# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_1



_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         
'C16 H12 O2'

_chemical_formula_sum            
'C16 H12 O2'

_chemical_formula_weight         236.26



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'



_space_group_crystal_system      orthorhombic

_space_group_IT_number           33

_space_group_name_H-M_alt        'P n a 21'

_space_group_name_Hall           'P 2c -2n'



_shelx_space_group_comment       
;

The symmetry employed for this shelxl refinement is uniquely defined

by the following loop, which should always be used as a source of

symmetry information in preference to the above space-group names.

They are only intended as comments.

;



loop_

_space_group_symop_operation_xyz




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



_cell_length_a                   18.696(2)

_cell_length_b                   5.1480(7)

_cell_length_c                   12.7045(18)

_cell_angle_alpha                90

_cell_angle_beta                 90

_cell_angle_gamma                90

_cell_volume                     1222.8(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    2007

_cell_measurement_theta_min      2.70

_cell_measurement_theta_max      21.51



_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    ?

_exptl_crystal_density_diffrn    1.283

_exptl_crystal_F_000             496

_exptl_transmission_factor_min   ?

_exptl_transmission_factor_max   ?

_exptl_crystal_size_max          0.498

_exptl_crystal_size_mid          0.275

_exptl_crystal_size_min          0.152

_exptl_absorpt_coefficient_mu    0.084

_shelx_estimated_absorpt_T_min   0.959

_shelx_estimated_absorpt_T_max   0.987

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6178

_exptl_absorpt_correction_T_max  0.7456

_exptl_absorpt_process_details   '(Sheldrick, 2008)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'

_diffrn_measurement_method       ω-scans

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            7878

_diffrn_reflns_av_unetI/netI     0.0821

_diffrn_reflns_av_R_equivalents  0.0561

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       24

_diffrn_reflns_limit_k_min       -6

_diffrn_reflns_limit_k_max       6

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         2.179

_diffrn_reflns_theta_max         27.998

_diffrn_reflns_theta_full        25.242

_diffrn_measured_fraction_theta_max 0.997

_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_Laue_measured_fraction_max 0.997

_diffrn_reflns_Laue_measured_fraction_full 0.999

_diffrn_reflns_point_group_measured_fraction_max 0.982

_diffrn_reflns_point_group_measured_fraction_full 0.996

_reflns_number_total             2896

_reflns_number_gt                1399

_reflns_threshold_expression     'I > 2σ(I)'

_reflns_Friedel_coverage         0.885

_reflns_Friedel_fraction_max     0.965

_reflns_Friedel_fraction_full    0.993



_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       'APEX2 v2012.10.0(Bruker, 2012)'

_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'

_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'

_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'



_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)+(0.0133P)²]

 where P=(Fo²+2Fc²)/3

;

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   mixed

_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       .

_refine_ls_abs_structure_details 
;

?

;

_refine_ls_abs_structure_Flack   ?

_chemical_absolute_configuration ?

