?
C4 C5 C1 108.4(2) . . ?
C4 C5 Fe1 69.91(15) . . ?
C1 C5 Fe1 70.47(15) . . ?
C4 C5 H5 125.8 . . ?
C1 C5 H5 125.8 . . ?
Fe1 C5 H5 125.4 . . ?
C7 C6 C10 107.5(3) . . ?
C7 C6 Fe1 70.00(16) . . ?
C10 C6 Fe1 69.67(16) . . ?
C7 C6 H6 126.2 . . ?
C10 C6 H6 126.2 . . ?
Fe1 C6 H6 125.7 . . ?
C8 C7 C6 108.0(3) . . ?
C8 C7 Fe1 70.51(16) . . ?
C6 C7 Fe1 69.66(17) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe1 C7 H7 125.4 . . ?
C9 C8 C7 108.5(3) . . ?
C9 C8 Fe1 69.94(16) . . ?
C7 C8 Fe1 69.60(16) . . ?
C9 C8 H8 125.7 . . ?
C7 C8 H8 125.7 . . ?
Fe1 C8 H8 126.3 . . ?
C8 C9 C10 108.1(3) . . ?
C8 C9 Fe1 70.28(16) . . ?
C10 C9 Fe1 69.45(16) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 125.9 . . ?
C9 C10 C6 107.8(3) . . ?
C9 C10 Fe1 70.39(16) . . ?
C6 C10 Fe1 69.70(16) . . ?
C9 C10 H10 126.1 . . ?
C6 C10 H10 126.1 . . ?
Fe1 C10 H10 125.4 . . ?
C12 C11 C20 117.9(3) . . ?
C12 C11 C1 121.7(2) . . ?
C20 C11 C1 120.2(2) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 C18 119.0(3) . . ?
C12 C13 C18 119.1(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 122.8(2) . . ?
C17 C18 C13 118.9(2) . . ?
C19 C18 C13 118.3(2) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C11 122.0(3) . . ?
C19 C20 H20 119.0 . . ?
C11 C20 H20 119.0 . . ?
C10 Fe1 C6 40.63(12) . . ?
C10 Fe1 C5 120.87(13) . . ?
C6 Fe1 C5 156.21(13) . . ?
C10 Fe1 C7 67.82(13) . . ?
C6 Fe1 C7 40.34(12) . . ?
C5 Fe1 C7 161.72(12) . . ?
C10 Fe1 C4 155.83(13) . . ?
C6 Fe1 C4 162.12(13) . . ?
C5 Fe1 C4 40.39(10) . . ?
C7 Fe1 C4 125.52(12) . . ?
C10 Fe1 C9 40.16(11) . . ?
C6 Fe1 C9 67.71(12) . . ?
C5 Fe1 C9 107.99(11) . . ?
C7 Fe1 C9 67.31(12) . . ?
C4 Fe1 C9 121.36(12) . . ?
C10 Fe1 C3 162.22(12) . . ?
C6 Fe1 C3 125.30(12) . . ?
C5 Fe1 C3 68.27(11) . . ?
C7 Fe1 C3 108.43(12) . . ?
C4 Fe1 C3 40.52(11) . . ?
C9 Fe1 C3 156.18(12) . . ?
C10 Fe1 C2 125.40(12) . . ?
C6 Fe1 C2 108.10(11) . . ?
C5 Fe1 C2 68.40(10) . . ?
C7 Fe1 C2 121.58(11) . . ?
C4 Fe1 C2 68.03(11) . . ?
C9 Fe1 C2 162.13(12) . . ?
C3 Fe1 C2 40.42(11) . . ?
C10 Fe1 C8 67.26(12) . . ?
C6 Fe1 C8 67.36(12) . . ?
C5 Fe1 C8 125.31(11) . . ?
C7 Fe1 C8 39.89(11) . . ?
C4 Fe1 C8 108.77(11) . . ?
C9 Fe1 C8 39.78(11) . . ?
C3 Fe1 C8 121.85(12) . . ?
C2 Fe1 C8 156.45(12) . . ?
C10 Fe1 C1 107.60(12) . . ?
C6 Fe1 C1 120.95(12) . . ?
C5 Fe1 C1 40.94(10) . . ?
C7 Fe1 C1 156.27(11) . . ?
C4 Fe1 C1 68.33(11) . . ?
C9 Fe1 C1 125.19(11) . . ?
C3 Fe1 C1 68.40(11) . . ?
C2 Fe1 C1 40.70(10) . . ?
C8 Fe1 C1 161.88(11) . . ?

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 0.8(3) . . . . ?
C11 C1 C2 C3 -175.1(2) . . . . ?
Fe1 C1 C2 C3 59.35(18) . . . . ?
C5 C1 C2 Fe1 -58.57(17) . . . . ?
C11 C1 C2 Fe1 125.6(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
Fe1 C2 C3 C4 59.23(18) . . . . ?
C1 C2 C3 Fe1 -59.57(18) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
Fe1 C3 C4 C5 59.25(18) . . . . ?
C2 C3 C4 Fe1 -59.50(18) . . . . ?
C3 C4 C5 C1 0.7(3) . . . . ?
Fe1 C4 C5 C1 60.24(17) . . . . ?
C3 C4 C5 Fe1 -59.49(19) . . . . ?
C2 C1 C5 C4 -0.9(3) . . . . ?
C11 C1 C5 C4 174.9(2) . . . . ?
Fe1 C1 C5 C4 -59.89(18) . . . . ?
C2 C1 C5 Fe1 58.95(17) . . . . ?
C11 C1 C5 Fe1 -125.2(3) . . . . ?
C10 C6 C7 C8 -0.5(3) . . . . ?
Fe1 C6 C7 C8 -60.33(19) . . . . ?
C10 C6 C7 Fe1 59.81(19) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
Fe1 C7 C8 C9 -59.29(19) . . . . ?
C6 C7 C8 Fe1 59.80(19) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
Fe1 C8 C9 C10 -59.38(19) . . . . ?
C7 C8 C9 Fe1 59.08(19) . . . . ?
C8 C9 C10 C6 0.0(3) . . . . ?
Fe1 C9 C10 C6 -59.92(19) . . . . ?
C8 C9 C10 Fe1 59.90(19) . . . . ?
C7 C6 C10 C9 0.3(3) . . . . ?
Fe1 C6 C10 C9 60.36(19) . . . . ?
C7 C6 C10 Fe1 -60.02(19) . . . . ?
C2 C1 C11 C12 178.0(2) . . . . ?
C5 C1 C11 C12 2.9(4) . . . . ?
Fe1 C1 C11 C12 -89.1(3) . . . . ?
C2 C1 C11 C20 2.1(4) . . . . ?
C5 C1 C11 C20 -173.0(2) . . . . ?
Fe1 C1 C11 C20 95.0(3) . . . . ?
C20 C11 C12 C13 2.2(4) . . . . ?
C1 C11 C12 C13 -173.7(2) . . . . ?
C11 C12 C13 C14 178.0(2) . . . . ?
C11 C12 C13 C18 -0.9(4) . . . . ?
C12 C13 C14 C15 -178.5(2) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 179.5(2) . . . . ?
C16 C17 C18 C13 1.1(4) . . . . ?
C14 C13 C18 C17 -1.3(4) . . . . ?
C12 C13 C18 C17 177.6(2) . . . . ?
C14 C13 C18 C19 -179.9(2) . . . . ?
C12 C13 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 -177.2(2) . . . . ?
C13 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C11 0.1(4) . . . . ?
C12 C11 C20 C19 -1.9(4) . . . . ?
C1 C11 C20 C19 174.1(2) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.066

_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_AP-DA-AP088-1
_database_code_depnum_ccdc_archive 'CCDC 1897603'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 Fe O'
_chemical_formula_sum            'C21 H16 Fe O'
_chemical_formula_weight         340.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   8.707(10)
_cell_length_b                   9.473(3)
_cell_length_c                   36.37(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3000(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    121(1)
_cell_measurement_reflns_used    2200
_cell_measurement_theta_min      4.8200
_cell_measurement_theta_max      68.2040

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    8.054
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.22897
_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.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      121(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8386
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         4.824
_diffrn_reflns_theta_max         64.990
_diffrn_reflns_theta_full        65.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             4410
_reflns_number_gt                3702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.729
_reflns_Friedel_fraction_full    0.729

_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0835P)²+14.7631P] 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_abs_structure_details 
;
 Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.003(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4410
_refine_ls_number_parameters     415
_refine_ls_number_restraints     547
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.1957
_refine_ls_wR_factor_gt          0.1836
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2880(14) -0.1178(12) 0.2512(4) 0.023(2) Uani 1 1 d . U . . .
C2 C 0.3137(13) -0.1934(13) 0.2846(4) 0.020(2) Uani 1 1 d . U . . .
H2 H 0.3862 -0.2643 0.2881 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2113(14) -0.1429(12) 0.3115(4) 0.023(2) Uani 1 1 d . U . . .
H3 H 0.2036 -0.1750 0.3356 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1212(13) -0.0330(11) 0.2951(4) 0.022(2) Uani 1 1 d . U . . .
H4 H 0.0442 0.0188 0.3066 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1706(15) -0.0175(12) 0.2582(4) 0.025(2) Uani 1 1 d . U . . .
H5 H 0.1324 0.0476 0.2414 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5465(14) 0.1239(13) 0.2808(4) 0.024(2) Uani 1 1 d . U . . .
H6 H 0.6037 0.1166 0.2593 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5642(14) 0.0411(14) 0.3125(4) 0.026(2) Uani 1 1 d . U . . .
H7 H 0.6357 -0.0310 0.3156 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4540(14) 0.0857(14) 0.3396(4) 0.025(2) Uani 1 1 d . U . . .
H8 H 0.4402 0.0477 0.3629 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3694(15) 0.1999(13) 0.3236(4) 0.023(2) Uani 1 1 d . U . . .
H9 H 0.2916 0.2511 0.3350 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4251(14) 0.2210(12) 0.2875(4) 0.022(2) Uani 1 1 d . U . . .
H10 H 0.3884 0.2875 0.2709 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3657(14) -0.1521(13) 0.2161(3) 0.021(2) Uani 1 1 d . U . . .
C12 C 0.3847(14) -0.2939(13) 0.2066(4) 0.022(2) Uani 1 1 d . U . . .
C13 C 0.4774(16) -0.3345(14) 0.1762(4) 0.029(3) Uani 1 1 d . U . . .
H13 H 0.4893 -0.4298 0.1707 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5479(16) -0.2371(14) 0.1554(4) 0.030(3) Uani 1 1 d . U . . .
H14 H 0.6106 -0.2658 0.1361 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5279(16) -0.0902(14) 0.1625(4) 0.027(3) Uani 1 1 d . U . . .
C16 C 0.5980(16) 0.0121(14) 0.1405(4) 0.029(3) Uani 1 1 d . U . . .
H16 H 0.6605 -0.0165 0.1212 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5765(16) 0.1545(15) 0.1468(4) 0.033(3) Uani 1 1 d . U . . .
H17 H 0.6270 0.2209 0.1323 0.040 Uiso 1 1 calc R U . . .
C18 C 0.4773(17) 0.1986(16) 0.1752(4) 0.034(3) Uani 1 1 d . U . . .
H18 H 0.4579 0.2942 0.1788 0.040 Uiso 1 1 calc R U . . .
C19 C 0.4103(16) 0.1005(13) 0.1974(3) 0.025(3) Uani 1 1 d . U . . .
H19 H 0.3479 0.1314 0.2165 0.030 Uiso 1 1 calc R U . . .
C20 C 0.4318(14) -0.0479(13) 0.1925(4) 0.022(2) Uani 1 1 d . U . . .
C21 C 0.2980(15) -0.4087(13) 0.2253(4) 0.024(2) Uani 1 1 d . U . . .
H21 H 0.2164 -0.3829 0.2404 0.029 Uiso 1 1 calc R U . . .
C22 C 0.0187(14) 0.1180(12) 0.4667(3) 0.021(2) Uani 1 1 d . U . . .
C23 C 0.1394(14) 0.0190(12) 0.4593(4) 0.022(2) Uani 1 1 d . U . . .
H23 H 0.1824 -0.0431 0.4762 0.026 Uiso 1 1 calc R U . . .
C24 C 0.1815(12) 0.0313(11) 0.4224(4) 0.020(2) Uani 1 1 d . U . . .
H24 H 0.2546 -0.0240 0.4106 0.024 Uiso 1 1 calc R U . . .
C25 C 0.0943(14) 0.1428(12) 0.4056(4) 0.024(2) Uani 1 1 d . U . . .
H25 H 0.1029 0.1748 0.3815 0.028 Uiso 1 1 calc R U . . .
C26 C -0.0058(13) 0.1935(12) 0.4325(3) 0.020(2) Uani 1 1 d . U . . .
H26 H -0.0776 0.2650 0.4290 0.024 Uiso 1 1 calc R U . . .
C27 C -0.2400(14) -0.1236(13) 0.4363(3) 0.024(2) Uani 1 1 d . U . . .
H27 H -0.2972 -0.1165 0.4578 0.029 Uiso 1 1 calc R U . . .
C28 C -0.1179(14) -0.2209(12) 0.4299(4) 0.021(2) Uani 1 1 d . U . . .
H28 H -0.0808 -0.2869 0.4466 0.026 Uiso 1 1 calc R U . . .
C29 C -0.0632(14) -0.1994(14) 0.3938(4) 0.024(2) Uani 1 1 d . U . . .
H29 H 0.0145 -0.2499 0.3822 0.029 Uiso 1 1 calc R U . . .
C30 C -0.1492(15) -0.0862(15) 0.3785(4) 0.027(3) Uani 1 1 d . U . . .
H30 H -0.1352 -0.0485 0.3552 0.033 Uiso 1 1 calc R U . . .
C31 C -0.2595(15) -0.0400(14) 0.4045(4) 0.027(2) Uani 1 1 d . U . . .
H31 H -0.3311 0.0318 0.4012 0.033 Uiso 1 1 calc R U . . .
C32 C -0.0593(13) 0.1543(13) 0.5009(4) 0.020(2) Uani 1 1 d . U . . .
C33 C -0.0770(14) 0.2963(13) 0.5103(4) 0.022(2) Uani 1 1 d . U . . .
C34 C -0.1703(13) 0.3384(14) 0.5400(4) 0.023(2) Uani 1 1 d . U . . .
H34 H -0.1827 0.4338 0.5453 0.027 Uiso 1 1 calc R U . . .
C35 C -0.2418(15) 0.2403(14) 0.5609(4) 0.026(3) Uani 1 1 d . U . . .
H35 H -0.3070 0.2694 0.5797 0.032 Uiso 1 1 calc R U . . .
C36 C -0.2195(15) 0.0936(13) 0.5547(4) 0.024(2) Uani 1 1 d . U . . .
C37 C -0.2927(16) -0.0100(15) 0.5769(4) 0.031(3) Uani 1 1 d . U . . .
H37 H -0.3556 0.0191 0.5961 0.037 Uiso 1 1 calc R U . . .
C38 C -0.2733(15) -0.1500(14) 0.5707(4) 0.030(3) Uani 1 1 d . U . . .
H38 H -0.3245 -0.2160 0.5852 0.036 Uiso 1 1 calc R U . . .
C39 C -0.1753(16) -0.1947(15) 0.5424(4) 0.032(3) Uani 1 1 d . U . . .
H39 H -0.1581 -0.2907 0.5389 0.038 Uiso 1 1 calc R U . . .
C40 C -0.1041(16) -0.0984(12) 0.5196(4) 0.024(3) Uani 1 1 d . U . . .
H40 H -0.0416 -0.1306 0.5006 0.029 Uiso 1 1 calc R U . . .
C41 C -0.1245(14) 0.0496(13) 0.5246(4) 0.021(2) Uani 1 1 d . U . . .
C42 C 0.0098(13) 0.4087(12) 0.4910(4) 0.021(2) Uani 1 1 d . U . . .
H42 H 0.0896 0.3822 0.4755 0.025 Uiso 1 1 calc R U . . .
O1 O 0.3263(10) -0.5337(9) 0.2224(3) 0.026(2) Uani 1 1 d . U . . .
O2 O -0.0183(10) 0.5356(9) 0.4945(3) 0.027(2) Uani 1 1 d . U . . .
Fe1 Fe 0.3478(2) 0.01770(18) 0.29330(5) 0.0186(4) Uani 1 1 d . U . . .
Fe2 Fe -0.04070(19) -0.01738(18) 0.42385(5) 0.0173(4) Uani 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
C1 C5 1.419(18) . ?
C1 C2 1.429(18) . ?
C1 C11 1.480(18) . ?
C1 Fe1 2.065(12) . ?
C2 C3 1.407(17) . ?
C2 Fe1 2.046(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.434(17) . ?
C3 Fe1 2.041(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.42(2) . ?
C4 Fe1 2.032(11) . ?
C4 H4 0.9300 . ?
C5 Fe1 2.029(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(19) . ?
C6 C10 1.422(17) . ?
C6 Fe1 2.053(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.438(19) . ?
C7 Fe1 2.023(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.431(18) . ?
C8 Fe1 2.025(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.413(19) . ?
C9 Fe1 2.057(13) . ?
C9 H9 0.9300 . ?
C10 Fe1 2.051(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(18) . ?
C11 C20 1.430(18) . ?
C12 C13 1.42(2) . ?
C12 C21 1.489(18) . ?
C13 C14 1.34(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.427(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(19) . ?
C15 C20 1.430(19) . ?
C16 C17 1.381(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.41(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.36(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.430(18) . ?
C19 H19 0.9300 . ?
C21 O1 1.214(16) . ?
C21 H21 0.9300 . ?
C22 C23 1.435(17) . ?
C22 C26 1.452(17) . ?
C22 C32 1.458(18) . ?
C22 Fe2 2.084(12) . ?
C23 C24 1.394(19) . ?
C23 Fe2 2.058(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.438(17) . ?
C24 Fe2 1.990(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.396(18) . ?
C25 Fe2 2.031(12) . ?
C25 H25 0.9300 . ?
C26 Fe2 2.045(11) . ?
C26 H26 0.9300 . ?
C27 C31 1.413(19) . ?
C27 C28 1.426(18) . ?
C27 Fe2 2.057(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.410(19) . ?
C28 Fe2 2.053(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.420(19) . ?
C29 Fe2 2.051(13) . ?
C29 H29 0.9300 . ?
C30 C31 1.42(2) . ?
C30 Fe2 2.008(13) . ?
C30 H30 0.9300 . ?
C31 Fe2 2.043(14) . ?
C31 H31 0.9300 . ?
C32 C33 1.396(17) . ?
C32 C41 1.431(18) . ?
C33 C34 1.411(18) . ?
C33 C42 1.482(17) . ?
C34 C35 1.351(19) . ?
C34 H34 0.9300 . ?
C35 C36 1.422(18) . ?
C35 H35 0.9300 . ?
C36 C37 1.422(19) . ?
C36 C41 1.433(18) . ?
C37 C38 1.36(2) . ?
C37 H37 0.9300 . ?
C38 C39 1.40(2) . ?
C38 H38 0.9300 . ?
C39 C40 1.380(19) . ?
C39 H39 0.9300 . ?
C40 C41 1.424(17) . ?
C40 H40 0.9300 . ?
C42 O2 1.234(15) . ?
C42 H42 0.9300 . ?

