# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 2060977'
loop_
_audit_author_name
_audit_author_address
'Jean-Claude Daran'
;CNRS
France
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 Cl Fe O4'
_chemical_formula_sum            'C19 H11 Cl Fe O4'
_chemical_formula_weight         394.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5931(2)
_cell_length_b                   8.5797(2)
_cell_length_c                   15.3443(4)
_cell_angle_alpha                104.201(2)
_cell_angle_beta                 98.461(2)
_cell_angle_gamma                95.747(2)
_cell_volume                     823.85(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15193
_cell_measurement_theta_min      3.9110
_cell_measurement_theta_max      29.2890

_exptl_crystal_description       box
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.102
_shelx_estimated_absorpt_T_min   0.609
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro (Rigaku Oxford Diffraction, 2015)
;

_diffrn_ambient_temperature      173(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1978
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            33334
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        26.400
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3369
_reflns_number_gt                3181
_reflns_threshold_expression     'I > 2σ(I)'


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2016)'
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXt (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-2015

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.6642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3369
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.55721(4) 0.48999(3) 0.77418(2) 0.02326(11) Uani 1 1 d . . . . .
Cl1 Cl -0.25150(10) 0.02710(7) 0.37651(4) 0.04297(16) Uani 1 1 d . . . . .
O11 O 0.7641(3) 0.5702(2) 0.96492(12) 0.0490(5) Uani 1 1 d . . . . .
O12 O 0.1571(3) 0.3649(3) 0.81767(13) 0.0506(5) Uani 1 1 d . . . . .
O13 O 0.7140(3) 0.1819(2) 0.70910(13) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.9554(3) 0.6708(2) 0.75886(14) 0.0471(4) Uani 1 1 d . . . . .
C1 C 0.4452(3) 0.4941(2) 0.63325(13) 0.0250(4) Uani 1 1 d . . . . .
H1 H 0.581768 0.470498 0.629146 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4209(3) 0.6367(2) 0.69786(13) 0.0245(4) Uani 1 1 d . . . . .
H2 H 0.288334 0.670217 0.700171 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5980(3) 0.7282(2) 0.75885(14) 0.0261(4) Uani 1 1 d . . . . .
C4 C 0.7748(3) 0.6415(2) 0.75541(14) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.6803(3) 0.5367(2) 0.89109(15) 0.0310(4) Uani 1 1 d . . . . .
C12 C 0.3065(3) 0.4129(3) 0.79912(15) 0.0335(5) Uani 1 1 d . . . . .
C13 C 0.6518(3) 0.2998(3) 0.73488(14) 0.0286(4) Uani 1 1 d . . . . .
C31 C 0.6039(3) 0.8850(2) 0.82732(14) 0.0279(4) Uani 1 1 d . . . . .
C32 C 0.4236(4) 0.9476(3) 0.84589(15) 0.0328(5) Uani 1 1 d . . . . .
H32 H 0.292905 0.888623 0.814366 0.039 Uiso 1 1 calc R U . . .
C33 C 0.4321(4) 1.0947(3) 0.90972(16) 0.0392(5) Uani 1 1 d . . . . .
H33 H 0.307591 1.136127 0.921370 0.047 Uiso 1 1 calc R U . . .
C34 C 0.6206(4) 1.1812(3) 0.95640(17) 0.0436(6) Uani 1 1 d . . . . .
H34 H 0.626402 1.281561 1.000648 0.052 Uiso 1 1 calc R U . . .
C35 C 0.7995(5) 1.1214(3) 0.9385(2) 0.0540(7) Uani 1 1 d . . . . .
H35 H 0.929523 1.181166 0.970294 0.065 Uiso 1 1 calc R U . . .
C36 C 0.7930(4) 0.9741(3) 0.87429(19) 0.0452(6) Uani 1 1 d . . . . .
H36 H 0.918286 0.934313 0.862488 0.054 Uiso 1 1 calc R U . . .
C111 C 0.2707(3) 0.3796(2) 0.57179(13) 0.0241(4) Uani 1 1 d . . . . .
