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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_adg7
_database_code_depnum_ccdc_archive 'CCDC 1567218'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_audit_creation_date             2015-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Fe O5 Si'
_chemical_formula_sum            'C20 H20 Fe O5 Si'
_chemical_formula_weight         424.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O3 Fe'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.56456(12)
_cell_length_b                   15.9301(3)
_cell_length_c                   19.5077(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2040.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19088
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.0780
_cell_measurement_theta_min      3.2590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38542
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.391
_diffrn_reflns_theta_min         2.557
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  94.00   1.00   50.00    --   17.41  77.00-150.00  109
  2  ω    -15.00  94.00   1.00   50.00    --   17.41  77.00  90.00  109
  3  ω    -15.00  94.00   1.00   50.00    --   17.41  77.00 -30.00  109
  4  ω    -51.00  58.00   1.00   50.00    --  -18.35  77.00-180.00  109
  5  ω    -25.00  37.00   1.00   50.00    --   17.41 -99.00  90.00   62
  6  ω   -107.00 -57.00   1.00   50.00    --  -18.35-178.00-180.00   50
  7  ω   -107.00 -57.00   1.00   50.00    --  -18.35-178.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0045449000
_diffrn_orient_matrix_UB_12      0.0175522000
_diffrn_orient_matrix_UB_13      -0.0333896000
_diffrn_orient_matrix_UB_21      0.0184709000
_diffrn_orient_matrix_UB_22      0.0401757000
_diffrn_orient_matrix_UB_23      0.0143788000
_diffrn_orient_matrix_UB_31      0.1063596000
_diffrn_orient_matrix_UB_32      -0.0077100000
_diffrn_orient_matrix_UB_33      -0.0010574000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                6379
_reflns_number_total             6932
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 Flack x =   -0.015(10) by classical fit to all intensities  (Shelx 2014)
             -0.018(4) from 2542 selected quotients (Parsons' method)
 Hooft y: -0.018(3)  Olex2
;
_refine_ls_abs_structure_Flack   -0.018(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0638
_refine_special_details          ?
_olex2_refinement_description    
;

The OH was located in a difference map and refined with a DFIX restraint and given thermal 
ellipsoids Uiso 1.5 times the Uequiv of the parent oxygen.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-H6A
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.9401(2) 0.39284(9) 0.28027(9) 0.0201(3) Uani 1 1 d . . . . .
Fe1 Fe 0.61966(3) 0.32565(2) 0.27979(2) 0.01961(6) Uani 1 1 d . . . . .
O1 O 1.0059(2) 0.46322(7) 0.26457(7) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.8525(2) 0.36922(9) 0.34780(8) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.8367(2) 0.27982(9) 0.34734(8) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.8089(3) 0.20922(10) 0.39741(9) 0.0252(3) Uani 1 1 d . . . . .
H4A H 0.6937 0.2202 0.4289 0.030 Uiso 1 1 calc R . . . .
H4B H 0.9341 0.1996 0.4246 0.030 Uiso 1 1 calc R . . . .
C5 C 0.7635(3) 0.13407(10) 0.34949(10) 0.0306(4) Uani 1 1 d . . . . .
H5A H 0.8185 0.0815 0.3693 0.037 Uiso 1 1 calc R . . . .
H5B H 0.6147 0.1275 0.3432 0.037 Uiso 1 1 calc R . . . .
C6 C 0.8674(3) 0.15333(9) 0.28021(9) 0.0256(3) Uani 1 1 d . . . . .
H6 H 0.7876 0.1305 0.2407 0.031 Uiso 1 1 calc R . . . .
O6 O 1.0744(2) 0.12686(8) 0.27811(8) 0.0328(3) Uani 1 1 d D . . . .
H6A H 1.081(4) 0.0758(13) 0.2664(13) 0.049 Uiso 1 1 d DR . . . .
C7 C 0.8707(2) 0.24846(9) 0.28018(8) 0.0190(2) Uani 1 1 d . . . . .
C8 C 0.9170(2) 0.31767(9) 0.23536(8) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.9663(2) 0.31505(11) 0.16168(9) 0.0241(3) Uani 1 1 d . . . . .
C10 C 0.9907(3) 0.23903(12) 0.12724(10) 0.0327(4) Uani 1 1 d . . . . .
H10 H 0.9758 0.1877 0.1516 0.039 Uiso 1 1 calc R . . . .
C11 C 1.0368(4) 0.23750(15) 0.05749(11) 0.0407(5) Uani 1 1 d . . . . .
H11 H 1.0525 0.1852 0.0346 0.049 Uiso 1 1 calc R . . . .
C12 C 1.0596(4) 0.31120(16) 0.02159(10) 0.0421(5) Uani 1 1 d . . . . .
H12 H 1.0915 0.3100 -0.0259 0.050 Uiso 1 1 calc R . . . .
C13 C 1.0359(4) 0.38667(16) 0.05504(11) 0.0461(5) Uani 1 1 d . . . . .
H13 H 1.0514 0.4377 0.0303 0.055 Uiso 1 1 calc R . . . .
C14 C 0.9895(4) 0.38911(13) 0.12444(10) 0.0383(5) Uani 1 1 d . . . . .
H14 H 0.9733 0.4417 0.1467 0.046 Uiso 1 1 calc R . . . .
Si15 Si 0.83361(7) 0.44690(3) 0.41972(3) 0.02418(10) Uani 1 1 d . . . . .
C16 C 0.6781(3) 0.53777(11) 0.39057(11) 0.0340(4) Uani 1 1 d . . . . .
H16A H 0.7358 0.5605 0.3481 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.6786 0.5813 0.4260 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.5378 0.5193 0.3822 0.051 Uiso 1 1 calc GR . . . .
C17 C 1.0958(4) 0.48247(15) 0.44172(15) 0.0517(6) Uani 1 1 d . . . . .
H17A H 1.1755 0.4346 0.4584 0.078 Uiso 1 1 calc GR . . . .
H17B H 1.0887 0.5256 0.4775 0.078 Uiso 1 1 calc GR . . . .
H17C H 1.1612 0.5059 0.4008 0.078 Uiso 1 1 calc GR . . . .
C18 C 0.7143(4) 0.39483(14) 0.49548(10) 0.0421(5) Uani 1 1 d . . . . .
H18A H 0.5759 0.3768 0.4837 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.7087 0.4345 0.5338 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.7956 0.3458 0.5087 0.063 Uiso 1 1 calc GR . . . .
C19 C 0.5355(3) 0.42639(13) 0.24630(11) 0.0329(4) Uani 1 1 d . . . . .
O19 O 0.4929(3) 0.48961(11) 0.22463(11) 0.0578(5) Uani 1 1 d . . . . .
C20 C 0.4232(3) 0.30535(11) 0.34188(10) 0.0271(4) Uani 1 1 d . . . . .
O20 O 0.3061(2) 0.29085(11) 0.38298(9) 0.0422(4) Uani 1 1 d . . . . .
O21 O 0.4531(3) 0.22180(12) 0.16939(10) 0.0547(5) Uani 1 1 d . . . . .
C21 C 0.5077(3) 0.26228(12) 0.21345(11) 0.0333(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 Fe1 2.3601(15) . ?
C1 O1 1.2399(18) . ?
C1 C2 1.486(2) . ?
C1 C8 1.492(2) . ?
Fe1 C2 2.1397(15) . ?
Fe1 C3 2.0734(15) . ?
Fe1 C7 2.0563(15) . ?
Fe1 C8 2.1393(15) . ?
Fe1 C19 1.8185(19) . ?
Fe1 C20 1.7988(18) . ?
Fe1 C21 1.798(2) . ?
C2 C3 1.4280(19) . ?
C2 Si15 1.8748(16) . ?
C3 C4 1.501(2) . ?
C3 C7 1.420(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.548(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.545(3) . ?
C6 H6 1.0000 . ?
C6 O6 1.423(2) . ?
C6 C7 1.5156(19) . ?
O6 H6A 0.85(2) . ?
C7 C8 1.439(2) . ?
C8 C9 1.474(2) . ?
C9 C10 1.394(3) . ?
C9 C14 1.394(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.375(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
Si15 C16 1.861(2) . ?
Si15 C17 1.862(2) . ?
Si15 C18 1.867(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O19 1.127(2) . ?
C20 O20 1.135(2) . ?
O21 C21 1.133(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
O1 C1 Fe1 136.02(12) . . ?
O1 C1 C2 125.66(15) . . ?
O1 C1 C8 128.04(16) . . ?
C2 C1 Fe1 62.86(8) . . ?
C2 C1 C8 106.15(12) . . ?
C8 C1 Fe1 62.80(8) . . ?
C2 Fe1 C1 38.16(6) . . ?
C3 Fe1 C1 62.92(6) . . ?
C3 Fe1 C2 39.59(5) . . ?
C3 Fe1 C8 67.03(6) . . ?
C7 Fe1 C1 63.69(6) . . ?
C7 Fe1 C2 67.61(6) . . ?
C7 Fe1 C3 40.22(6) . . ?
C7 Fe1 C8 40.07(6) . . ?
C8 Fe1 C1 38.32(6) . . ?
C8 Fe1 C2 67.59(6) . . ?
C19 Fe1 C1 82.64(7) . . ?
C19 Fe1 C2 98.83(8) . . ?
C19 Fe1 C3 138.39(8) . . ?
C19 Fe1 C7 140.58(7) . . ?
C19 Fe1 C8 100.60(7) . . ?
C20 Fe1 C1 135.89(7) . . ?
C20 Fe1 C2 98.80(7) . . ?
C20 Fe1 C3 90.08(7) . . ?
C20 Fe1 C7 117.70(7) . . ?
C20 Fe1 C8 156.40(7) . . ?
C20 Fe1 C19 100.53(8) . . ?
C21 Fe1 C1 128.45(8) . . ?
C21 Fe1 C2 156.97(7) . . ?
C21 Fe1 C3 122.72(8) . . ?
C21 Fe1 C7 89.69(7) . . ?
C21 Fe1 C8 92.76(7) . . ?
C21 Fe1 C19 96.47(9) . . ?
C21 Fe1 C20 95.19(9) . . ?
C1 C2 Fe1 78.98(9) . . ?
C1 C2 Si15 121.46(10) . . ?
C3 C2 C1 105.97(13) . . ?
C3 C2 Fe1 67.71(9) . . ?
C3 C2 Si15 131.16(12) . . ?
Si15 C2 Fe1 129.12(8) . . ?
C2 C3 Fe1 72.71(9) . . ?
C2 C3 C4 138.78(15) . . ?
C4 C3 Fe1 126.45(11) . . ?
C7 C3 Fe1 69.24(9) . . ?
C7 C3 C2 110.20(13) . . ?
C7 C3 C4 110.85(13) . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
C3 C4 C5 102.12(14) . . ?
H4A C4 H4B 109.2 . . ?
C5 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C4 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C6 C5 C4 106.84(13) . . ?
C6 C5 H5A 110.4 . . ?
C6 C5 H5B 110.4 . . ?
C5 C6 H6 111.7 . . ?
O6 C6 C5 112.83(15) . . ?
O6 C6 H6 111.7 . . ?
O6 C6 C7 106.40(13) . . ?
C7 C6 C5 101.85(13) . . ?
C7 C6 H6 111.7 . . ?
C6 O6 H6A 110.0(19) . . ?
C3 C7 Fe1 70.54(8) . . ?
C3 C7 C6 110.44(13) . . ?
C3 C7 C8 108.92(12) . . ?
C6 C7 Fe1 125.90(11) . . ?
C8 C7 Fe1 73.07(8) . . ?
C8 C7 C6 140.28(15) . . ?
C1 C8 Fe1 78.88(9) . . ?
C7 C8 C1 106.23(13) . . ?
C7 C8 Fe1 66.86(8) . . ?
C7 C8 C9 128.09(14) . . ?
C9 C8 C1 124.98(14) . . ?
C9 C8 Fe1 126.68(11) . . ?
C10 C9 C8 121.31(16) . . ?
C14 C9 C8 120.54(16) . . ?
C14 C9 C10 118.14(17) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.69(19) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.45(19) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C16 Si15 C2 108.73(8) . . ?
C16 Si15 C17 109.93(11) . . ?
C16 Si15 C18 110.94(10) . . ?
C17 Si15 C2 108.19(9) . . ?
C17 Si15 C18 109.91(13) . . ?
C18 Si15 C2 109.09(8) . . ?
Si15 C16 H16A 109.5 . . ?
Si15 C16 H16B 109.5 . . ?
Si15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si15 C17 H17A 109.5 . . ?
Si15 C17 H17B 109.5 . . ?
Si15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si15 C18 H18A 109.5 . . ?
Si15 C18 H18B 109.5 . . ?
Si15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O19 C19 Fe1 176.63(18) . . ?
O20 C20 Fe1 176.73(17) . . ?
O21 C21 Fe1 174.21(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6A O1 0.85(2) 1.98(2) 2.7868(17) 160(3) 3_745

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 Fe1 -70.60(10) . . . . ?