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 C1 C2 107.2(11) . . ?
C5 C1 C11 129.2(12) . . ?
C2 C1 C11 123.5(11) . . ?
C5 C1 Fe1 68.4(7) . . ?
C2 C1 Fe1 69.0(7) . . ?
C11 C1 Fe1 131.3(9) . . ?
C3 C2 C1 108.8(11) . . ?
C3 C2 Fe1 69.7(7) . . ?
C1 C2 Fe1 70.4(7) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
Fe1 C2 H2 125.9 . . ?
C2 C3 C4 107.7(12) . . ?
C2 C3 Fe1 70.1(7) . . ?
C4 C3 Fe1 69.0(7) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Fe1 C3 H3 126.3 . . ?
C5 C4 C3 107.6(11) . . ?
C5 C4 Fe1 69.5(7) . . ?
C3 C4 Fe1 69.7(7) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
Fe1 C4 H4 126.2 . . ?
C4 C5 C1 108.7(11) . . ?
C4 C5 Fe1 69.7(7) . . ?
C1 C5 Fe1 71.1(7) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.7 . . ?
Fe1 C5 H5 125.2 . . ?
C7 C6 C10 107.5(12) . . ?
C7 C6 Fe1 68.7(7) . . ?
C10 C6 Fe1 69.6(7) . . ?
C7 C6 H6 126.3 . . ?
C10 C6 H6 126.3 . . ?
Fe1 C6 H6 127.0 . . ?
C6 C7 C8 108.9(11) . . ?
C6 C7 Fe1 71.0(7) . . ?
C8 C7 Fe1 69.3(7) . . ?
C6 C7 H7 125.5 . . ?
C8 C7 H7 125.5 . . ?
Fe1 C7 H7 125.8 . . ?
C9 C8 C7 106.8(12) . . ?
C9 C8 Fe1 70.7(7) . . ?
C7 C8 Fe1 69.1(8) . . ?
C9 C8 H8 126.6 . . ?
C7 C8 H8 126.6 . . ?
Fe1 C8 H8 125.2 . . ?
C10 C9 C8 107.8(11) . . ?
C10 C9 Fe1 69.6(7) . . ?
C8 C9 Fe1 68.3(7) . . ?
C10 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
Fe1 C9 H9 127.5 . . ?
C9 C10 C6 109.0(11) . . ?
C9 C10 Fe1 70.1(7) . . ?
C6 C10 Fe1 69.8(7) . . ?
C9 C10 H10 125.5 . . ?
C6 C10 H10 125.5 . . ?
Fe1 C10 H10 126.1 . . ?
C12 C11 C20 117.8(12) . . ?
C12 C11 C1 118.6(11) . . ?
C20 C11 C1 123.5(11) . . ?
C11 C12 C13 121.3(12) . . ?
C11 C12 C21 122.0(12) . . ?
C13 C12 C21 116.5(11) . . ?
C14 C13 C12 120.8(13) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.9(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 121.3(13) . . ?
C16 C15 C20 119.9(12) . . ?
C14 C15 C20 118.9(12) . . ?
C17 C16 C15 121.6(13) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.5(13) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 119.7(14) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 122.7(13) . . ?
C18 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C19 C20 C15 116.6(12) . . ?
C19 C20 C11 123.4(12) . . ?
C15 C20 C11 120.0(11) . . ?
O1 C21 C12 124.7(13) . . ?
O1 C21 H21 117.7 . . ?
C12 C21 H21 117.7 . . ?
C23 C22 C26 105.5(11) . . ?
C23 C22 C32 131.1(12) . . ?
C26 C22 C32 123.2(11) . . ?
C23 C22 Fe2 68.8(7) . . ?
C26 C22 Fe2 68.0(7) . . ?
C32 C22 Fe2 131.8(9) . . ?
C24 C23 C22 108.7(11) . . ?
C24 C23 Fe2 67.2(7) . . ?
C22 C23 Fe2 70.7(7) . . ?
C24 C23 H23 125.7 . . ?
C22 C23 H23 125.7 . . ?
Fe2 C23 H23 127.9 . . ?
C23 C24 C25 109.3(11) . . ?
C23 C24 Fe2 72.5(7) . . ?
C25 C24 Fe2 70.6(6) . . ?
C23 C24 H24 125.3 . . ?
C25 C24 H24 125.3 . . ?
Fe2 C24 H24 123.2 . . ?
C26 C25 C24 106.6(11) . . ?
C26 C25 Fe2 70.5(7) . . ?
C24 C25 Fe2 67.5(6) . . ?
C26 C25 H25 126.7 . . ?
C24 C25 H25 126.7 . . ?
Fe2 C25 H25 126.7 . . ?
C25 C26 C22 109.8(11) . . ?
C25 C26 Fe2 69.4(7) . . ?
C22 C26 Fe2 70.9(6) . . ?
C25 C26 H26 125.1 . . ?
C22 C26 H26 125.1 . . ?
Fe2 C26 H26 126.2 . . ?
C31 C27 C28 108.5(12) . . ?
C31 C27 Fe2 69.3(7) . . ?
C28 C27 Fe2 69.6(7) . . ?
C31 C27 H27 125.7 . . ?
C28 C27 H27 125.7 . . ?
Fe2 C27 H27 127.0 . . ?
C29 C28 C27 108.1(11) . . ?
C29 C28 Fe2 69.8(7) . . ?
C27 C28 Fe2 69.8(7) . . ?
C29 C28 H28 126.0 . . ?
C27 C28 H28 126.0 . . ?
Fe2 C28 H28 126.0 . . ?
C28 C29 C30 107.1(11) . . ?
C28 C29 Fe2 70.0(7) . . ?
C30 C29 Fe2 67.9(7) . . ?
C28 C29 H29 126.4 . . ?
C30 C29 H29 126.4 . . ?
Fe2 C29 H29 127.2 . . ?
C31 C30 C29 109.3(12) . . ?
C31 C30 Fe2 70.8(8) . . ?
C29 C30 Fe2 71.1(7) . . ?
C31 C30 H30 125.4 . . ?
C29 C30 H30 125.4 . . ?
Fe2 C30 H30 124.3 . . ?
C27 C31 C30 106.9(12) . . ?
C27 C31 Fe2 70.4(8) . . ?
C30 C31 Fe2 68.2(7) . . ?
C27 C31 H31 126.6 . . ?
C30 C31 H31 126.6 . . ?
Fe2 C31 H31 126.4 . . ?
C33 C32 C41 118.5(12) . . ?
C33 C32 C22 119.1(11) . . ?
C41 C32 C22 122.3(11) . . ?
C32 C33 C34 121.6(12) . . ?
C32 C33 C42 121.4(11) . . ?
C34 C33 C42 116.9(11) . . ?
C35 C34 C33 120.1(12) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 121.3(12) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C37 C36 C35 121.5(12) . . ?
C37 C36 C41 119.4(12) . . ?
C35 C36 C41 119.0(12) . . ?
C38 C37 C36 121.8(13) . . ?
C38 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
C37 C38 C39 119.4(13) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C40 C39 C38 121.0(13) . . ?
C40 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C39 C40 C41 121.2(13) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C40 C41 C32 123.8(12) . . ?
C40 C41 C36 117.1(12) . . ?
C32 C41 C36 119.1(11) . . ?
O2 C42 C33 123.4(11) . . ?
O2 C42 H42 118.3 . . ?
C33 C42 H42 118.3 . . ?
C7 Fe1 C8 41.6(5) . . ?
C7 Fe1 C5 160.7(6) . . ?
C8 Fe1 C5 157.2(5) . . ?
C7 Fe1 C4 156.9(6) . . ?
C8 Fe1 C4 119.4(6) . . ?
C5 Fe1 C4 40.8(6) . . ?
C7 Fe1 C3 120.8(5) . . ?
C8 Fe1 C3 103.5(5) . . ?
C5 Fe1 C3 68.8(5) . . ?
C4 Fe1 C3 41.2(5) . . ?
C7 Fe1 C2 107.2(5) . . ?
C8 Fe1 C2 120.3(5) . . ?
C5 Fe1 C2 68.4(5) . . ?
C4 Fe1 C2 68.5(4) . . ?
C3 Fe1 C2 40.3(5) . . ?
C7 Fe1 C10 68.1(5) . . ?
C8 Fe1 C10 68.7(5) . . ?
C5 Fe1 C10 109.9(5) . . ?
C4 Fe1 C10 123.0(5) . . ?
C3 Fe1 C10 157.6(5) . . ?
C2 Fe1 C10 161.7(5) . . ?
C7 Fe1 C6 40.3(5) . . ?
C8 Fe1 C6 69.1(5) . . ?
C5 Fe1 C6 125.6(5) . . ?
C4 Fe1 C6 160.3(5) . . ?
C3 Fe1 C6 158.1(5) . . ?
C2 Fe1 C6 124.5(5) . . ?
C10 Fe1 C6 40.6(5) . . ?
C7 Fe1 C9 68.7(5) . . ?
C8 Fe1 C9 41.0(5) . . ?
C5 Fe1 C9 123.0(5) . . ?
C4 Fe1 C9 105.6(5) . . ?
C3 Fe1 C9 120.3(5) . . ?
C2 Fe1 C9 156.3(5) . . ?
C10 Fe1 C9 40.2(5) . . ?
C6 Fe1 C9 68.3(5) . . ?
C7 Fe1 C1 124.0(5) . . ?
C8 Fe1 C1 158.3(5) . . ?
C5 Fe1 C1 40.6(5) . . ?
C4 Fe1 C1 68.4(5) . . ?
C3 Fe1 C1 68.3(5) . . ?
C2 Fe1 C1 40.7(5) . . ?
C10 Fe1 C1 126.2(5) . . ?
C6 Fe1 C1 110.6(5) . . ?
C9 Fe1 C1 160.5(5) . . ?
C24 Fe2 C30 120.7(6) . . ?
C24 Fe2 C25 41.9(5) . . ?
C30 Fe2 C25 104.3(6) . . ?
C24 Fe2 C31 157.3(5) . . ?
C30 Fe2 C31 40.9(6) . . ?
C25 Fe2 C31 120.4(5) . . ?
C24 Fe2 C26 68.5(5) . . ?
C30 Fe2 C26 120.9(5) . . ?
C25 Fe2 C26 40.1(5) . . ?
C31 Fe2 C26 107.1(5) . . ?
C24 Fe2 C29 105.9(5) . . ?
C30 Fe2 C29 40.9(5) . . ?
C25 Fe2 C29 120.6(5) . . ?
C31 Fe2 C29 68.8(5) . . ?
C26 Fe2 C29 156.6(5) . . ?
C24 Fe2 C28 122.6(5) . . ?
C30 Fe2 C28 68.2(5) . . ?
C25 Fe2 C28 157.8(5) . . ?
C31 Fe2 C28 68.5(5) . . ?
C26 Fe2 C28 161.7(5) . . ?
C29 Fe2 C28 40.2(5) . . ?
C24 Fe2 C27 160.0(5) . . ?
C30 Fe2 C27 68.0(5) . . ?
C25 Fe2 C27 157.8(5) . . ?
C31 Fe2 C27 40.3(5) . . ?
C26 Fe2 C27 124.7(5) . . ?
C29 Fe2 C27 68.0(5) . . ?
C28 Fe2 C27 40.6(5) . . ?
C24 Fe2 C23 40.2(5) . . ?
C30 Fe2 C23 157.8(5) . . ?
C25 Fe2 C23 68.8(5) . . ?
C31 Fe2 C23 160.7(5) . . ?
C26 Fe2 C23 68.1(5) . . ?
C29 Fe2 C23 123.2(5) . . ?
C28 Fe2 C23 109.9(5) . . ?
C27 Fe2 C23 126.0(5) . . ?
C24 Fe2 C22 68.6(5) . . ?
C30 Fe2 C22 158.5(5) . . ?
C25 Fe2 C22 69.0(5) . . ?
C31 Fe2 C22 123.6(5) . . ?
C26 Fe2 C22 41.1(5) . . ?
C29 Fe2 C22 160.0(5) . . ?
C28 Fe2 C22 125.4(5) . . ?
C27 Fe2 C22 110.2(5) . . ?
C23 Fe2 C22 40.5(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 1.4(14) . . . . ?
C11 C1 C2 C3 -174.3(11) . . . . ?
Fe1 C1 C2 C3 59.3(9) . . . . ?
C5 C1 C2 Fe1 -57.9(8) . . . . ?
C11 C1 C2 Fe1 126.4(12) . . . . ?
C1 C2 C3 C4 -0.7(14) . . . . ?
Fe1 C2 C3 C4 59.0(8) . . . . ?
C1 C2 C3 Fe1 -59.7(8) . . . . ?
C2 C3 C4 C5 -0.2(14) . . . . ?
Fe1 C3 C4 C5 59.4(8) . . . . ?
C2 C3 C4 Fe1 -59.6(8) . . . . ?
C3 C4 C5 C1 1.1(14) . . . . ?
Fe1 C4 C5 C1 60.6(9) . . . . ?
C3 C4 C5 Fe1 -59.5(8) . . . . ?
C2 C1 C5 C4 -1.6(14) . . . . ?
C11 C1 C5 C4 173.9(12) . . . . ?
Fe1 C1 C5 C4 -59.8(9) . . . . ?
C2 C1 C5 Fe1 58.2(8) . . . . ?
C11 C1 C5 Fe1 -126.4(13) . . . . ?
C10 C6 C7 C8 -0.1(14) . . . . ?
Fe1 C6 C7 C8 -59.1(9) . . . . ?
C10 C6 C7 Fe1 59.0(8) . . . . ?
C6 C7 C8 C9 -0.8(14) . . . . ?
Fe1 C7 C8 C9 -61.0(8) . . . . ?
C6 C7 C8 Fe1 60.2(9) . . . . ?
C7 C8 C9 C10 1.4(14) . . . . ?
Fe1 C8 C9 C10 -58.6(9) . . . . ?
C7 C8 C9 Fe1 59.9(8) . . . . ?
C8 C9 C10 C6 -1.4(14) . . . . ?
Fe1 C9 C10 C6 -59.2(8) . . . . ?
C8 C9 C10 Fe1 57.7(8) . . . . ?
C7 C6 C10 C9 0.9(14) . . . . ?
Fe1 C6 C10 C9 59.4(9) . . . . ?
C7 C6 C10 Fe1 -58.4(8) . . . . ?
C5 C1 C11 C12 -133.9(13) . . . . ?
C2 C1 C11 C12 40.9(18) . . . . ?
Fe1 C1 C11 C12 131.4(11) . . . . ?
C5 C1 C11 C20 50.4(19) . . . . ?
C2 C1 C11 C20 -134.8(13) . . . . ?
Fe1 C1 C11 C20 -44.3(18) . . . . ?
C20 C11 C12 C13 5.2(18) . . . . ?
C1 C11 C12 C13 -170.7(12) . . . . ?
C20 C11 C12 C21 -168.9(11) . . . . ?
C1 C11 C12 C21 15.2(18) . . . . ?
C11 C12 C13 C14 -1(2) . . . . ?
C21 C12 C13 C14 173.5(12) . . . . ?
C12 C13 C14 C15 -2(2) . . . . ?
C13 C14 C15 C16 -178.5(13) . . . . ?
C13 C14 C15 C20 0(2) . . . . ?
C14 C15 C16 C17 178.6(13) . . . . ?
C20 C15 C16 C17 0(2) . . . . ?
C15 C16 C17 C18 -2(2) . . . . ?
C16 C17 C18 C19 3(2) . . . . ?
C17 C18 C19 C20 -2(2) . . . . ?
C18 C19 C20 C15 0(2) . . . . ?
C18 C19 C20 C11 178.2(13) . . . . ?
C16 C15 C20 C19 1.5(19) . . . . ?
C14 C15 C20 C19 -177.3(12) . . . . ?
C16 C15 C20 C11 -177.1(12) . . . . ?
C14 C15 C20 C11 4.1(19) . . . . ?
C12 C11 C20 C19 174.8(12) . . . . ?
C1 C11 C20 C19 -9.5(19) . . . . ?
C12 C11 C20 C15 -6.7(18) . . . . ?
C1 C11 C20 C15 169.0(12) . . . . ?
C11 C12 C21 O1 -168.1(12) . . . . ?
C13 C12 C21 O1 17.6(19) . . . . ?
C26 C22 C23 C24 -1.7(13) . . . . ?
C32 C22 C23 C24 -175.8(12) . . . . ?
Fe2 C22 C23 C24 56.6(8) . . . . ?
C26 C22 C23 Fe2 -58.3(8) . . . . ?
C32 C22 C23 Fe2 127.6(13) . . . . ?
C22 C23 C24 C25 2.6(13) . . . . ?
Fe2 C23 C24 C25 61.3(8) . . . . ?
C22 C23 C24 Fe2 -58.7(8) . . . . ?
C23 C24 C25 C26 -2.5(13) . . . . ?
Fe2 C24 C25 C26 60.0(8) . . . . ?
C23 C24 C25 Fe2 -62.5(8) . . . . ?
C24 C25 C26 C22 1.4(13) . . . . ?
Fe2 C25 C26 C22 59.5(8) . . . . ?
C24 C25 C26 Fe2 -58.1(8) . . . . ?
C23 C22 C26 C25 0.2(13) . . . . ?
C32 C22 C26 C25 174.8(11) . . . . ?
Fe2 C22 C26 C25 -58.6(8) . . . . ?
C23 C22 C26 Fe2 58.8(8) . . . . ?
C32 C22 C26 Fe2 -126.5(11) . . . . ?
C31 C27 C28 C29 -1.0(14) . . . . ?
Fe2 C27 C28 C29 -59.5(8) . . . . ?
C31 C27 C28 Fe2 58.5(9) . . . . ?
C27 C28 C29 C30 1.6(14) . . . . ?
Fe2 C28 C29 C30 -57.9(8) . . . . ?
C27 C28 C29 Fe2 59.5(8) . . . . ?
C28 C29 C30 C31 -1.6(14) . . . . ?
Fe2 C29 C30 C31 -60.8(9) . . . . ?
C28 C29 C30 Fe2 59.2(9) . . . . ?
C28 C27 C31 C30 0.1(14) . . . . ?
Fe2 C27 C31 C30 58.7(9) . . . . ?
C28 C27 C31 Fe2 -58.6(8) . . . . ?
C29 C30 C31 C27 1.0(14) . . . . ?
Fe2 C30 C31 C27 -60.1(9) . . . . ?
C29 C30 C31 Fe2 61.0(9) . . . . ?
C23 C22 C32 C33 131.6(13) . . . . ?
C26 C22 C32 C33 -41.6(17) . . . . ?
Fe2 C22 C32 C33 -130.6(11) . . . . ?
C23 C22 C32 C41 -51.1(19) . . . . ?
C26 C22 C32 C41 135.7(12) . . . . ?
Fe2 C22 C32 C41 46.7(17) . . . . ?
C41 C32 C33 C34 -6.8(18) . . . . ?
C22 C32 C33 C34 170.6(11) . . . . ?
C41 C32 C33 C42 169.0(11) . . . . ?
C22 C32 C33 C42 -13.6(18) . . . . ?
C32 C33 C34 C35 1.9(19) . . . . ?
C42 C33 C34 C35 -174.1(11) . . . . ?
C33 C34 C35 C36 3(2) . . . . ?
C34 C35 C36 C37 179.1(13) . . . . ?
C34 C35 C36 C41 -3(2) . . . . ?
C35 C36 C37 C38 179.1(13) . . . . ?
C41 C36 C37 C38 1(2) . . . . ?
C36 C37 C38 C39 2(2) . . . . ?
C37 C38 C39 C40 -3(2) . . . . ?
C38 C39 C40 C41 2(2) . . . . ?
C39 C40 C41 C32 -177.1(12) . . . . ?
C39 C40 C41 C36 1.2(19) . . . . ?
C33 C32 C41 C40 -174.9(12) . . . . ?
C22 C32 C41 C40 7.8(19) . . . . ?
C33 C32 C41 C36 6.8(17) . . . . ?
C22 C32 C41 C36 -170.5(11) . . . . ?
C37 C36 C41 C40 -2.5(18) . . . . ?
C35 C36 C41 C40 179.4(12) . . . . ?
C37 C36 C41 C32 176.0(12) . . . . ?
C35 C36 C41 C32 -2.2(18) . . . . ?
C32 C33 C42 O2 168.9(12) . . . . ?
C34 C33 C42 O2 -15.1(18) . . . . ?

_refine_diff_density_max         1.170
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.117

_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_DA-AP135-2
_database_code_depnum_ccdc_archive 'CCDC 1897604'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 Fe'
_chemical_formula_sum            'C30 H22 Fe'
_chemical_formula_weight         438.32

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

_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                   12.8866(8)
_cell_length_b                   7.5244(4)
_cell_length_c                   21.0448(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.335(7)
_cell_angle_gamma                90
_cell_volume                     2000.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(14)
_cell_measurement_reflns_used    1882
_cell_measurement_theta_min      3.5280
_cell_measurement_theta_max      27.8240

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.769
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.922
_oxdiff_exptl_absorpt_empirical_full_max 1.175
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.00(14)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini S'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6221
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6221
_reflns_number_gt                4703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0051P)²+22.6428P] 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         6221
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2182(5) 0.0722(7) 0.5678(3) 0.0161(13) Uani 1 1 d . . . . .
C2 C 0.1354(5) 0.0706(8) 0.5121(3) 0.0187(14) Uani 1 1 d . . . . .
H2 H 0.1135 -0.0272 0.4859 0.022 Uiso 1 1 calc R U . . .
C3 C 0.0923(4) 0.2429(9) 0.5035(3) 0.0218(14) Uani 1 1 d . . . . .
H3 H 0.0367 0.2778 0.4707 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1478(5) 0.3547(8) 0.5532(3) 0.0207(15) Uani 1 1 d . . . . .
H4 H 0.1356 0.4751 0.5585 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2254(5) 0.2482(8) 0.5934(3) 0.0193(13) Uani 1 1 d . . . . .
H5 H 0.2727 0.2868 0.6300 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2781(5) -0.0824(7) 0.6015(3) 0.0148(13) Uani 1 1 d . . . . .
C7 C 0.3827(5) -0.1126(8) 0.6009(3) 0.0202(14) Uani 1 1 d . . . . .
H7 H 0.4169 -0.0396 0.5759 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4401(5) -0.2506(8) 0.6370(3) 0.0211(13) Uani 1 1 d . . . . .
H8 H 0.5110 -0.2682 0.6354 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3919(5) -0.3577(8) 0.6741(3) 0.0215(15) Uani 1 1 d . . . . .
H9 H 0.4303 -0.4482 0.6981 0.026 Uiso 1 1 calc R U . . .
C10 C 0.2840(5) -0.3339(7) 0.6769(3) 0.0162(14) Uani 1 1 d . . . . .
C11 C 0.2317(5) -0.4436(7) 0.7157(3) 0.0190(14) Uani 1 1 d . . . . .
H11 H 0.2695 -0.5337 0.7402 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1284(5) -0.4205(8) 0.7178(3) 0.0212(15) Uani 1 1 d . . . . .
H12 H 0.0964 -0.4928 0.7442 0.025 Uiso 1 1 calc R U . . .
C13 C 0.0690(5) -0.2865(7) 0.6799(3) 0.0194(14) Uani 1 1 d . . . . .
H13 H -0.0024 -0.2723 0.6806 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1170(5) -0.1776(7) 0.6422(3) 0.0160(13) Uani 1 1 d . . . . .
H14 H 0.0774 -0.0890 0.6179 0.019 Uiso 1 1 calc R U . . .
C15 C 0.2242(5) -0.1963(7) 0.6394(3) 0.0163(14) Uani 1 1 d . . . . .
Fe1 Fe 0.2500 0.2500 0.5000 0.0145(3) Uani 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.422(8) . ?
C1 C5 1.426(8) . ?
C1 C6 1.495(8) . ?
C1 Fe1 2.056(6) . ?
C2 C3 1.408(8) . ?
C2 Fe1 2.053(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.421(8) . ?
C3 Fe1 2.049(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.423(8) . ?
C4 Fe1 2.047(6) . ?
C4 H4 0.9300 . ?
C5 Fe1 2.051(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(8) . ?
C6 C15 1.440(8) . ?
C7 C8 1.408(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.355(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.414(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(8) . ?
C10 C15 1.432(8) . ?
C11 C12 1.352(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.414(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(8) . ?
C14 H14 0.9300 . ?
Fe1 C4 2.047(6) 7_556 ?
Fe1 C3 2.049(5) 7_556 ?
Fe1 C5 2.051(5) 7_556 ?
Fe1 C2 2.053(6) 7_556 ?
Fe1 C1 2.056(6) 7_556 ?

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 C1 C5 107.5(5) . . ?
C2 C1 C6 128.2(5) . . ?
C5 C1 C6 123.7(5) . . ?
C2 C1 Fe1 69.6(3) . . ?
C5 C1 Fe1 69.5(3) . . ?
C6 C1 Fe1 132.9(4) . . ?
C3 C2 C1 108.1(5) . . ?
C3 C2 Fe1 69.8(3) . . ?
C1 C2 Fe1 69.8(3) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 126.0 . . ?
C2 C3 C4 108.8(5) . . ?
C2 C3 Fe1 70.1(3) . . ?
C4 C3 Fe1 69.6(3) . . ?
C2 C3 H3 125.6 . . ?
C4 C3 H3 125.6 . . ?
Fe1 C3 H3 126.3 . . ?
C3 C4 C5 107.3(5) . . ?
C3 C4 Fe1 69.8(3) . . ?
C5 C4 Fe1 69.8(3) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
Fe1 C4 H4 125.6 . . ?
C4 C5 C1 108.3(5) . . ?
C4 C5 Fe1 69.5(3) . . ?
C1 C5 Fe1 69.9(3) . . ?
C4 C5 H5 125.9 . . ?
C1 C5 H5 125.9 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C15 119.3(5) . . ?
C7 C6 C1 122.9(5) . . ?
C15 C6 C1 117.7(5) . . ?
C6 C7 C8 122.1(6) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.0(6) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 122.1(6) . . ?
C9 C10 C15 119.7(5) . . ?
C11 C10 C15 118.2(6) . . ?
C12 C11 C10 121.7(6) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.0(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.7(6) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 118.5(5) . . ?
C14 C15 C6 123.4(5) . . ?
C10 C15 C6 118.0(5) . . ?
C4 Fe1 C4 180.0(3) 7_556 . ?
C4 Fe1 C3 40.6(2) 7_556 7_556 ?
C4 Fe1 C3 139.4(2) . 7_556 ?
C4 Fe1 C3 139.4(2) 7_556 . ?
C4 Fe1 C3 40.6(2) . . ?
C3 Fe1 C3 180.0 7_556 . ?
C4 Fe1 C5 139.4(2) 7_556 . ?
C4 Fe1 C5 40.6(2) . . ?
C3 Fe1 C5 112.1(2) 7_556 . ?
C3 Fe1 C5 67.9(2) . . ?
C4 Fe1 C5 40.6(2) 7_556 7_556 ?
C4 Fe1 C5 139.4(2) . 7_556 ?
C3 Fe1 C5 67.9(2) 7_556 7_556 ?
C3 Fe1 C5 112.1(2) . 7_556 ?
C5 Fe1 C5 180.0(3) . 7_556 ?
C4 Fe1 C2 68.3(2) 7_556 7_556 ?
C4 Fe1 C2 111.7(2) . 7_556 ?
C3 Fe1 C2 40.2(2) 7_556 7_556 ?
C3 Fe1 C2 139.8(2) . 7_556 ?
C5 Fe1 C2 111.9(2) . 7_556 ?
C5 Fe1 C2 68.1(2) 7_556 7_556 ?
C4 Fe1 C2 111.7(2) 7_556 . ?
C4 Fe1 C2 68.3(2) . . ?
C3 Fe1 C2 139.8(2) 7_556 . ?
C3 Fe1 C2 40.2(2) . . ?
C5 Fe1 C2 68.1(2) . . ?
C5 Fe1 C2 111.9(2) 7_556 . ?
C2 Fe1 C2 180.0 7_556 . ?
C4 Fe1 C1 111.5(2) 7_556 . ?
C4 Fe1 C1 68.5(2) . . ?
C3 Fe1 C1 112.1(2) 7_556 . ?
C3 Fe1 C1 67.9(2) . . ?
C5 Fe1 C1 40.6(2) . . ?
C5 Fe1 C1 139.4(2) 7_556 . ?
C2 Fe1 C1 139.5(2) 7_556 . ?
C2 Fe1 C1 40.5(2) . . ?
C4 Fe1 C1 68.5(2) 7_556 7_556 ?
C4 Fe1 C1 111.5(2) . 7_556 ?
C3 Fe1 C1 67.9(2) 7_556 7_556 ?
C3 Fe1 C1 112.1(2) . 7_556 ?
C5 Fe1 C1 139.4(2) . 7_556 ?
C5 Fe1 C1 40.6(2) 7_556 7_556 ?
C2 Fe1 C1 40.5(2) 7_556 7_556 ?
C2 Fe1 C1 139.5(2) . 7_556 ?
C1 Fe1 C1 180.0(2) . 7_556 ?

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 0.0(6) . . . . ?
C6 C1 C2 C3 171.4(6) . . . . ?
Fe1 C1 C2 C3 -59.5(4) . . . . ?
C5 C1 C2 Fe1 59.4(4) . . . . ?
C6 C1 C2 Fe1 -129.2(6) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
Fe1 C2 C3 C4 -59.1(4) . . . . ?
C1 C2 C3 Fe1 59.5(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
Fe1 C3 C4 C5 -60.0(4) . . . . ?
C2 C3 C4 Fe1 59.3(4) . . . . ?
C3 C4 C5 C1 0.7(6) . . . . ?
Fe1 C4 C5 C1 -59.3(4) . . . . ?
C3 C4 C5 Fe1 60.0(4) . . . . ?
C2 C1 C5 C4 -0.4(6) . . . . ?
C6 C1 C5 C4 -172.3(5) . . . . ?
Fe1 C1 C5 C4 59.1(4) . . . . ?
C2 C1 C5 Fe1 -59.5(4) . . . . ?
C6 C1 C5 Fe1 128.6(6) . . . . ?
C2 C1 C6 C7 111.0(7) . . . . ?
C5 C1 C6 C7 -78.9(8) . . . . ?
Fe1 C1 C6 C7 13.7(9) . . . . ?
C2 C1 C6 C15 -73.3(8) . . . . ?
C5 C1 C6 C15 96.9(7) . . . . ?
Fe1 C1 C6 C15 -170.5(4) . . . . ?
C15 C6 C7 C8 -0.8(9) . . . . ?
C1 C6 C7 C8 174.9(6) . . . . ?
C6 C7 C8 C9 -0.4(9) . . . . ?
C7 C8 C9 C10 0.4(9) . . . . ?
C8 C9 C10 C11 -179.7(6) . . . . ?
C8 C9 C10 C15 0.9(9) . . . . ?
C9 C10 C11 C12 -179.6(6) . . . . ?
C15 C10 C11 C12 -0.1(9) . . . . ?
C10 C11 C12 C13 1.2(9) . . . . ?
C11 C12 C13 C14 -1.5(9) . . . . ?
C12 C13 C14 C15 0.7(9) . . . . ?
C13 C14 C15 C10 0.3(9) . . . . ?
C13 C14 C15 C6 -178.7(5) . . . . ?
C9 C10 C15 C14 178.9(5) . . . . ?
C11 C10 C15 C14 -0.6(8) . . . . ?
C9 C10 C15 C6 -2.1(8) . . . . ?
C11 C10 C15 C6 178.5(5) . . . . ?
C7 C6 C15 C14 -179.0(6) . . . . ?
C1 C6 C15 C14 5.1(8) . . . . ?
C7 C6 C15 C10 2.0(8) . . . . ?
C1 C6 C15 C10 -173.9(5) . . . . ?