C112 C 0.3061(3) 0.2771(3) 0.49167(14) 0.0283(4) Uani 1 1 d . . . . .
H112 H 0.442608 0.281338 0.478543 0.034 Uiso 1 1 calc R U . . .
C113 C 0.1480(4) 0.1692(3) 0.43045(14) 0.0322(5) Uani 1 1 d . . . . .
H113 H 0.174760 0.101250 0.375614 0.039 Uiso 1 1 calc R U . . .
C114 C -0.0492(3) 0.1624(2) 0.45081(14) 0.0295(4) Uani 1 1 d . . . . .
C115 C -0.0902(3) 0.2614(3) 0.53008(15) 0.0337(5) Uani 1 1 d . . . . .
H115 H -0.226641 0.254779 0.543298 0.040 Uiso 1 1 calc R U . . .
C116 C 0.0689(3) 0.3704(3) 0.59018(14) 0.0297(4) Uani 1 1 d . . . . .
H116 H 0.040586 0.439504 0.644329 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C11 1.786(2) . ?
Fe C13 1.802(2) . ?
Fe C12 1.846(2) . ?
Fe C4 1.9397(19) . ?
Fe C2 2.0985(19) . ?
Fe C3 2.110(2) . ?
Fe C1 2.190(2) . ?
Cl1 C114 1.738(2) . ?
O11 C11 1.138(3) . ?
O12 C12 1.132(3) . ?
O13 C13 1.132(3) . ?
O1 C4 1.183(3) . ?
C1 C2 1.413(3) . ?
C1 C111 1.476(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.410(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.445(3) . ?
C3 C31 1.483(3) . ?
C31 C36 1.390(3) . ?
C31 C32 1.391(3) . ?
C32 C33 1.385(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.370(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C111 C112 1.391(3) . ?
C111 C116 1.399(3) . ?
C112 C113 1.385(3) . ?
C112 H112 0.9500 . ?
C113 C114 1.380(3) . ?
C113 H113 0.9500 . ?
C114 C115 1.382(3) . ?
C115 C116 1.386(3) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Fe C13 97.80(10) . . ?
C11 Fe C12 92.71(10) . . ?
C13 Fe C12 99.31(10) . . ?
C11 Fe C4 88.06(9) . . ?
C13 Fe C4 101.05(9) . . ?
C12 Fe C4 159.34(10) . . ?
C11 Fe C2 130.88(9) . . ?
C13 Fe C2 129.18(9) . . ?
C12 Fe C2 92.79(9) . . ?
C4 Fe C2 71.48(8) . . ?
C11 Fe C3 97.33(9) . . ?
C13 Fe C3 138.71(9) . . ?
C12 Fe C3 118.07(9) . . ?
C4 Fe C3 41.54(8) . . ?
C2 Fe C3 39.16(8) . . ?
C11 Fe C1 165.51(9) . . ?
C13 Fe C1 90.94(9) . . ?
C12 Fe C1 97.27(8) . . ?
C4 Fe C1 78.90(8) . . ?
C2 Fe C1 38.41(8) . . ?
C3 Fe C1 68.70(8) . . ?
C2 C1 C111 123.80(18) . . ?
C2 C1 Fe 67.30(11) . . ?
C111 C1 Fe 123.95(13) . . ?
C2 C1 H1 118.1 . . ?
C111 C1 H1 118.1 . . ?
Fe C1 H1 79.4 . . ?
C3 C2 C1 118.51(18) . . ?
C3 C2 Fe 70.84(11) . . ?
C1 C2 Fe 74.29(12) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
Fe C2 H2 125.9 . . ?
C2 C3 C4 111.65(18) . . ?
C2 C3 C31 125.95(18) . . ?
C4 C3 C31 122.00(18) . . ?
C2 C3 Fe 69.99(11) . . ?
C4 C3 Fe 62.92(11) . . ?
C31 C3 Fe 129.25(14) . . ?
O1 C4 C3 138.1(2) . . ?
O1 C4 Fe 144.52(18) . . ?
C3 C4 Fe 75.54(11) . . ?
O11 C11 Fe 177.5(2) . . ?
O12 C12 Fe 177.2(2) . . ?
O13 C13 Fe 178.4(2) . . ?
C36 C31 C32 118.3(2) . . ?
C36 C31 C3 120.0(2) . . ?
C32 C31 C3 121.67(19) . . ?
C33 C32 C31 120.9(2) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 120.2(2) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 119.5(2) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 120.8(2) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C31 120.3(2) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C112 C111 C116 118.12(19) . . ?
C112 C111 C1 119.19(18) . . ?
C116 C111 C1 122.69(18) . . ?
C113 C112 C111 121.9(2) . . ?
C113 C112 H112 119.1 . . ?
C111 C112 H112 119.1 . . ?
C114 C113 C112 118.6(2) . . ?
C114 C113 H113 120.7 . . ?
C112 C113 H113 120.7 . . ?
C113 C114 C115 121.22(19) . . ?
C113 C114 Cl1 120.10(17) . . ?
C115 C114 Cl1 118.68(17) . . ?
C114 C115 C116 119.6(2) . . ?
C114 C115 H115 120.2 . . ?
C116 C115 H115 120.2 . . ?
C115 C116 C111 120.6(2) . . ?
C115 C116 H116 119.7 . . ?
C111 C116 H116 119.7 . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.064