C1 C2 C3 C4 163.32(19) . . . . ?
C1 C2 C3 C7 -11.26(17) . . . . ?
C1 C2 Si15 C16 58.41(14) . . . . ?
C1 C2 Si15 C17 -60.95(16) . . . . ?
C1 C2 Si15 C18 179.51(14) . . . . ?
C1 C8 C9 C10 163.41(17) . . . . ?
C1 C8 C9 C14 -16.8(3) . . . . ?
Fe1 C1 C2 C3 62.76(10) . . . . ?
Fe1 C1 C2 Si15 -129.38(12) . . . . ?
Fe1 C1 C8 C7 -61.68(10) . . . . ?
Fe1 C1 C8 C9 127.26(16) . . . . ?
Fe1 C2 C3 C4 -126.1(2) . . . . ?
Fe1 C2 C3 C7 59.34(11) . . . . ?
Fe1 C2 Si15 C16 -43.64(12) . . . . ?
Fe1 C2 Si15 C17 -163.00(13) . . . . ?
Fe1 C2 Si15 C18 77.46(13) . . . . ?
Fe1 C3 C4 C5 62.04(18) . . . . ?
Fe1 C3 C7 C6 -122.14(12) . . . . ?
Fe1 C3 C7 C8 63.41(10) . . . . ?
Fe1 C7 C8 C1 69.95(10) . . . . ?
Fe1 C7 C8 C9 -119.37(16) . . . . ?
Fe1 C8 C9 C10 -93.44(19) . . . . ?
Fe1 C8 C9 C14 86.4(2) . . . . ?
O1 C1 C2 Fe1 128.86(16) . . . . ?
O1 C1 C2 C3 -168.38(16) . . . . ?
O1 C1 C2 Si15 -0.5(2) . . . . ?
O1 C1 C8 Fe1 -128.69(16) . . . . ?
O1 C1 C8 C7 169.63(15) . . . . ?
O1 C1 C8 C9 -1.4(3) . . . . ?
C2 C1 C8 Fe1 46.93(10) . . . . ?
C2 C1 C8 C7 -14.75(16) . . . . ?
C2 C1 C8 C9 174.19(14) . . . . ?
C2 C3 C4 C5 168.44(19) . . . . ?
C2 C3 C7 Fe1 -61.44(11) . . . . ?
C2 C3 C7 C6 176.42(13) . . . . ?
C2 C3 C7 C8 1.97(18) . . . . ?
C3 C2 Si15 C16 -137.16(16) . . . . ?
C3 C2 Si15 C17 103.48(18) . . . . ?
C3 C2 Si15 C18 -16.06(19) . . . . ?
C3 C4 C5 C6 27.15(18) . . . . ?
C3 C7 C8 C1 8.14(17) . . . . ?
C3 C7 C8 Fe1 -61.81(10) . . . . ?
C3 C7 C8 C9 178.83(15) . . . . ?
C4 C3 C7 Fe1 122.38(13) . . . . ?
C4 C3 C7 C6 0.24(19) . . . . ?
C4 C3 C7 C8 -174.21(13) . . . . ?
C4 C5 C6 O6 86.75(16) . . . . ?
C4 C5 C6 C7 -26.91(18) . . . . ?
C5 C6 C7 Fe1 -63.61(17) . . . . ?
C5 C6 C7 C3 16.65(17) . . . . ?
C5 C6 C7 C8 -171.58(19) . . . . ?
C6 C7 C8 C1 -163.71(19) . . . . ?
C6 C7 C8 Fe1 126.3(2) . . . . ?
C6 C7 C8 C9 7.0(3) . . . . ?
O6 C6 C7 Fe1 178.03(12) . . . . ?
O6 C6 C7 C3 -101.71(16) . . . . ?
O6 C6 C7 C8 70.1(3) . . . . ?
C7 C3 C4 C5 -17.00(19) . . . . ?
C7 C8 C9 C10 -5.7(3) . . . . ?
C7 C8 C9 C14 174.18(18) . . . . ?
C8 C1 C2 Fe1 -46.90(10) . . . . ?
C8 C1 C2 C3 15.86(16) . . . . ?
C8 C1 C2 Si15 -176.28(11) . . . . ?
C8 C9 C10 C11 179.80(19) . . . . ?
C8 C9 C14 C13 -180.0(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 0.1(4) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
Si15 C2 C3 Fe1 123.18(14) . . . . ?
Si15 C2 C3 C4 -2.9(3) . . . . ?
Si15 C2 C3 C7 -177.48(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.119
_oxdiff_exptl_absorpt_empirical_full_min 0.926
####################################################################### 
# 
# 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_adg11
_database_code_depnum_ccdc_archive 'CCDC 1567220'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H34 Fe O8'
_chemical_formula_sum            'C40 H34 Fe O8'
_chemical_formula_weight         698.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.64408(12)
_cell_length_b                   8.04710(9)
_cell_length_c                   21.6608(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.7335(11)
_cell_angle_gamma                90
_cell_volume                     1679.12(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14346
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.8010
_cell_measurement_theta_min      4.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34729
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.268
_diffrn_reflns_theta_min         4.086
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00  -9.00   1.00    5.00    --  -41.46 -77.00-180.00  109
  2  ω    -70.00  32.00   1.00    5.00    --  -41.46  57.00 -60.00  102
  3  ω    -70.00  32.00   1.00    5.00    --  -41.46  57.00-180.00  102
  4  ω     17.00 116.00   1.00    5.00    --   41.46  38.00  60.00   99
  5  ω     -4.00  82.00   1.00    5.00    --   41.46 -99.00  30.00   86
  6  ω     81.00 178.00   1.00   25.00    --  114.00  77.00 -60.00   97
  7  ω     57.00 151.00   1.00   25.00    --  114.00 178.00-150.00   94
  8  ω     32.00 167.00   1.00   25.00    --  114.00 -15.00 120.00  135
  9  ω     86.00 178.00   1.00   25.00    --  114.00  30.00  30.00   92
 10  ω     42.00 143.00   1.00   25.00    --  114.00 -61.00-150.00  101
 11  ω     38.00 116.00   1.00   25.00    --  114.00-111.00-120.00   78
 12  ω     38.00 116.00   1.00   25.00    --  114.00-111.00   0.00   78
 13  ω    100.00 178.00   1.00   25.00    --  114.00 111.00 120.00   78
 14  ω     32.00 109.00   1.00   25.00    --  114.00 -95.00 150.00   77
 15  ω     38.00 116.00   1.00   25.00    --  114.00-111.00 120.00   78
 16  ω     57.00 151.00   1.00   25.00    --  114.00 178.00 150.00   94
 17  ω   -118.00 -14.00   1.00    5.00    --  -41.46 -77.00  60.00  104
 18  ω   -114.00 -13.00   1.00    5.00    --  -41.46 -57.00 -90.00  101
 19  ω      9.00 118.00   1.00    5.00    --   41.46  77.00 150.00  109
 20  ω     17.00 116.00   1.00    5.00    --   41.46  38.00 -90.00   99
 21  ω      9.00 118.00   1.00    5.00    --   41.46  77.00 -60.00  109
 22  ω     85.00 178.00   1.00   25.00    --  114.00  61.00 120.00   93
 23  ω     81.00 178.00   1.00   25.00    --  114.00  77.00  30.00   97
 24  ω     61.00 178.00   1.00   25.00    --  114.00  15.00-120.00  117
 25  ω     81.00 178.00   1.00   25.00    --  114.00  77.00-150.00   97
 26  ω     81.00 178.00   1.00   25.00    --  114.00  77.00 150.00   97
 27  ω     81.00 178.00   1.00   25.00    --  114.00  77.00  60.00   97
 28  ω     81.00 178.00   1.00   25.00    --  114.00  77.00 -30.00   97
 29  ω     85.00 178.00   1.00   25.00    --  114.00  61.00  90.00   93
 30  ω     81.00 178.00   1.00   25.00    --  114.00  77.00-120.00   97
 31  ω     85.00 178.00   1.00   25.00    --  114.00  61.00 -90.00   93
 32  ω     18.00  97.00   1.00    5.00    --   41.46-125.00 -90.00   79
 33  ω      9.00 118.00   1.00    5.00    --   41.46  77.00  30.00  109
 34  ω     13.00 114.00   1.00    5.00    --   41.46  57.00 120.00  101
 35  ω      9.00 118.00   1.00    5.00    --   41.46  77.00-150.00  109
 36  ω     -4.00  82.00   1.00    5.00    --   41.46 -99.00  60.00   86
 37  ω     81.00 124.00   1.00   25.00    --  114.00  77.00-180.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650685000
_diffrn_orient_matrix_UB_12      -0.1318253000
_diffrn_orient_matrix_UB_13      0.0413493000
_diffrn_orient_matrix_UB_21      -0.0163510000
_diffrn_orient_matrix_UB_22      -0.1185124000
_diffrn_orient_matrix_UB_23      -0.0557315000
_diffrn_orient_matrix_UB_31      0.1451621000
_diffrn_orient_matrix_UB_32      -0.0722443000
_diffrn_orient_matrix_UB_33      0.0159878000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6587
_reflns_number_total             7091
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 2745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Hooft y: -0.0086(19)  Olex2
Flack x: -0.010(2)    Shelx 2014
;
_refine_ls_abs_structure_Flack   -0.010(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         7091
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C26(H26A,H26B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20), C21(H21),
 C22(H22), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C35(H35), C36(H36),
  C37(H37), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.30663(5) 0.54443(6) 0.19644(2) 0.02998(13) Uani 1 1 d . . . . .
C1 C 0.3616(4) 0.3098(4) 0.26238(15) 0.0301(6) Uani 1 1 d . . . . .
O1 O 0.3215(3) 0.1658(3) 0.26651(12) 0.0382(6) Uani 1 1 d . . . . .
C2 C 0.4666(3) 0.3760(4) 0.22160(14) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.5000(3) 0.5421(4) 0.24091(12) 0.0276(5) Uani 1 1 d . . . . .
O4 O 0.6548(2) 0.6215(3) 0.16426(10) 0.0320(5) Uani 1 1 d . . . . .
C4 C 0.6228(4) 0.6465(4) 0.22671(14) 0.0292(6) Uani 1 1 d . . . . .
H4 H 0.7039 0.6091 0.2537 0.035 Uiso 1 1 calc R . . . .
C5 C 0.5939(4) 0.8294(4) 0.24101(16) 0.0349(7) Uani 1 1 d . . . . .
H5A H 0.6787 0.8961 0.2358 0.042 Uiso 1 1 calc R . . . .
H5B H 0.5200 0.8722 0.2119 0.042 Uiso 1 1 calc R . . . .
C6 C 0.5483(4) 0.8453(4) 0.30732(16) 0.0365(7) Uani 1 1 d . . . . .
H6A H 0.6198 0.7947 0.3357 0.044 Uiso 1 1 calc R . . . .
H6B H 0.5412 0.9645 0.3180 0.044 Uiso 1 1 calc R . . . .
O7 O 0.3913(3) 0.7270(3) 0.38028(10) 0.0308(5) Uani 1 1 d . . . . .
C7 C 0.4089(4) 0.7612(4) 0.31665(14) 0.0301(6) Uani 1 1 d . . . . .
H7 H 0.3321 0.8352 0.3006 0.036 Uiso 1 1 calc R . . . .
C8 C 0.3995(3) 0.5955(4) 0.28336(13) 0.0262(6) Uani 1 1 d . . . . .
C9 C 0.3041(3) 0.4628(4) 0.29191(14) 0.0276(6) Uani 1 1 d . . . . .
C10 C 0.1948(4) 0.4515(4) 0.33764(15) 0.0308(6) Uani 1 1 d . . . . .
C11 C 0.1932(4) 0.3099(4) 0.37580(16) 0.0373(7) Uani 1 1 d . . . . .
H11 H 0.2597 0.2244 0.3707 0.045 Uiso 1 1 calc R . . . .
C12 C 0.0961(5) 0.2929(5) 0.42092(18) 0.0444(9) Uani 1 1 d . . . . .
H12 H 0.0973 0.1967 0.4464 0.053 Uiso 1 1 calc R . . . .
C13 C -0.0011(4) 0.4143(6) 0.42870(19) 0.0469(9) Uani 1 1 d . . . . .
H13 H -0.0671 0.4024 0.4596 0.056 Uiso 1 1 calc R . . . .
C14 C -0.0031(4) 0.5549(6) 0.39136(17) 0.0433(8) Uani 1 1 d . . . . .
H14 H -0.0712 0.6384 0.3964 0.052 Uiso 1 1 calc R . . . .
C15 C 0.0946(4) 0.5736(4) 0.34652(16) 0.0354(7) Uani 1 1 d . . . . .
O16 O 0.0990(3) 0.7095(4) 0.30884(13) 0.0450(6) Uani 1 1 d . . . . .
C17 C 0.0051(6) 0.8419(7) 0.3177(3) 0.0663(14) Uani 1 1 d . . . . .