_refine_diff_density_max         1.502
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.113

_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_DA-AP124-1
_database_code_depnum_ccdc_archive 'CCDC 1897605'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Br Fe'
_chemical_formula_sum            'C20 H15 Br Fe'
_chemical_formula_weight         391.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   12.3825(5)
_cell_length_b                   7.7378(4)
_cell_length_c                   15.7332(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.903(4)
_cell_angle_gamma                90
_cell_volume                     1503.95(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    3752
_cell_measurement_theta_min      3.4130
_cell_measurement_theta_max      28.3720

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    3.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.786
_oxdiff_exptl_absorpt_empirical_full_max 1.606
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10528
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2950
_reflns_number_gt                2487
_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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0289P)²+0.4961P] 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         2950
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0555
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74043(16) 0.8318(3) 1.04987(12) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.77555(16) 0.9463(3) 1.11769(13) 0.0206(4) Uani 1 1 d . . . . .
H2 H 0.8466 0.9601 1.1399 0.025 Uiso 1 1 calc R U . . .
C3 C 0.68415(17) 1.0353(3) 1.14540(13) 0.0226(5) Uani 1 1 d . . . . .
H3 H 0.6849 1.1175 1.1886 0.027 Uiso 1 1 calc R U . . .
C4 C 0.59176(17) 0.9771(3) 1.09589(13) 0.0229(5) Uani 1 1 d . . . . .
H4 H 0.5210 1.0143 1.1008 0.028 Uiso 1 1 calc R U . . .
C5 C 0.62564(16) 0.8521(3) 1.03728(12) 0.0199(4) Uani 1 1 d . . . . .
H5 H 0.5807 0.7931 0.9973 0.024 Uiso 1 1 calc R U . . .
C6 C 0.70638(18) 0.5316(3) 1.19890(13) 0.0251(5) Uani 1 1 d . . . . .
H6 H 0.7521 0.4564 1.1725 0.030 Uiso 1 1 calc R U . . .
C7 C 0.73794(18) 0.6544(3) 1.26309(13) 0.0261(5) Uani 1 1 d . . . . .
H7 H 0.8081 0.6736 1.2862 0.031 Uiso 1 1 calc R U . . .
C8 C 0.64349(19) 0.7426(3) 1.28575(14) 0.0262(5) Uani 1 1 d . . . . .
H8 H 0.6409 0.8295 1.3264 0.031 Uiso 1 1 calc R U . . .
C9 C 0.55382(17) 0.6752(3) 1.23561(13) 0.0256(5) Uani 1 1 d . . . . .
H9 H 0.4822 0.7106 1.2374 0.031 Uiso 1 1 calc R U . . .
C10 C 0.59242(18) 0.5445(3) 1.18230(13) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.5504 0.4786 1.1432 0.029 Uiso 1 1 calc R U . . .
C11 C 0.81511(16) 0.7323(3) 0.99817(13) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.91084(17) 0.8112(3) 0.98168(14) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.9260 0.9202 1.0044 0.031 Uiso 1 1 calc R U . . .
C13 C 0.98691(18) 0.7321(3) 0.93134(14) 0.0260(5) Uani 1 1 d . . . . .
H13 H 1.0520 0.7876 0.9229 0.031 Uiso 1 1 calc R U . . .
C14 C 0.96561(16) 0.5756(3) 0.89514(12) 0.0218(5) Uani 1 1 d . . . . .
H14 H 1.0155 0.5252 0.8612 0.026 Uiso 1 1 calc R U . . .
C15 C 0.86743(16) 0.4885(3) 0.90885(12) 0.0183(4) Uani 1 1 d . . . . .
C16 C 0.84068(16) 0.3243(3) 0.87337(13) 0.0217(5) Uani 1 1 d . . . . .
C17 C 0.74948(19) 0.2360(3) 0.88965(14) 0.0259(5) Uani 1 1 d . . . . .
H17 H 0.7350 0.1281 0.8653 0.031 Uiso 1 1 calc R U . . .
C18 C 0.67700(17) 0.3123(3) 0.94454(13) 0.0248(5) Uani 1 1 d . . . . .
H18 H 0.6148 0.2529 0.9572 0.030 Uiso 1 1 calc R U . . .
C19 C 0.69700(15) 0.4707(3) 0.97895(12) 0.0183(4) Uani 1 1 d . . . . .
H19 H 0.6475 0.5186 1.0141 0.022 Uiso 1 1 calc R U . . .
C20 C 0.79174(15) 0.5654(3) 0.96253(12) 0.0168(4) Uani 1 1 d . . . . .
Fe1 Fe 0.66531(2) 0.77556(4) 1.15945(2) 0.01462(9) Uani 1 1 d . . . . .
Br1 Br 0.93632(2) 0.22158(3) 0.79750(2) 0.03302(9) 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
C1 C5 1.430(3) . ?
C1 C2 1.432(3) . ?
C1 C11 1.488(3) . ?
C1 Fe1 2.0606(19) . ?
C2 C3 1.418(3) . ?
C2 Fe1 2.0404(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(3) . ?
C3 Fe1 2.037(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.420(3) . ?
C4 Fe1 2.034(2) . ?
C4 H4 0.9300 . ?
C5 Fe1 2.0392(19) . ?
C5 H5 0.9300 . ?
C6 C10 1.421(3) . ?
C6 C7 1.422(3) . ?
C6 Fe1 2.040(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.420(3) . ?
C7 Fe1 2.036(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(3) . ?
C8 Fe1 2.039(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.418(3) . ?
C9 Fe1 2.0419(19) . ?
C9 H9 0.9300 . ?
C10 Fe1 2.045(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C11 C20 1.429(3) . ?
C12 C13 1.411(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.419(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.418(3) . ?
C15 C20 1.433(3) . ?
C16 C17 1.359(3) . ?
C16 Br1 1.911(2) . ?
C17 C18 1.416(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.356(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.422(3) . ?
C19 H19 0.9300 . ?

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 C1 C2 106.50(17) . . ?
C5 C1 C11 129.04(18) . . ?
C2 C1 C11 124.02(18) . . ?
C5 C1 Fe1 68.78(11) . . ?
C2 C1 Fe1 68.81(10) . . ?
C11 C1 Fe1 132.91(14) . . ?
C3 C2 C1 108.74(18) . . ?
C3 C2 Fe1 69.52(11) . . ?
C1 C2 Fe1 70.32(11) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
Fe1 C2 H2 126.1 . . ?
C4 C3 C2 107.99(18) . . ?
C4 C3 Fe1 69.58(12) . . ?
C2 C3 Fe1 69.77(11) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.2 . . ?
C3 C4 C5 108.14(18) . . ?
C3 C4 Fe1 69.80(12) . . ?
C5 C4 Fe1 69.79(11) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 126.1 . . ?
C4 C5 C1 108.63(18) . . ?
C4 C5 Fe1 69.42(11) . . ?
C1 C5 Fe1 70.39(11) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.7 . . ?
Fe1 C5 H5 126.1 . . ?
C10 C6 C7 107.78(19) . . ?
C10 C6 Fe1 69.84(12) . . ?
C7 C6 Fe1 69.44(12) . . ?
C10 C6 H6 126.1 . . ?
C7 C6 H6 126.1 . . ?
Fe1 C6 H6 126.2 . . ?
C8 C7 C6 107.9(2) . . ?
C8 C7 Fe1 69.72(12) . . ?
C6 C7 Fe1 69.74(12) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe1 C7 H7 126.1 . . ?
C9 C8 C7 108.1(2) . . ?
C9 C8 Fe1 69.78(12) . . ?
C7 C8 Fe1 69.48(12) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Fe1 C8 H8 126.4 . . ?
C8 C9 C10 108.0(2) . . ?
C8 C9 Fe1 69.59(12) . . ?
C10 C9 Fe1 69.84(11) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 126.1 . . ?
C9 C10 C6 108.17(19) . . ?
C9 C10 Fe1 69.57(12) . . ?
C6 C10 Fe1 69.45(12) . . ?
C9 C10 H10 125.9 . . ?
C6 C10 H10 125.9 . . ?
Fe1 C10 H10 126.6 . . ?
C12 C11 C20 118.81(18) . . ?
C12 C11 C1 116.70(18) . . ?
C20 C11 C1 124.44(18) . . ?
C11 C12 C13 122.1(2) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 120.31(19) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.27(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 123.04(18) . . ?
C14 C15 C20 119.59(18) . . ?
C16 C15 C20 117.36(18) . . ?
C17 C16 C15 123.44(18) . . ?
C17 C16 Br1 117.84(16) . . ?
C15 C16 Br1 118.71(15) . . ?
C16 C17 C18 118.33(19) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 120.95(19) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.60(18) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C11 122.81(17) . . ?
C19 C20 C15 118.28(18) . . ?
C11 C20 C15 118.90(17) . . ?
C4 Fe1 C3 40.62(8) . . ?
C4 Fe1 C7 154.84(9) . . ?
C3 Fe1 C7 119.57(9) . . ?
C4 Fe1 C5 40.79(8) . . ?
C3 Fe1 C5 68.49(8) . . ?
C7 Fe1 C5 162.44(9) . . ?
C4 Fe1 C8 119.35(9) . . ?
C3 Fe1 C8 104.64(9) . . ?
C7 Fe1 C8 40.79(9) . . ?
C5 Fe1 C8 156.25(9) . . ?
C4 Fe1 C2 68.41(8) . . ?
C3 Fe1 C2 40.71(8) . . ?
C7 Fe1 C2 106.70(9) . . ?
C5 Fe1 C2 68.40(8) . . ?
C8 Fe1 C2 122.04(9) . . ?
C4 Fe1 C6 162.31(9) . . ?
C3 Fe1 C6 156.58(9) . . ?
C7 Fe1 C6 40.82(9) . . ?
C5 Fe1 C6 126.47(9) . . ?
C8 Fe1 C6 68.59(9) . . ?
C2 Fe1 C6 122.60(9) . . ?
C4 Fe1 C9 106.38(9) . . ?
C3 Fe1 C9 121.72(9) . . ?
C7 Fe1 C9 68.56(9) . . ?
C5 Fe1 C9 122.31(9) . . ?
C8 Fe1 C9 40.63(9) . . ?
C2 Fe1 C9 158.28(9) . . ?
C6 Fe1 C9 68.55(9) . . ?
C4 Fe1 C10 124.63(9) . . ?
C3 Fe1 C10 159.48(9) . . ?
C7 Fe1 C10 68.48(9) . . ?
C5 Fe1 C10 109.79(8) . . ?
C8 Fe1 C10 68.30(9) . . ?
C2 Fe1 C10 159.31(8) . . ?
C6 Fe1 C10 40.70(9) . . ?
C9 Fe1 C10 40.59(9) . . ?
C4 Fe1 C1 68.84(8) . . ?
C3 Fe1 C1 68.85(8) . . ?
C7 Fe1 C1 124.57(9) . . ?
C5 Fe1 C1 40.83(8) . . ?
C8 Fe1 C1 159.88(9) . . ?
C2 Fe1 C1 40.86(8) . . ?
C6 Fe1 C1 109.43(8) . . ?
C9 Fe1 C1 158.92(9) . . ?
C10 Fe1 C1 124.16(8) . . ?

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) . . . . ?
C11 C1 C2 C3 172.64(18) . . . . ?
Fe1 C1 C2 C3 -59.09(14) . . . . ?
C5 C1 C2 Fe1 58.69(13) . . . . ?
C11 C1 C2 Fe1 -128.27(18) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
Fe1 C2 C3 C4 -59.29(14) . . . . ?
C1 C2 C3 Fe1 59.59(13) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
Fe1 C3 C4 C5 -59.48(14) . . . . ?
C2 C3 C4 Fe1 59.41(14) . . . . ?
C3 C4 C5 C1 -0.2(2) . . . . ?
Fe1 C4 C5 C1 -59.67(14) . . . . ?
C3 C4 C5 Fe1 59.49(14) . . . . ?
C2 C1 C5 C4 0.4(2) . . . . ?
C11 C1 C5 C4 -172.22(19) . . . . ?
Fe1 C1 C5 C4 59.07(14) . . . . ?
C2 C1 C5 Fe1 -58.71(13) . . . . ?
C11 C1 C5 Fe1 128.7(2) . . . . ?
C10 C6 C7 C8 -0.1(2) . . . . ?
Fe1 C6 C7 C8 59.48(14) . . . . ?
C10 C6 C7 Fe1 -59.55(14) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
Fe1 C7 C8 C9 59.29(15) . . . . ?
C6 C7 C8 Fe1 -59.49(14) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
Fe1 C8 C9 C10 59.50(14) . . . . ?
C7 C8 C9 Fe1 -59.11(15) . . . . ?
C8 C9 C10 C6 -0.4(2) . . . . ?
Fe1 C9 C10 C6 58.91(14) . . . . ?
C8 C9 C10 Fe1 -59.35(14) . . . . ?
C7 C6 C10 C9 0.3(2) . . . . ?
Fe1 C6 C10 C9 -58.98(14) . . . . ?
C7 C6 C10 Fe1 59.30(14) . . . . ?
C5 C1 C11 C12 136.6(2) . . . . ?
C2 C1 C11 C12 -34.8(3) . . . . ?
Fe1 C1 C11 C12 -126.6(2) . . . . ?
C5 C1 C11 C20 -40.8(3) . . . . ?
C2 C1 C11 C20 147.8(2) . . . . ?
Fe1 C1 C11 C20 55.9(3) . . . . ?
C20 C11 C12 C13 -0.5(3) . . . . ?
C1 C11 C12 C13 -178.1(2) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 -179.5(2) . . . . ?
C13 C14 C15 C20 -1.2(3) . . . . ?
C14 C15 C16 C17 176.5(2) . . . . ?
C20 C15 C16 C17 -1.9(3) . . . . ?
C14 C15 C16 Br1 -4.3(3) . . . . ?
C20 C15 C16 Br1 177.33(14) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
Br1 C16 C17 C18 -178.85(16) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C11 -179.7(2) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C12 C11 C20 C19 177.31(19) . . . . ?
C1 C11 C20 C19 -5.3(3) . . . . ?
C12 C11 C20 C15 -1.8(3) . . . . ?
C1 C11 C20 C15 175.60(18) . . . . ?
C14 C15 C20 C19 -176.49(18) . . . . ?
C16 C15 C20 C19 2.0(3) . . . . ?
C14 C15 C20 C11 2.7(3) . . . . ?
C16 C15 C20 C11 -178.90(18) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.059

_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_DA-AP123-2
_database_code_depnum_ccdc_archive 'CCDC 1897608'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Fe2'
_chemical_formula_sum            'C30 H24 Fe2'
_chemical_formula_weight         496.19

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   12.1550(4)
_cell_length_b                   12.9938(3)
_cell_length_c                   13.7119(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2165.65(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    129.95(10)
_cell_measurement_reflns_used    3767
_cell_measurement_theta_min      3.5500
_cell_measurement_theta_max      27.4970

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.356
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.898
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      129.95(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8109
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3646
_reflns_number_gt                3265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3646
_refine_ls_number_parameters     318
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C 1.0235(4) 1.0003(3) 0.6509(3) 0.0298(9) Uani 1 1 d . . . . .
C2 C 1.0122(4) 1.0374(3) 0.7489(4) 0.0367(10) Uani 1 1 d . . . . .
H2 H 1.0694 1.0551 0.7908 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8981(4) 1.0421(3) 0.7706(4) 0.0438(12) Uani 1 1 d . . . . .
H3 H 0.8672 1.0648 0.8288 0.053 Uiso 1 1 calc R U . . .
C4 C 0.8403(4) 1.0069(3) 0.6896(4) 0.0452(13) Uani 1 1 d . . . . .
H4 H 0.7643 1.0009 0.6851 0.054 Uiso 1 1 calc R U . . .
C5 C 0.9156(4) 0.9818(3) 0.6160(4) 0.0367(10) Uani 1 1 d . . . . .
H5 H 0.8977 0.9570 0.5543 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0052(16) 0.7536(12) 0.7315(9) 0.049(6) Uani 0.53(3) 1 d G . P A 1
H6 H 1.0548 0.7309 0.6845 0.058 Uiso 0.53(3) 1 calc R U P A 1
C7 C 1.0326(6) 0.7990(14) 0.8225(12) 0.040(6) Uani 0.53(3) 1 d G . P A 1
H7 H 1.1033 0.8113 0.8456 0.049 Uiso 0.53(3) 1 calc R U P A 1
C8 C 0.9331(10) 0.8223(9) 0.8720(7) 0.043(4) Uani 0.53(3) 1 d G . P A 1
H8 H 0.9272 0.8525 0.9333 0.052 Uiso 0.53(3) 1 calc R U P A 1
C9 C 0.8442(6) 0.7913(11) 0.8116(14) 0.053(7) Uani 0.53(3) 1 d G . P A 1
H9 H 0.7698 0.7977 0.8264 0.064 Uiso 0.53(3) 1 calc R U P A 1
C10 C 0.8887(17) 0.7488(9) 0.7248(11) 0.051(5) Uani 0.53(3) 1 d G . P A 1
H10 H 0.8486 0.7225 0.6726 0.061 Uiso 0.53(3) 1 calc R U P A 1
C6' C 0.9447(17) 0.7382(7) 0.6964(9) 0.044(4) Uani 0.47(3) 1 d G . P A 2
H6' H 0.9430 0.7096 0.6342 0.053 Uiso 0.47(3) 1 calc R U P A 2
C7' C 0.8519(7) 0.7612(13) 0.7554(17) 0.055(5) Uani 0.47(3) 1 d G . P A 2
H7' H 0.7787 0.7503 0.7386 0.066 Uiso 0.47(3) 1 calc R U P A 2
C8' C 0.891(2) 0.8039(14) 0.8444(13) 0.077(9) Uani 0.47(3) 1 d G . P A 2
H8' H 0.8470 0.8257 0.8962 0.093 Uiso 0.47(3) 1 calc R U P A 2
C9' C 1.007(2) 0.8072(18) 0.8404(15) 0.079(10) Uani 0.47(3) 1 d G . P A 2
H9' H 1.0535 0.8317 0.8891 0.095 Uiso 0.47(3) 1 calc R U P A 2
C10' C 1.0407(7) 0.7667(16) 0.7489(19) 0.057(6) Uani 0.47(3) 1 d G . P A 2
H10' H 1.1129 0.7599 0.7272 0.069 Uiso 0.47(3) 1 calc R U P A 2
C11 C 1.3987(3) 0.9321(3) 0.3990(4) 0.0312(8) Uani 1 1 d . . . . .
C12 C 1.4462(3) 0.8323(3) 0.3819(4) 0.0376(10) Uani 1 1 d . . . . .
H12 H 1.4370 0.7747 0.4214 0.045 Uiso 1 1 calc R U . . .
C13 C 1.5094(4) 0.8358(4) 0.2946(4) 0.0462(12) Uani 1 1 d . . . . .
H13 H 1.5482 0.7814 0.2671 0.055 Uiso 1 1 calc R U . . .
C14 C 1.5026(4) 0.9372(4) 0.2574(4) 0.0469(12) Uani 1 1 d . . . . .
H14 H 1.5362 0.9610 0.2009 0.056 Uiso 1 1 calc R U . . .
C15 C 1.4358(4) 0.9960(4) 0.3210(3) 0.0385(10) Uani 1 1 d . . . . .
H15 H 1.4188 1.0653 0.3132 0.046 Uiso 1 1 calc R U . . .
C16 C 1.6325(4) 0.9920(3) 0.5211(3) 0.0410(11) Uani 1 1 d . . . . .
H16 H 1.5919 1.0080 0.5766 0.049 Uiso 1 1 calc R U . . .
C17 C 1.6770(4) 0.8947(3) 0.4981(3) 0.0374(10) Uani 1 1 d . . . . .
H17 H 1.6723 0.8356 0.5362 0.045 Uiso 1 1 calc R U . . .
C18 C 1.7305(4) 0.9032(3) 0.4064(4) 0.0384(10) Uani 1 1 d . . . . .
H18 H 1.7662 0.8504 0.3733 0.046 Uiso 1 1 calc R U . . .
C19 C 1.7198(4) 1.0058(3) 0.3746(4) 0.0415(11) Uani 1 1 d . . . . .
H19 H 1.7475 1.0327 0.3167 0.050 Uiso 1 1 calc R U . . .
C20 C 1.6599(4) 1.0606(3) 0.4457(4) 0.0407(11) Uani 1 1 d . . . . .
H20 H 1.6417 1.1301 0.4432 0.049 Uiso 1 1 calc R U . . .
C21 C 1.1261(4) 0.9844(3) 0.5950(3) 0.0296(9) Uani 1 1 d . . . . .
C22 C 1.1450(4) 0.8932(3) 0.5478(3) 0.0334(10) Uani 1 1 d . . . . .
H22 H 1.0952 0.8396 0.5557 0.040 Uiso 1 1 calc R U . . .
C23 C 1.2367(4) 0.8784(3) 0.4882(3) 0.0336(10) Uani 1 1 d . . . . .
H23 H 1.2457 0.8151 0.4576 0.040 Uiso 1 1 calc R U . . .
C24 C 1.3141(4) 0.9536(3) 0.4731(3) 0.0296(9) Uani 1 1 d . . . . .
C25 C 1.2988(3) 1.0507(3) 0.5230(3) 0.0267(9) Uani 1 1 d . . . . .
C26 C 1.3754(4) 1.1326(3) 0.5138(3) 0.0308(9) Uani 1 1 d . . . . .
H26 H 1.4385 1.1233 0.4765 0.037 Uiso 1 1 calc R U . . .
C27 C 1.3578(4) 1.2245(3) 0.5588(3) 0.0354(10) Uani 1 1 d . . . . .
H27 H 1.4091 1.2771 0.5520 0.042 Uiso 1 1 calc R U . . .
C28 C 1.2639(4) 1.2406(3) 0.6150(3) 0.0372(10) Uani 1 1 d . . . . .
H28 H 1.2522 1.3041 0.6445 0.045 Uiso 1 1 calc R U . . .
C29 C 1.1891(4) 1.1636(3) 0.6267(3) 0.0327(9) Uani 1 1 d . . . . .
H29 H 1.1265 1.1754 0.6641 0.039 Uiso 1 1 calc R U . . .
C30 C 1.2049(3) 1.0658(3) 0.5829(3) 0.0287(9) Uani 1 1 d . . . . .
Fe1 Fe 0.94194(5) 0.89551(4) 0.73765(5) 0.03375(17) Uani 1 1 d . . . . .
Fe2 Fe 1.56889(5) 0.93953(4) 0.39279(4) 0.03034(16) 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
C1 C5 1.417(6) . ?
C1 C2 1.434(7) . ?
C1 C21 1.478(6) . ?
C1 Fe1 2.062(4) . ?
C2 C3 1.420(7) . ?
C2 Fe1 2.037(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(7) . ?
C3 Fe1 2.029(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(7) . ?
C4 Fe1 2.013(4) . ?
C4 H4 0.9300 . ?
C5 Fe1 2.035(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.4200 . ?
C6 C10 1.4200 . ?
C6 Fe1 2.000(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.4200 . ?
C7 Fe1 2.035(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.4200 . ?
C8 Fe1 2.076(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.4200 . ?
C9 Fe1 2.068(10) . ?
C9 H9 0.9300 . ?
C10 Fe1 2.020(11) . ?
C10 H10 0.9300 . ?
C6' C10' 1.4200 . ?
C6' C7' 1.4200 . ?
C6' Fe1 2.121(10) . ?
C6' H6' 0.9300 . ?
C7' C8' 1.4200 . ?
C7' Fe1 2.074(13) . ?
C7' H7' 0.9300 . ?
C8' C9' 1.4200 . ?
C8' Fe1 1.987(17) . ?
C8' H8' 0.9300 . ?
C9' C10' 1.4200 . ?
C9' Fe1 1.98(2) . ?
C9' H9' 0.9300 . ?
C10' Fe1 2.066(17) . ?
C10' H10' 0.9300 . ?
C11 C15 1.427(6) . ?
C11 C12 1.440(6) . ?
C11 C24 1.472(6) . ?
C11 Fe2 2.072(4) . ?
C12 C13 1.422(7) . ?
C12 Fe2 2.047(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.415(7) . ?
C13 Fe2 2.037(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(6) . ?
C14 Fe2 2.024(5) . ?
C14 H14 0.9300 . ?
C15 Fe2 2.030(5) . ?
C15 H15 0.9300 . ?
C16 C20 1.405(6) . ?
C16 C17 1.411(6) . ?
C16 Fe2 2.039(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.419(6) . ?
C17 Fe2 2.038(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.409(5) . ?
C18 Fe2 2.029(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.410(7) . ?
C19 Fe2 2.042(4) . ?
C19 H19 0.9300 . ?
C20 Fe2 2.056(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(5) . ?
C21 C30 1.437(5) . ?
C22 C23 1.395(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.447(5) . ?
C25 C26 1.419(6) . ?
C25 C30 1.420(6) . ?
C26 C27 1.361(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.393(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.361(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.418(5) . ?
C29 H29 0.9300 . ?