####################################################################### 
# 
# 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_4f
_database_code_depnum_ccdc_archive 'CCDC 2060978'
loop_
_audit_author_name
_audit_author_address
'Jean-Claude Daran'
;CNRS
France
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Fe O3'
_chemical_formula_sum            'C21 H18 Fe O3'
_chemical_formula_weight         374.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.0467(3)
_cell_length_b                   16.3769(5)
_cell_length_c                   11.6631(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.644(3)
_cell_angle_gamma                90
_cell_volume                     1686.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5477
_cell_measurement_theta_min      4.0580
_cell_measurement_theta_max      27.6310

_exptl_crystal_description       box
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.911
_shelx_estimated_absorpt_T_min   0.723
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_T_min  0.76729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro (Rigaku Oxford Diffraction, 2015)
;

_diffrn_ambient_temperature      173(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1978
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            15920
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        26.400
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3374
_reflns_number_gt                2925
_reflns_threshold_expression     'I > 2σ(I)'


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2016)'
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXt (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-2015


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0228P)²+0.9407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.24415(3) 0.33698(2) 0.07312(2) 0.02124(8) Uani 1 1 d . . . . .
O1 O 0.78752(13) 0.42888(7) 0.24527(10) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.71337(14) 0.35301(8) 0.08310(10) 0.0320(3) Uani 1 1 d . . . . .
O3 O 0.83805(15) 0.37589(8) 0.78413(10) 0.0336(3) Uani 1 1 d . . . . .
C1 C 0.39720(19) 0.42650(9) 0.06248(13) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.25262(19) 0.46138(10) 0.06257(14) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.2311 0.4991 0.1186 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1465(2) 0.42997(10) -0.03561(14) 0.0264(4) Uani 1 1 d . . . . .
H3 H 0.0417 0.4431 -0.0567 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2240(2) 0.37568(10) -0.09656(14) 0.0269(4) Uani 1 1 d . . . . .
H4 H 0.1800 0.3461 -0.1657 0.032 Uiso 1 1 calc R U . . .
C5 C 0.37857(19) 0.37298(10) -0.03698(14) 0.0248(4) Uani 1 1 d . . . . .
H5 H 0.4559 0.3414 -0.0590 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3350(2) 0.26510(12) 0.21271(17) 0.0399(5) Uani 1 1 d . . . . .
H6 H 0.4355 0.2687 0.2584 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2865(2) 0.21649(11) 0.11219(19) 0.0384(5) Uani 1 1 d . . . . .
H7 H 0.3486 0.1813 0.0782 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1297(2) 0.22896(12) 0.07063(19) 0.0416(5) Uani 1 1 d . . . . .
H8 H 0.0680 0.2037 0.0036 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0807(2) 0.28477(13) 0.1448(2) 0.0457(5) Uani 1 1 d . . . . .