H17A H 0.0278 0.9352 0.2910 0.099 Uiso 1 1 calc GR . . . .
H17B H 0.0124 0.8776 0.3610 0.099 Uiso 1 1 calc GR . . . .
H17C H -0.0898 0.8044 0.3074 0.099 Uiso 1 1 calc GR . . . .
C18 C 0.5464(4) 0.2690(4) 0.18006(14) 0.0297(6) Uani 1 1 d . . . . .
C19 C 0.4845(4) 0.1957(4) 0.12690(15) 0.0346(7) Uani 1 1 d . . . . .
H19 H 0.3884 0.2130 0.1173 0.041 Uiso 1 1 calc R . . . .
C20 C 0.5609(4) 0.0984(5) 0.08805(17) 0.0415(8) Uani 1 1 d . . . . .
H20 H 0.5172 0.0493 0.0523 0.050 Uiso 1 1 calc R . . . .
C21 C 0.7004(4) 0.0732(4) 0.10145(17) 0.0398(8) Uani 1 1 d . . . . .
H21 H 0.7532 0.0087 0.0743 0.048 Uiso 1 1 calc R . . . .
C22 C 0.7641(4) 0.1416(4) 0.15434(16) 0.0349(7) Uani 1 1 d . . . . .
H22 H 0.8603 0.1238 0.1634 0.042 Uiso 1 1 calc R . . . .
C23 C 0.6870(4) 0.2362(4) 0.19392(15) 0.0307(6) Uani 1 1 d . . . . .
O24 O 0.7395(3) 0.3035(3) 0.24805(11) 0.0356(5) Uani 1 1 d . . . . .
C25 C 0.8736(5) 0.2535(6) 0.2705(2) 0.0503(10) Uani 1 1 d . . . . .
H25A H 0.8925 0.2997 0.3119 0.075 Uiso 1 1 calc GR . . . .
H25B H 0.9431 0.2943 0.2426 0.075 Uiso 1 1 calc GR . . . .
H25C H 0.8778 0.1319 0.2725 0.075 Uiso 1 1 calc GR . . . .
C26 C 0.7978(4) 0.6479(5) 0.15307(16) 0.0364(7) Uani 1 1 d . . . . .
H26A H 0.8562 0.5708 0.1787 0.044 Uiso 1 1 calc R . . . .
H26B H 0.8245 0.7631 0.1643 0.044 Uiso 1 1 calc R . . . .
C27 C 0.8204(4) 0.6181(4) 0.08553(15) 0.0324(7) Uani 1 1 d . . . . .
C28 C 0.9200(4) 0.7086(5) 0.05620(17) 0.0383(7) Uani 1 1 d . . . . .
H28 H 0.9741 0.7881 0.0790 0.046 Uiso 1 1 calc R . . . .
C29 C 0.9422(4) 0.6851(5) -0.00587(17) 0.0431(8) Uani 1 1 d . . . . .
H29 H 1.0104 0.7487 -0.0255 0.052 Uiso 1 1 calc R . . . .
C30 C 0.8642(4) 0.5680(5) -0.03916(15) 0.0408(8) Uani 1 1 d . . . . .
H30 H 0.8789 0.5511 -0.0818 0.049 Uiso 1 1 calc R . . . .
C31 C 0.7653(4) 0.4763(5) -0.01041(18) 0.0419(8) Uani 1 1 d . . . . .
H31 H 0.7118 0.3962 -0.0333 0.050 Uiso 1 1 calc R . . . .
C32 C 0.7434(4) 0.5004(4) 0.05199(17) 0.0377(8) Uani 1 1 d . . . . .
H32 H 0.6756 0.4362 0.0717 0.045 Uiso 1 1 calc R . . . .
C33 C 0.3525(4) 0.8688(4) 0.41419(17) 0.0393(8) Uani 1 1 d . . . . .
H33A H 0.2607 0.9096 0.3984 0.047 Uiso 1 1 calc R . . . .
H33B H 0.4212 0.9588 0.4096 0.047 Uiso 1 1 calc R . . . .
C34 C 0.3463(4) 0.8208(4) 0.48103(15) 0.0337(7) Uani 1 1 d . . . . .
C35 C 0.3932(4) 0.9314(6) 0.52686(19) 0.0456(9) Uani 1 1 d . . . . .
H35 H 0.4279 1.0371 0.5156 0.055 Uiso 1 1 calc R . . . .
C36 C 0.3898(5) 0.8891(7) 0.5882(2) 0.0572(12) Uani 1 1 d . . . . .
H36 H 0.4202 0.9664 0.6191 0.069 Uiso 1 1 calc R . . . .
C37 C 0.3426(5) 0.7352(7) 0.60510(18) 0.0574(13) Uani 1 1 d . . . . .
H37 H 0.3431 0.7048 0.6475 0.069 Uiso 1 1 calc R . . . .
C38 C 0.2942(5) 0.6246(6) 0.55997(18) 0.0490(10) Uani 1 1 d . . . . .
H38 H 0.2598 0.5191 0.5716 0.059 Uiso 1 1 calc R . . . .
C39 C 0.2956(4) 0.6668(5) 0.49805(16) 0.0368(7) Uani 1 1 d . . . . .
H39 H 0.2621 0.5907 0.4673 0.044 Uiso 1 1 calc R . . . .
C40 C 0.2089(4) 0.7362(5) 0.19307(16) 0.0419(8) Uani 1 1 d . . . . .
O40 O 0.1498(4) 0.8578(4) 0.18748(14) 0.0553(8) Uani 1 1 d . . . . .
C41 C 0.1682(4) 0.4095(5) 0.16830(17) 0.0417(8) Uani 1 1 d . . . . .
O41 O 0.0814(3) 0.3242(5) 0.15085(15) 0.0592(9) Uani 1 1 d . . . . .
O42 O 0.4041(3) 0.6064(4) 0.07228(12) 0.0554(8) Uani 1 1 d . . . . .
C42 C 0.3713(4) 0.5857(5) 0.12079(16) 0.0409(8) 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
Fe1 C1 2.411(3) . ?
Fe1 C2 2.106(3) . ?
Fe1 C3 2.058(3) . ?
Fe1 C8 2.087(3) . ?
Fe1 C9 2.171(3) . ?
Fe1 C40 1.808(4) . ?
Fe1 C41 1.804(4) . ?
Fe1 C42 1.811(4) . ?
C1 O1 1.226(4) . ?
C1 C2 1.475(4) . ?
C1 C9 1.505(4) . ?
C2 C3 1.433(5) . ?
C2 C18 1.486(4) . ?
C3 C4 1.496(4) . ?
C3 C8 1.434(4) . ?
O4 C4 1.416(4) . ?
O4 C26 1.427(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.532(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.527(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(5) . ?
O7 C7 1.424(4) . ?
O7 C33 1.417(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.516(4) . ?
C8 C9 1.428(4) . ?
C9 C10 1.483(4) . ?
C10 C11 1.408(5) . ?
C10 C15 1.398(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(5) . ?
C15 O16 1.366(5) . ?
O16 C17 1.417(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.402(5) . ?
C18 C23 1.400(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(5) . ?
C23 O24 1.367(4) . ?
O24 C25 1.418(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.508(5) . ?
C27 C28 1.384(5) . ?
C27 C32 1.387(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.386(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.391(5) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.502(5) . ?
C34 C35 1.393(5) . ?
C34 C39 1.388(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.374(7) . ?
C36 H36 0.9500 . ?
C36 C37 1.375(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.386(7) . ?
C38 H38 0.9500 . ?
C38 C39 1.385(5) . ?
C39 H39 0.9500 . ?
C40 O40 1.136(5) . ?
C41 O41 1.134(5) . ?
O42 C42 1.124(5) . ?

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 Fe1 C1 37.34(11) . . ?
C2 Fe1 C9 66.42(12) . . ?
C3 Fe1 C1 63.06(12) . . ?
C3 Fe1 C2 40.24(13) . . ?
C3 Fe1 C8 40.46(12) . . ?
C3 Fe1 C9 66.58(12) . . ?
C8 Fe1 C1 63.07(11) . . ?
C8 Fe1 C2 67.41(12) . . ?
C8 Fe1 C9 39.11(12) . . ?
C9 Fe1 C1 37.89(11) . . ?
C40 Fe1 C1 142.35(14) . . ?
C40 Fe1 C2 159.05(15) . . ?
C40 Fe1 C3 119.04(16) . . ?
C40 Fe1 C8 93.93(14) . . ?
C40 Fe1 C9 105.51(14) . . ?
C40 Fe1 C42 90.47(17) . . ?
C41 Fe1 C1 82.36(16) . . ?
C41 Fe1 C2 102.77(16) . . ?
C41 Fe1 C3 142.38(17) . . ?
C41 Fe1 C8 134.60(15) . . ?
C41 Fe1 C9 95.62(15) . . ?
C41 Fe1 C40 97.15(19) . . ?
C41 Fe1 C42 94.92(18) . . ?
C42 Fe1 C1 127.16(14) . . ?
C42 Fe1 C2 94.17(15) . . ?
C42 Fe1 C3 94.69(15) . . ?
C42 Fe1 C8 128.95(16) . . ?
C42 Fe1 C9 159.56(15) . . ?
O1 C1 Fe1 136.2(3) . . ?
O1 C1 C2 127.8(3) . . ?
O1 C1 C9 128.2(3) . . ?
C2 C1 Fe1 60.02(16) . . ?
C2 C1 C9 103.7(3) . . ?
C9 C1 Fe1 62.38(16) . . ?
C1 C2 Fe1 82.64(19) . . ?
C1 C2 C18 123.0(3) . . ?
C3 C2 Fe1 68.07(17) . . ?
C3 C2 C1 108.3(3) . . ?
C3 C2 C18 127.0(3) . . ?
C18 C2 Fe1 127.6(2) . . ?
C2 C3 Fe1 71.68(18) . . ?
C2 C3 C4 129.3(3) . . ?
C2 C3 C8 108.5(3) . . ?
C4 C3 Fe1 127.4(2) . . ?
C8 C3 Fe1 70.85(17) . . ?
C8 C3 C4 122.0(3) . . ?
C4 O4 C26 113.4(3) . . ?
C3 C4 H4 108.4 . . ?
C3 C4 C5 110.1(3) . . ?
O4 C4 C3 109.1(3) . . ?
O4 C4 H4 108.4 . . ?
O4 C4 C5 112.3(3) . . ?
C5 C4 H4 108.4 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 C4 109.5(3) . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.5(3) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C33 O7 C7 113.1(2) . . ?
C6 C7 H7 109.4 . . ?
O7 C7 C6 111.1(3) . . ?
O7 C7 H7 109.4 . . ?
O7 C7 C8 106.4(2) . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 H7 109.4 . . ?
C3 C8 Fe1 68.68(16) . . ?
C3 C8 C7 122.8(3) . . ?
C7 C8 Fe1 128.0(2) . . ?
C9 C8 Fe1 73.64(18) . . ?
C9 C8 C3 108.6(3) . . ?
C9 C8 C7 128.4(3) . . ?
C1 C9 Fe1 79.72(17) . . ?
C8 C9 Fe1 67.25(17) . . ?
C8 C9 C1 107.7(3) . . ?
C8 C9 C10 128.0(3) . . ?
C10 C9 Fe1 134.0(2) . . ?
C10 C9 C1 121.4(3) . . ?
C11 C10 C9 118.0(3) . . ?
C15 C10 C9 124.5(3) . . ?
C15 C10 C11 117.5(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 121.0(3) . . ?
O16 C15 C10 116.0(3) . . ?
O16 C15 C14 123.0(3) . . ?
C15 O16 C17 118.8(3) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C2 121.9(3) . . ?
C23 C18 C2 120.2(3) . . ?
C23 C18 C19 117.8(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.9(3) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C18 120.8(3) . . ?
O24 C23 C18 115.2(3) . . ?
O24 C23 C22 124.0(3) . . ?
C23 O24 C25 118.5(3) . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 H26A 109.9 . . ?
O4 C26 H26B 109.9 . . ?
O4 C26 C27 109.1(3) . . ?
H26A C26 H26B 108.3 . . ?
C27 C26 H26A 109.9 . . ?
C27 C26 H26B 109.9 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 C32 119.0(3) . . ?
C32 C27 C26 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.1(4) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 120.2 . . ?
C28 C29 C30 119.5(4) . . ?
C30 C29 H29 120.2 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.3(4) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 120.1(3) . . ?
C27 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
O7 C33 H33A 110.0 . . ?
O7 C33 H33B 110.0 . . ?
O7 C33 C34 108.4(3) . . ?
H33A C33 H33B 108.4 . . ?
C34 C33 H33A 110.0 . . ?
C34 C33 H33B 110.0 . . ?
C35 C34 C33 119.7(3) . . ?
C39 C34 C33 121.1(3) . . ?
C39 C34 C35 119.2(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.6(4) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.3(4) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 120.2 . . ?