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 C1 C2 106.6(4) . . ?
C5 C1 C21 125.6(4) . . ?
C2 C1 C21 127.8(4) . . ?
C5 C1 Fe1 68.8(2) . . ?
C2 C1 Fe1 68.6(2) . . ?
C21 C1 Fe1 127.7(3) . . ?
C3 C2 C1 107.7(4) . . ?
C3 C2 Fe1 69.2(2) . . ?
C1 C2 Fe1 70.4(2) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
Fe1 C2 H2 125.7 . . ?
C4 C3 C2 108.1(4) . . ?
C4 C3 Fe1 69.3(3) . . ?
C2 C3 Fe1 69.9(2) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.5 . . ?
C3 C4 C5 108.8(4) . . ?
C3 C4 Fe1 70.5(3) . . ?
C5 C4 Fe1 70.6(3) . . ?
C3 C4 H4 125.6 . . ?
C5 C4 H4 125.6 . . ?
Fe1 C4 H4 124.9 . . ?
C4 C5 C1 108.7(4) . . ?
C4 C5 Fe1 68.9(3) . . ?
C1 C5 Fe1 70.8(2) . . ?
C4 C5 H5 125.6 . . ?
C1 C5 H5 125.6 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C10 108.0 . . ?
C7 C6 Fe1 70.7(5) . . ?
C10 C6 Fe1 70.1(6) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 H6 126.0 . . ?
Fe1 C6 H6 124.8 . . ?
C6 C7 C8 108.0 . . ?
C6 C7 Fe1 68.1(4) . . ?
C8 C7 Fe1 71.4(5) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
Fe1 C7 H7 126.1 . . ?
C7 C8 C9 108.0 . . ?
C7 C8 Fe1 68.2(6) . . ?
C9 C8 Fe1 69.6(5) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
Fe1 C8 H8 127.7 . . ?
C10 C9 C8 108.0 . . ?
C10 C9 Fe1 67.9(4) . . ?
C8 C9 Fe1 70.3(5) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
Fe1 C9 H9 127.4 . . ?
C6 C10 C9 108.0 . . ?
C6 C10 Fe1 68.5(6) . . ?
C9 C10 Fe1 71.5(4) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 125.6 . . ?
C10' C6' C7' 108.0 . . ?
C10' C6' Fe1 68.1(7) . . ?
C7' C6' Fe1 68.4(6) . . ?
C10' C6' H6' 126.0 . . ?
C7' C6' H6' 126.0 . . ?
Fe1 C6' H6' 129.0 . . ?
C8' C7' C6' 108.0 . . ?
C8' C7' Fe1 66.3(6) . . ?
C6' C7' Fe1 72.0(5) . . ?
C8' C7' H7' 126.0 . . ?
C6' C7' H7' 126.0 . . ?
Fe1 C7' H7' 127.2 . . ?
C9' C8' C7' 108.0 . . ?
C9' C8' Fe1 68.9(7) . . ?
C7' C8' Fe1 72.8(6) . . ?
C9' C8' H8' 126.0 . . ?
C7' C8' H8' 126.0 . . ?
Fe1 C8' H8' 123.9 . . ?
C8' C9' C10' 108.0 . . ?
C8' C9' Fe1 69.2(6) . . ?
C10' C9' Fe1 72.7(5) . . ?
C8' C9' H9' 126.0 . . ?
C10' C9' H9' 126.0 . . ?
Fe1 C9' H9' 123.7 . . ?
C9' C10' C6' 108.0 . . ?
C9' C10' Fe1 66.3(6) . . ?
C6' C10' Fe1 72.3(6) . . ?
C9' C10' H10' 126.0 . . ?
C6' C10' H10' 126.0 . . ?
Fe1 C10' H10' 126.9 . . ?
C15 C11 C12 106.0(4) . . ?
C15 C11 C24 128.9(4) . . ?
C12 C11 C24 124.3(4) . . ?
C15 C11 Fe2 68.1(2) . . ?
C12 C11 Fe2 68.6(2) . . ?
C24 C11 Fe2 135.8(3) . . ?
C13 C12 C11 109.0(4) . . ?
C13 C12 Fe2 69.3(2) . . ?
C11 C12 Fe2 70.5(2) . . ?
C13 C12 H12 125.5 . . ?
C11 C12 H12 125.5 . . ?
Fe2 C12 H12 126.3 . . ?
C14 C13 C12 107.5(4) . . ?
C14 C13 Fe2 69.1(3) . . ?
C12 C13 Fe2 70.0(3) . . ?
C14 C13 H13 126.2 . . ?
C12 C13 H13 126.2 . . ?
Fe2 C13 H13 126.3 . . ?
C15 C14 C13 108.3(4) . . ?
C15 C14 Fe2 69.8(3) . . ?
C13 C14 Fe2 70.1(3) . . ?
C15 C14 H14 125.8 . . ?
C13 C14 H14 125.8 . . ?
Fe2 C14 H14 125.8 . . ?
C14 C15 C11 109.2(4) . . ?
C14 C15 Fe2 69.3(3) . . ?
C11 C15 Fe2 71.2(3) . . ?
C14 C15 H15 125.4 . . ?
C11 C15 H15 125.4 . . ?
Fe2 C15 H15 125.6 . . ?
C20 C16 C17 108.2(4) . . ?
C20 C16 Fe2 70.6(3) . . ?
C17 C16 Fe2 69.7(3) . . ?
C20 C16 H16 125.9 . . ?
C17 C16 H16 125.9 . . ?
Fe2 C16 H16 125.4 . . ?
C16 C17 C18 107.7(4) . . ?
C16 C17 Fe2 69.8(3) . . ?
C18 C17 Fe2 69.2(3) . . ?
C16 C17 H17 126.2 . . ?
C18 C17 H17 126.2 . . ?
Fe2 C17 H17 126.4 . . ?
C19 C18 C17 107.8(4) . . ?
C19 C18 Fe2 70.3(3) . . ?
C17 C18 Fe2 69.9(3) . . ?
C19 C18 H18 126.1 . . ?
C17 C18 H18 126.1 . . ?
Fe2 C18 H18 125.3 . . ?
C18 C19 C20 108.1(4) . . ?
C18 C19 Fe2 69.2(2) . . ?
C20 C19 Fe2 70.4(3) . . ?
C18 C19 H19 125.9 . . ?
C20 C19 H19 125.9 . . ?
Fe2 C19 H19 126.0 . . ?
C16 C20 C19 108.1(4) . . ?
C16 C20 Fe2 69.3(2) . . ?
C19 C20 Fe2 69.4(2) . . ?
C16 C20 H20 125.9 . . ?
C19 C20 H20 125.9 . . ?
Fe2 C20 H20 127.0 . . ?
C22 C21 C30 118.1(4) . . ?
C22 C21 C1 120.5(4) . . ?
C30 C21 C1 121.3(3) . . ?
C21 C22 C23 122.0(4) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C24 C23 C22 122.6(4) . . ?
C24 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
C23 C24 C25 117.4(4) . . ?
C23 C24 C11 116.7(3) . . ?
C25 C24 C11 125.5(4) . . ?
C26 C25 C30 118.3(4) . . ?
C26 C25 C24 121.8(4) . . ?
C30 C25 C24 119.9(3) . . ?
C27 C26 C25 121.0(4) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 120.7(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 121.2(4) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C25 118.5(4) . . ?
C29 C30 C21 121.4(4) . . ?
C25 C30 C21 120.0(3) . . ?
C9' Fe1 C8' 41.9(4) . . ?
C9' Fe1 C4 153.4(9) . . ?
C8' Fe1 C4 118.6(7) . . ?
C6 Fe1 C4 152.2(6) . . ?
C6 Fe1 C10 41.4(2) . . ?
C4 Fe1 C10 116.9(5) . . ?
C9' Fe1 C3 119.4(7) . . ?
C8' Fe1 C3 108.4(4) . . ?
C6 Fe1 C3 167.5(5) . . ?
C4 Fe1 C3 40.3(2) . . ?
C10 Fe1 C3 145.2(7) . . ?
C6 Fe1 C7 41.2(3) . . ?
C4 Fe1 C7 164.2(5) . . ?
C10 Fe1 C7 69.0(3) . . ?
C3 Fe1 C7 126.4(5) . . ?
C9' Fe1 C5 164.6(9) . . ?
C8' Fe1 C5 152.1(9) . . ?
C6 Fe1 C5 122.2(4) . . ?
C4 Fe1 C5 40.48(19) . . ?
C10 Fe1 C5 113.4(3) . . ?
C3 Fe1 C5 67.9(2) . . ?
C7 Fe1 C5 153.3(4) . . ?
C9' Fe1 C2 107.6(5) . . ?
C8' Fe1 C2 128.2(6) . . ?
C6 Fe1 C2 132.6(6) . . ?
C4 Fe1 C2 68.4(2) . . ?
C10 Fe1 C2 173.9(7) . . ?
C3 Fe1 C2 40.88(19) . . ?
C7 Fe1 C2 106.7(4) . . ?
C5 Fe1 C2 68.27(19) . . ?
C9' Fe1 C1 126.9(7) . . ?
C8' Fe1 C1 166.3(8) . . ?
C6 Fe1 C1 113.6(4) . . ?
C4 Fe1 C1 68.37(19) . . ?
C10 Fe1 C1 136.6(6) . . ?
C3 Fe1 C1 68.57(18) . . ?
C7 Fe1 C1 118.5(3) . . ?
C5 Fe1 C1 40.45(17) . . ?
C2 Fe1 C1 40.95(18) . . ?
C9' Fe1 C10' 41.0(4) . . ?
C8' Fe1 C10' 69.0(5) . . ?
C4 Fe1 C10' 164.5(7) . . ?
C3 Fe1 C10' 153.8(7) . . ?
C5 Fe1 C10' 126.8(7) . . ?
C2 Fe1 C10' 118.9(5) . . ?
C1 Fe1 C10' 107.4(5) . . ?
C6 Fe1 C9 68.8(2) . . ?
C4 Fe1 C9 106.2(3) . . ?
C10 Fe1 C9 40.63(19) . . ?
C3 Fe1 C9 110.8(5) . . ?
C7 Fe1 C9 68.1(3) . . ?
C5 Fe1 C9 132.3(3) . . ?
C2 Fe1 C9 142.8(6) . . ?
C1 Fe1 C9 172.7(4) . . ?
C14 Fe2 C18 117.8(2) . . ?
C14 Fe2 C15 40.85(19) . . ?
C18 Fe2 C15 154.15(19) . . ?
C14 Fe2 C13 40.8(2) . . ?
C18 Fe2 C13 104.5(2) . . ?
C15 Fe2 C13 68.7(2) . . ?
C14 Fe2 C17 154.50(19) . . ?
C18 Fe2 C17 40.85(18) . . ?
C15 Fe2 C17 163.86(19) . . ?
C13 Fe2 C17 120.5(2) . . ?
C14 Fe2 C16 161.33(19) . . ?
C18 Fe2 C16 68.37(19) . . ?
C15 Fe2 C16 126.8(2) . . ?
C13 Fe2 C16 157.8(2) . . ?
C17 Fe2 C16 40.51(17) . . ?
C14 Fe2 C19 104.6(2) . . ?
C18 Fe2 C19 40.50(16) . . ?
C15 Fe2 C19 120.26(19) . . ?
C13 Fe2 C19 121.1(2) . . ?
C17 Fe2 C19 68.14(18) . . ?
C16 Fe2 C19 67.9(2) . . ?
C14 Fe2 C12 68.4(2) . . ?
C18 Fe2 C12 123.63(16) . . ?
C15 Fe2 C12 68.30(19) . . ?
C13 Fe2 C12 40.8(2) . . ?
C17 Fe2 C12 109.10(19) . . ?
C16 Fe2 C12 124.5(2) . . ?
C19 Fe2 C12 158.89(18) . . ?
C14 Fe2 C20 123.3(2) . . ?
C18 Fe2 C20 67.95(18) . . ?
C15 Fe2 C20 108.85(19) . . ?
C13 Fe2 C20 158.5(2) . . ?
C17 Fe2 C20 67.76(18) . . ?
C16 Fe2 C20 40.14(18) . . ?
C19 Fe2 C20 40.26(18) . . ?
C12 Fe2 C20 159.9(2) . . ?
C14 Fe2 C11 68.9(2) . . ?
C18 Fe2 C11 162.13(16) . . ?
C15 Fe2 C11 40.69(18) . . ?
C13 Fe2 C11 69.05(19) . . ?
C17 Fe2 C11 126.97(19) . . ?
C16 Fe2 C11 111.0(2) . . ?
C19 Fe2 C11 157.11(15) . . ?
C12 Fe2 C11 40.91(15) . . ?
C20 Fe2 C11 123.91(18) . . ?

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 -1.0(5) . . . . ?
C21 C1 C2 C3 178.7(4) . . . . ?
Fe1 C1 C2 C3 -59.5(3) . . . . ?
C5 C1 C2 Fe1 58.5(3) . . . . ?
C21 C1 C2 Fe1 -121.9(4) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
Fe1 C2 C3 C4 -58.9(3) . . . . ?
C1 C2 C3 Fe1 60.2(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
Fe1 C3 C4 C5 -60.5(3) . . . . ?
C2 C3 C4 Fe1 59.2(3) . . . . ?
C3 C4 C5 C1 0.6(5) . . . . ?
Fe1 C4 C5 C1 -59.8(3) . . . . ?
C3 C4 C5 Fe1 60.4(3) . . . . ?
C2 C1 C5 C4 0.2(5) . . . . ?
C21 C1 C5 C4 -179.4(4) . . . . ?
Fe1 C1 C5 C4 58.6(3) . . . . ?
C2 C1 C5 Fe1 -58.4(3) . . . . ?
C21 C1 C5 Fe1 122.0(4) . . . . ?
C10 C6 C7 C8 0.0 . . . . ?
Fe1 C6 C7 C8 60.5(5) . . . . ?
C10 C6 C7 Fe1 -60.5(5) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
Fe1 C7 C8 C9 58.4(4) . . . . ?
C6 C7 C8 Fe1 -58.4(4) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
Fe1 C8 C9 C10 57.5(5) . . . . ?
C7 C8 C9 Fe1 -57.5(5) . . . . ?
C7 C6 C10 C9 0.0 . . . . ?
Fe1 C6 C10 C9 -60.9(4) . . . . ?
C7 C6 C10 Fe1 60.9(4) . . . . ?
C8 C9 C10 C6 0.0 . . . . ?
Fe1 C9 C10 C6 59.0(6) . . . . ?
C8 C9 C10 Fe1 -59.0(6) . . . . ?
C10' C6' C7' C8' 0.0 . . . . ?
Fe1 C6' C7' C8' -56.6(7) . . . . ?
C10' C6' C7' Fe1 56.6(7) . . . . ?
C6' C7' C8' C9' 0.0 . . . . ?
Fe1 C7' C8' C9' -60.2(7) . . . . ?
C6' C7' C8' Fe1 60.2(7) . . . . ?
C7' C8' C9' C10' 0.0 . . . . ?
Fe1 C8' C9' C10' -62.7(5) . . . . ?
C7' C8' C9' Fe1 62.7(5) . . . . ?
C8' C9' C10' C6' 0.0 . . . . ?
Fe1 C9' C10' C6' -60.5(6) . . . . ?
C8' C9' C10' Fe1 60.5(6) . . . . ?
C7' C6' C10' C9' 0.0 . . . . ?
Fe1 C6' C10' C9' 56.8(6) . . . . ?
C7' C6' C10' Fe1 -56.8(6) . . . . ?
C15 C11 C12 C13 -0.7(5) . . . . ?
C24 C11 C12 C13 169.6(4) . . . . ?
Fe2 C11 C12 C13 -58.7(3) . . . . ?
C15 C11 C12 Fe2 58.0(3) . . . . ?
C24 C11 C12 Fe2 -131.7(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
Fe2 C12 C13 C14 -59.1(3) . . . . ?
C11 C12 C13 Fe2 59.5(3) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
Fe2 C13 C14 C15 -59.6(3) . . . . ?
C12 C13 C14 Fe2 59.7(3) . . . . ?
C13 C14 C15 C11 -0.5(5) . . . . ?
Fe2 C14 C15 C11 -60.3(3) . . . . ?
C13 C14 C15 Fe2 59.8(3) . . . . ?
C12 C11 C15 C14 0.7(5) . . . . ?
C24 C11 C15 C14 -168.9(4) . . . . ?
Fe2 C11 C15 C14 59.1(3) . . . . ?
C12 C11 C15 Fe2 -58.4(3) . . . . ?
C24 C11 C15 Fe2 131.9(5) . . . . ?
C20 C16 C17 C18 -1.2(5) . . . . ?
Fe2 C16 C17 C18 59.1(3) . . . . ?
C20 C16 C17 Fe2 -60.3(3) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
Fe2 C17 C18 C19 60.3(3) . . . . ?
C16 C17 C18 Fe2 -59.4(3) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
Fe2 C18 C19 C20 59.9(3) . . . . ?
C17 C18 C19 Fe2 -60.1(3) . . . . ?
C17 C16 C20 C19 1.1(5) . . . . ?
Fe2 C16 C20 C19 -58.7(3) . . . . ?
C17 C16 C20 Fe2 59.8(3) . . . . ?
C18 C19 C20 C16 -0.5(5) . . . . ?
Fe2 C19 C20 C16 58.6(3) . . . . ?
C18 C19 C20 Fe2 -59.2(3) . . . . ?
C5 C1 C21 C22 -50.4(6) . . . . ?
C2 C1 C21 C22 130.1(5) . . . . ?
Fe1 C1 C21 C22 39.1(6) . . . . ?
C5 C1 C21 C30 125.3(5) . . . . ?
C2 C1 C21 C30 -54.3(6) . . . . ?
Fe1 C1 C21 C30 -145.3(3) . . . . ?
C30 C21 C22 C23 -0.9(6) . . . . ?
C1 C21 C22 C23 174.9(4) . . . . ?
C21 C22 C23 C24 0.2(7) . . . . ?
C22 C23 C24 C25 1.0(6) . . . . ?
C22 C23 C24 C11 -172.5(4) . . . . ?
C15 C11 C24 C23 131.7(5) . . . . ?
C12 C11 C24 C23 -36.3(6) . . . . ?
Fe2 C11 C24 C23 -130.2(4) . . . . ?
C15 C11 C24 C25 -41.2(7) . . . . ?
C12 C11 C24 C25 150.8(4) . . . . ?
Fe2 C11 C24 C25 57.0(6) . . . . ?
C23 C24 C25 C26 178.7(4) . . . . ?
C11 C24 C25 C26 -8.5(6) . . . . ?
C23 C24 C25 C30 -1.5(6) . . . . ?
C11 C24 C25 C30 171.3(4) . . . . ?
C30 C25 C26 C27 -1.9(6) . . . . ?
C24 C25 C26 C27 177.9(4) . . . . ?
C25 C26 C27 C28 -0.2(6) . . . . ?
C26 C27 C28 C29 1.0(7) . . . . ?
C27 C28 C29 C30 0.3(7) . . . . ?
C28 C29 C30 C25 -2.4(6) . . . . ?
C28 C29 C30 C21 -179.9(4) . . . . ?
C26 C25 C30 C29 3.2(6) . . . . ?
C24 C25 C30 C29 -176.7(4) . . . . ?
C26 C25 C30 C21 -179.3(4) . . . . ?
C24 C25 C30 C21 0.9(5) . . . . ?
C22 C21 C30 C29 177.8(4) . . . . ?
C1 C21 C30 C29 2.0(6) . . . . ?
C22 C21 C30 C25 0.3(6) . . . . ?
C1 C21 C30 C25 -175.4(4) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.053

_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_DA-AP149-1
_database_code_depnum_ccdc_archive 'CCDC 1897602'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Fe'
_chemical_formula_sum            'C21 H18 Fe'
_chemical_formula_weight         326.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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                   9.662(5)
_cell_length_b                   10.031(5)
_cell_length_c                   15.390(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.773(5)
_cell_angle_gamma                90
_cell_volume                     1486.4(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      5.2170
_cell_measurement_theta_max      66.6546
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    8.046
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.0532
_exptl_absorpt_correction_T_max  0.1108
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω π scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            17497
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.217
_diffrn_reflns_theta_max         65.987
_diffrn_reflns_theta_full        66.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2589
_reflns_number_gt                2478
_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       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0384P)²+0.7421P] 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         2589
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.43544(18) 0.13834(17) 0.69189(11) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.57922(18) 0.13550(17) 0.67354(11) 0.0214(4) Uani 1 1 d . . . . .
H2 H 0.6149 0.1720 0.6246 0.026 Uiso 1 1 calc R U . . .
C3 C 0.65751(19) 0.06807(17) 0.74207(12) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.7529 0.0538 0.7462 0.029 Uiso 1 1 calc R U . . .
C4 C 0.56435(18) 0.02613(18) 0.80341(11) 0.0231(4) Uani 1 1 d . . . . .
H4 H 0.5882 -0.0210 0.8545 0.028 Uiso 1 1 calc R U . . .
C5 C 0.42871(18) 0.06852(16) 0.77319(11) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.3485 0.0537 0.8013 0.026 Uiso 1 1 calc R U . . .
C6 C 0.40055(18) -0.15370(17) 0.58409(11) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.3274 -0.1191 0.5479 0.026 Uiso 1 1 calc R U . . .
C7 C 0.54376(18) -0.14846(17) 0.56861(11) 0.0216(4) Uani 1 1 d . . . . .
H7 H 0.5806 -0.1100 0.5206 0.026 Uiso 1 1 calc R U . . .
C8 C 0.62023(18) -0.21251(17) 0.63952(11) 0.0221(4) Uani 1 1 d . . . . .
H8 H 0.7161 -0.2236 0.6460 0.027 Uiso 1 1 calc R U . . .
C9 C 0.52484(18) -0.25674(17) 0.69906(11) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.5473 -0.3012 0.7514 0.027 Uiso 1 1 calc R U . . .
C10 C 0.38895(18) -0.22080(16) 0.66429(11) 0.0219(4) Uani 1 1 d . . . . .
H10 H 0.3068 -0.2382 0.6897 0.026 Uiso 1 1 calc R U . . .
C11 C 0.32163(18) 0.20841(17) 0.63851(10) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.34696(19) 0.33194(17) 0.60190(11) 0.0236(4) Uani 1 1 d . . . . .
C13 C 0.2405(2) 0.39588(18) 0.54769(12) 0.0275(4) Uani 1 1 d . . . . .
H13 H 0.2594 0.4773 0.5224 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1124(2) 0.34192(18) 0.53174(11) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.0457 0.3857 0.4951 0.032 Uiso 1 1 calc R U . . .
C15 C 0.07956(19) 0.21948(18) 0.57040(11) 0.0235(4) Uani 1 1 d . . . . .
C16 C -0.05488(18) 0.16412(19) 0.55599(11) 0.0257(4) Uani 1 1 d . . . . .
H16 H -0.1228 0.2109 0.5222 0.031 Uiso 1 1 calc R U . . .
C17 C -0.08774(18) 0.04389(18) 0.59035(12) 0.0253(4) Uani 1 1 d . . . . .
H17 H -0.1766 0.0088 0.5797 0.030 Uiso 1 1 calc R U . . .
C18 C 0.01496(18) -0.02642(18) 0.64219(11) 0.0229(4) Uani 1 1 d . . . . .
H18 H -0.0060 -0.1089 0.6654 0.028 Uiso 1 1 calc R U . . .
C19 C 0.14609(18) 0.02633(17) 0.65869(11) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.2118 -0.0212 0.6938 0.025 Uiso 1 1 calc R U . . .
C20 C 0.18440(17) 0.15054(17) 0.62397(10) 0.0206(4) Uani 1 1 d . . . . .
C21 C 0.4834(2) 0.40621(18) 0.61413(13) 0.0294(4) Uani 1 1 d . . . . .
H21A H 0.5297 0.3840 0.6699 0.044 Uiso 1 1 calc R U . . .
H21B H 0.4662 0.5004 0.6114 0.044 Uiso 1 1 calc R U . . .
H21C H 0.5410 0.3813 0.5689 0.044 Uiso 1 1 calc R U . . .
Fe1 Fe 0.51049(2) -0.05475(2) 0.68356(2) 0.01589(10) 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
C1 C5 1.440(2) . ?
C1 C2 1.441(3) . ?
C1 C11 1.493(2) . ?
C1 Fe1 2.0758(19) . ?
C2 C3 1.417(3) . ?
C2 Fe1 2.0306(19) . ?
C3 C4 1.421(3) . ?
C3 Fe1 2.0331(18) . ?
C4 C5 1.419(3) . ?
C4 Fe1 2.0424(18) . ?
C5 Fe1 2.0586(18) . ?
C6 C10 1.419(3) . ?
C6 C7 1.424(3) . ?
C6 Fe1 2.0461(17) . ?
C7 C8 1.420(2) . ?
C7 Fe1 2.0521(17) . ?
C8 C9 1.424(2) . ?
C8 Fe1 2.0512(18) . ?
C9 C10 1.422(2) . ?
C9 Fe1 2.044(2) . ?
C10 Fe1 2.0454(18) . ?
C11 C12 1.391(3) . ?
C11 C20 1.448(3) . ?
C12 C13 1.422(3) . ?
C12 C21 1.513(3) . ?
C13 C14 1.355(3) . ?
C14 C15 1.412(3) . ?
C15 C16 1.413(3) . ?
C15 C20 1.430(2) . ?
C16 C17 1.365(3) . ?
C17 C18 1.409(3) . ?
C18 C19 1.377(3) . ?
C19 C20 1.417(3) . ?