H9 H -0.0200 0.3040 0.1369 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2071(3) 0.30784(13) 0.23397(18) 0.0457(5) Uani 1 1 d . . . . .
H10 H 0.2063 0.3450 0.2964 0.055 Uiso 1 1 calc R U . . .
C21 C 0.53489(18) 0.44169(9) 0.15203(13) 0.0214(3) Uani 1 1 d . . . . .
C22 C 0.5569(2) 0.49006(10) 0.24595(14) 0.0266(4) Uani 1 1 d . . . . .
H22 H 0.4804 0.5226 0.2676 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7176(2) 0.48639(10) 0.31286(14) 0.0280(4) Uani 1 1 d . . . . .
H23 H 0.7655 0.5413 0.3114 0.034 Uiso 1 1 calc R U . . .
C24 C 0.68190(19) 0.40217(10) 0.15076(14) 0.0240(4) Uani 1 1 d . . . . .
C231 C 0.74183(19) 0.45704(10) 0.43845(14) 0.0261(4) Uani 1 1 d . . . . .
C232 C 0.8295(2) 0.50211(10) 0.52951(15) 0.0285(4) Uani 1 1 d . . . . .
H232 H 0.8699 0.5532 0.5130 0.034 Uiso 1 1 calc R U . . .
C233 C 0.8586(2) 0.47353(11) 0.64376(15) 0.0302(4) Uani 1 1 d . . . . .
H233 H 0.9183 0.5051 0.7052 0.036 Uiso 1 1 calc R U . . .
C234 C 0.80088(19) 0.39880(10) 0.66867(14) 0.0246(4) Uani 1 1 d . . . . .
C235 C 0.7125(2) 0.35303(10) 0.57956(15) 0.0291(4) Uani 1 1 d . . . . .
H235 H 0.6725 0.3019 0.5963 0.035 Uiso 1 1 calc R U . . .
C236 C 0.6833(2) 0.38302(11) 0.46543(15) 0.0325(4) Uani 1 1 d . . . . .
H236 H 0.6217 0.3520 0.4043 0.039 Uiso 1 1 calc R U . . .
C237 C 0.7831(2) 0.30034(12) 0.81662(15) 0.0363(4) Uani 1 1 d . . . . .
H23A H 0.6721 0.3004 0.7958 0.054 Uiso 1 1 calc R U . . .
H23B H 0.8177 0.2924 0.9016 0.054 Uiso 1 1 calc R U . . .
H23C H 0.8215 0.2559 0.7750 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C6 2.0312(18) . ?
Fe1 C10 2.0334(19) . ?
Fe1 C9 2.0387(19) . ?
Fe1 C1 2.0388(16) . ?
Fe1 C5 2.0393(16) . ?
Fe1 C7 2.0424(18) . ?
Fe1 C2 2.0434(16) . ?
Fe1 C8 2.0467(18) . ?
Fe1 C4 2.0478(16) . ?
Fe1 C3 2.0537(16) . ?
O1 C24 1.363(2) . ?
O1 C23 1.458(2) . ?
O2 C24 1.204(2) . ?
O3 C234 1.367(2) . ?
O3 C237 1.416(2) . ?
C1 C2 1.427(2) . ?
C1 C5 1.434(2) . ?
C1 C21 1.461(2) . ?
C2 C3 1.420(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.406(3) . ?
C6 C10 1.419(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C21 C22 1.331(2) . ?
C21 C24 1.482(2) . ?
C22 C23 1.493(2) . ?
C22 H22 0.9500 . ?
C23 C231 1.511(2) . ?
C23 H23 1.0000 . ?
C231 C236 1.386(2) . ?
C231 C232 1.390(2) . ?
C232 C233 1.382(2) . ?
C232 H232 0.9500 . ?
C233 C234 1.386(2) . ?
C233 H233 0.9500 . ?
C234 C235 1.385(2) . ?
C235 C236 1.389(2) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C237 H23A 0.9800 . ?
C237 H23B 0.9800 . ?
C237 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Fe1 C10 40.88(9) . . ?
C6 Fe1 C9 68.32(8) . . ?
C10 Fe1 C9 40.76(9) . . ?
C6 Fe1 C1 107.73(7) . . ?
C10 Fe1 C1 118.44(8) . . ?
C9 Fe1 C1 152.82(8) . . ?
C6 Fe1 C5 118.68(8) . . ?
C10 Fe1 C5 152.90(9) . . ?
C9 Fe1 C5 164.86(8) . . ?
C1 Fe1 C5 41.18(6) . . ?
C6 Fe1 C7 40.37(8) . . ?
C10 Fe1 C7 68.17(9) . . ?
C9 Fe1 C7 67.70(8) . . ?
C1 Fe1 C7 127.71(7) . . ?
C5 Fe1 C7 108.14(7) . . ?
C6 Fe1 C2 127.75(7) . . ?
C10 Fe1 C2 107.79(8) . . ?
C9 Fe1 C2 118.88(8) . . ?
C1 Fe1 C2 40.94(6) . . ?
C5 Fe1 C2 68.81(7) . . ?
C7 Fe1 C2 165.69(8) . . ?
C6 Fe1 C8 67.98(8) . . ?
C10 Fe1 C8 67.99(9) . . ?
C9 Fe1 C8 39.95(9) . . ?
C1 Fe1 C8 165.64(8) . . ?
C5 Fe1 C8 127.62(8) . . ?