C36 C37 C38 119.7(4) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 H38 119.8 . . ?
C39 C38 C37 120.4(4) . . ?
C39 C38 H38 119.8 . . ?
C34 C39 H39 120.1 . . ?
C38 C39 C34 119.8(4) . . ?
C38 C39 H39 120.1 . . ?
O40 C40 Fe1 176.0(4) . . ?
O41 C41 Fe1 179.6(4) . . ?
O42 C42 Fe1 175.6(4) . . ?

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
Fe1 C1 C2 C3 64.0(2) . . . . ?
Fe1 C1 C2 C18 -130.5(3) . . . . ?
Fe1 C1 C9 C8 -61.9(2) . . . . ?
Fe1 C1 C9 C10 135.8(3) . . . . ?
Fe1 C2 C3 C4 -123.8(3) . . . . ?
Fe1 C2 C3 C8 61.6(2) . . . . ?
Fe1 C2 C18 C19 -36.3(4) . . . . ?
Fe1 C2 C18 C23 144.9(3) . . . . ?
Fe1 C3 C4 O4 -56.8(4) . . . . ?
Fe1 C3 C4 C5 66.9(3) . . . . ?
Fe1 C3 C8 C7 -122.3(3) . . . . ?
Fe1 C3 C8 C9 63.3(2) . . . . ?
Fe1 C8 C9 C1 70.3(2) . . . . ?
Fe1 C8 C9 C10 -129.0(3) . . . . ?
Fe1 C9 C10 C11 139.0(3) . . . . ?
Fe1 C9 C10 C15 -42.5(5) . . . . ?
C1 C2 C3 Fe1 -73.8(2) . . . . ?
C1 C2 C3 C4 162.4(3) . . . . ?
C1 C2 C3 C8 -12.2(3) . . . . ?
C1 C2 C18 C19 71.6(4) . . . . ?
C1 C2 C18 C23 -107.3(4) . . . . ?
C1 C9 C10 C11 31.5(5) . . . . ?
C1 C9 C10 C15 -150.0(3) . . . . ?
O1 C1 C2 Fe1 127.4(4) . . . . ?
O1 C1 C2 C3 -168.6(4) . . . . ?
O1 C1 C2 C18 -3.1(6) . . . . ?
O1 C1 C9 Fe1 -128.7(4) . . . . ?
O1 C1 C9 C8 169.3(3) . . . . ?
O1 C1 C9 C10 7.1(5) . . . . ?
C2 C1 C9 Fe1 44.9(2) . . . . ?
C2 C1 C9 C8 -17.0(3) . . . . ?
C2 C1 C9 C10 -179.2(3) . . . . ?
C2 C3 C4 O4 39.8(4) . . . . ?
C2 C3 C4 C5 163.4(3) . . . . ?
C2 C3 C8 Fe1 -62.2(2) . . . . ?
C2 C3 C8 C7 175.5(3) . . . . ?
C2 C3 C8 C9 1.1(3) . . . . ?
C2 C18 C19 C20 178.9(3) . . . . ?
C2 C18 C23 C22 -177.6(3) . . . . ?
C2 C18 C23 O24 2.4(4) . . . . ?
C3 C2 C18 C19 -125.7(4) . . . . ?
C3 C2 C18 C23 55.5(4) . . . . ?
C3 C4 C5 C6 53.4(4) . . . . ?
C3 C8 C9 Fe1 -60.1(2) . . . . ?
C3 C8 C9 C1 10.2(3) . . . . ?
C3 C8 C9 C10 170.9(3) . . . . ?
O4 C4 C5 C6 175.2(3) . . . . ?
O4 C26 C27 C28 147.5(3) . . . . ?
O4 C26 C27 C32 -32.9(4) . . . . ?
C4 C3 C8 Fe1 122.8(3) . . . . ?
C4 C3 C8 C7 0.4(4) . . . . ?
C4 C3 C8 C9 -174.0(3) . . . . ?
C4 O4 C26 C27 180.0(3) . . . . ?
C4 C5 C6 C7 -65.9(4) . . . . ?
C5 C6 C7 O7 159.9(3) . . . . ?
C5 C6 C7 C8 41.6(4) . . . . ?
C6 C7 C8 Fe1 -96.9(3) . . . . ?
C6 C7 C8 C3 -9.5(4) . . . . ?
C6 C7 C8 C9 163.7(3) . . . . ?
O7 C7 C8 Fe1 142.0(2) . . . . ?
O7 C7 C8 C3 -130.6(3) . . . . ?
O7 C7 C8 C9 42.6(4) . . . . ?
O7 C33 C34 C35 141.2(3) . . . . ?
O7 C33 C34 C39 -38.1(5) . . . . ?
C7 O7 C33 C34 -176.3(3) . . . . ?
C7 C8 C9 Fe1 125.9(3) . . . . ?
C7 C8 C9 C1 -163.8(3) . . . . ?
C7 C8 C9 C10 -3.1(5) . . . . ?
C8 C3 C4 O4 -146.3(3) . . . . ?
C8 C3 C4 C5 -22.6(4) . . . . ?
C8 C9 C10 C11 -126.9(4) . . . . ?
C8 C9 C10 C15 51.6(5) . . . . ?
C9 C1 C2 Fe1 -46.3(2) . . . . ?
C9 C1 C2 C3 17.7(3) . . . . ?
C9 C1 C2 C18 -176.8(3) . . . . ?
C9 C10 C11 C12 178.2(3) . . . . ?
C9 C10 C15 C14 -178.7(3) . . . . ?
C9 C10 C15 O16 1.4(5) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C10 C15 O16 C17 -176.6(4) . . . . ?
C11 C10 C15 C14 -0.2(5) . . . . ?
C11 C10 C15 O16 179.9(3) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C13 C14 C15 C10 0.8(6) . . . . ?
C13 C14 C15 O16 -179.3(4) . . . . ?
C14 C15 O16 C17 3.5(6) . . . . ?
C15 C10 C11 C12 -0.4(5) . . . . ?
C18 C2 C3 Fe1 121.3(3) . . . . ?
C18 C2 C3 C4 -2.4(5) . . . . ?
C18 C2 C3 C8 -177.0(3) . . . . ?
C18 C19 C20 C21 -0.3(6) . . . . ?
C18 C23 O24 C25 169.6(3) . . . . ?
C19 C18 C23 C22 3.5(5) . . . . ?
C19 C18 C23 O24 -176.5(3) . . . . ?
C19 C20 C21 C22 1.5(6) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C21 C22 C23 C18 -2.4(5) . . . . ?
C21 C22 C23 O24 177.6(3) . . . . ?
C22 C23 O24 C25 -10.5(5) . . . . ?
C23 C18 C19 C20 -2.2(5) . . . . ?
C26 O4 C4 C3 -152.5(3) . . . . ?
C26 O4 C4 C5 85.1(4) . . . . ?
C26 C27 C28 C29 -179.4(4) . . . . ?
C26 C27 C32 C31 179.4(3) . . . . ?
C27 C28 C29 C30 -0.5(6) . . . . ?
C28 C27 C32 C31 -0.9(5) . . . . ?
C28 C29 C30 C31 0.1(6) . . . . ?
C29 C30 C31 C32 -0.1(6) . . . . ?
C30 C31 C32 C27 0.5(6) . . . . ?
C32 C27 C28 C29 1.0(6) . . . . ?
C33 O7 C7 C6 78.3(4) . . . . ?
C33 O7 C7 C8 -160.6(3) . . . . ?
C33 C34 C35 C36 -179.3(4) . . . . ?
C33 C34 C39 C38 178.5(4) . . . . ?
C34 C35 C36 C37 1.4(7) . . . . ?
C35 C34 C39 C38 -0.9(6) . . . . ?
C35 C36 C37 C38 -2.0(7) . . . . ?
C36 C37 C38 C39 1.3(7) . . . . ?
C37 C38 C39 C34 0.2(6) . . . . ?
C39 C34 C35 C36 0.1(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.611
_oxdiff_exptl_absorpt_empirical_full_min 0.740
####################################################################### 
# 
# 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_adg12
_database_code_depnum_ccdc_archive 'CCDC 1567221'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 Fe O8'
_chemical_formula_sum            'C26 H22 Fe O8'
_chemical_formula_weight         518.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Fe'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   8.60374(7)
_cell_length_b                   14.16447(11)
_cell_length_c                   19.76246(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2408.40(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16485
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9410
_cell_measurement_theta_min      3.8270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.204
_diffrn_reflns_theta_min         3.840
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00  -9.00   1.00    5.50    --  -41.46 -77.00   0.00  109
  2  ω    -33.00  66.00   1.00    5.50    --   41.46 -38.00-180.00   99
  3  ω     32.00 109.00   1.00   22.00    --  114.00 -95.00 150.00   77
  4  ω     88.00 178.00   1.00   22.00    --  114.00  45.00 -90.00   90
  5  ω     38.00 116.00   1.00   22.00    --  114.00-111.00 -30.00   78
  6  ω     88.00 178.00   1.00   22.00    --  114.00  45.00   0.00   90
  7  ω     38.00 142.00   1.00   22.00    --  114.00 -30.00 -30.00  104
  8  ω   -114.00 -13.00   1.00    5.50    --  -41.46 -57.00-180.00  101
  9  ω     18.00  97.00   1.00    5.50    --   41.46-125.00  60.00   79
 10  ω     61.00 178.00   1.00   22.00    --  114.00  15.00 150.00  117
 11  ω     86.00 178.00   1.00   22.00    --  114.00  30.00-150.00   92
 12  ω     81.00 178.00   1.00   22.00    --  114.00  77.00 -60.00   97
 13  ω     81.00 178.00   1.00   22.00    --  114.00  77.00  30.00   97
 14  ω   -114.00 -13.00   1.00    5.50    --  -41.46 -57.00  90.00  101
 15  ω   -116.00 -17.00   1.00    5.50    --  -41.46 -38.00-120.00   99
 16  ω     32.00 109.00   1.00   22.00    --  114.00 -95.00  30.00   77
 17  ω     88.00 178.00   1.00   22.00    --  114.00  45.00 150.00   90
 18  ω     38.00 147.00   1.00   22.00    --  114.00 -77.00-150.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1421843000
_diffrn_orient_matrix_UB_12      -0.0434544000
_diffrn_orient_matrix_UB_13      0.0356396000
_diffrn_orient_matrix_UB_21      0.0748996000
_diffrn_orient_matrix_UB_22      -0.0985734000
_diffrn_orient_matrix_UB_23      -0.0051311000
_diffrn_orient_matrix_UB_31      0.0790574000
_diffrn_orient_matrix_UB_32      0.0150712000
_diffrn_orient_matrix_UB_33      0.0691087000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                5009
_reflns_number_total             5094
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Hooft y: -0.0063(13) Shelx 2014
Flack x: -0.008(2)   Olex2

;
_refine_ls_abs_structure_Flack   -0.0076(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0719
_refine_special_details          ?
_olex2_refinement_description    
;

The OHs were located in a difference map and allowed to refine with 
thermal parameters Uiso 1.5 x times Uequiv of the parent oxygen. 
O7-H7 was refined with a DFIX distance restraint

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O7-H7
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4A), C7(H7A)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C22(H22)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.57850(4) 0.57704(2) 0.60686(2) 0.02019(9) Uani 1 1 d . . . . .
O1 O 0.5606(2) 0.34899(11) 0.66151(8) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.5097(3) 0.42984(16) 0.65914(10) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.5527(3) 0.51162(15) 0.70229(11) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.4386(2) 0.58352(14) 0.69243(10) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.4010(3) 0.66824(16) 0.73684(12) 0.0276(5) Uani 1 1 d . . . . .
H4A H 0.4034 0.6484 0.7854 0.033 Uiso 1 1 calc R . . . .
O4 O 0.5158(2) 0.73891(13) 0.72612(11) 0.0363(4) Uani 1 1 d . . . . .
H4 H 0.509(5) 0.776(3) 0.759(2) 0.054 Uiso 1 1 d R . . . .
C5 C 0.2382(3) 0.70504(18) 0.71967(15) 0.0354(6) Uani 1 1 d . . . . .
H5A H 0.1599 0.6627 0.7403 0.043 Uiso 1 1 calc R . . . .
H5B H 0.2249 0.7685 0.7399 0.043 Uiso 1 1 calc R . . . .
C6 C 0.2082(3) 0.71128(18) 0.64391(15) 0.0353(5) Uani 1 1 d . . . . .
H6A H 0.2898 0.7505 0.6225 0.042 Uiso 1 1 calc R . . . .
H6B H 0.1066 0.7421 0.6359 0.042 Uiso 1 1 calc R . . . .
C7 C 0.2080(3) 0.61347(17) 0.61195(14) 0.0296(5) Uani 1 1 d . . . . .
H7A H 0.2085 0.6192 0.5615 0.035 Uiso 1 1 calc R . . . .