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 C1 C2 105.94(15) . . ?
C5 C1 C11 128.52(16) . . ?
C2 C1 C11 125.43(16) . . ?
C5 C1 Fe1 68.97(10) . . ?
C2 C1 Fe1 67.79(9) . . ?
C11 C1 Fe1 130.58(12) . . ?
C3 C2 C1 109.10(15) . . ?
C3 C2 Fe1 69.68(10) . . ?
C1 C2 Fe1 71.15(9) . . ?
C2 C3 C4 107.89(16) . . ?
C2 C3 Fe1 69.49(10) . . ?
C4 C3 Fe1 69.94(10) . . ?
C5 C4 C3 108.20(16) . . ?
C5 C4 Fe1 70.37(10) . . ?
C3 C4 Fe1 69.24(10) . . ?
C4 C5 C1 108.86(15) . . ?
C4 C5 Fe1 69.15(10) . . ?
C1 C5 Fe1 70.26(10) . . ?
C10 C6 C7 108.13(15) . . ?
C10 C6 Fe1 69.68(10) . . ?
C7 C6 Fe1 69.89(9) . . ?
C8 C7 C6 107.79(15) . . ?
C8 C7 Fe1 69.72(10) . . ?
C6 C7 Fe1 69.44(9) . . ?
C7 C8 C9 108.20(15) . . ?
C7 C8 Fe1 69.79(10) . . ?
C9 C8 Fe1 69.37(10) . . ?
C8 C9 C10 107.79(16) . . ?
C8 C9 Fe1 69.94(10) . . ?
C10 C9 Fe1 69.71(10) . . ?
C6 C10 C9 108.08(15) . . ?
C6 C10 Fe1 69.74(10) . . ?
C9 C10 Fe1 69.58(10) . . ?
C12 C11 C20 118.96(16) . . ?
C12 C11 C1 119.73(16) . . ?
C20 C11 C1 121.30(15) . . ?
C11 C12 C13 119.75(17) . . ?
C11 C12 C21 124.69(16) . . ?
C13 C12 C21 115.55(16) . . ?
C14 C13 C12 122.11(17) . . ?
C13 C14 C15 120.32(17) . . ?
C14 C15 C16 120.74(16) . . ?
C14 C15 C20 119.37(17) . . ?
C16 C15 C20 119.88(16) . . ?
C17 C16 C15 121.79(16) . . ?
C16 C17 C18 119.07(17) . . ?
C19 C18 C17 120.38(17) . . ?
C18 C19 C20 122.24(16) . . ?
C19 C20 C15 116.61(16) . . ?
C19 C20 C11 123.98(15) . . ?
C15 C20 C11 119.40(16) . . ?
C2 Fe1 C3 40.83(7) . . ?
C2 Fe1 C4 68.59(7) . . ?
C3 Fe1 C4 40.82(7) . . ?
C2 Fe1 C9 157.11(7) . . ?
C3 Fe1 C9 120.73(8) . . ?
C4 Fe1 C9 106.18(8) . . ?
C2 Fe1 C10 160.35(7) . . ?
C3 Fe1 C10 158.32(7) . . ?
C4 Fe1 C10 123.67(7) . . ?
C9 Fe1 C10 40.71(7) . . ?
C2 Fe1 C6 123.49(7) . . ?
C3 Fe1 C6 157.73(7) . . ?
C4 Fe1 C6 161.04(7) . . ?
C9 Fe1 C6 68.43(7) . . ?
C10 Fe1 C6 40.57(7) . . ?
C2 Fe1 C8 121.24(7) . . ?
C3 Fe1 C8 104.63(8) . . ?
C4 Fe1 C8 120.33(7) . . ?
C9 Fe1 C8 40.69(7) . . ?
C10 Fe1 C8 68.29(8) . . ?
C6 Fe1 C8 68.22(7) . . ?
C2 Fe1 C7 106.82(7) . . ?
C3 Fe1 C7 120.37(8) . . ?
C4 Fe1 C7 156.08(7) . . ?
C9 Fe1 C7 68.44(7) . . ?
C10 Fe1 C7 68.36(7) . . ?
C6 Fe1 C7 40.68(7) . . ?
C8 Fe1 C7 40.48(7) . . ?
C2 Fe1 C5 68.44(7) . . ?
C3 Fe1 C5 68.42(8) . . ?
C4 Fe1 C5 40.48(7) . . ?
C9 Fe1 C5 122.91(7) . . ?
C10 Fe1 C5 109.79(7) . . ?
C6 Fe1 C5 126.04(7) . . ?
C8 Fe1 C5 157.31(7) . . ?
C7 Fe1 C5 161.66(7) . . ?
C2 Fe1 C1 41.06(8) . . ?
C3 Fe1 C1 69.03(8) . . ?
C4 Fe1 C1 68.76(7) . . ?
C9 Fe1 C1 159.81(7) . . ?
C10 Fe1 C1 124.71(8) . . ?
C6 Fe1 C1 109.67(7) . . ?
C8 Fe1 C1 158.92(7) . . ?
C7 Fe1 C1 124.14(7) . . ?
C5 Fe1 C1 40.77(7) . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.048

_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_DA-AP87-1
_database_code_depnum_ccdc_archive 'CCDC 1897601'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Fe O'
_chemical_formula_sum            'C21 H18 Fe O'
_chemical_formula_weight         342.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   15.3517(15)
_cell_length_b                   7.3645(7)
_cell_length_c                   14.7940(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.885(3)
_cell_angle_gamma                90
_cell_volume                     1504.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7266
_cell_measurement_theta_min      2.9498
_cell_measurement_theta_max      25.6593
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear intense orange'

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.004
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.942
_exptl_crystal_density_method    'not measured'



_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 Ventture'
_diffrn_measurement_method       'ω π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12484
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.761
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2626
_reflns_number_gt                2283
_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       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0408P)²+0.6918P] 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         2626
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77771(15) 0.7999(3) 0.42033(15) 0.0146(4) Uani 1 1 d . . . . .
C2 C 0.88022(15) 0.8268(3) 0.46652(15) 0.0153(4) Uani 1 1 d . . . . .
H2 H 0.9265 0.7772 0.4417 0.018 Uiso 1 1 calc R U . . .
C3 C 0.90539(16) 0.9365(3) 0.55376(15) 0.0187(5) Uani 1 1 d . . . . .
H3 H 0.9721 0.9779 0.6004 0.022 Uiso 1 1 calc R U . . .
C4 C 0.81957(16) 0.9744(3) 0.56351(15) 0.0187(5) Uani 1 1 d . . . . .
H4 H 0.8150 1.0479 0.6181 0.022 Uiso 1 1 calc R U . . .
C5 C 0.74126(15) 0.8904(3) 0.48282(14) 0.0160(4) Uani 1 1 d . . . . .
H5 H 0.6720 0.8941 0.4710 0.019 Uiso 1 1 calc R U . . .
C6 C 0.80684(17) 0.4333(3) 0.56587(16) 0.0216(5) Uani 1 1 d . . . . .
H6 H 0.7648 0.3601 0.5056 0.026 Uiso 1 1 calc R U . . .
C7 C 0.90809(17) 0.4555(3) 0.60402(16) 0.0236(5) Uani 1 1 d . . . . .
H7 H 0.9500 0.4011 0.5750 0.028 Uiso 1 1 calc R U . . .
C8 C 0.94022(16) 0.5703(3) 0.68991(16) 0.0248(5) Uani 1 1 d . . . . .
H8 H 1.0084 0.6098 0.7321 0.030 Uiso 1 1 calc R U . . .
C9 C 0.85761(16) 0.6191(3) 0.70480(15) 0.0236(5) Uani 1 1 d . . . . .
H9 H 0.8575 0.6991 0.7594 0.028 Uiso 1 1 calc R U . . .
C10 C 0.77522(16) 0.5338(3) 0.62823(15) 0.0217(5) Uani 1 1 d . . . . .
H10 H 0.7070 0.5437 0.6194 0.026 Uiso 1 1 calc R U . . .
C11 C 0.71737(15) 0.7092(3) 0.32385(15) 0.0144(4) Uani 1 1 d . . . . .
C12 C 0.74107(14) 0.5406(3) 0.29917(14) 0.0159(4) Uani 1 1 d . . . . .
C13 C 0.67722(15) 0.4468(3) 0.21249(15) 0.0192(5) Uani 1 1 d . . . . .
H13 H 0.6929 0.3280 0.1992 0.023 Uiso 1 1 calc R U . . .
C14 C 0.59301(15) 0.5268(3) 0.14775(15) 0.0205(5) Uani 1 1 d . . . . .
H14 H 0.5493 0.4606 0.0909 0.025 Uiso 1 1 calc R U . . .
C15 C 0.56905(15) 0.7051(3) 0.16290(15) 0.0177(4) Uani 1 1 d . . . . .
C16 C 0.48375(16) 0.7917(3) 0.09355(16) 0.0219(5) Uani 1 1 d . . . . .
H16 H 0.4398 0.7265 0.0364 0.026 Uiso 1 1 calc R U . . .
C17 C 0.46351(16) 0.9670(3) 0.10723(16) 0.0237(5) Uani 1 1 d . . . . .
H17 H 0.4060 1.0234 0.0600 0.028 Uiso 1 1 calc R U . . .
C18 C 0.52843(15) 1.0636(3) 0.19175(15) 0.0200(5) Uani 1 1 d . . . . .
H18 H 0.5158 1.1872 0.2002 0.024 Uiso 1 1 calc R U . . .
C19 C 0.60967(15) 0.9814(3) 0.26195(15) 0.0167(4) Uani 1 1 d . . . . .
H19 H 0.6516 1.0487 0.3193 0.020 Uiso 1 1 calc R U . . .
C20 C 0.63328(15) 0.7985(3) 0.25177(15) 0.0153(4) Uani 1 1 d . . . . .
C21 C 0.84939(16) 0.2861(3) 0.35087(18) 0.0231(5) Uani 1 1 d . . . . .
H20A H 0.8470 0.2700 0.2841 0.035 Uiso 1 1 calc R U . . .
H20B H 0.8012 0.2072 0.3576 0.035 Uiso 1 1 calc R U . . .
H20C H 0.9141 0.2544 0.4023 0.035 Uiso 1 1 calc R U . . .
Fe1 Fe 0.84054(2) 0.70208(4) 0.56629(2) 0.01434(12) Uani 1 1 d . . . . .
O1 O 0.82887(10) 0.4706(2) 0.36334(10) 0.0197(3) 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
C1 C2 1.430(3) . ?
C1 C5 1.437(3) . ?
C1 C11 1.479(3) . ?
C1 Fe1 2.072(2) . ?
C2 C3 1.425(3) . ?
C2 Fe1 2.044(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.414(3) . ?
C3 Fe1 2.041(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.414(3) . ?
C4 Fe1 2.028(2) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.032(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.413(3) . ?
C6 C10 1.423(3) . ?
C6 Fe1 2.045(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.423(3) . ?
C7 Fe1 2.044(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.425(3) . ?
C8 Fe1 2.046(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.424(3) . ?
C9 Fe1 2.043(2) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.045(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.387(3) . ?
C11 C20 1.426(3) . ?
C12 O1 1.366(2) . ?
C12 C13 1.409(3) . ?
C13 C14 1.362(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(3) . ?
C15 C20 1.429(3) . ?
C16 C17 1.364(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.367(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.420(3) . ?
C19 H19 0.9500 . ?
C21 O1 1.425(2) . ?
C21 H20A 0.9800 . ?
C21 H20B 0.9800 . ?
C21 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 106.54(17) . . ?
C2 C1 C11 128.25(18) . . ?
C5 C1 C11 125.09(19) . . ?
C2 C1 Fe1 68.63(11) . . ?
C5 C1 Fe1 68.01(11) . . ?
C11 C1 Fe1 131.26(14) . . ?
C3 C2 C1 108.56(18) . . ?
C3 C2 Fe1 69.47(12) . . ?
C1 C2 Fe1 70.73(11) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe1 C2 H2 125.7 . . ?
C4 C3 C2 107.92(18) . . ?
C4 C3 Fe1 69.18(12) . . ?
C2 C3 Fe1 69.69(11) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.0 . . ?
C5 C4 C3 108.31(18) . . ?
C5 C4 Fe1 69.75(12) . . ?
C3 C4 Fe1 70.15(12) . . ?
C5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 108.64(18) . . ?
C4 C5 Fe1 69.49(12) . . ?
C1 C5 Fe1 71.01(11) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.7 . . ?
Fe1 C5 H5 125.7 . . ?
C7 C6 C10 107.94(19) . . ?
C7 C6 Fe1 69.74(12) . . ?
C10 C6 Fe1 69.65(12) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 H6 126.0 . . ?
Fe1 C6 H6 126.0 . . ?
C6 C7 C8 108.52(19) . . ?
C6 C7 Fe1 69.84(12) . . ?
C8 C7 Fe1 69.71(12) . . ?
C6 C7 H7 125.7 . . ?
C8 C7 H7 125.7 . . ?
Fe1 C7 H7 125.7 . . ?
C7 C8 C9 107.6(2) . . ?
C7 C8 Fe1 69.58(12) . . ?
C9 C8 Fe1 69.49(12) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 H8 126.2 . . ?
Fe1 C8 H8 126.2 . . ?
C10 C9 C8 107.9(2) . . ?
C10 C9 Fe1 69.73(12) . . ?
C8 C9 Fe1 69.72(12) . . ?
C10 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
Fe1 C9 H9 126.1 . . ?
C6 C10 C9 108.0(2) . . ?
C6 C10 Fe1 69.64(12) . . ?
C9 C10 Fe1 69.51(12) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
C12 C11 C20 118.15(18) . . ?
C12 C11 C1 122.18(18) . . ?
C20 C11 C1 119.65(17) . . ?
O1 C12 C11 116.58(17) . . ?
O1 C12 C13 122.06(18) . . ?
C11 C12 C13 121.37(19) . . ?
C14 C13 C12 119.83(19) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.69(19) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 121.90(19) . . ?
C14 C15 C20 118.19(19) . . ?
C16 C15 C20 119.90(19) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 122.00(19) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C11 123.21(18) . . ?
C19 C20 C15 116.67(18) . . ?
C11 C20 C15 120.11(18) . . ?
O1 C21 H20A 109.5 . . ?
O1 C21 H20B 109.5 . . ?
H20A C21 H20B 109.5 . . ?
O1 C21 H20C 109.5 . . ?
H20A C21 H20C 109.5 . . ?
H20B C21 H20C 109.5 . . ?
C4 Fe1 C5 40.76(8) . . ?
C4 Fe1 C3 40.67(9) . . ?
C5 Fe1 C3 68.51(9) . . ?
C4 Fe1 C9 105.41(9) . . ?
C5 Fe1 C9 123.20(9) . . ?
C3 Fe1 C9 119.35(9) . . ?
C4 Fe1 C7 160.18(9) . . ?
C5 Fe1 C7 158.26(9) . . ?
C3 Fe1 C7 124.51(9) . . ?
C9 Fe1 C7 68.45(9) . . ?
C4 Fe1 C2 68.64(8) . . ?
C5 Fe1 C2 68.61(8) . . ?
C3 Fe1 C2 40.84(8) . . ?
C9 Fe1 C2 155.60(9) . . ?
C7 Fe1 C2 108.71(9) . . ?
C4 Fe1 C6 156.77(10) . . ?
C5 Fe1 C6 122.49(9) . . ?
C3 Fe1 C6 161.98(9) . . ?
C9 Fe1 C6 68.59(9) . . ?
C7 Fe1 C6 40.42(9) . . ?
C2 Fe1 C6 125.98(8) . . ?
C4 Fe1 C10 120.23(9) . . ?
C5 Fe1 C10 107.55(9) . . ?
C3 Fe1 C10 155.10(9) . . ?
C9 Fe1 C10 40.76(9) . . ?
C7 Fe1 C10 68.21(9) . . ?
C2 Fe1 C10 162.69(8) . . ?
C6 Fe1 C10 40.71(9) . . ?
C4 Fe1 C8 122.50(9) . . ?
C5 Fe1 C8 159.57(9) . . ?
C3 Fe1 C8 106.16(9) . . ?
C9 Fe1 C8 40.79(9) . . ?
C7 Fe1 C8 40.72(9) . . ?
C2 Fe1 C8 121.09(9) . . ?
C6 Fe1 C8 68.46(9) . . ?
C10 Fe1 C8 68.50(9) . . ?
C4 Fe1 C1 68.76(8) . . ?
C5 Fe1 C1 40.97(8) . . ?
C3 Fe1 C1 68.59(8) . . ?
C9 Fe1 C1 161.25(9) . . ?
C7 Fe1 C1 122.90(8) . . ?
C2 Fe1 C1 40.64(8) . . ?
C6 Fe1 C1 109.34(8) . . ?
C10 Fe1 C1 125.54(8) . . ?
C8 Fe1 C1 157.34(9) . . ?
C12 O1 C21 118.46(16) . . ?

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 -1.8(2) . . . . ?
C11 C1 C2 C3 174.23(19) . . . . ?
Fe1 C1 C2 C3 -59.39(14) . . . . ?
C5 C1 C2 Fe1 57.62(13) . . . . ?
C11 C1 C2 Fe1 -126.4(2) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
Fe1 C2 C3 C4 -58.80(14) . . . . ?
C1 C2 C3 Fe1 60.17(14) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
Fe1 C3 C4 C5 -59.53(14) . . . . ?
C2 C3 C4 Fe1 59.12(14) . . . . ?
C3 C4 C5 C1 -0.7(2) . . . . ?
Fe1 C4 C5 C1 -60.47(14) . . . . ?
C3 C4 C5 Fe1 59.78(14) . . . . ?
C2 C1 C5 C4 1.5(2) . . . . ?
C11 C1 C5 C4 -174.64(18) . . . . ?
Fe1 C1 C5 C4 59.53(14) . . . . ?
C2 C1 C5 Fe1 -58.00(13) . . . . ?
C11 C1 C5 Fe1 125.84(19) . . . . ?
C10 C6 C7 C8 -0.2(2) . . . . ?
Fe1 C6 C7 C8 59.16(15) . . . . ?
C10 C6 C7 Fe1 -59.40(14) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
Fe1 C7 C8 C9 59.28(15) . . . . ?
C6 C7 C8 Fe1 -59.25(14) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
Fe1 C8 C9 C10 59.51(15) . . . . ?
C7 C8 C9 Fe1 -59.34(15) . . . . ?
C7 C6 C10 C9 0.3(2) . . . . ?
Fe1 C6 C10 C9 -59.12(15) . . . . ?
C7 C6 C10 Fe1 59.45(14) . . . . ?
C8 C9 C10 C6 -0.3(2) . . . . ?
Fe1 C9 C10 C6 59.19(14) . . . . ?
C8 C9 C10 Fe1 -59.51(15) . . . . ?
C2 C1 C11 C12 48.5(3) . . . . ?
C5 C1 C11 C12 -136.1(2) . . . . ?
Fe1 C1 C11 C12 -45.7(3) . . . . ?
C2 C1 C11 C20 -129.6(2) . . . . ?
C5 C1 C11 C20 45.7(3) . . . . ?
Fe1 C1 C11 C20 136.11(17) . . . . ?
C20 C11 C12 O1 170.99(17) . . . . ?
C1 C11 C12 O1 -7.2(3) . . . . ?
C20 C11 C12 C13 -9.3(3) . . . . ?
C1 C11 C12 C13 172.46(19) . . . . ?
O1 C12 C13 C14 -176.16(18) . . . . ?
C11 C12 C13 C14 4.2(3) . . . . ?
C12 C13 C14 C15 2.4(3) . . . . ?
C13 C14 C15 C16 177.1(2) . . . . ?
C13 C14 C15 C20 -3.4(3) . . . . ?
C14 C15 C16 C17 -177.3(2) . . . . ?
C20 C15 C16 C17 3.2(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -2.4(3) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C18 C19 C20 C11 -179.88(19) . . . . ?
C18 C19 C20 C15 1.5(3) . . . . ?
C12 C11 C20 C19 -170.37(19) . . . . ?
C1 C11 C20 C19 7.9(3) . . . . ?
C12 C11 C20 C15 8.2(3) . . . . ?
C1 C11 C20 C15 -173.57(18) . . . . ?
C14 C15 C20 C19 176.65(18) . . . . ?
C16 C15 C20 C19 -3.9(3) . . . . ?
C14 C15 C20 C11 -2.0(3) . . . . ?
C16 C15 C20 C11 177.51(18) . . . . ?
C11 C12 O1 C21 169.41(18) . . . . ?
C13 C12 O1 C21 -10.3(3) . . . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.065

_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_AP-DA-AP124-2
_database_code_depnum_ccdc_archive 'CCDC 1897609'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Fe2'
_chemical_formula_sum            'C30 H24 Fe2'
_chemical_formula_weight         496.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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                   9.6644(16)
_cell_length_b                   10.7292(16)
_cell_length_c                   10.9942(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.625(18)
_cell_angle_gamma                90
_cell_volume                     1066.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    117.00(10)
_cell_measurement_reflns_used    1539
_cell_measurement_theta_min      4.2760
_cell_measurement_theta_max      68.4460

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    11.006
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.24691
_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.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      117.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3123
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.252
_diffrn_reflns_theta_max         64.967
_diffrn_reflns_theta_full        65.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1782
_reflns_number_gt                1475
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1397P)²] 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         1782
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.1985
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0694(6) 0.1825(6) 0.7426(5) 0.0174(12) Uani 1 1 d . . . . .
C2 C -0.0385(6) 0.1754(6) 0.8025(6) 0.0202(12) Uani 1 1 d . . . . .
H2 H -0.1336 0.1436 0.7644 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0230(7) 0.2254(6) 0.9318(6) 0.0240(13) Uani 1 1 d . . . . .
H3 H -0.0234 0.2298 0.9928 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1684(6) 0.2669(6) 0.9488(5) 0.0216(13) Uani 1 1 d . . . . .
H4 H 0.2334 0.3046 1.0232 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1983(6) 0.2413(5) 0.8332(6) 0.0204(12) Uani 1 1 d . . . . .
H5 H 0.2855 0.2594 0.8189 0.025 Uiso 1 1 calc R U . . .
C6 C -0.0727(7) 0.4574(5) 0.6280(6) 0.0225(13) Uani 1 1 d . . . . .
H6 H -0.0951 0.4285 0.5434 0.027 Uiso 1 1 calc R U . . .
C7 C -0.1686(7) 0.4558(6) 0.6990(6) 0.0228(13) Uani 1 1 d . . . . .
H7 H -0.2651 0.4258 0.6694 0.027 Uiso 1 1 calc R U . . .
C8 C -0.0925(7) 0.5083(6) 0.8246(6) 0.0263(13) Uani 1 1 d . . . . .
H8 H -0.1306 0.5176 0.8909 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0522(7) 0.5441(6) 0.8306(6) 0.0251(13) Uani 1 1 d . . . . .
H9 H 0.1244 0.5818 0.9007 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0657(6) 0.5110(5) 0.7079(6) 0.0201(12) Uani 1 1 d . . . . .
H10 H 0.1488 0.5223 0.6850 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0582(6) 0.1401(5) 0.6099(6) 0.0162(12) Uani 1 1 d . . . . .
C12 C 0.1053(6) 0.2181(5) 0.5329(6) 0.0183(12) Uani 1 1 d . . . . .
H12 H 0.1438 0.2960 0.5643 0.022 Uiso 1 1 calc R U . . .
C13 C 0.0960(6) 0.1815(6) 0.4067(6) 0.0206(12) Uani 1 1 d . . . . .
H13 H 0.1288 0.2353 0.3562 0.025 Uiso 1 1 calc R U . . .
C14 C 0.0397(6) 0.0687(6) 0.3586(6) 0.0213(13) Uani 1 1 d . . . . .
H14 H 0.0289 0.0483 0.2735 0.026 Uiso 1 1 calc R U . . .
C15 C 0.0033(6) 0.0194(5) 0.5640(5) 0.0166(11) Uani 1 1 d . . . . .
Fe1 Fe 0.01956(8) 0.35649(8) 0.79515(8) 0.0149(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
C1 C2 1.419(8) . ?
C1 C5 1.438(8) . ?
C1 C11 1.495(8) . ?
C1 Fe1 2.061(6) . ?
C2 C3 1.438(8) . ?
C2 Fe1 2.032(6) . ?
C3 C4 1.422(9) . ?
C3 Fe1 2.050(6) . ?
C4 C5 1.426(8) . ?
C4 Fe1 2.033(5) . ?
C5 Fe1 2.044(6) . ?
C6 C7 1.407(9) . ?
C6 C10 1.437(9) . ?
C6 Fe1 2.047(6) . ?
C7 C8 1.432(9) . ?
C7 Fe1 2.051(6) . ?
C8 C9 1.428(9) . ?
C8 Fe1 2.044(6) . ?
C9 C10 1.445(8) . ?
C9 Fe1 2.053(6) . ?
C10 Fe1 2.041(6) . ?
C11 C12 1.377(8) . ?
C11 C15 1.422(8) . ?
C12 C13 1.414(8) . ?
C13 C14 1.356(9) . ?
C14 C15 1.429(9) 3_556 ?
C15 C14 1.428(9) 3_556 ?
C15 C15 1.448(10) 3_556 ?