C7 Fe1 C8 40.32(8) . . ?
C2 Fe1 C8 152.43(8) . . ?
C6 Fe1 C4 152.72(8) . . ?
C10 Fe1 C4 165.12(8) . . ?
C9 Fe1 C4 127.37(8) . . ?
C1 Fe1 C4 68.69(6) . . ?
C5 Fe1 C4 40.64(7) . . ?
C7 Fe1 C4 119.16(8) . . ?
C2 Fe1 C4 68.27(6) . . ?
C8 Fe1 C4 108.43(8) . . ?
C6 Fe1 C3 165.60(8) . . ?
C10 Fe1 C3 127.46(8) . . ?
C9 Fe1 C3 108.15(8) . . ?
C1 Fe1 C3 68.62(7) . . ?
C5 Fe1 C3 68.42(7) . . ?
C7 Fe1 C3 152.68(8) . . ?
C2 Fe1 C3 40.56(6) . . ?
C8 Fe1 C3 118.96(7) . . ?
C4 Fe1 C3 40.41(7) . . ?
C24 O1 C23 109.51(13) . . ?
C234 O3 C237 118.59(13) . . ?
C2 C1 C5 107.43(14) . . ?
C2 C1 C21 124.70(14) . . ?
C5 C1 C21 127.82(15) . . ?
C2 C1 Fe1 69.70(9) . . ?
C5 C1 Fe1 69.43(9) . . ?
C21 C1 Fe1 124.26(11) . . ?
C3 C2 C1 108.22(14) . . ?
C3 C2 Fe1 70.11(9) . . ?
C1 C2 Fe1 69.36(9) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.06(15) . . ?
C4 C3 Fe1 69.57(9) . . ?
C2 C3 Fe1 69.33(9) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.7 . . ?
C3 C4 C5 108.48(14) . . ?
C3 C4 Fe1 70.02(9) . . ?
C5 C4 Fe1 69.36(9) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 126.4 . . ?
C4 C5 C1 107.80(15) . . ?
C4 C5 Fe1 70.00(10) . . ?
C1 C5 Fe1 69.40(9) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 126.1 . . ?
Fe1 C5 H5 126.1 . . ?
C7 C6 C10 107.91(18) . . ?
C7 C6 Fe1 70.24(11) . . ?
C10 C6 Fe1 69.64(11) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 H6 126.0 . . ?
Fe1 C6 H6 125.6 . . ?
C6 C7 C8 108.16(18) . . ?
C6 C7 Fe1 69.39(10) . . ?
C8 C7 Fe1 70.00(10) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
Fe1 C7 H7 126.3 . . ?
C9 C8 C7 108.29(19) . . ?
C9 C8 Fe1 69.72(11) . . ?
C7 C8 Fe1 69.68(11) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Fe1 C8 H8 126.3 . . ?
C8 C9 C10 108.34(18) . . ?
C8 C9 Fe1 70.33(11) . . ?
C10 C9 Fe1 69.42(11) . . ?
C8 C9 H9 125.8 . . ?
C10 C9 H9 125.8 . . ?
Fe1 C9 H9 126.0 . . ?
C9 C10 C6 107.30(19) . . ?
C9 C10 Fe1 69.82(11) . . ?
C6 C10 Fe1 69.48(11) . . ?
C9 C10 H10 126.3 . . ?
C6 C10 H10 126.3 . . ?
Fe1 C10 H10 125.9 . . ?
C22 C21 C1 129.79(16) . . ?
C22 C21 C24 107.18(14) . . ?
C1 C21 C24 123.03(14) . . ?
C21 C22 C23 111.05(15) . . ?
C21 C22 H22 124.5 . . ?
C23 C22 H22 124.5 . . ?
O1 C23 C22 103.38(13) . . ?
O1 C23 C231 109.29(13) . . ?
C22 C23 C231 115.96(15) . . ?
O1 C23 H23 109.3 . . ?
C22 C23 H23 109.3 . . ?
C231 C23 H23 109.3 . . ?
O2 C24 O1 121.33(15) . . ?
O2 C24 C21 129.78(15) . . ?
O1 C24 C21 108.88(14) . . ?
C236 C231 C232 118.24(15) . . ?
C236 C231 C23 121.09(15) . . ?
C232 C231 C23 120.61(15) . . ?
C233 C232 C231 120.88(16) . . ?
C233 C232 H232 119.6 . . ?
C231 C232 H232 119.6 . . ?
C232 C233 C234 120.00(15) . . ?
C232 C233 H233 120.0 . . ?
C234 C233 H233 120.0 . . ?
O3 C234 C235 124.60(16) . . ?
O3 C234 C233 115.22(14) . . ?
C235 C234 C233 120.18(15) . . ?
C234 C235 C236 119.04(16) . . ?
C234 C235 H235 120.5 . . ?
C236 C235 H235 120.5 . . ?
C231 C236 C235 121.66(16) . . ?
C231 C236 H236 119.2 . . ?
C235 C236 H236 119.2 . . ?
O3 C237 H23A 109.5 . . ?
O3 C237 H23B 109.5 . . ?
H23A C237 H23B 109.5 . . ?
O3 C237 H23C 109.5 . . ?
H23A C237 H23C 109.5 . . ?
H23B C237 H23C 109.5 . . ?

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
C235 H235 O2 0.95 2.57 3.375(2) 142.3 4_566

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6