O7 O 0.0715(2) 0.56457(14) 0.63347(12) 0.0430(5) Uani 1 1 d D . . . .
H7 H 0.097(5) 0.5079(19) 0.630(2) 0.065 Uiso 1 1 d DR . . . .
C8 C 0.3490(2) 0.55939(15) 0.63494(11) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.4047(2) 0.47183(14) 0.60803(11) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.3306(3) 0.41640(16) 0.55289(11) 0.0252(4) Uani 1 1 d . . . . .
C11 C 0.3793(3) 0.41799(18) 0.48611(12) 0.0299(5) Uani 1 1 d . . . . .
H11 H 0.4652 0.4564 0.4736 0.036 Uiso 1 1 calc R . . . .
C12 C 0.3042(4) 0.36407(19) 0.43711(13) 0.0368(6) Uani 1 1 d . . . . .
H12 H 0.3374 0.3668 0.3913 0.044 Uiso 1 1 calc R . . . .
C13 C 0.1819(4) 0.3069(2) 0.45515(16) 0.0420(6) Uani 1 1 d . . . . .
H13 H 0.1320 0.2693 0.4218 0.050 Uiso 1 1 calc R . . . .
C14 C 0.1307(4) 0.3036(2) 0.52166(17) 0.0461(7) Uani 1 1 d . . . . .
H14 H 0.0460 0.2641 0.5340 0.055 Uiso 1 1 calc R . . . .
C15 C 0.2048(3) 0.35857(19) 0.57007(15) 0.0376(6) Uani 1 1 d . . . . .
O16 O 0.1598(3) 0.36494(17) 0.63664(12) 0.0528(6) Uani 1 1 d . . . . .
C17 C 0.0593(6) 0.2935(3) 0.6628(2) 0.0769(14) Uani 1 1 d . . . . .
H17A H 0.0388 0.3058 0.7108 0.115 Uiso 1 1 calc GR . . . .
H17B H 0.1089 0.2316 0.6578 0.115 Uiso 1 1 calc GR . . . .
H17C H -0.0390 0.2941 0.6377 0.115 Uiso 1 1 calc GR . . . .
C18 C 0.6657(3) 0.50060(15) 0.75870(12) 0.0288(5) Uani 1 1 d . . . . .
C19 C 0.8241(3) 0.5074(2) 0.74806(15) 0.0399(6) Uani 1 1 d . . . . .
H19 H 0.8614 0.5268 0.7050 0.048 Uiso 1 1 calc R . . . .
C20 C 0.9302(4) 0.4866(2) 0.79920(19) 0.0548(8) Uani 1 1 d . . . . .
H20 H 1.0389 0.4908 0.7912 0.066 Uiso 1 1 calc R . . . .
C21 C 0.8746(5) 0.4598(2) 0.86139(19) 0.0588(10) Uani 1 1 d . . . . .
H21 H 0.9461 0.4451 0.8965 0.071 Uiso 1 1 calc R . . . .
C22 C 0.7181(5) 0.4537(2) 0.87398(15) 0.0512(9) Uani 1 1 d . . . . .
H22 H 0.6825 0.4358 0.9177 0.061 Uiso 1 1 calc R . . . .
C23 C 0.6106(4) 0.47361(17) 0.82267(13) 0.0363(6) Uani 1 1 d . . . . .
O24 O 0.4536(3) 0.46636(14) 0.82841(10) 0.0443(5) Uani 1 1 d . . . . .
C25 C 0.3942(5) 0.4261(2) 0.88941(17) 0.0627(10) Uani 1 1 d . . . . .
H25A H 0.4376 0.3627 0.8955 0.094 Uiso 1 1 calc GR . . . .
H25B H 0.2806 0.4221 0.8867 0.094 Uiso 1 1 calc GR . . . .
H25C H 0.4236 0.4659 0.9279 0.094 Uiso 1 1 calc GR . . . .
O26 O 0.4811(3) 0.69306(17) 0.49167(11) 0.0515(6) Uani 1 1 d . . . . .
C26 C 0.5204(3) 0.64699(17) 0.53555(13) 0.0308(5) Uani 1 1 d . . . . .
C27 C 0.7243(3) 0.50175(17) 0.56781(12) 0.0282(5) Uani 1 1 d . . . . .
O27 O 0.8121(2) 0.45287(15) 0.54389(11) 0.0432(5) Uani 1 1 d . . . . .
O28 O 0.8038(2) 0.72243(14) 0.64848(12) 0.0438(5) Uani 1 1 d . . . . .
C28 C 0.7139(3) 0.66801(17) 0.63470(13) 0.0297(5) 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
Fe1 C1 2.401(2) . ?
Fe1 C2 2.113(2) . ?
Fe1 C3 2.078(2) . ?
Fe1 C8 2.067(2) . ?
Fe1 C9 2.111(2) . ?
Fe1 C26 1.794(3) . ?
Fe1 C27 1.818(2) . ?
Fe1 C28 1.822(2) . ?
O1 C1 1.227(3) . ?
C1 C2 1.485(3) . ?
C1 C9 1.480(3) . ?
C2 C3 1.428(3) . ?
C2 C18 1.487(3) . ?
C3 C4 1.522(3) . ?
C3 C8 1.415(3) . ?
C4 H4A 1.0000 . ?
C4 O4 1.422(3) . ?
C4 C5 1.532(4) . ?
O4 H4 0.83(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.522(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.523(3) . ?
C7 H7A 1.0000 . ?
C7 O7 1.428(3) . ?
C7 C8 1.504(3) . ?
O7 H7 0.84(2) . ?
C8 C9 1.432(3) . ?
C9 C10 1.487(3) . ?
C10 C11 1.385(3) . ?
C10 C15 1.399(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(4) . ?
C15 O16 1.374(3) . ?
O16 C17 1.428(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.383(4) . ?
C18 C23 1.403(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.372(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.401(4) . ?
C23 O24 1.360(4) . ?
O24 C25 1.428(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O26 C26 1.137(3) . ?
C27 O27 1.128(3) . ?
O28 C28 1.126(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
C2 Fe1 C1 37.74(8) . . ?
C3 Fe1 C1 62.96(8) . . ?
C3 Fe1 C2 39.84(8) . . ?
C3 Fe1 C9 67.16(8) . . ?
C8 Fe1 C1 62.86(8) . . ?
C8 Fe1 C2 66.86(9) . . ?
C8 Fe1 C3 39.93(9) . . ?
C8 Fe1 C9 40.07(8) . . ?
C9 Fe1 C1 37.61(8) . . ?
C9 Fe1 C2 66.82(9) . . ?
C26 Fe1 C1 138.51(10) . . ?
C26 Fe1 C2 156.09(10) . . ?
C26 Fe1 C3 116.97(10) . . ?
C26 Fe1 C8 90.65(11) . . ?
C26 Fe1 C9 101.59(10) . . ?
C26 Fe1 C27 100.54(11) . . ?
C26 Fe1 C28 91.43(12) . . ?
C27 Fe1 C1 80.99(9) . . ?
C27 Fe1 C2 101.19(10) . . ?
C27 Fe1 C3 140.44(10) . . ?
C27 Fe1 C8 134.61(10) . . ?
C27 Fe1 C9 94.55(10) . . ?
C27 Fe1 C28 95.85(11) . . ?
C28 Fe1 C1 129.91(10) . . ?
C28 Fe1 C2 96.18(10) . . ?
C28 Fe1 C3 95.35(10) . . ?
C28 Fe1 C8 127.98(10) . . ?
C28 Fe1 C9 161.56(10) . . ?
O1 C1 Fe1 137.65(16) . . ?
O1 C1 C2 128.1(2) . . ?
O1 C1 C9 128.2(2) . . ?
C2 C1 Fe1 60.56(11) . . ?
C9 C1 Fe1 60.52(11) . . ?
C9 C1 C2 103.33(18) . . ?
C1 C2 Fe1 81.70(13) . . ?
C1 C2 C18 120.76(19) . . ?
C3 C2 Fe1 68.75(12) . . ?
C3 C2 C1 107.85(19) . . ?
C3 C2 C18 128.8(2) . . ?
C18 C2 Fe1 130.28(16) . . ?
C2 C3 Fe1 71.41(12) . . ?
C2 C3 C4 129.0(2) . . ?
C4 C3 Fe1 128.87(15) . . ?
C8 C3 Fe1 69.61(12) . . ?
C8 C3 C2 108.18(18) . . ?
C8 C3 C4 122.5(2) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 C5 109.56(19) . . ?
O4 C4 C3 108.74(18) . . ?
O4 C4 H4A 109.1 . . ?
O4 C4 C5 111.3(2) . . ?
C5 C4 H4A 109.1 . . ?
C4 O4 H4 106(3) . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 113.1(2) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 C7 110.8(2) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.8 . . ?
O7 C7 C6 108.6(2) . . ?
O7 C7 H7A 109.8 . . ?
O7 C7 C8 109.0(2) . . ?
C8 C7 C6 109.7(2) . . ?
C8 C7 H7A 109.8 . . ?
C7 O7 H7 103(3) . . ?
C3 C8 Fe1 70.46(12) . . ?
C3 C8 C7 124.0(2) . . ?
C3 C8 C9 108.96(19) . . ?
C7 C8 Fe1 128.86(16) . . ?
C9 C8 Fe1 71.65(12) . . ?
C9 C8 C7 126.8(2) . . ?
C1 C9 Fe1 81.86(12) . . ?
C1 C9 C10 123.35(19) . . ?
C8 C9 Fe1 68.28(11) . . ?
C8 C9 C1 107.39(19) . . ?
C8 C9 C10 125.9(2) . . ?
C10 C9 Fe1 131.94(16) . . ?
C11 C10 C9 124.1(2) . . ?
C11 C10 C15 118.4(2) . . ?
C15 C10 C9 117.6(2) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.1(3) . . ?
O16 C15 C10 114.3(2) . . ?
O16 C15 C14 124.5(3) . . ?
C15 O16 C17 118.1(2) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C2 121.5(2) . . ?
C19 C18 C23 119.3(3) . . ?
C23 C18 C2 118.9(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.7(4) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 118.9(3) . . ?
O24 C23 C18 115.5(2) . . ?
O24 C23 C22 125.5(3) . . ?
C23 O24 C25 117.1(3) . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O26 C26 Fe1 177.9(2) . . ?
O27 C27 Fe1 178.0(2) . . ?
O28 C28 Fe1 175.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O1 0.83(4) 1.98(4) 2.792(3) 166(4) 3_656
O7 H7 O16 0.84(2) 2.10(3) 2.928(3) 171(4) .

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
Fe1 C1 C2 C3 64.42(14) . . . . ?
Fe1 C1 C2 C18 -132.3(2) . . . . ?
Fe1 C1 C9 C8 -64.11(13) . . . . ?
Fe1 C1 C9 C10 135.6(2) . . . . ?
Fe1 C2 C3 C4 -125.4(2) . . . . ?
Fe1 C2 C3 C8 60.18(14) . . . . ?
Fe1 C2 C18 C19 -20.8(3) . . . . ?
Fe1 C2 C18 C23 165.51(18) . . . . ?
Fe1 C3 C4 O4 -19.7(3) . . . . ?
Fe1 C3 C4 C5 102.1(2) . . . . ?
Fe1 C3 C8 C7 -124.3(2) . . . . ?
Fe1 C3 C8 C9 61.63(14) . . . . ?
Fe1 C8 C9 C1 73.47(14) . . . . ?
Fe1 C8 C9 C10 -126.9(2) . . . . ?
Fe1 C9 C10 C11 7.6(3) . . . . ?
Fe1 C9 C10 C15 -172.99(19) . . . . ?
O1 C1 C2 Fe1 129.5(2) . . . . ?
O1 C1 C2 C3 -166.1(2) . . . . ?
O1 C1 C2 C18 -2.9(4) . . . . ?
O1 C1 C9 Fe1 -129.5(2) . . . . ?
O1 C1 C9 C8 166.4(2) . . . . ?
O1 C1 C9 C10 6.1(4) . . . . ?
C1 C2 C3 Fe1 -73.26(15) . . . . ?
C1 C2 C3 C4 161.3(2) . . . . ?
C1 C2 C3 C8 -13.1(2) . . . . ?
C1 C2 C18 C19 85.7(3) . . . . ?
C1 C2 C18 C23 -88.0(3) . . . . ?
C1 C9 C10 C11 -103.7(3) . . . . ?
C1 C9 C10 C15 75.7(3) . . . . ?
C2 C1 C9 Fe1 44.43(14) . . . . ?
C2 C1 C9 C8 -19.7(2) . . . . ?
C2 C1 C9 C10 180.00(19) . . . . ?
C2 C3 C4 O4 77.6(3) . . . . ?
C2 C3 C4 C5 -160.6(2) . . . . ?
C2 C3 C8 Fe1 -61.31(14) . . . . ?
C2 C3 C8 C7 174.4(2) . . . . ?
C2 C3 C8 C9 0.3(2) . . . . ?
C2 C18 C19 C20 -172.6(3) . . . . ?