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 C1 C5 107.5(5) . . ?
C2 C1 C11 128.6(5) . . ?
C5 C1 C11 123.8(5) . . ?
C2 C1 Fe1 68.6(3) . . ?
C5 C1 Fe1 68.9(3) . . ?
C11 C1 Fe1 127.3(4) . . ?
C1 C2 C3 108.9(5) . . ?
C1 C2 Fe1 70.8(3) . . ?
C3 C2 Fe1 70.0(4) . . ?
C4 C3 C2 107.0(5) . . ?
C4 C3 Fe1 69.0(3) . . ?
C2 C3 Fe1 68.7(4) . . ?
C3 C4 C5 108.9(5) . . ?
C3 C4 Fe1 70.2(3) . . ?
C5 C4 Fe1 69.9(3) . . ?
C4 C5 C1 107.7(5) . . ?
C4 C5 Fe1 69.1(3) . . ?
C1 C5 Fe1 70.1(3) . . ?
C7 C6 C10 108.6(5) . . ?
C7 C6 Fe1 70.1(3) . . ?
C10 C6 Fe1 69.2(3) . . ?
C6 C7 C8 108.4(5) . . ?
C6 C7 Fe1 69.8(3) . . ?
C8 C7 Fe1 69.3(3) . . ?
C9 C8 C7 108.2(5) . . ?
C9 C8 Fe1 69.9(4) . . ?
C7 C8 Fe1 69.8(4) . . ?
C8 C9 C10 107.5(5) . . ?
C8 C9 Fe1 69.3(4) . . ?
C10 C9 Fe1 68.9(3) . . ?
C6 C10 C9 107.4(5) . . ?
C6 C10 Fe1 69.6(3) . . ?
C9 C10 Fe1 69.8(3) . . ?
C12 C11 C15 119.9(5) . . ?
C12 C11 C1 119.3(5) . . ?
C15 C11 C1 120.9(5) . . ?
C11 C12 C13 120.9(6) . . ?
C14 C13 C12 120.6(6) . . ?
C13 C14 C15 121.3(5) . 3_556 ?
C11 C15 C14 122.8(5) . 3_556 ?
C11 C15 C15 119.3(7) . 3_556 ?
C14 C15 C15 117.8(7) 3_556 3_556 ?
C2 Fe1 C4 68.9(2) . . ?
C2 Fe1 C10 154.7(2) . . ?
C4 Fe1 C10 124.5(2) . . ?
C2 Fe1 C5 68.9(2) . . ?
C4 Fe1 C5 40.9(2) . . ?
C10 Fe1 C5 106.1(2) . . ?
C2 Fe1 C8 125.9(2) . . ?
C4 Fe1 C8 120.3(2) . . ?
C10 Fe1 C8 69.1(3) . . ?
C5 Fe1 C8 155.0(3) . . ?
C2 Fe1 C6 120.1(2) . . ?
C4 Fe1 C6 162.3(3) . . ?
C10 Fe1 C6 41.2(2) . . ?
C5 Fe1 C6 124.9(2) . . ?
C8 Fe1 C6 68.5(2) . . ?
C2 Fe1 C3 41.2(2) . . ?
C4 Fe1 C3 40.8(2) . . ?
C10 Fe1 C3 162.1(2) . . ?
C5 Fe1 C3 69.0(2) . . ?
C8 Fe1 C3 107.7(2) . . ?
C6 Fe1 C3 155.6(3) . . ?
C2 Fe1 C7 108.1(2) . . ?
C4 Fe1 C7 156.0(3) . . ?
C10 Fe1 C7 68.7(2) . . ?
C5 Fe1 C7 162.1(2) . . ?
C8 Fe1 C7 40.9(2) . . ?
C6 Fe1 C7 40.2(2) . . ?
C3 Fe1 C7 121.1(2) . . ?
C2 Fe1 C9 162.9(3) . . ?
C4 Fe1 C9 106.8(3) . . ?
C10 Fe1 C9 41.3(2) . . ?
C5 Fe1 C9 119.4(3) . . ?
C8 Fe1 C9 40.8(3) . . ?
C6 Fe1 C9 69.0(2) . . ?
C3 Fe1 C9 124.9(3) . . ?
C7 Fe1 C9 68.7(2) . . ?
C2 Fe1 C1 40.6(2) . . ?
C4 Fe1 C1 68.8(2) . . ?
C10 Fe1 C1 119.5(2) . . ?
C5 Fe1 C1 41.0(2) . . ?
C8 Fe1 C1 162.9(2) . . ?
C6 Fe1 C1 107.3(2) . . ?
C3 Fe1 C1 68.8(2) . . ?
C7 Fe1 C1 125.3(2) . . ?
C9 Fe1 C1 154.9(2) . . ?

_refine_diff_density_max         1.444
_refine_diff_density_min         -1.340
_refine_diff_density_rms         0.155

_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_DA-AP125-2
_database_code_depnum_ccdc_archive 'CCDC 1897611'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Fe2'
_chemical_formula_sum            'C30 H24 Fe2'
_chemical_formula_weight         496.19

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

_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                   13.6264(18)
_cell_length_b                   9.7347(13)
_cell_length_c                   8.1052(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.977(4)
_cell_angle_gamma                90
_cell_volume                     1069.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3529
_cell_measurement_theta_min      3.2813
_cell_measurement_theta_max      24.9712
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.373
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9776
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.664
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1866
_reflns_number_gt                1465
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0512P)²+1.3732P] 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         1866
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7565(3) 0.3910(3) 0.8382(5) 0.0197(8) Uani 1 1 d . . . . .
C2 C 0.7866(3) 0.2911(3) 0.7228(5) 0.0209(9) Uani 1 1 d . . . . .
H2 H 0.7419 0.2257 0.6560 0.025 Uiso 1 1 calc R U . . .
C3 C 0.8898(3) 0.3021(4) 0.7178(5) 0.0215(9) Uani 1 1 d . . . . .
H3 H 0.9305 0.2458 0.6473 0.026 Uiso 1 1 calc R U . . .
C4 C 0.9258(3) 0.4081(4) 0.8294(5) 0.0219(9) Uani 1 1 d . . . . .
H4 H 0.9959 0.4390 0.8515 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8435(3) 0.4630(4) 0.9024(5) 0.0198(8) Uani 1 1 d . . . . .
H5 H 0.8461 0.5398 0.9847 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7211(3) 0.6190(4) 0.5440(5) 0.0263(9) Uani 1 1 d . . . . .
H6 H 0.6540 0.6358 0.5792 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7451(3) 0.5194(4) 0.4261(5) 0.0234(8) Uani 1 1 d . . . . .
H7 H 0.6980 0.4544 0.3638 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8483(3) 0.5292(4) 0.4129(5) 0.0240(9) Uani 1 1 d . . . . .
H8 H 0.8868 0.4717 0.3402 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8871(3) 0.6338(4) 0.5229(5) 0.0271(9) Uani 1 1 d . . . . .
H9 H 0.9578 0.6628 0.5411 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8087(3) 0.6894(4) 0.6042(5) 0.0277(10) Uani 1 1 d . . . . .
H10 H 0.8142 0.7647 0.6885 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6548(3) 0.4175(3) 0.8781(5) 0.0181(8) Uani 1 1 d . . . . .
C12 C 0.5740(3) 0.3480(4) 0.7926(5) 0.0209(8) Uani 1 1 d . . . . .
H12 H 0.5853 0.2843 0.7079 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4802(3) 0.3706(4) 0.8293(5) 0.0235(9) Uani 1 1 d . . . . .
H13 H 0.4272 0.3224 0.7697 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5400(3) 0.5344(3) 1.0441(5) 0.0165(7) Uani 1 1 d . . . . .
C15 C 0.6368(3) 0.5093(3) 1.0019(4) 0.0190(8) Uani 1 1 d . . . . .
H15 H 0.6907 0.5567 1.0600 0.023 Uiso 1 1 calc R U . . .
Fe1 Fe 0.82261(4) 0.48435(5) 0.65168(7) 0.0182(2) 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
C1 C5 1.428(5) . ?
C1 C2 1.438(5) . ?
C1 C11 1.478(5) . ?
C1 Fe1 2.051(4) . ?
C2 C3 1.416(5) . ?
C2 Fe1 2.043(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.425(5) . ?
C3 Fe1 2.043(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.426(5) . ?
C4 Fe1 2.045(4) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.033(4) . ?
C5 H5 1.0000 . ?
C6 C10 1.418(6) . ?
C6 C7 1.422(5) . ?
C6 Fe1 2.035(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.425(6) . ?
C7 Fe1 2.043(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.418(6) . ?
C8 Fe1 2.049(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.419(6) . ?
C9 Fe1 2.042(4) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.038(4) . ?
C10 H10 1.0000 . ?
C11 C15 1.385(5) . ?
C11 C12 1.411(5) . ?
C12 C13 1.360(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.429(5) 3_667 ?
C13 H13 0.9500 . ?
C14 C14 1.409(7) 3_667 ?
C14 C15 1.419(5) . ?
C14 C13 1.429(5) 3_667 ?
C15 H15 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 C1 C2 106.7(3) . . ?
C5 C1 C11 126.6(3) . . ?
C2 C1 C11 126.7(3) . . ?
C5 C1 Fe1 68.9(2) . . ?
C2 C1 Fe1 69.1(2) . . ?
C11 C1 Fe1 125.3(3) . . ?
C3 C2 C1 108.6(3) . . ?
C3 C2 Fe1 69.7(2) . . ?
C1 C2 Fe1 69.7(2) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe1 C2 H2 125.7 . . ?
C2 C3 C4 108.3(3) . . ?
C2 C3 Fe1 69.7(2) . . ?
C4 C3 Fe1 69.7(2) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C5 C4 C3 107.6(3) . . ?
C5 C4 Fe1 69.1(2) . . ?
C3 C4 Fe1 69.5(2) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
Fe1 C4 H4 126.2 . . ?
C4 C5 C1 108.9(3) . . ?
C4 C5 Fe1 70.0(2) . . ?
C1 C5 Fe1 70.2(2) . . ?
C4 C5 H5 125.6 . . ?
C1 C5 H5 125.6 . . ?
Fe1 C5 H5 125.6 . . ?
C10 C6 C7 108.5(4) . . ?
C10 C6 Fe1 69.7(2) . . ?
C7 C6 Fe1 69.9(2) . . ?
C10 C6 H6 125.8 . . ?
C7 C6 H6 125.8 . . ?
Fe1 C6 H6 125.8 . . ?
C6 C7 C8 107.6(3) . . ?
C6 C7 Fe1 69.3(2) . . ?
C8 C7 Fe1 69.9(2) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
Fe1 C7 H7 126.2 . . ?
C9 C8 C7 107.8(3) . . ?
C9 C8 Fe1 69.4(2) . . ?
C7 C8 Fe1 69.4(2) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
C10 C9 C8 108.5(4) . . ?
C10 C9 Fe1 69.5(2) . . ?
C8 C9 Fe1 70.0(2) . . ?
C10 C9 H9 125.8 . . ?
C8 C9 H9 125.8 . . ?
Fe1 C9 H9 125.8 . . ?
C6 C10 C9 107.6(4) . . ?
C6 C10 Fe1 69.5(2) . . ?
C9 C10 Fe1 69.8(2) . . ?
C6 C10 H10 126.2 . . ?
C9 C10 H10 126.2 . . ?
Fe1 C10 H10 126.2 . . ?
C15 C11 C12 118.5(3) . . ?
C15 C11 C1 120.8(3) . . ?
C12 C11 C1 120.7(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.1(4) . 3_667 ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 3_667 . ?
C14 C14 C15 119.0(4) 3_667 . ?
C14 C14 C13 118.5(4) 3_667 3_667 ?
C15 C14 C13 122.5(3) . 3_667 ?
C11 C15 C14 121.7(3) . . ?
C11 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C5 Fe1 C6 120.83(15) . . ?
C5 Fe1 C10 106.83(15) . . ?
C6 Fe1 C10 40.74(16) . . ?
C5 Fe1 C9 124.13(16) . . ?
C6 Fe1 C9 68.34(17) . . ?
C10 Fe1 C9 40.70(16) . . ?
C5 Fe1 C3 68.70(15) . . ?
C6 Fe1 C3 159.76(16) . . ?
C10 Fe1 C3 158.55(16) . . ?
C9 Fe1 C3 123.25(16) . . ?
C5 Fe1 C2 68.68(15) . . ?
C6 Fe1 C2 122.80(16) . . ?
C10 Fe1 C2 159.24(17) . . ?
C9 Fe1 C2 158.37(16) . . ?
C3 Fe1 C2 40.56(15) . . ?
C5 Fe1 C7 156.50(16) . . ?
C6 Fe1 C7 40.83(15) . . ?
C10 Fe1 C7 68.76(15) . . ?
C9 Fe1 C7 68.47(16) . . ?
C3 Fe1 C7 123.79(15) . . ?
C2 Fe1 C7 106.83(16) . . ?
C5 Fe1 C4 40.94(15) . . ?
C6 Fe1 C4 157.34(15) . . ?
C10 Fe1 C4 122.17(16) . . ?
C9 Fe1 C4 108.55(16) . . ?
C3 Fe1 C4 40.80(15) . . ?
C2 Fe1 C4 68.56(15) . . ?
C7 Fe1 C4 160.86(15) . . ?
C5 Fe1 C8 161.06(16) . . ?
C6 Fe1 C8 68.47(16) . . ?
C10 Fe1 C8 68.56(15) . . ?
C9 Fe1 C8 40.57(15) . . ?
C3 Fe1 C8 108.47(15) . . ?
C2 Fe1 C8 122.18(15) . . ?
C7 Fe1 C8 40.76(16) . . ?
C4 Fe1 C8 124.74(16) . . ?
C5 Fe1 C1 40.92(15) . . ?
C6 Fe1 C1 105.69(16) . . ?
C10 Fe1 C1 122.27(15) . . ?
C9 Fe1 C1 159.70(15) . . ?
C3 Fe1 C1 68.97(15) . . ?
C2 Fe1 C1 41.14(14) . . ?
C7 Fe1 C1 120.52(16) . . ?
C4 Fe1 C1 69.06(15) . . ?
C8 Fe1 C1 157.20(16) . . ?

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 0.2(4) . . . . ?
C11 C1 C2 C3 178.2(3) . . . . ?
Fe1 C1 C2 C3 59.1(2) . . . . ?
C5 C1 C2 Fe1 -58.9(2) . . . . ?
C11 C1 C2 Fe1 119.1(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
Fe1 C2 C3 C4 59.2(2) . . . . ?
C1 C2 C3 Fe1 -59.1(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
Fe1 C3 C4 C5 58.8(3) . . . . ?
C2 C3 C4 Fe1 -59.2(2) . . . . ?
C3 C4 C5 C1 0.5(4) . . . . ?
Fe1 C4 C5 C1 59.6(3) . . . . ?
C3 C4 C5 Fe1 -59.1(3) . . . . ?
C2 C1 C5 C4 -0.5(4) . . . . ?
C11 C1 C5 C4 -178.5(3) . . . . ?
Fe1 C1 C5 C4 -59.5(3) . . . . ?
C2 C1 C5 Fe1 59.0(2) . . . . ?
C11 C1 C5 Fe1 -119.0(4) . . . . ?
C10 C6 C7 C8 -0.3(4) . . . . ?
Fe1 C6 C7 C8 -59.6(2) . . . . ?
C10 C6 C7 Fe1 59.3(3) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
Fe1 C7 C8 C9 -59.0(3) . . . . ?
C6 C7 C8 Fe1 59.2(3) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
Fe1 C8 C9 C10 -59.0(3) . . . . ?
C7 C8 C9 Fe1 58.9(2) . . . . ?
C7 C6 C10 C9 0.3(4) . . . . ?
Fe1 C6 C10 C9 59.6(3) . . . . ?
C7 C6 C10 Fe1 -59.4(3) . . . . ?
C8 C9 C10 C6 -0.1(4) . . . . ?
Fe1 C9 C10 C6 -59.4(3) . . . . ?
C8 C9 C10 Fe1 59.3(3) . . . . ?
C5 C1 C11 C15 -7.7(6) . . . . ?
C2 C1 C11 C15 174.7(3) . . . . ?
Fe1 C1 C11 C15 -96.3(4) . . . . ?
C5 C1 C11 C12 173.4(4) . . . . ?
C2 C1 C11 C12 -4.3(6) . . . . ?
Fe1 C1 C11 C12 84.8(4) . . . . ?
C15 C11 C12 C13 0.4(5) . . . . ?
C1 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C14 0.0(6) . . . 3_667 ?
C12 C11 C15 C14 0.1(5) . . . . ?
C1 C11 C15 C14 -178.9(3) . . . . ?
C14 C14 C15 C11 -1.0(6) 3_667 . . . ?
C13 C14 C15 C11 -179.6(3) 3_667 . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.094

_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_AP-DA-AP122-1
_database_code_depnum_ccdc_archive 'CCDC 1897606'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Br Fe'
_chemical_formula_sum            'C20 H15 Br Fe'
_chemical_formula_weight         391.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   13.8326(7)
_cell_length_b                   11.0072(7)
_cell_length_c                   10.0041(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.575(4)
_cell_angle_gamma                90
_cell_volume                     1513.19(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    119(4)
_cell_measurement_reflns_used    2162
_cell_measurement_theta_min      5.0680
_cell_measurement_theta_max      68.0140

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    10.999
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.18971
_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.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      119(4)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4355
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.148
_diffrn_reflns_theta_max         62.489
_diffrn_reflns_theta_full        62.500
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2364
_reflns_number_gt                2050
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0785P)²] 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         2364
_refine_ls_number_parameters     199
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.052
_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
C1 C 0.6986(3) 0.3310(3) 0.1476(4) 0.0136(8) Uani 1 1 d . U . . .
C2 C 0.6763(3) 0.3369(4) 0.2822(4) 0.0180(8) Uani 1 1 d . U . . .
H2 H 0.7180 0.3160 0.3583 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5794(3) 0.3803(4) 0.2813(4) 0.0205(9) Uani 1 1 d . . . . .
H3 H 0.5464 0.3915 0.3563 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5417(3) 0.4036(4) 0.1450(4) 0.0186(9) Uani 1 1 d . . . . .
H4 H 0.4800 0.4334 0.1155 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6155(3) 0.3732(4) 0.0621(4) 0.0167(8) Uani 1 1 d . U . . .
H5 H 0.6104 0.3797 -0.0312 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7830(3) 0.6170(4) 0.2042(4) 0.0199(9) Uani 1 1 d . . . . .
H6 H 0.8459 0.5923 0.1932 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7107(3) 0.6556(4) 0.1001(4) 0.0235(9) Uani 1 1 d . . . . .
H7 H 0.7181 0.6613 0.0090 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6255(3) 0.6837(4) 0.1604(5) 0.0264(10) Uani 1 1 d . . . . .
H8 H 0.5669 0.7103 0.1150 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6442(3) 0.6649(4) 0.2994(5) 0.0280(10) Uani 1 1 d . . . . .
H9 H 0.6006 0.6775 0.3623 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7421(3) 0.6229(4) 0.3274(4) 0.0234(9) Uani 1 1 d . . . . .
H10 H 0.7735 0.6029 0.4118 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7907(3) 0.2842(4) 0.1027(4) 0.0156(8) Uani 1 1 d . U . . .
C12 C 0.8458(3) 0.3612(4) 0.0334(4) 0.0199(8) Uani 1 1 d . . . . .
H12 H 0.8216 0.4375 0.0075 0.024 Uiso 1 1 calc R U . . .
C13 C 0.9391(3) 0.3258(4) 0.0008(4) 0.0198(9) Uani 1 1 d . . . . .
H13 H 0.9733 0.3761 -0.0519 0.024 Uiso 1 1 calc R U . . .
C14 C 0.9780(3) 0.2196(4) 0.0460(4) 0.0251(10) Uani 1 1 d . . . . .
H14 H 1.0419 0.2014 0.0332 0.030 Uiso 1 1 calc R U . . .
C15 C 0.9234(3) 0.1352(4) 0.1126(4) 0.0227(9) Uani 1 1 d . . . . .
C16 C 0.9636(3) 0.0205(5) 0.1546(5) 0.0287(11) Uani 1 1 d . . . . .
H16 H 1.0285 0.0045 0.1451 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9100(4) -0.0655(5) 0.2078(4) 0.0335(12) Uani 1 1 d . . . . .
H17 H 0.9392 -0.1378 0.2393 0.040 Uiso 1 1 calc R U . . .
C18 C 0.8108(4) -0.0466(5) 0.2157(4) 0.0286(10) Uani 1 1 d . . . . .
H18 H 0.7728 -0.1084 0.2457 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7697(3) 0.0647(4) 0.1786(4) 0.0213(9) Uani 1 1 d . . . . .
C20 C 0.8245(3) 0.1632(4) 0.1337(4) 0.0175(9) Uani 1 1 d . . . . .
Fe1 Fe 0.66325(4) 0.50665(6) 0.19826(6) 0.0138(2) Uani 1 1 d . U . . .
Br1 Br 0.63116(3) 0.06708(4) 0.17032(4) 0.0273(2) 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
C1 C2 1.417(6) . ?
C1 C5 1.430(5) . ?
C1 C11 1.490(5) . ?
C1 Fe1 2.071(4) . ?
C2 C3 1.421(6) . ?
C2 Fe1 2.048(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.426(6) . ?
C3 Fe1 2.047(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.427(6) . ?
C4 Fe1 2.047(4) . ?
C4 H4 0.9300 . ?
C5 Fe1 2.060(4) . ?
C5 H5 0.9300 . ?
C6 C10 1.415(6) . ?
C6 C7 1.423(6) . ?
C6 Fe1 2.049(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.418(6) . ?
C7 Fe1 2.057(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(7) . ?
C8 Fe1 2.042(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.428(6) . ?
C9 Fe1 2.047(4) . ?
C9 H9 0.9300 . ?
C10 Fe1 2.043(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(6) . ?
C11 C20 1.433(6) . ?
C12 C13 1.421(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.342(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.412(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.423(7) . ?
C15 C20 1.441(6) . ?
C16 C17 1.349(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.425(6) . ?
C19 Br1 1.908(4) . ?

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 C1 C5 107.8(3) . . ?
C2 C1 C11 126.1(3) . . ?
C5 C1 C11 126.1(3) . . ?
C2 C1 Fe1 69.0(2) . . ?
C5 C1 Fe1 69.4(2) . . ?
C11 C1 Fe1 129.1(3) . . ?
C1 C2 C3 108.5(3) . . ?
C1 C2 Fe1 70.8(2) . . ?
C3 C2 Fe1 69.7(2) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
Fe1 C2 H2 125.4 . . ?
C2 C3 C4 107.9(3) . . ?
C2 C3 Fe1 69.7(2) . . ?
C4 C3 Fe1 69.6(2) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 126.2 . . ?
C3 C4 C5 107.8(3) . . ?
C3 C4 Fe1 69.6(2) . . ?
C5 C4 Fe1 70.2(2) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Fe1 C4 H4 125.7 . . ?
C4 C5 C1 107.9(3) . . ?
C4 C5 Fe1 69.2(2) . . ?
C1 C5 Fe1 70.2(2) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.2 . . ?
C10 C6 C7 107.9(4) . . ?
C10 C6 Fe1 69.5(2) . . ?
C7 C6 Fe1 70.0(2) . . ?
C10 C6 H6 126.1 . . ?
C7 C6 H6 126.1 . . ?
Fe1 C6 H6 126.0 . . ?
C8 C7 C6 107.6(4) . . ?
C8 C7 Fe1 69.2(3) . . ?
C6 C7 Fe1 69.4(2) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
Fe1 C7 H7 126.8 . . ?
C9 C8 C7 108.8(4) . . ?
C9 C8 Fe1 70.1(3) . . ?
C7 C8 Fe1 70.3(3) . . ?
C9 C8 H8 125.6 . . ?
C7 C8 H8 125.6 . . ?
Fe1 C8 H8 125.5 . . ?
C8 C9 C10 107.8(4) . . ?
C8 C9 Fe1 69.8(3) . . ?
C10 C9 Fe1 69.4(3) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
Fe1 C9 H9 126.3 . . ?
C6 C10 C9 108.0(4) . . ?
C6 C10 Fe1 70.0(2) . . ?
C9 C10 Fe1 69.7(2) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 125.8 . . ?
C12 C11 C20 119.6(4) . . ?
C12 C11 C1 118.7(4) . . ?
C20 C11 C1 121.7(3) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.1(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 C20 119.7(4) . . ?
C16 C15 C20 119.5(4) . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.5(5) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 122.8(4) . . ?
C18 C19 Br1 113.8(3) . . ?
C20 C19 Br1 122.9(3) . . ?
C19 C20 C11 127.1(4) . . ?
C19 C20 C15 115.5(4) . . ?
C11 C20 C15 117.3(4) . . ?
C8 Fe1 C10 68.05(17) . . ?
C8 Fe1 C9 40.08(19) . . ?
C10 Fe1 C9 40.87(18) . . ?
C8 Fe1 C3 125.39(17) . . ?
C10 Fe1 C3 117.07(17) . . ?
C9 Fe1 C3 105.46(18) . . ?
C8 Fe1 C4 107.19(17) . . ?
C10 Fe1 C4 150.99(17) . . ?
C9 Fe1 C4 116.86(17) . . ?
C3 Fe1 C4 40.77(16) . . ?
C8 Fe1 C2 162.85(17) . . ?
C10 Fe1 C2 107.25(17) . . ?
C9 Fe1 C2 125.72(19) . . ?
C3 Fe1 C2 40.63(17) . . ?
C4 Fe1 C2 68.43(16) . . ?
C8 Fe1 C6 68.17(17) . . ?
C10 Fe1 C6 40.47(17) . . ?
C9 Fe1 C6 68.31(17) . . ?
C3 Fe1 C6 152.20(17) . . ?
C4 Fe1 C6 166.60(17) . . ?
C2 Fe1 C6 119.75(16) . . ?
C8 Fe1 C7 40.48(18) . . ?
C10 Fe1 C7 68.06(17) . . ?
C9 Fe1 C7 67.92(19) . . ?
C3 Fe1 C7 164.14(17) . . ?
C4 Fe1 C7 127.93(17) . . ?
C2 Fe1 C7 154.83(17) . . ?
C6 Fe1 C7 40.57(17) . . ?
C8 Fe1 C5 120.13(16) . . ?
C10 Fe1 C5 166.51(16) . . ?
C9 Fe1 C5 152.14(17) . . ?
C3 Fe1 C5 68.30(16) . . ?
C4 Fe1 C5 40.65(16) . . ?
C2 Fe1 C5 68.11(16) . . ?
C6 Fe1 C5 129.71(16) . . ?
C7 Fe1 C5 110.37(17) . . ?
C8 Fe1 C1 155.21(17) . . ?
C10 Fe1 C1 128.00(17) . . ?
C9 Fe1 C1 164.31(18) . . ?
C3 Fe1 C1 68.02(16) . . ?
C4 Fe1 C1 68.22(16) . . ?
C2 Fe1 C1 40.25(16) . . ?
C6 Fe1 C1 110.36(16) . . ?
C7 Fe1 C1 121.99(17) . . ?
C5 Fe1 C1 40.49(15) . . ?

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 1.0(5) . . . . ?
C11 C1 C2 C3 -176.6(4) . . . . ?
Fe1 C1 C2 C3 59.7(3) . . . . ?
C5 C1 C2 Fe1 -58.6(3) . . . . ?
C11 C1 C2 Fe1 123.7(4) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
Fe1 C2 C3 C4 59.4(3) . . . . ?
C1 C2 C3 Fe1 -60.4(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
Fe1 C3 C4 C5 60.0(3) . . . . ?
C2 C3 C4 Fe1 -59.4(3) . . . . ?
C3 C4 C5 C1 0.0(5) . . . . ?
Fe1 C4 C5 C1 59.7(3) . . . . ?
C3 C4 C5 Fe1 -59.7(3) . . . . ?
C2 C1 C5 C4 -0.7(5) . . . . ?
C11 C1 C5 C4 177.0(4) . . . . ?
Fe1 C1 C5 C4 -59.1(3) . . . . ?
C2 C1 C5 Fe1 58.4(3) . . . . ?
C11 C1 C5 Fe1 -124.0(4) . . . . ?
C10 C6 C7 C8 -0.6(5) . . . . ?
Fe1 C6 C7 C8 58.9(3) . . . . ?
C10 C6 C7 Fe1 -59.5(3) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
Fe1 C7 C8 C9 59.8(3) . . . . ?
C6 C7 C8 Fe1 -59.0(3) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
Fe1 C8 C9 C10 59.2(3) . . . . ?
C7 C8 C9 Fe1 -59.9(3) . . . . ?
C7 C6 C10 C9 0.2(5) . . . . ?
Fe1 C6 C10 C9 -59.6(3) . . . . ?
C7 C6 C10 Fe1 59.8(3) . . . . ?
C8 C9 C10 C6 0.3(5) . . . . ?
Fe1 C9 C10 C6 59.8(3) . . . . ?
C8 C9 C10 Fe1 -59.4(3) . . . . ?
C2 C1 C11 C12 -120.5(4) . . . . ?
C5 C1 C11 C12 62.3(5) . . . . ?
Fe1 C1 C11 C12 -29.4(5) . . . . ?
C2 C1 C11 C20 57.4(5) . . . . ?
C5 C1 C11 C20 -119.8(4) . . . . ?
Fe1 C1 C11 C20 148.5(3) . . . . ?
C20 C11 C12 C13 -4.8(5) . . . . ?
C1 C11 C12 C13 173.2(3) . . . . ?
C11 C12 C13 C14 -4.9(6) . . . . ?
C12 C13 C14 C15 7.5(6) . . . . ?
C13 C14 C15 C16 177.0(4) . . . . ?
C13 C14 C15 C20 -0.5(6) . . . . ?
C14 C15 C16 C17 -174.1(4) . . . . ?
C20 C15 C16 C17 3.4(6) . . . . ?
C15 C16 C17 C18 3.8(7) . . . . ?
C16 C17 C18 C19 -5.1(7) . . . . ?
C17 C18 C19 C20 -0.9(6) . . . . ?
C17 C18 C19 Br1 171.3(3) . . . . ?
C18 C19 C20 C11 -175.0(4) . . . . ?
Br1 C19 C20 C11 13.6(6) . . . . ?
C18 C19 C20 C15 7.6(6) . . . . ?
Br1 C19 C20 C15 -163.8(3) . . . . ?
C12 C11 C20 C19 -166.1(4) . . . . ?
C1 C11 C20 C19 16.0(6) . . . . ?
C12 C11 C20 C15 11.3(5) . . . . ?
C1 C11 C20 C15 -166.6(3) . . . . ?
C14 C15 C20 C19 168.8(4) . . . . ?
C16 C15 C20 C19 -8.7(5) . . . . ?
C14 C15 C20 C11 -8.9(5) . . . . ?
C16 C15 C20 C11 173.6(3) . . . . ?

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.152

_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_DA-AP125-1
_database_code_depnum_ccdc_archive 'CCDC 1897607'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Br Fe'
_chemical_formula_sum            'C20 H15 Br Fe'
_chemical_formula_weight         391.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.3319(10)
_cell_length_b                   7.7884(7)
_cell_length_c                   37.581(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3024.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    125.00(10)
_cell_measurement_reflns_used    1671
_cell_measurement_theta_min      3.3110
_cell_measurement_theta_max      27.6210

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    3.632
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.864
_oxdiff_exptl_absorpt_empirical_full_max 1.235
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8085
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.930
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2658
_reflns_number_gt                2085
_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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0238P)²] 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         2658
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
C11 C 1.3279(3) -0.1067(5) 0.15448(11) 0.0154(10) Uani 1 1 d . . . . .
H11 H 1.2536 -0.1679 0.1487 0.018 Uiso 1 1 calc R U . . .
C12 C 1.4144(3) -0.0654(5) 0.12778(12) 0.0149(10) Uani 1 1 d . . . . .
C13 C 1.5257(4) 0.0327(5) 0.13724(12) 0.0185(10) Uani 1 1 d . . . . .
H3 H 1.5844 0.0642 0.1196 0.022 Uiso 1 1 calc R U . . .
C14 C 1.5479(4) 0.0812(5) 0.17149(12) 0.0180(10) Uani 1 1 d . . . . .
H4 H 1.6213 0.1453 0.1768 0.022 Uiso 1 1 calc R U . . .
C15 C 1.4616(3) 0.0363(5) 0.19920(12) 0.0144(10) Uani 1 1 d . . . . .
C16 C 1.4843(4) 0.0781(5) 0.23538(12) 0.0169(10) Uani 1 1 d . . . . .
H6 H 1.5568 0.1419 0.2417 0.020 Uiso 1 1 calc R U . . .
C17 C 1.3993(4) 0.0241(5) 0.26084(12) 0.0164(10) Uani 1 1 d . . . . .
C18 C 1.2869(4) -0.0687(5) 0.25245(12) 0.0184(10) Uani 1 1 d . . . . .
H8 H 1.2297 -0.1022 0.2702 0.022 Uiso 1 1 calc R U . . .
C19 C 1.2632(4) -0.1087(5) 0.21775(12) 0.0166(10) Uani 1 1 d . . . . .
H9 H 1.1889 -0.1702 0.2120 0.020 Uiso 1 1 calc R U . . .
C20 C 1.3483(3) -0.0594(5) 0.19028(12) 0.0146(10) Uani 1 1 d . . . . .
C1 C 1.3923(4) -0.1193(5) 0.09082(12) 0.0166(10) Uani 1 1 d . . . . .
C2 C 1.3022(3) -0.2469(5) 0.07931(12) 0.0147(10) Uani 1 1 d . . . . .
H13 H 1.2478 -0.3098 0.0941 0.018 Uiso 1 1 calc R U . . .
C3 C 1.3091(3) -0.2623(6) 0.04169(12) 0.0182(11) Uani 1 1 d . . . . .
H14 H 1.2602 -0.3360 0.0276 0.022 Uiso 1 1 calc R U . . .
C4 C 1.4045(3) -0.1442(6) 0.02948(12) 0.0184(10) Uani 1 1 d . . . . .
H15 H 1.4292 -0.1277 0.0059 0.022 Uiso 1 1 calc R U . . .
C5 C 1.4557(4) -0.0554(5) 0.05959(11) 0.0155(10) Uani 1 1 d . . . . .
H16 H 1.5192 0.0292 0.0590 0.019 Uiso 1 1 calc R U . . .
C6 C 1.6343(4) -0.3942(6) 0.09603(12) 0.0228(11) Uani 1 1 d . . . . .
H17 H 1.6605 -0.3434 0.1172 0.027 Uiso 1 1 calc R U . . .
C7 C 1.5397(4) -0.5260(6) 0.09261(13) 0.0256(12) Uani 1 1 d . . . . .
H18 H 1.4934 -0.5770 0.1110 0.031 Uiso 1 1 calc R U . . .
C8 C 1.5290(4) -0.5651(6) 0.05604(13) 0.0239(11) Uani 1 1 d . . . . .
H19 H 1.4734 -0.6460 0.0462 0.029 Uiso 1 1 calc R U . . .
C9 C 1.6165(4) -0.4612(6) 0.03695(13) 0.0217(11) Uani 1 1 d . . . . .
H20 H 1.6294 -0.4625 0.0125 0.026 Uiso 1 1 calc R U . . .
C10 C 1.6815(4) -0.3539(6) 0.06182(12) 0.0215(11) Uani 1 1 d . . . . .
H21 H 1.7440 -0.2719 0.0565 0.026 Uiso 1 1 calc R U . . .
Fe1 Fe 1.48612(5) -0.31316(8) 0.06429(2) 0.01309(17) Uani 1 1 d . . . . .
Br1 Br 1.43272(4) 0.07807(6) 0.30934(2) 0.02525(16) 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
C11 C12 1.381(5) . ?
C11 C20 1.411(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.426(5) . ?
C12 C1 1.469(6) . ?
C13 C14 1.361(6) . ?
C13 H3 0.9300 . ?
C14 C15 1.415(6) . ?
C14 H4 0.9300 . ?
C15 C16 1.418(6) . ?
C15 C20 1.427(5) . ?
C16 C17 1.365(6) . ?
C16 H6 0.9300 . ?
C17 C18 1.404(5) . ?
C17 Br1 1.902(4) . ?
C18 C19 1.363(6) . ?
C18 H8 0.9300 . ?
C19 C20 1.409(6) . ?
C19 H9 0.9300 . ?
C1 C2 1.428(5) . ?
C1 C5 1.433(6) . ?
C1 Fe1 2.052(4) . ?
C2 C3 1.420(6) . ?
C2 Fe1 2.048(4) . ?
C2 H13 0.9300 . ?
C3 C4 1.424(6) . ?
C3 Fe1 2.055(4) . ?
C3 H14 0.9300 . ?
C4 C5 1.428(6) . ?
C4 Fe1 2.038(4) . ?
C4 H15 0.9300 . ?
C5 Fe1 2.040(4) . ?
C5 H16 0.9300 . ?
C6 C10 1.411(6) . ?
C6 C7 1.423(6) . ?
C6 Fe1 2.041(4) . ?
C6 H17 0.9300 . ?
C7 C8 1.412(6) . ?
C7 Fe1 2.046(5) . ?
C7 H18 0.9300 . ?
C8 C9 1.409(6) . ?
C8 Fe1 2.035(4) . ?
C8 H19 0.9300 . ?
C9 C10 1.422(6) . ?
C9 Fe1 2.049(4) . ?
C9 H20 0.9300 . ?
C10 Fe1 2.046(4) . ?
C10 H21 0.9300 . ?

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
C12 C11 C20 122.4(4) . . ?
C12 C11 H11 118.8 . . ?
C20 C11 H11 118.8 . . ?
C11 C12 C13 117.7(4) . . ?
C11 C12 C1 121.3(4) . . ?
C13 C12 C1 120.9(4) . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H3 119.3 . . ?
C12 C13 H3 119.3 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H4 119.3 . . ?
C15 C14 H4 119.3 . . ?
C14 C15 C16 123.0(4) . . ?
C14 C15 C20 118.2(4) . . ?
C16 C15 C20 118.8(4) . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H6 120.2 . . ?
C15 C16 H6 120.2 . . ?
C16 C17 C18 122.2(4) . . ?
C16 C17 Br1 119.1(3) . . ?
C18 C17 Br1 118.6(3) . . ?
C19 C18 C17 118.8(4) . . ?
C19 C18 H8 120.6 . . ?
C17 C18 H8 120.6 . . ?
C18 C19 C20 121.7(4) . . ?
C18 C19 H9 119.1 . . ?
C20 C19 H9 119.1 . . ?
C19 C20 C11 122.3(4) . . ?
C19 C20 C15 118.8(4) . . ?
C11 C20 C15 118.9(4) . . ?
C2 C1 C5 107.0(4) . . ?
C2 C1 C12 125.9(4) . . ?
C5 C1 C12 127.1(4) . . ?
C2 C1 Fe1 69.5(2) . . ?
C5 C1 Fe1 69.0(2) . . ?
C12 C1 Fe1 126.6(3) . . ?
C3 C2 C1 109.1(4) . . ?
C3 C2 Fe1 70.0(2) . . ?
C1 C2 Fe1 69.8(2) . . ?
C3 C2 H13 125.4 . . ?
C1 C2 H13 125.4 . . ?
Fe1 C2 H13 126.4 . . ?
C2 C3 C4 107.5(4) . . ?
C2 C3 Fe1 69.5(2) . . ?
C4 C3 Fe1 69.0(2) . . ?
C2 C3 H14 126.2 . . ?
C4 C3 H14 126.2 . . ?
Fe1 C3 H14 126.8 . . ?
C3 C4 C5 108.3(4) . . ?
C3 C4 Fe1 70.3(2) . . ?
C5 C4 Fe1 69.6(2) . . ?
C3 C4 H15 125.9 . . ?
C5 C4 H15 125.9 . . ?
Fe1 C4 H15 125.9 . . ?
C4 C5 C1 108.1(4) . . ?
C4 C5 Fe1 69.4(2) . . ?
C1 C5 Fe1 70.0(2) . . ?
C4 C5 H16 125.9 . . ?
C1 C5 H16 125.9 . . ?
Fe1 C5 H16 126.2 . . ?
C10 C6 C7 108.4(4) . . ?
C10 C6 Fe1 70.0(2) . . ?
C7 C6 Fe1 69.8(2) . . ?
C10 C6 H17 125.8 . . ?
C7 C6 H17 125.8 . . ?
Fe1 C6 H17 126.0 . . ?
C8 C7 C6 107.2(4) . . ?
C8 C7 Fe1 69.3(3) . . ?
C6 C7 Fe1 69.4(3) . . ?
C8 C7 H18 126.4 . . ?
C6 C7 H18 126.4 . . ?
Fe1 C7 H18 126.4 . . ?
C9 C8 C7 108.8(4) . . ?
C9 C8 Fe1 70.4(2) . . ?
C7 C8 Fe1 70.2(3) . . ?
C9 C8 H19 125.6 . . ?
C7 C8 H19 125.6 . . ?
Fe1 C8 H19 125.4 . . ?
C8 C9 C10 107.8(4) . . ?
C8 C9 Fe1 69.3(2) . . ?
C10 C9 Fe1 69.5(2) . . ?
C8 C9 H20 126.1 . . ?
C10 C9 H20 126.1 . . ?
Fe1 C9 H20 126.6 . . ?
C6 C10 C9 107.7(4) . . ?
C6 C10 Fe1 69.6(2) . . ?
C9 C10 Fe1 69.8(2) . . ?
C6 C10 H21 126.1 . . ?
C9 C10 H21 126.1 . . ?
Fe1 C10 H21 126.0 . . ?
C8 Fe1 C4 127.93(19) . . ?
C8 Fe1 C5 165.74(19) . . ?
C4 Fe1 C5 40.99(16) . . ?
C8 Fe1 C6 68.12(18) . . ?
C4 Fe1 C6 152.27(17) . . ?
C5 Fe1 C6 118.07(18) . . ?
C8 Fe1 C10 68.20(17) . . ?
C4 Fe1 C10 118.63(17) . . ?
C5 Fe1 C10 107.49(17) . . ?
C6 Fe1 C10 40.38(16) . . ?
C8 Fe1 C7 40.48(18) . . ?
C4 Fe1 C7 165.65(18) . . ?
C5 Fe1 C7 152.15(19) . . ?
C6 Fe1 C7 40.76(17) . . ?
C10 Fe1 C7 68.36(17) . . ?
C8 Fe1 C2 119.15(17) . . ?
C4 Fe1 C2 68.31(16) . . ?
C5 Fe1 C2 68.47(16) . . ?
C6 Fe1 C2 127.80(18) . . ?
C10 Fe1 C2 165.26(18) . . ?
C7 Fe1 C2 108.16(17) . . ?
C8 Fe1 C9 40.36(17) . . ?
C4 Fe1 C9 108.25(18) . . ?
C5 Fe1 C9 127.69(17) . . ?
C6 Fe1 C9 68.04(18) . . ?
C10 Fe1 C9 40.65(16) . . ?
C7 Fe1 C9 68.12(19) . . ?
C2 Fe1 C9 152.83(17) . . ?
C8 Fe1 C1 152.38(18) . . ?
C4 Fe1 C1 68.99(17) . . ?
C5 Fe1 C1 41.01(16) . . ?
C6 Fe1 C1 107.34(18) . . ?
C10 Fe1 C1 127.03(17) . . ?
C7 Fe1 C1 118.10(19) . . ?
C2 Fe1 C1 40.77(15) . . ?
C9 Fe1 C1 165.42(17) . . ?
C8 Fe1 C3 108.47(17) . . ?
C4 Fe1 C3 40.72(16) . . ?
C5 Fe1 C3 68.74(16) . . ?
C6 Fe1 C3 165.64(18) . . ?
C10 Fe1 C3 152.80(18) . . ?
C7 Fe1 C3 127.72(17) . . ?
C2 Fe1 C3 40.50(16) . . ?
C9 Fe1 C3 119.09(18) . . ?
C1 Fe1 C3 68.81(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
C20 C11 C12 C13 -1.8(6) . . . . ?
C20 C11 C12 C1 178.7(4) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C1 C12 C13 C14 -179.1(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C13 C14 C15 C16 177.2(4) . . . . ?
C13 C14 C15 C20 -1.1(6) . . . . ?
C14 C15 C16 C17 -177.3(4) . . . . ?
C20 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C18 -1.7(6) . . . . ?
C15 C16 C17 Br1 179.0(3) . . . . ?
C16 C17 C18 C19 1.2(6) . . . . ?
Br1 C17 C18 C19 -179.5(3) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C11 177.0(4) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C12 C11 C20 C19 -176.9(4) . . . . ?
C12 C11 C20 C15 0.7(6) . . . . ?
C14 C15 C20 C19 178.4(4) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
C14 C15 C20 C11 0.7(6) . . . . ?
C16 C15 C20 C11 -177.6(4) . . . . ?
C11 C12 C1 C2 -15.1(6) . . . . ?
C13 C12 C1 C2 165.4(4) . . . . ?
C11 C12 C1 C5 164.9(4) . . . . ?
C13 C12 C1 C5 -14.7(6) . . . . ?
C11 C12 C1 Fe1 -104.9(4) . . . . ?
C13 C12 C1 Fe1 75.5(5) . . . . ?
C5 C1 C2 C3 0.0(4) . . . . ?
C12 C1 C2 C3 179.9(4) . . . . ?
Fe1 C1 C2 C3 -59.1(3) . . . . ?
C5 C1 C2 Fe1 59.1(3) . . . . ?
C12 C1 C2 Fe1 -121.0(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
Fe1 C2 C3 C4 -58.7(3) . . . . ?
C1 C2 C3 Fe1 59.0(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
Fe1 C3 C4 C5 -59.4(3) . . . . ?
C2 C3 C4 Fe1 59.0(3) . . . . ?
C3 C4 C5 C1 0.3(4) . . . . ?
Fe1 C4 C5 C1 -59.5(3) . . . . ?
C3 C4 C5 Fe1 59.8(3) . . . . ?
C2 C1 C5 C4 -0.2(4) . . . . ?
C12 C1 C5 C4 179.9(4) . . . . ?
Fe1 C1 C5 C4 59.2(3) . . . . ?
C2 C1 C5 Fe1 -59.3(3) . . . . ?
C12 C1 C5 Fe1 120.7(4) . . . . ?
C10 C6 C7 C8 -0.3(5) . . . . ?
Fe1 C6 C7 C8 59.2(3) . . . . ?
C10 C6 C7 Fe1 -59.6(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
Fe1 C7 C8 C9 60.0(3) . . . . ?
C6 C7 C8 Fe1 -59.3(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
Fe1 C8 C9 C10 59.1(3) . . . . ?
C7 C8 C9 Fe1 -59.9(3) . . . . ?
C7 C6 C10 C9 -0.2(5) . . . . ?
Fe1 C6 C10 C9 -59.6(3) . . . . ?
C7 C6 C10 Fe1 59.5(3) . . . . ?
C8 C9 C10 C6 0.6(5) . . . . ?
Fe1 C9 C10 C6 59.5(3) . . . . ?
C8 C9 C10 Fe1 -58.9(3) . . . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.105

_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_DA-AP-1-8-Fc2Naph
_database_code_depnum_ccdc_archive 'CCDC 1897610'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Fe2'
_chemical_formula_sum            'C30 H24 Fe2'
_chemical_formula_weight         496.19

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

_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                   17.0392(7)
_cell_length_b                   10.0481(5)
_cell_length_c                   12.2011(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.020(3)
_cell_angle_gamma                90
_cell_volume                     2087.67(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    125.00(10)
_cell_measurement_reflns_used    4688
_cell_measurement_theta_min      3.5130
_cell_measurement_theta_max      27.6530