C2 C18 C23 C22 173.4(2) . . . . ?
C2 C18 C23 O24 -4.6(3) . . . . ?
C3 C2 C18 C19 -114.9(3) . . . . ?
C3 C2 C18 C23 71.4(3) . . . . ?
C3 C4 C5 C6 -44.6(3) . . . . ?
C3 C8 C9 Fe1 -60.89(14) . . . . ?
C3 C8 C9 C1 12.6(2) . . . . ?
C3 C8 C9 C10 172.3(2) . . . . ?
C4 C3 C8 Fe1 123.85(19) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C4 C3 C8 C9 -174.52(19) . . . . ?
C4 C5 C6 C7 65.5(3) . . . . ?
O4 C4 C5 C6 75.7(3) . . . . ?
C5 C6 C7 O7 70.6(3) . . . . ?
C5 C6 C7 C8 -48.5(3) . . . . ?
C6 C7 C8 Fe1 -73.3(3) . . . . ?
C6 C7 C8 C3 18.2(3) . . . . ?
C6 C7 C8 C9 -168.8(2) . . . . ?
C7 C8 C9 Fe1 125.3(2) . . . . ?
C7 C8 C9 C1 -161.3(2) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
O7 C7 C8 Fe1 167.98(17) . . . . ?
O7 C7 C8 C3 -100.6(2) . . . . ?
O7 C7 C8 C9 72.4(3) . . . . ?
C8 C3 C4 O4 -108.7(2) . . . . ?
C8 C3 C4 C5 13.1(3) . . . . ?
C8 C9 C10 C11 99.7(3) . . . . ?
C8 C9 C10 C15 -80.9(3) . . . . ?
C9 C1 C2 Fe1 -44.41(14) . . . . ?
C9 C1 C2 C3 20.0(2) . . . . ?
C9 C1 C2 C18 -176.7(2) . . . . ?
C9 C10 C11 C12 180.0(2) . . . . ?
C9 C10 C15 C14 -179.1(3) . . . . ?
C9 C10 C15 O16 3.6(4) . . . . ?
C10 C11 C12 C13 -1.3(4) . . . . ?
C10 C15 O16 C17 -165.2(3) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C11 C10 C15 O16 -177.0(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C10 -0.5(5) . . . . ?
C13 C14 C15 O16 176.5(3) . . . . ?
C14 C15 O16 C17 17.5(5) . . . . ?
C15 C10 C11 C12 0.6(4) . . . . ?
C18 C2 C3 Fe1 125.3(2) . . . . ?
C18 C2 C3 C4 -0.2(4) . . . . ?
C18 C2 C3 C8 -174.6(2) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
C18 C23 O24 C25 171.2(2) . . . . ?
C19 C18 C23 C22 -0.4(4) . . . . ?
C19 C18 C23 O24 -178.5(2) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C21 C22 C23 C18 -0.5(4) . . . . ?
C21 C22 C23 O24 177.3(3) . . . . ?
C22 C23 O24 C25 -6.7(4) . . . . ?
C23 C18 C19 C20 1.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_adg3
_database_code_depnum_ccdc_archive 'CCDC 1567222'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_audit_creation_date             2015-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 Fe O5 Si2'
_chemical_formula_sum            'C17 H24 Fe O5 Si2'
_chemical_formula_weight         420.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Fe'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.72990(5)
_cell_length_b                   16.17780(13)
_cell_length_c                   19.24565(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2095.37(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8451
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.8740
_cell_measurement_theta_min      4.5680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36946
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.019
_diffrn_reflns_theta_min         3.569
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -111.00  -74.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109 -135.0000  103.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00  -17.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -38.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega -108.00  -17.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -38.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   48.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       41.7109  -99.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   80.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       41.7109  -99.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega   55.00   83.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       41.7109  -99.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   62.00   94.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -135.0000  103.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega  101.00  178.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00  116.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  120.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00  170.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   15.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   67.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   77.00  113.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  139.00  166.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   96.00  124.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -135.0000  103.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   32.00  109.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -95.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega   88.00  123.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
 17 omega   85.00  174.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
 18 omega  110.00  141.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   82.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 20 omega   52.00   91.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 21 omega   51.00   98.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 22 omega   44.00  140.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000  -90.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0083746000
_diffrn_orient_matrix_UB_12      -0.0681643000
_diffrn_orient_matrix_UB_13      0.0558211000
_diffrn_orient_matrix_UB_21      0.0105468000
_diffrn_orient_matrix_UB_22      0.0665294000
_diffrn_orient_matrix_UB_23      0.0571431000
_diffrn_orient_matrix_UB_31      -0.2285374000
_diffrn_orient_matrix_UB_32      0.0005514000
_diffrn_orient_matrix_UB_33      0.0046648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4330
_reflns_number_total             4436
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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_collection       
;
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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0763
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.80654(5) 0.67460(2) 0.70637(2) 0.02175(11) Uani 1 1 d . . . . .
O1 O 0.4615(3) 0.53408(11) 0.75292(10) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.5078(4) 0.60256(14) 0.72998(12) 0.0214(5) Uani 1 1 d . . . . .
C2 C 0.5515(3) 0.67826(14) 0.77210(12) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.5557(4) 0.74470(14) 0.72311(13) 0.0214(4) Uani 1 1 d . . . . .
O4 O 0.6606(3) 0.87651(11) 0.77208(11) 0.0333(4) Uani 1 1 d . . . . .
H4 H 0.6418 0.9278 0.7709 0.050 Uiso 1 1 calc GR . . . .
C4 C 0.5428(4) 0.83818(14) 0.72146(13) 0.0247(5) Uani 1 1 d . . . . .
H4A H 0.4013 0.8551 0.7283 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6055(5) 0.85792(15) 0.64539(15) 0.0310(6) Uani 1 1 d . . . . .
H5A H 0.5367 0.9082 0.6285 0.037 Uiso 1 1 calc R . . . .
H5B H 0.7507 0.8671 0.6425 0.037 Uiso 1 1 calc R . . . .
C6 C 0.5445(5) 0.78183(15) 0.60163(14) 0.0291(5) Uani 1 1 d . . . . .
H6A H 0.4086 0.7882 0.5827 0.035 Uiso 1 1 calc R . . . .
H6B H 0.6385 0.7724 0.5629 0.035 Uiso 1 1 calc R . . . .
C7 C 0.5540(4) 0.71287(14) 0.65418(13) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.5489(4) 0.62457(14) 0.65555(12) 0.0224(4) Uani 1 1 d . . . . .
Si9 Si 0.53765(11) 0.54706(4) 0.58323(3) 0.02564(15) Uani 1 1 d . . . . .
C10 C 0.6027(8) 0.59994(19) 0.50005(16) 0.0499(9) Uani 1 1 d . . . . .
H10A H 0.5148 0.6475 0.4932 0.075 Uiso 1 1 calc GR . . . .
H10B H 0.5866 0.5612 0.4613 0.075 Uiso 1 1 calc GR . . . .
H10C H 0.7410 0.6188 0.5020 0.075 Uiso 1 1 calc GR . . . .
C11 C 0.7123(5) 0.46076(17) 0.60174(16) 0.0345(6) Uani 1 1 d . . . . .
H11A H 0.8493 0.4811 0.5992 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.6932 0.4167 0.5674 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.6865 0.4390 0.6484 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.2781(5) 0.50684(18) 0.57715(17) 0.0365(6) Uani 1 1 d . . . . .
H12A H 0.2349 0.4874 0.6229 0.055 Uiso 1 1 calc GR . . . .
H12B H 0.2737 0.4609 0.5440 0.055 Uiso 1 1 calc GR . . . .
H12C H 0.1896 0.5511 0.5613 0.055 Uiso 1 1 calc GR . . . .
Si13 Si 0.54464(11) 0.67090(4) 0.86968(3) 0.02653(15) Uani 1 1 d . . . . .
C14 C 0.2834(5) 0.6485(3) 0.89524(17) 0.0501(9) Uani 1 1 d . . . . .
H14A H 0.2001 0.6967 0.8851 0.075 Uiso 1 1 calc GR . . . .
H14B H 0.2780 0.6363 0.9451 0.075 Uiso 1 1 calc GR . . . .
H14C H 0.2347 0.6007 0.8690 0.075 Uiso 1 1 calc GR . . . .
C15 C 0.7017(5) 0.58203(19) 0.89774(16) 0.0377(6) Uani 1 1 d . . . . .
H15A H 0.6743 0.5342 0.8680 0.057 Uiso 1 1 calc GR . . . .
H15B H 0.6710 0.5681 0.9461 0.057 Uiso 1 1 calc GR . . . .
H15C H 0.8423 0.5971 0.8938 0.057 Uiso 1 1 calc GR . . . .
C16 C 0.6381(8) 0.7666(2) 0.91228(18) 0.0533(10) Uani 1 1 d . . . . .
H16A H 0.7804 0.7727 0.9029 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.6164 0.7628 0.9625 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.5666 0.8145 0.8938 0.080 Uiso 1 1 calc GR . . . .
O17 O 1.0637(4) 0.78809(15) 0.78466(15) 0.0477(6) Uani 1 1 d . . . . .
C17 C 0.9605(4) 0.74522(17) 0.75541(16) 0.0326(6) Uani 1 1 d . . . . .
O18 O 1.0442(4) 0.70279(16) 0.58146(13) 0.0475(6) Uani 1 1 d . . . . .
C18 C 0.9538(4) 0.69029(17) 0.63024(16) 0.0323(5) Uani 1 1 d . . . . .
O19 O 0.9816(4) 0.51729(14) 0.75487(14) 0.0442(5) Uani 1 1 d . . . . .
C19 C 0.9179(4) 0.57776(17) 0.73661(16) 0.0308(5) 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
Fe1 C1 2.368(3) . ?
Fe1 C2 2.133(2) . ?
Fe1 C3 2.059(2) . ?
Fe1 C7 2.069(2) . ?
Fe1 C8 2.149(3) . ?
Fe1 C17 1.808(3) . ?
Fe1 C18 1.787(3) . ?
Fe1 C19 1.832(3) . ?
O1 C1 1.233(3) . ?
C1 C2 1.498(3) . ?
C1 C8 1.502(3) . ?
C2 C3 1.430(3) . ?
C2 Si13 1.882(2) . ?
C3 C4 1.515(3) . ?
C3 C7 1.423(3) . ?
O4 H4 0.8400 . ?
O4 C4 1.401(3) . ?
C4 H4A 1.0000 . ?
C4 C5 1.557(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.547(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.507(3) . ?
C7 C8 1.429(3) . ?
C8 Si9 1.875(2) . ?
Si9 C10 1.867(3) . ?
Si9 C11 1.860(3) . ?
Si9 C12 1.867(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Si13 C14 1.861(4) . ?
Si13 C15 1.864(3) . ?
Si13 C16 1.861(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O17 C17 1.131(4) . ?
O18 C18 1.137(4) . ?
O19 C19 1.124(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 Fe1 C1 38.43(8) . . ?
C2 Fe1 C8 68.35(9) . . ?
C3 Fe1 C1 62.93(8) . . ?
C3 Fe1 C2 39.84(9) . . ?
C3 Fe1 C7 40.33(9) . . ?
C3 Fe1 C8 67.48(9) . . ?
C7 Fe1 C1 62.80(9) . . ?
C7 Fe1 C2 67.58(9) . . ?
C7 Fe1 C8 39.55(8) . . ?
C8 Fe1 C1 38.45(8) . . ?
C17 Fe1 C1 134.21(11) . . ?
C17 Fe1 C2 97.70(11) . . ?
C17 Fe1 C3 92.29(12) . . ?
C17 Fe1 C7 122.34(11) . . ?
C17 Fe1 C8 159.68(11) . . ?
C17 Fe1 C19 98.07(14) . . ?
C18 Fe1 C1 134.27(11) . . ?
C18 Fe1 C2 158.21(11) . . ?
C18 Fe1 C3 120.31(11) . . ?
C18 Fe1 C7 90.85(12) . . ?
C18 Fe1 C8 97.34(12) . . ?
C18 Fe1 C17 91.18(14) . . ?
C18 Fe1 C19 98.93(13) . . ?
C19 Fe1 C1 82.27(11) . . ?
C19 Fe1 C2 99.47(11) . . ?
C19 Fe1 C3 139.19(11) . . ?
C19 Fe1 C7 138.27(12) . . ?
C19 Fe1 C8 98.78(12) . . ?
O1 C1 Fe1 136.52(18) . . ?
O1 C1 C2 126.2(2) . . ?
O1 C1 C8 127.0(2) . . ?
C2 C1 Fe1 62.26(12) . . ?
C2 C1 C8 106.63(19) . . ?
C8 C1 Fe1 62.87(13) . . ?
C1 C2 Fe1 79.31(14) . . ?
C1 C2 Si13 118.90(17) . . ?
C3 C2 Fe1 67.30(13) . . ?
C3 C2 C1 105.17(19) . . ?
C3 C2 Si13 134.89(18) . . ?
Si13 C2 Fe1 127.57(12) . . ?
C2 C3 Fe1 72.85(13) . . ?
C2 C3 C4 139.7(2) . . ?
C4 C3 Fe1 126.39(17) . . ?
C7 C3 Fe1 70.21(14) . . ?
C7 C3 C2 110.0(2) . . ?
C7 C3 C4 109.9(2) . . ?
C4 O4 H4 109.5 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 C5 102.07(19) . . ?
O4 C4 C3 113.3(2) . . ?
O4 C4 H4A 109.0 . . ?
O4 C4 C5 114.2(2) . . ?
C5 C4 H4A 109.0 . . ?
C4 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 C4 106.1(2) . . ?
C6 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C5 C6 H6A 111.3 . . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C7 C6 C5 102.3(2) . . ?
C7 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
C3 C7 Fe1 69.46(14) . . ?
C3 C7 C6 111.0(2) . . ?
C3 C7 C8 110.2(2) . . ?
C6 C7 Fe1 125.61(19) . . ?
C8 C7 Fe1 73.25(15) . . ?
C8 C7 C6 138.7(2) . . ?
C1 C8 Fe1 78.68(14) . . ?
C1 C8 Si9 122.83(16) . . ?
C7 C8 Fe1 67.20(15) . . ?
C7 C8 C1 105.0(2) . . ?
C7 C8 Si9 130.97(19) . . ?
Si9 C8 Fe1 128.47(13) . . ?
C10 Si9 C8 108.71(12) . . ?
C10 Si9 C12 108.98(19) . . ?
C11 Si9 C8 109.54(13) . . ?
C11 Si9 C10 111.10(17) . . ?
C11 Si9 C12 109.98(14) . . ?
C12 Si9 C8 108.49(12) . . ?
Si9 C10 H10A 109.5 . . ?
Si9 C10 H10B 109.5 . . ?
Si9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si9 C11 H11A 109.5 . . ?
Si9 C11 H11B 109.5 . . ?
Si9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si9 C12 H12A 109.5 . . ?
Si9 C12 H12B 109.5 . . ?
Si9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 Si13 C2 107.41(13) . . ?
C14 Si13 C15 108.00(17) . . ?
C15 Si13 C2 108.89(12) . . ?
C16 Si13 C2 112.25(14) . . ?
C16 Si13 C14 111.4(2) . . ?
C16 Si13 C15 108.80(17) . . ?
Si13 C14 H14A 109.5 . . ?
Si13 C14 H14B 109.5 . . ?
Si13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si13 C15 H15A 109.5 . . ?
Si13 C15 H15B 109.5 . . ?
Si13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si13 C16 H16A 109.5 . . ?
Si13 C16 H16B 109.5 . . ?
Si13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C17 Fe1 177.1(3) . . ?
O18 C18 Fe1 177.7(3) . . ?
O19 C19 Fe1 178.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O1 0.84 1.91 2.721(3) 161.9 3_656

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
Fe1 C1 C2 C3 62.74(15) . . . . ?
Fe1 C1 C2 Si13 -127.20(17) . . . . ?
Fe1 C1 C8 C7 -62.42(17) . . . . ?
Fe1 C1 C8 Si9 128.8(2) . . . . ?
Fe1 C2 C3 C4 -126.6(3) . . . . ?
Fe1 C2 C3 C7 60.69(17) . . . . ?
Fe1 C2 Si13 C14 -164.56(19) . . . . ?
Fe1 C2 Si13 C15 -47.85(19) . . . . ?
Fe1 C2 Si13 C16 72.7(2) . . . . ?
Fe1 C3 C4 O4 -62.1(3) . . . . ?
Fe1 C3 C4 C5 61.1(3) . . . . ?
Fe1 C3 C7 C6 -121.5(2) . . . . ?
Fe1 C3 C7 C8 62.27(19) . . . . ?
Fe1 C7 C8 C1 70.54(17) . . . . ?
Fe1 C7 C8 Si9 -121.9(2) . . . . ?
Fe1 C8 Si9 C10 -76.7(2) . . . . ?
Fe1 C8 Si9 C11 44.90(19) . . . . ?
Fe1 C8 Si9 C12 164.96(16) . . . . ?
O1 C1 C2 Fe1 129.1(3) . . . . ?
O1 C1 C2 C3 -168.1(2) . . . . ?
O1 C1 C2 Si13 1.9(3) . . . . ?
O1 C1 C8 Fe1 -129.4(3) . . . . ?
O1 C1 C8 C7 168.2(3) . . . . ?
O1 C1 C8 Si9 -0.7(4) . . . . ?
C1 C2 C3 Fe1 -71.23(16) . . . . ?
C1 C2 C3 C4 162.2(3) . . . . ?
C1 C2 C3 C7 -10.5(3) . . . . ?
C1 C2 Si13 C14 -65.5(2) . . . . ?
C1 C2 Si13 C15 51.2(2) . . . . ?
C1 C2 Si13 C16 171.7(2) . . . . ?
C1 C8 Si9 C10 -179.0(3) . . . . ?
C1 C8 Si9 C11 -57.5(2) . . . . ?
C1 C8 Si9 C12 62.6(2) . . . . ?
C2 C1 C8 Fe1 45.67(17) . . . . ?
C2 C1 C8 C7 -16.8(3) . . . . ?
C2 C1 C8 Si9 174.42(17) . . . . ?
C2 C3 C4 O4 45.5(4) . . . . ?
C2 C3 C4 C5 168.8(3) . . . . ?
C2 C3 C7 Fe1 -62.32(17) . . . . ?
C2 C3 C7 C6 176.2(2) . . . . ?
C2 C3 C7 C8 0.0(3) . . . . ?
C3 C2 Si13 C14 100.9(3) . . . . ?
C3 C2 Si13 C15 -142.4(3) . . . . ?
C3 C2 Si13 C16 -21.9(3) . . . . ?
C3 C4 C5 C6 28.5(3) . . . . ?
C3 C7 C8 Fe1 -59.95(18) . . . . ?
C3 C7 C8 C1 10.6(3) . . . . ?
C3 C7 C8 Si9 178.13(19) . . . . ?
O4 C4 C5 C6 151.2(2) . . . . ?
C4 C3 C7 Fe1 122.69(19) . . . . ?
C4 C3 C7 C6 1.2(3) . . . . ?
C4 C3 C7 C8 -175.0(2) . . . . ?
C4 C5 C6 C7 -27.8(3) . . . . ?
C5 C6 C7 Fe1 -62.4(3) . . . . ?
C5 C6 C7 C3 16.8(3) . . . . ?
C5 C6 C7 C8 -168.6(3) . . . . ?
C6 C7 C8 Fe1 125.4(4) . . . . ?
C6 C7 C8 C1 -164.1(3) . . . . ?
C6 C7 C8 Si9 3.4(5) . . . . ?
C7 C3 C4 O4 -141.8(2) . . . . ?
C7 C3 C4 C5 -18.5(3) . . . . ?
C7 C8 Si9 C10 15.3(3) . . . . ?
C7 C8 Si9 C11 136.9(3) . . . . ?
C7 C8 Si9 C12 -103.1(3) . . . . ?
C8 C1 C2 Fe1 -45.99(17) . . . . ?
C8 C1 C2 C3 16.7(3) . . . . ?
C8 C1 C2 Si13 -173.19(16) . . . . ?
Si13 C2 C3 Fe1 121.1(2) . . . . ?
Si13 C2 C3 C4 -5.5(5) . . . . ?
Si13 C2 C3 C7 -178.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_adg10
_database_code_depnum_ccdc_archive 'CCDC 1567219'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Fe O5 Si'
_chemical_formula_sum            'C20 H20 Fe O5 Si'
_chemical_formula_weight         424.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H20 O2 Fe'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.66446(13)
_cell_length_b                   16.1511(3)
_cell_length_c                   19.2420(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2071.18(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25675
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      37.4990
_cell_measurement_theta_min      3.0780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            104348
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         37.810
_diffrn_reflns_theta_min         3.235
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 117.00   1.00    5.00    --   30.19-178.00 120.00   85
  2  ω    -44.00  55.00   1.00    5.00    --   30.19 -38.00  90.00   99
  3  ω      6.00 104.00   1.00    5.00    --   30.19  38.00   0.00   98
  4  ω    -44.00  55.00   1.00    5.00    --   30.19 -38.00-180.00   99
  5  ω    -58.00 118.00   1.00    5.00    --   30.19   0.00-120.00  176
  6  ω   -108.00 -38.00   1.00    5.00    --  -31.13 156.00 105.00   70
  7  ω     -2.00 106.00   1.00    5.00    --   30.19  77.00-150.00  108
  8  ω      2.00 103.00   1.00    5.00    --   30.19  57.00 150.00  101
  9  ω      2.00 103.00   1.00    5.00    --   30.19  57.00  90.00  101
 10  ω   -120.00 -57.00   1.00    5.00    --  -31.13-178.00-150.00   63
 11  ω   -107.00   1.00   1.00    5.00    --  -31.13 -77.00 -90.00  108
 12  ω   -107.00 -19.00   1.00    5.00    --  -31.13 -77.00   0.00   88
 13  ω   -120.00 -57.00   1.00    5.00    --  -31.13-178.00 -30.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0786294000
_diffrn_orient_matrix_UB_12      -0.0295361000
_diffrn_orient_matrix_UB_13      -0.0017730000
_diffrn_orient_matrix_UB_21      -0.0125057000
_diffrn_orient_matrix_UB_22      -0.0025629000
_diffrn_orient_matrix_UB_23      -0.0365434000
_diffrn_orient_matrix_UB_31      0.0706072000
_diffrn_orient_matrix_UB_32      0.0324083000
_diffrn_orient_matrix_UB_33      -0.0044933000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                9377
_reflns_number_total             10846
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 3704 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Flack x: -0.012(4) Shelx 2014
Hooft y: -0.012(3) Olex2
;
_refine_ls_abs_structure_Flack   -0.012(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         10846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.1789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          ?
_olex2_refinement_description    
;

OH located in a difference map but was placed at calculate position during refinement

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.64969(3) 0.32265(2) 0.72957(2) 0.02169(5) Uani 1 1 d . . . . .
O1 O 1.0325(2) 0.46029(7) 0.73925(7) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.9643(2) 0.39123(8) 0.72430(9) 0.0242(2) Uani 1 1 d . . . . .
C2 C 0.94642(18) 0.31796(7) 0.77124(8) 0.0216(2) Uani 1 1 d . . . . .
C3 C 0.90187(19) 0.24876(7) 0.72648(8) 0.0223(2) Uani 1 1 d . . . . .
C4 C 0.9122(3) 0.15519(8) 0.72471(10) 0.0307(3) Uani 1 1 d . . . . .
H4 H 1.0558 0.1378 0.7207 0.037 Uiso 1 1 calc R . . . .
O4 O 0.8263(2) 0.11620(7) 0.78319(7) 0.0378(3) Uani 1 1 d . . . . .
H4A H 0.8460 0.0649 0.7808 0.057 Uiso 1 1 calc GR . . . .
C5 C 0.8030(3) 0.13463(10) 0.65623(10) 0.0404(4) Uani 1 1 d . . . . .
H5A H 0.6584 0.1250 0.6649 0.049 Uiso 1 1 calc R . . . .
H5B H 0.8606 0.0842 0.6349 0.049 Uiso 1 1 calc R . . . .
C6 C 0.8322(3) 0.20981(9) 0.60778(9) 0.0325(3) Uani 1 1 d . . . . .
H6A H 0.9529 0.2033 0.5783 0.039 Uiso 1 1 calc R . . . .
H6B H 0.7135 0.2186 0.5777 0.039 Uiso 1 1 calc R . . . .
C7 C 0.8574(2) 0.27936(8) 0.65905(7) 0.0220(2) Uani 1 1 d . . . . .
C8 C 0.8686(2) 0.36739(8) 0.65790(7) 0.0219(2) Uani 1 1 d . . . . .
Si9 Si 0.83543(8) 0.44336(3) 0.58504(2) 0.02952(9) Uani 1 1 d . . . . .
C10 C 1.0886(4) 0.47796(17) 0.55605(14) 0.0562(6) Uani 1 1 d . . . . .
H10A H 1.1597 0.5034 0.5952 0.084 Uiso 1 1 calc GR . . . .
H10B H 1.0743 0.5185 0.5185 0.084 Uiso 1 1 calc GR . . . .
H10C H 1.1650 0.4302 0.5392 0.084 Uiso 1 1 calc GR . . . .
C11 C 0.7040(4) 0.39127(13) 0.51095(10) 0.0455(5) Uani 1 1 d . . . . .
H11A H 0.7825 0.3433 0.4957 0.068 Uiso 1 1 calc GR . . . .
H11B H 0.6900 0.4303 0.4723 0.068 Uiso 1 1 calc GR . . . .