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    1.406
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.98176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.945
_oxdiff_exptl_absorpt_empirical_full_max 1.045
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10121
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3653
_reflns_number_gt                3254
_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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0261P)²+1.1694P] 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         3653
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C21 C 0.20595(10) 0.92146(19) 0.17177(14) 0.0128(4) Uani 1 1 d . . . . .
C22 C 0.17844(11) 1.0029(2) 0.08829(15) 0.0173(4) Uani 1 1 d . . . . .
H2 H 0.1533 0.9647 0.0271 0.021 Uiso 1 1 calc R U . . .
C23 C 0.18712(11) 1.1416(2) 0.09251(16) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.1717 1.1936 0.0325 0.025 Uiso 1 1 calc R U . . .
C24 C 0.21814(11) 1.1995(2) 0.18450(17) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.2192 1.2918 0.1901 0.024 Uiso 1 1 calc R U . . .
C25 C 0.24887(10) 1.1213(2) 0.27185(15) 0.0159(4) Uani 1 1 d . . . . .
C26 C 0.27765(11) 1.1813(2) 0.36991(16) 0.0195(4) Uani 1 1 d . . . . .
H6 H 0.2739 1.2731 0.3782 0.023 Uiso 1 1 calc R U . . .
C27 C 0.31088(11) 1.1069(2) 0.45262(16) 0.0197(4) Uani 1 1 d . . . . .
H7 H 0.3252 1.1460 0.5194 0.024 Uiso 1 1 calc R U . . .
C28 C 0.32319(11) 0.9705(2) 0.43578(15) 0.0158(4) Uani 1 1 d . . . . .
H8 H 0.3502 0.9219 0.4898 0.019 Uiso 1 1 calc R U . . .
C29 C 0.29670(10) 0.90626(19) 0.34222(14) 0.0124(4) Uani 1 1 d . . . . .
C30 C 0.25051(10) 0.9791(2) 0.26173(14) 0.0129(4) Uani 1 1 d . . . . .
C1 C 0.18312(10) 0.77903(19) 0.17070(14) 0.0116(4) Uani 1 1 d . . . . .
C2 C 0.15500(11) 0.70453(19) 0.26082(15) 0.0144(4) Uani 1 1 d . . . . .
H12 H 0.1475 0.7373 0.3310 0.017 Uiso 1 1 calc R U . . .
C3 C 0.14039(11) 0.5725(2) 0.22551(15) 0.0169(4) Uani 1 1 d . . . . .
H13 H 0.1223 0.5034 0.2685 0.020 Uiso 1 1 calc R U . . .
C4 C 0.15821(11) 0.5638(2) 0.11296(16) 0.0175(4) Uani 1 1 d . . . . .
H14 H 0.1540 0.4881 0.0693 0.021 Uiso 1 1 calc R U . . .
C5 C 0.18353(10) 0.69078(19) 0.07895(15) 0.0140(4) Uani 1 1 d . . . . .
H15 H 0.1980 0.7131 0.0085 0.017 Uiso 1 1 calc R U . . .
C6 C -0.00241(11) 0.8609(2) 0.12678(16) 0.0205(4) Uani 1 1 d . . . . .
H16 H 0.0097 0.9479 0.1472 0.025 Uiso 1 1 calc R U . . .
C7 C -0.03263(11) 0.7609(2) 0.19557(17) 0.0232(5) Uani 1 1 d . . . . .
H17 H -0.0438 0.7706 0.2692 0.028 Uiso 1 1 calc R U . . .
C8 C -0.04284(11) 0.6436(2) 0.13233(17) 0.0221(5) Uani 1 1 d . . . . .
H18 H -0.0621 0.5629 0.1572 0.027 Uiso 1 1 calc R U . . .
C9 C -0.01883(11) 0.6704(2) 0.02504(16) 0.0202(4) Uani 1 1 d . . . . .
H19 H -0.0193 0.6104 -0.0330 0.024 Uiso 1 1 calc R U . . .
C10 C 0.00605(11) 0.8048(2) 0.02145(16) 0.0187(4) Uani 1 1 d . . . . .
H20 H 0.0247 0.8486 -0.0395 0.022 Uiso 1 1 calc R U . . .
C11 C 0.32152(10) 0.76717(19) 0.32304(14) 0.0118(4) Uani 1 1 d . . . . .
C15 C 0.34713(10) 0.71517(19) 0.22141(14) 0.0134(4) Uani 1 1 d . . . . .
H22 H 0.3515 0.7629 0.1566 0.016 Uiso 1 1 calc R U . . .
C14 C 0.36469(10) 0.57832(19) 0.23619(15) 0.0153(4) Uani 1 1 d . . . . .
H23 H 0.3817 0.5204 0.1825 0.018 Uiso 1 1 calc R U . . .
C13 C 0.35180(10) 0.54504(19) 0.34683(15) 0.0153(4) Uani 1 1 d . . . . .
H24 H 0.3590 0.4616 0.3786 0.018 Uiso 1 1 calc R U . . .
C12 C 0.32592(10) 0.66118(19) 0.40059(15) 0.0137(4) Uani 1 1 d . . . . .
H25 H 0.3138 0.6672 0.4742 0.016 Uiso 1 1 calc R U . . .
C16 C 0.50508(11) 0.8427(2) 0.39189(15) 0.0190(4) Uani 1 1 d . . . . .
H26 H 0.4886 0.9282 0.4090 0.023 Uiso 1 1 calc R U . . .
C20 C 0.51131(12) 0.7345(2) 0.46544(16) 0.0234(5) Uani 1 1 d . . . . .
H27 H 0.4997 0.7361 0.5393 0.028 Uiso 1 1 calc R U . . .
C19 C 0.53842(11) 0.6228(2) 0.40653(18) 0.0258(5) Uani 1 1 d . . . . .
H28 H 0.5478 0.5383 0.4351 0.031 Uiso 1 1 calc R U . . .
C18 C 0.54878(11) 0.6625(2) 0.29683(17) 0.0234(5) Uani 1 1 d . . . . .
H29 H 0.5661 0.6086 0.2406 0.028 Uiso 1 1 calc R U . . .
C17 C 0.52814(11) 0.7989(2) 0.28766(16) 0.0199(5) Uani 1 1 d . . . . .
H30 H 0.5295 0.8504 0.2244 0.024 Uiso 1 1 calc R U . . .
Fe1 Fe 0.07256(2) 0.70338(3) 0.13511(2) 0.01170(9) Uani 1 1 d . . . . .
Fe2 Fe 0.43428(2) 0.69183(3) 0.33876(2) 0.01134(9) 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
C21 C22 1.376(3) . ?
C21 C30 1.435(2) . ?
C21 C1 1.483(3) . ?
C22 C23 1.402(3) . ?
C22 H2 0.9300 . ?
C23 C24 1.355(3) . ?
C23 H3 0.9300 . ?
C24 C25 1.410(3) . ?
C24 H4 0.9300 . ?
C25 C26 1.412(3) . ?
C25 C30 1.434(3) . ?
C26 C27 1.363(3) . ?
C26 H6 0.9300 . ?
C27 C28 1.402(3) . ?
C27 H7 0.9300 . ?
C28 C29 1.374(3) . ?
C28 H8 0.9300 . ?
C29 C30 1.437(3) . ?
C29 C11 1.481(3) . ?
C1 C2 1.427(3) . ?
C1 C5 1.428(3) . ?
C1 Fe1 2.0635(18) . ?
C2 C3 1.414(3) . ?
C2 Fe1 2.0430(18) . ?
C2 H12 0.9300 . ?
C3 C4 1.420(3) . ?
C3 Fe1 2.0474(19) . ?
C3 H13 0.9300 . ?
C4 C5 1.413(3) . ?
C4 Fe1 2.0486(19) . ?
C4 H14 0.9300 . ?
C5 Fe1 2.0377(18) . ?
C5 H15 0.9300 . ?
C6 C10 1.415(3) . ?
C6 C7 1.418(3) . ?
C6 Fe1 2.034(2) . ?
C6 H16 0.9300 . ?
C7 C8 1.416(3) . ?
C7 Fe1 2.0455(19) . ?
C7 H17 0.9300 . ?
C8 C9 1.411(3) . ?
C8 Fe1 2.0552(19) . ?
C8 H18 0.9300 . ?
C9 C10 1.417(3) . ?
C9 Fe1 2.0472(19) . ?
C9 H19 0.9300 . ?
C10 Fe1 2.0335(19) . ?
C10 H20 0.9300 . ?
C11 C12 1.425(3) . ?
C11 C15 1.428(3) . ?
C11 Fe2 2.0677(18) . ?
C15 C14 1.417(3) . ?
C15 Fe2 2.0397(17) . ?
C15 H22 0.9300 . ?
C14 C13 1.415(3) . ?
C14 Fe2 2.0418(18) . ?
C14 H23 0.9300 . ?
C13 C12 1.417(3) . ?
C13 Fe2 2.0421(19) . ?
C13 H24 0.9300 . ?
C12 Fe2 2.0423(18) . ?
C12 H25 0.9300 . ?
C16 C20 1.411(3) . ?
C16 C17 1.414(3) . ?
C16 Fe2 2.0293(19) . ?
C16 H26 0.9300 . ?
C20 C19 1.419(3) . ?
C20 Fe2 2.0377(19) . ?
C20 H27 0.9300 . ?
C19 C18 1.414(3) . ?
C19 Fe2 2.0518(19) . ?
C19 H28 0.9300 . ?
C18 C17 1.418(3) . ?
C18 Fe2 2.0555(19) . ?
C18 H29 0.9300 . ?
C17 Fe2 2.0430(19) . ?
C17 H30 0.9300 . ?

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
C22 C21 C30 118.92(18) . . ?
C22 C21 C1 119.02(16) . . ?
C30 C21 C1 121.86(16) . . ?
C21 C22 C23 122.09(18) . . ?
C21 C22 H2 119.0 . . ?
C23 C22 H2 119.0 . . ?
C24 C23 C22 119.65(18) . . ?
C24 C23 H3 120.2 . . ?
C22 C23 H3 120.2 . . ?
C23 C24 C25 120.69(19) . . ?
C23 C24 H4 119.7 . . ?
C25 C24 H4 119.7 . . ?
C24 C25 C26 120.70(19) . . ?
C24 C25 C30 119.87(17) . . ?
C26 C25 C30 119.43(17) . . ?
C27 C26 C25 121.01(19) . . ?
C27 C26 H6 119.5 . . ?
C25 C26 H6 119.5 . . ?
C26 C27 C28 119.22(18) . . ?
C26 C27 H7 120.4 . . ?
C28 C27 H7 120.4 . . ?
C29 C28 C27 122.31(18) . . ?
C29 C28 H8 118.8 . . ?
C27 C28 H8 118.8 . . ?
C28 C29 C30 118.97(18) . . ?
C28 C29 C11 119.18(17) . . ?
C30 C29 C11 121.68(16) . . ?
C25 C30 C21 117.17(16) . . ?
C25 C30 C29 117.41(16) . . ?
C21 C30 C29 125.42(18) . . ?
C2 C1 C5 106.81(16) . . ?
C2 C1 C21 126.49(16) . . ?
C5 C1 C21 126.69(16) . . ?
C2 C1 Fe1 68.90(10) . . ?
C5 C1 Fe1 68.65(10) . . ?
C21 C1 Fe1 126.48(13) . . ?
C3 C2 C1 108.53(16) . . ?
C3 C2 Fe1 69.94(10) . . ?
C1 C2 Fe1 70.44(10) . . ?
C3 C2 H12 125.7 . . ?
C1 C2 H12 125.7 . . ?
Fe1 C2 H12 125.5 . . ?
C2 C3 C4 108.11(17) . . ?
C2 C3 Fe1 69.61(11) . . ?
C4 C3 Fe1 69.77(11) . . ?
C2 C3 H13 125.9 . . ?
C4 C3 H13 125.9 . . ?
Fe1 C3 H13 126.3 . . ?
C5 C4 C3 107.85(17) . . ?
C5 C4 Fe1 69.35(11) . . ?
C3 C4 Fe1 69.68(11) . . ?
C5 C4 H14 126.1 . . ?
C3 C4 H14 126.1 . . ?
Fe1 C4 H14 126.5 . . ?
C4 C5 C1 108.68(16) . . ?
C4 C5 Fe1 70.18(11) . . ?
C1 C5 Fe1 70.59(10) . . ?
C4 C5 H15 125.7 . . ?
C1 C5 H15 125.7 . . ?
Fe1 C5 H15 125.2 . . ?
C10 C6 C7 107.83(18) . . ?
C10 C6 Fe1 69.61(11) . . ?
C7 C6 Fe1 70.10(11) . . ?
C10 C6 H16 126.1 . . ?
C7 C6 H16 126.1 . . ?
Fe1 C6 H16 125.8 . . ?
C8 C7 C6 107.91(18) . . ?
C8 C7 Fe1 70.16(11) . . ?
C6 C7 Fe1 69.24(11) . . ?
C8 C7 H17 126.0 . . ?
C6 C7 H17 126.0 . . ?
Fe1 C7 H17 126.1 . . ?
C9 C8 C7 108.23(19) . . ?
C9 C8 Fe1 69.58(11) . . ?
C7 C8 Fe1 69.43(11) . . ?
C9 C8 H18 125.9 . . ?
C7 C8 H18 125.9 . . ?
Fe1 C8 H18 126.7 . . ?
C8 C9 C10 107.89(18) . . ?
C8 C9 Fe1 70.19(11) . . ?
C10 C9 Fe1 69.16(11) . . ?
C8 C9 H19 126.1 . . ?
C10 C9 H19 126.1 . . ?
Fe1 C9 H19 126.2 . . ?
C6 C10 C9 108.15(18) . . ?
C6 C10 Fe1 69.67(11) . . ?
C9 C10 Fe1 70.20(11) . . ?
C6 C10 H20 125.9 . . ?
C9 C10 H20 125.9 . . ?
Fe1 C10 H20 125.8 . . ?
C12 C11 C15 107.01(16) . . ?
C12 C11 C29 127.51(16) . . ?
C15 C11 C29 125.46(16) . . ?
C12 C11 Fe2 68.76(10) . . ?
C15 C11 Fe2 68.61(10) . . ?
C29 C11 Fe2 126.90(13) . . ?
C14 C15 C11 108.31(16) . . ?
C14 C15 Fe2 69.76(10) . . ?
C11 C15 Fe2 70.71(10) . . ?
C14 C15 H22 125.8 . . ?
C11 C15 H22 125.8 . . ?
Fe2 C15 H22 125.3 . . ?
C13 C14 C15 108.14(16) . . ?
C13 C14 Fe2 69.74(10) . . ?
C15 C14 Fe2 69.60(10) . . ?
C13 C14 H23 125.9 . . ?
C15 C14 H23 125.9 . . ?
Fe2 C14 H23 126.3 . . ?
C14 C13 C12 107.96(17) . . ?
C14 C13 Fe2 69.71(11) . . ?
C12 C13 Fe2 69.72(11) . . ?
C14 C13 H24 126.0 . . ?
C12 C13 H24 126.0 . . ?
Fe2 C13 H24 126.1 . . ?
C13 C12 C11 108.55(16) . . ?
C13 C12 Fe2 69.70(10) . . ?
C11 C12 Fe2 70.68(10) . . ?
C13 C12 H25 125.7 . . ?
C11 C12 H25 125.7 . . ?
Fe2 C12 H25 125.5 . . ?
C20 C16 C17 108.36(19) . . ?
C20 C16 Fe2 70.01(11) . . ?
C17 C16 Fe2 70.20(11) . . ?
C20 C16 H26 125.8 . . ?
C17 C16 H26 125.8 . . ?
Fe2 C16 H26 125.6 . . ?
C16 C20 C19 107.80(18) . . ?
C16 C20 Fe2 69.38(11) . . ?
C19 C20 Fe2 70.24(11) . . ?
C16 C20 H27 126.1 . . ?
C19 C20 H27 126.1 . . ?
Fe2 C20 H27 125.9 . . ?
C18 C19 C20 108.09(19) . . ?
C18 C19 Fe2 70.01(11) . . ?
C20 C19 Fe2 69.17(11) . . ?
C18 C19 H28 126.0 . . ?
C20 C19 H28 126.0 . . ?
Fe2 C19 H28 126.4 . . ?
C19 C18 C17 107.95(19) . . ?
C19 C18 Fe2 69.73(11) . . ?
C17 C18 Fe2 69.28(11) . . ?
C19 C18 H29 126.0 . . ?
C17 C18 H29 126.0 . . ?
Fe2 C18 H29 126.5 . . ?
C16 C17 C18 107.80(18) . . ?
C16 C17 Fe2 69.16(11) . . ?
C18 C17 Fe2 70.23(11) . . ?
C16 C17 H30 126.1 . . ?
C18 C17 H30 126.1 . . ?
Fe2 C17 H30 126.1 . . ?
C10 Fe1 C6 40.72(8) . . ?
C10 Fe1 C5 107.65(8) . . ?
C6 Fe1 C5 128.32(8) . . ?
C10 Fe1 C2 149.44(8) . . ?
C6 Fe1 C2 116.56(8) . . ?
C5 Fe1 C2 68.36(7) . . ?
C10 Fe1 C7 68.28(8) . . ?
C6 Fe1 C7 40.66(8) . . ?
C5 Fe1 C7 166.93(8) . . ?
C2 Fe1 C7 108.40(8) . . ?
C10 Fe1 C9 40.64(8) . . ?
C6 Fe1 C9 68.38(8) . . ?
C5 Fe1 C9 117.57(8) . . ?
C2 Fe1 C9 168.62(8) . . ?
C7 Fe1 C9 68.07(8) . . ?
C10 Fe1 C3 168.44(8) . . ?
C6 Fe1 C3 150.25(8) . . ?
C5 Fe1 C3 68.18(8) . . ?
C2 Fe1 C3 40.45(8) . . ?
C7 Fe1 C3 118.19(8) . . ?
C9 Fe1 C3 130.63(8) . . ?
C10 Fe1 C4 129.46(8) . . ?
C6 Fe1 C4 167.15(8) . . ?
C5 Fe1 C4 40.47(8) . . ?
C2 Fe1 C4 68.21(8) . . ?
C7 Fe1 C4 151.45(9) . . ?
C9 Fe1 C4 109.36(8) . . ?
C3 Fe1 C4 40.55(8) . . ?
C10 Fe1 C8 68.00(8) . . ?
C6 Fe1 C8 68.15(8) . . ?
C5 Fe1 C8 151.04(8) . . ?
C2 Fe1 C8 130.25(8) . . ?
C7 Fe1 C8 40.40(9) . . ?
C9 Fe1 C8 40.24(8) . . ?
C3 Fe1 C8 110.04(8) . . ?
C4 Fe1 C8 118.91(8) . . ?
C10 Fe1 C1 116.21(8) . . ?
C6 Fe1 C1 106.92(8) . . ?
C5 Fe1 C1 40.76(7) . . ?
C2 Fe1 C1 40.66(7) . . ?
C7 Fe1 C1 128.69(8) . . ?
C9 Fe1 C1 149.94(8) . . ?
C3 Fe1 C1 68.25(7) . . ?
C4 Fe1 C1 68.32(7) . . ?
C8 Fe1 C1 167.70(8) . . ?
C16 Fe2 C20 40.61(8) . . ?
C16 Fe2 C15 123.25(8) . . ?
C20 Fe2 C15 160.36(9) . . ?
C16 Fe2 C14 159.87(8) . . ?
C20 Fe2 C14 157.98(9) . . ?
C15 Fe2 C14 40.64(7) . . ?
C16 Fe2 C13 157.90(8) . . ?
C20 Fe2 C13 122.78(8) . . ?
C15 Fe2 C13 68.38(7) . . ?
C14 Fe2 C13 40.56(7) . . ?
C16 Fe2 C12 121.98(8) . . ?
C20 Fe2 C12 108.55(8) . . ?
C15 Fe2 C12 68.36(7) . . ?
C14 Fe2 C12 68.23(7) . . ?
C13 Fe2 C12 40.59(7) . . ?
C16 Fe2 C17 40.64(8) . . ?
C20 Fe2 C17 68.32(8) . . ?
C15 Fe2 C17 106.47(8) . . ?
C14 Fe2 C17 123.44(8) . . ?
C13 Fe2 C17 160.47(8) . . ?
C12 Fe2 C17 156.89(8) . . ?
C16 Fe2 C19 68.15(9) . . ?
C20 Fe2 C19 40.59(9) . . ?
C15 Fe2 C19 156.88(8) . . ?
C14 Fe2 C19 122.25(8) . . ?
C13 Fe2 C19 108.87(8) . . ?
C12 Fe2 C19 125.48(8) . . ?
C17 Fe2 C19 68.03(8) . . ?
C16 Fe2 C18 68.15(8) . . ?
C20 Fe2 C18 68.12(8) . . ?
C15 Fe2 C18 121.04(8) . . ?
C14 Fe2 C18 107.65(8) . . ?
C13 Fe2 C18 124.70(8) . . ?
C12 Fe2 C18 161.55(8) . . ?
C17 Fe2 C18 40.50(8) . . ?
C19 Fe2 C18 40.26(8) . . ?
C16 Fe2 C11 107.23(8) . . ?
C20 Fe2 C11 124.40(8) . . ?
C15 Fe2 C11 40.68(7) . . ?
C14 Fe2 C11 68.28(7) . . ?
C13 Fe2 C11 68.29(7) . . ?
C12 Fe2 C11 40.56(7) . . ?
C17 Fe2 C11 120.91(8) . . ?
C19 Fe2 C11 161.57(8) . . ?
C18 Fe2 C11 156.41(8) . . ?

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
C30 C21 C22 C23 -5.2(3) . . . . ?
C1 C21 C22 C23 169.75(17) . . . . ?
C21 C22 C23 C24 -5.1(3) . . . . ?
C22 C23 C24 C25 6.3(3) . . . . ?
C23 C24 C25 C26 -176.84(18) . . . . ?
C23 C24 C25 C30 2.7(3) . . . . ?
C24 C25 C26 C27 -176.82(18) . . . . ?
C30 C25 C26 C27 3.6(3) . . . . ?
C25 C26 C27 C28 6.0(3) . . . . ?
C26 C27 C28 C29 -5.9(3) . . . . ?
C27 C28 C29 C30 -4.0(3) . . . . ?
C27 C28 C29 C11 171.33(17) . . . . ?
C24 C25 C30 C21 -12.6(2) . . . . ?
C26 C25 C30 C21 166.97(16) . . . . ?
C24 C25 C30 C29 167.29(16) . . . . ?
C26 C25 C30 C29 -13.2(2) . . . . ?
C22 C21 C30 C25 13.7(2) . . . . ?
C1 C21 C30 C25 -161.14(16) . . . . ?
C22 C21 C30 C29 -166.17(17) . . . . ?
C1 C21 C30 C29 19.0(3) . . . . ?
C28 C29 C30 C25 13.3(2) . . . . ?
C11 C29 C30 C25 -161.93(16) . . . . ?
C28 C29 C30 C21 -166.87(17) . . . . ?
C11 C29 C30 C21 17.9(3) . . . . ?
C22 C21 C1 C2 -132.96(19) . . . . ?
C30 C21 C1 C2 41.9(3) . . . . ?
C22 C21 C1 C5 45.7(3) . . . . ?
C30 C21 C1 C5 -139.50(18) . . . . ?
C22 C21 C1 Fe1 -43.5(2) . . . . ?
C30 C21 C1 Fe1 131.28(15) . . . . ?
C5 C1 C2 C3 1.4(2) . . . . ?
C21 C1 C2 C3 -179.72(17) . . . . ?
Fe1 C1 C2 C3 59.80(12) . . . . ?
C5 C1 C2 Fe1 -58.39(12) . . . . ?
C21 C1 C2 Fe1 120.48(18) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
Fe1 C2 C3 C4 59.35(13) . . . . ?
C1 C2 C3 Fe1 -60.11(12) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
Fe1 C3 C4 C5 59.04(13) . . . . ?
C2 C3 C4 Fe1 -59.25(13) . . . . ?
C3 C4 C5 C1 1.1(2) . . . . ?
Fe1 C4 C5 C1 60.35(12) . . . . ?
C3 C4 C5 Fe1 -59.25(13) . . . . ?
C2 C1 C5 C4 -1.6(2) . . . . ?
C21 C1 C5 C4 179.59(17) . . . . ?
Fe1 C1 C5 C4 -60.09(13) . . . . ?
C2 C1 C5 Fe1 58.54(12) . . . . ?
C21 C1 C5 Fe1 -120.32(18) . . . . ?
C10 C6 C7 C8 -0.1(2) . . . . ?
Fe1 C6 C7 C8 -59.74(13) . . . . ?
C10 C6 C7 Fe1 59.63(13) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
Fe1 C7 C8 C9 -58.94(13) . . . . ?
C6 C7 C8 Fe1 59.16(13) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
Fe1 C8 C9 C10 -59.10(13) . . . . ?
C7 C8 C9 Fe1 58.85(13) . . . . ?
C7 C6 C10 C9 0.0(2) . . . . ?
Fe1 C6 C10 C9 59.90(13) . . . . ?
C7 C6 C10 Fe1 -59.93(13) . . . . ?
C8 C9 C10 C6 0.2(2) . . . . ?
Fe1 C9 C10 C6 -59.56(13) . . . . ?
C8 C9 C10 Fe1 59.74(13) . . . . ?
C28 C29 C11 C12 43.1(3) . . . . ?
C30 C29 C11 C12 -141.67(18) . . . . ?
C28 C29 C11 C15 -135.72(19) . . . . ?
C30 C29 C11 C15 39.5(3) . . . . ?
C28 C29 C11 Fe2 -47.2(2) . . . . ?
C30 C29 C11 Fe2 128.03(16) . . . . ?
C12 C11 C15 C14 1.7(2) . . . . ?
C29 C11 C15 C14 -179.29(16) . . . . ?
Fe2 C11 C15 C14 59.87(12) . . . . ?
C12 C11 C15 Fe2 -58.21(12) . . . . ?
C29 C11 C15 Fe2 120.84(18) . . . . ?
C11 C15 C14 C13 -1.2(2) . . . . ?
Fe2 C15 C14 C13 59.29(12) . . . . ?
C11 C15 C14 Fe2 -60.47(12) . . . . ?
C15 C14 C13 C12 0.2(2) . . . . ?
Fe2 C14 C13 C12 59.44(12) . . . . ?
C15 C14 C13 Fe2 -59.21(13) . . . . ?
C14 C13 C12 C11 0.8(2) . . . . ?
Fe2 C13 C12 C11 60.24(12) . . . . ?
C14 C13 C12 Fe2 -59.44(12) . . . . ?
C15 C11 C12 C13 -1.5(2) . . . . ?
C29 C11 C12 C13 179.46(17) . . . . ?
Fe2 C11 C12 C13 -59.63(12) . . . . ?
C15 C11 C12 Fe2 58.12(12) . . . . ?
C29 C11 C12 Fe2 -120.91(18) . . . . ?
C17 C16 C20 C19 0.0(2) . . . . ?
Fe2 C16 C20 C19 59.98(13) . . . . ?
C17 C16 C20 Fe2 -59.97(13) . . . . ?
C16 C20 C19 C18 0.0(2) . . . . ?
Fe2 C20 C19 C18 59.40(13) . . . . ?
C16 C20 C19 Fe2 -59.44(13) . . . . ?
C20 C19 C18 C17 0.0(2) . . . . ?
Fe2 C19 C18 C17 58.92(13) . . . . ?
C20 C19 C18 Fe2 -58.88(13) . . . . ?
C20 C16 C17 C18 0.0(2) . . . . ?
Fe2 C16 C17 C18 -59.84(13) . . . . ?
C20 C16 C17 Fe2 59.85(13) . . . . ?
C19 C18 C17 C16 0.0(2) . . . . ?
Fe2 C18 C17 C16 59.17(13) . . . . ?
C19 C18 C17 Fe2 -59.20(13) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