H11C H 0.5708 0.3729 0.5261 0.068 Uiso 1 1 calc GR . . . .
C12 C 0.6873(4) 0.53300(11) 0.61721(11) 0.0431(5) Uani 1 1 d . . . . .
H12A H 0.5471 0.5163 0.6235 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.6943 0.5782 0.5833 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.7422 0.5518 0.6617 0.065 Uiso 1 1 calc GR . . . .
C13 C 1.0005(2) 0.31876(9) 0.84544(8) 0.0256(2) Uani 1 1 d . . . . .
C14 C 1.0162(4) 0.39423(12) 0.88117(10) 0.0410(4) Uani 1 1 d . . . . .
H14 H 0.9914 0.4446 0.8572 0.049 Uiso 1 1 calc R . . . .
C15 C 1.0674(4) 0.39619(14) 0.95101(11) 0.0477(5) Uani 1 1 d . . . . .
H15 H 1.0768 0.4478 0.9745 0.057 Uiso 1 1 calc R . . . .
C16 C 1.1050(3) 0.32353(15) 0.98671(10) 0.0443(4) Uani 1 1 d . . . . .
H16 H 1.1444 0.3250 1.0342 0.053 Uiso 1 1 calc R . . . .
C17 C 1.0848(4) 0.24876(14) 0.95263(10) 0.0437(4) Uani 1 1 d . . . . .
H17 H 1.1066 0.1986 0.9773 0.052 Uiso 1 1 calc R . . . .
C18 C 1.0331(3) 0.24603(10) 0.88290(9) 0.0339(3) Uani 1 1 d . . . . .
H18 H 1.0196 0.1940 0.8603 0.041 Uiso 1 1 calc R . . . .
C19 C 0.4499(2) 0.30403(12) 0.66942(10) 0.0341(3) Uani 1 1 d . . . . .
O19 O 0.3280(2) 0.28991(12) 0.62951(9) 0.0548(4) Uani 1 1 d . . . . .
C20 C 0.5701(3) 0.42045(11) 0.76731(11) 0.0375(4) Uani 1 1 d . . . . .
O20 O 0.5290(3) 0.48150(11) 0.79247(11) 0.0648(5) Uani 1 1 d . . . . .
C21 C 0.5430(3) 0.25933(12) 0.79713(11) 0.0378(4) Uani 1 1 d . . . . .
O21 O 0.4789(3) 0.22092(12) 0.84153(11) 0.0640(5) 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
Fe1 C1 2.3736(14) . ?
Fe1 C2 2.1353(13) . ?
Fe1 C3 2.0621(12) . ?
Fe1 C7 2.0604(14) . ?
Fe1 C8 2.1334(14) . ?
Fe1 C19 1.7896(18) . ?
Fe1 C20 1.8177(16) . ?
Fe1 C21 1.8005(18) . ?
O1 C1 1.2384(17) . ?
C1 C2 1.4935(19) . ?
C1 C8 1.479(2) . ?
C2 C3 1.4417(19) . ?
C2 C13 1.473(2) . ?
C3 C4 1.5132(17) . ?
C3 C7 1.420(2) . ?
C4 H4 1.0000 . ?
C4 O4 1.411(2) . ?
C4 C5 1.542(3) . ?
O4 H4A 0.8400 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.543(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5044(19) . ?
C7 C8 1.4239(16) . ?
C8 Si9 1.8762(14) . ?
Si9 C10 1.863(2) . ?
Si9 C11 1.873(2) . ?
Si9 C12 1.858(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.403(2) . ?
C13 C18 1.395(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C19 O19 1.141(2) . ?
C20 O20 1.132(2) . ?
C21 O21 1.139(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Fe1 C1 38.23(5) . . ?
C3 Fe1 C1 63.18(5) . . ?
C3 Fe1 C2 40.13(5) . . ?
C3 Fe1 C8 67.67(5) . . ?
C7 Fe1 C1 62.41(5) . . ?
C7 Fe1 C2 67.24(6) . . ?
C7 Fe1 C3 40.29(6) . . ?
C7 Fe1 C8 39.65(5) . . ?
C8 Fe1 C1 37.84(5) . . ?
C8 Fe1 C2 67.76(5) . . ?
C19 Fe1 C1 135.08(7) . . ?
C19 Fe1 C2 157.80(7) . . ?
C19 Fe1 C3 119.37(7) . . ?
C19 Fe1 C7 90.96(7) . . ?
C19 Fe1 C8 98.49(7) . . ?
C19 Fe1 C20 100.80(9) . . ?
C19 Fe1 C21 94.46(9) . . ?
C20 Fe1 C1 82.50(7) . . ?
C20 Fe1 C2 98.70(7) . . ?
C20 Fe1 C3 138.79(8) . . ?
C20 Fe1 C7 138.95(8) . . ?
C20 Fe1 C8 99.42(8) . . ?
C21 Fe1 C1 130.14(8) . . ?
C21 Fe1 C2 94.26(7) . . ?
C21 Fe1 C3 90.79(7) . . ?
C21 Fe1 C7 123.22(7) . . ?
C21 Fe1 C8 158.29(7) . . ?
C21 Fe1 C20 95.15(10) . . ?
O1 C1 Fe1 137.28(12) . . ?
O1 C1 C2 127.05(15) . . ?
O1 C1 C8 126.41(14) . . ?
C2 C1 Fe1 62.22(7) . . ?
C8 C1 Fe1 62.24(7) . . ?
C8 C1 C2 106.36(10) . . ?
C1 C2 Fe1 79.56(8) . . ?
C3 C2 Fe1 67.20(7) . . ?
C3 C2 C1 105.63(12) . . ?
C3 C2 C13 129.52(13) . . ?
C13 C2 Fe1 126.18(10) . . ?
C13 C2 C1 124.04(12) . . ?
C2 C3 Fe1 72.67(7) . . ?
C2 C3 C4 141.10(15) . . ?
C4 C3 Fe1 128.00(10) . . ?
C7 C3 Fe1 69.79(8) . . ?
C7 C3 C2 108.61(11) . . ?
C7 C3 C4 109.67(13) . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C5 102.30(13) . . ?
O4 C4 C3 114.16(13) . . ?
O4 C4 H4 109.0 . . ?
O4 C4 C5 113.20(15) . . ?
C5 C4 H4 109.0 . . ?
C4 O4 H4A 109.5 . . ?
C4 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C4 C5 C6 106.69(13) . . ?
H5A C5 H5B 108.6 . . ?
C6 C5 H5A 110.4 . . ?
C6 C5 H5B 110.4 . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
H6A C6 H6B 109.3 . . ?
C7 C6 C5 101.85(13) . . ?
C7 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
C3 C7 Fe1 69.92(8) . . ?
C3 C7 C6 111.27(12) . . ?
C3 C7 C8 110.53(12) . . ?
C6 C7 Fe1 127.62(11) . . ?
C8 C7 Fe1 72.94(8) . . ?
C8 C7 C6 137.83(14) . . ?
C1 C8 Fe1 79.91(8) . . ?
C1 C8 Si9 121.73(9) . . ?
C7 C8 Fe1 67.41(8) . . ?
C7 C8 C1 105.61(12) . . ?
C7 C8 Si9 131.18(11) . . ?
Si9 C8 Fe1 128.61(8) . . ?
C10 Si9 C8 108.26(9) . . ?
C10 Si9 C11 109.28(12) . . ?
C11 Si9 C8 109.27(8) . . ?
C12 Si9 C8 108.85(8) . . ?
C12 Si9 C10 110.33(12) . . ?
C12 Si9 C11 110.79(10) . . ?
Si9 C10 H10A 109.5 . . ?
Si9 C10 H10B 109.5 . . ?
Si9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si9 C11 H11A 109.5 . . ?
Si9 C11 H11B 109.5 . . ?
Si9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si9 C12 H12A 109.5 . . ?
Si9 C12 H12B 109.5 . . ?
Si9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C2 120.06(14) . . ?
C18 C13 C2 122.12(14) . . ?
C18 C13 C14 117.81(15) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.85(18) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.45(19) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.24(17) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.80(18) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.80(17) . . ?
C17 C18 H18 119.6 . . ?
O19 C19 Fe1 177.01(17) . . ?
O20 C20 Fe1 176.7(2) . . ?
O21 C21 Fe1 177.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O1 0.84 1.91 2.7226(16) 161.5 3_746

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
Fe1 C1 C2 C3 62.57(8) . . . . ?
Fe1 C1 C2 C13 -126.86(13) . . . . ?
Fe1 C1 C8 C7 -62.95(10) . . . . ?
Fe1 C1 C8 Si9 129.43(11) . . . . ?
Fe1 C2 C3 C4 -129.8(2) . . . . ?
Fe1 C2 C3 C7 60.86(10) . . . . ?
Fe1 C2 C13 C14 -83.96(18) . . . . ?
Fe1 C2 C13 C18 94.55(17) . . . . ?
Fe1 C3 C4 O4 -61.1(2) . . . . ?
Fe1 C3 C4 C5 61.56(18) . . . . ?
Fe1 C3 C7 C6 -123.73(13) . . . . ?
Fe1 C3 C7 C8 61.93(11) . . . . ?
Fe1 C7 C8 C1 71.75(10) . . . . ?
Fe1 C7 C8 Si9 -122.28(14) . . . . ?
Fe1 C8 Si9 C10 165.65(12) . . . . ?
Fe1 C8 Si9 C11 -75.41(12) . . . . ?
Fe1 C8 Si9 C12 45.71(12) . . . . ?
O1 C1 C2 Fe1 130.00(17) . . . . ?
O1 C1 C2 C3 -167.43(16) . . . . ?
O1 C1 C2 C13 3.1(2) . . . . ?
O1 C1 C8 Fe1 -130.05(17) . . . . ?
O1 C1 C8 C7 167.00(17) . . . . ?
O1 C1 C8 Si9 -0.6(2) . . . . ?
C1 C2 C3 Fe1 -71.23(9) . . . . ?
C1 C2 C3 C4 158.96(18) . . . . ?
C1 C2 C3 C7 -10.37(15) . . . . ?
C1 C2 C13 C14 18.9(2) . . . . ?
C1 C2 C13 C18 -162.55(15) . . . . ?
C1 C8 Si9 C10 62.34(16) . . . . ?
C1 C8 Si9 C11 -178.73(13) . . . . ?
C1 C8 Si9 C12 -57.61(14) . . . . ?
C2 C1 C8 Fe1 45.30(9) . . . . ?
C2 C1 C8 C7 -17.65(16) . . . . ?
C2 C1 C8 Si9 174.73(10) . . . . ?
C2 C3 C4 O4 50.4(3) . . . . ?
C2 C3 C4 C5 173.04(18) . . . . ?
C2 C3 C7 Fe1 -62.68(9) . . . . ?
C2 C3 C7 C6 173.59(13) . . . . ?
C2 C3 C7 C8 -0.74(17) . . . . ?
C2 C13 C14 C15 -179.8(2) . . . . ?
C2 C13 C18 C17 179.66(17) . . . . ?
C3 C2 C13 C14 -172.87(16) . . . . ?
C3 C2 C13 C18 5.6(2) . . . . ?
C3 C4 C5 C6 27.83(18) . . . . ?
C3 C7 C8 Fe1 -60.11(10) . . . . ?
C3 C7 C8 C1 11.64(17) . . . . ?
C3 C7 C8 Si9 177.62(11) . . . . ?
C4 C3 C7 Fe1 124.42(11) . . . . ?
C4 C3 C7 C6 0.69(18) . . . . ?
C4 C3 C7 C8 -173.65(13) . . . . ?
C4 C5 C6 C7 -27.30(19) . . . . ?
O4 C4 C5 C6 151.14(14) . . . . ?
C5 C6 C7 Fe1 -63.91(18) . . . . ?
C5 C6 C7 C3 16.59(19) . . . . ?
C5 C6 C7 C8 -171.3(2) . . . . ?
C6 C7 C8 Fe1 127.8(2) . . . . ?
C6 C7 C8 C1 -160.49(19) . . . . ?
C6 C7 C8 Si9 5.5(3) . . . . ?
C7 C3 C4 O4 -140.37(15) . . . . ?
C7 C3 C4 C5 -17.70(17) . . . . ?
C7 C8 Si9 C10 -101.73(18) . . . . ?
C7 C8 Si9 C11 17.20(19) . . . . ?
C7 C8 Si9 C12 138.32(16) . . . . ?
C8 C1 C2 Fe1 -45.31(10) . . . . ?
C8 C1 C2 C3 17.26(15) . . . . ?
C8 C1 C2 C13 -172.17(13) . . . . ?
C13 C2 C3 Fe1 118.91(14) . . . . ?
C13 C2 C3 C4 -10.9(3) . . . . ?
C13 C2 C3 C7 179.77(13) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C13 C18 C17 -1.8(3) . . . . ?
C14 C15 C16 C17 -2.0(4) . . . . ?
C15 C16 C17 C18 1.8(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C18 C13 C14 C15 1.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.857