_refine_ls_number_reflns         2896

_refine_ls_number_parameters     296

_refine_ls_number_restraints     704

_refine_ls_R_factor_all          0.1246

_refine_ls_R_factor_gt           0.0520

_refine_ls_wR_factor_ref         0.1227

_refine_ls_wR_factor_gt          0.0951

_refine_ls_goodness_of_fit_ref   0.992

_refine_ls_restrained_S_all      0.936

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_site_symmetry_order

_atom_site_calc_flag

_atom_site_refinement_flags_posn

_atom_site_refinement_flags_adp

_atom_site_refinement_flags_occupancy

_atom_site_disorder_assembly

_atom_site_disorder_group




























































O1 O 0.5377(9) 0.576(3) 0.8676(7) 0.079(3) Uani 0.622(5) 1 d . U P A 1
O2 O 0.6210(12) 0.213(4) 0.8216(14) 0.080(3) Uani 0.622(5) 1 d D U P A 1
H21 H 0.591(5) 0.305(16) 0.863(7) 0.120 Uiso 0.622(5) 1 d D U P A 1
C1 C 0.4540(4) 0.9838(15) 0.5535(7) 0.0684(18) Uani 0.622(5) 1 d . U P A 1
H1 H 0.4601 0.9820 0.4809 0.082 Uiso 0.622(5) 1 calc R U P A 1
C2 C 0.4054(5) 1.1514(17) 0.6005(7) 0.074(2) Uani 0.622(5) 1 d . U P A 1
H2 H 0.3781 1.2611 0.5585 0.089 Uiso 0.622(5) 1 calc R U P A 1
C3 C 0.3970(5) 1.1582(18) 0.7067(6) 0.073(2) Uani 0.622(5) 1 d . U P A 1
H3 H 0.3655 1.2773 0.7364 0.087 Uiso 0.622(5) 1 calc R U P A 1
C4 C 0.4347(4) 0.9900(16) 0.7712(8) 0.0708(18) Uani 0.622(5) 1 d . U P A 1
H4 H 0.4277 0.9898 0.8437 0.085 Uiso 0.622(5) 1 calc R U P A 1
C5 C 0.4840(4) 0.8191(16) 0.7235(6) 0.0573(15) Uani 0.622(5) 1 d . U P A 1
C6 C 0.5296(4) 0.6254(16) 0.7700(7) 0.0566(16) Uani 0.622(5) 1 d . U P A 1
C7 C 0.5717(9) 0.498(3) 0.6887(13) 0.0537(19) Uani 0.622(5) 1 d . U P A 1
C8 C 0.6163(2) 0.3125(10) 0.7161(4) 0.064(2) Uani 0.622(5) 1 d . U P A 1
C9 C 0.6657(2) 0.1596(10) 0.6423(4) 0.0653(17) Uani 0.622(5) 1 d R U P A 1
C10 C 0.7053(2) -0.0397(10) 0.6878(4) 0.076(2) Uani 0.622(5) 1 d R U P A 1
H10 H 0.7013 -0.0731 0.7594 0.092 Uiso 0.622(5) 1 calc R U P A 1
C11 C 0.7509(2) -0.1889(10) 0.6260(4) 0.084(2) Uani 0.622(5) 1 d R U P A 1
H11 H 0.7774 -0.3221 0.6564 0.101 Uiso 0.622(5) 1 calc R U P A 1
C12 C 0.7569(2) -0.1388(10) 0.5189(4) 0.081(2) Uani 0.622(5) 1 d R U P A 1
H12 H 0.7875 -0.2387 0.4776 0.097 Uiso 0.622(5) 1 calc R U P A 1
C13 C 0.7174(2) 0.0604(10) 0.4735(4) 0.086(2) Uani 0.622(5) 1 d R U P A 1
H13 H 0.7214 0.0938 0.4018 0.103 Uiso 0.622(5) 1 calc R U P A 1
C14 C 0.6718(2) 0.2096(10) 0.5352(4) 0.076(2) Uani 0.622(5) 1 d R U P A 1
H14 H 0.6453 0.3429 0.5048 0.091 Uiso 0.622(5) 1 calc R U P A 1
C15 C 0.5494(3) 0.6206(11) 0.5860(5) 0.0559(14) Uani 0.622(5) 1 d . U P A 1
H15A H 0.5293 0.4920 0.5386 0.067 Uiso 0.622(5) 1 calc R U P A 1
H15B H 0.5897 0.7040 0.5518 0.067 Uiso 0.622(5) 1 calc R U P A 1
C16 C 0.4935(4) 0.8187(15) 0.6178(6) 0.0598(16) Uani 0.622(5) 1 d . U P A 1
O1B O 0.635(2) 0.262(7) 0.811(3) 0.077(5) Uani 0.378(5) 1 d . U P A 2
O2B O 0.5257(15) 0.550(6) 0.8413(15) 0.075(4) Uani 0.378(5) 1 d D U P A 2
H21B H 0.568(6) 0.48(3) 0.860(15) 0.112 Uiso 0.378(5) 1 d D U P A 2
C1B C 0.6907(7) 0.162(3) 0.4586(13) 0.081(3) Uani 0.378(5) 1 d . U P A 2
H1B H 0.6816 0.2305 0.3922 0.098 Uiso 0.378(5) 1 calc R U P A 2
C2B C 0.7421(8) -0.040(3) 0.4765(13) 0.084(3) Uani 0.378(5) 1 d . U P A 2
H2B H 0.7685 -0.1048 0.4204 0.101 Uiso 0.378(5) 1 calc R U P A 2
C3B C 0.7526(9) -0.136(3) 0.5741(14) 0.084(3) Uani 0.378(5) 1 d . U P A 2
H3B H 0.7853 -0.2707 0.5814 0.100 Uiso 0.378(5) 1 calc R U P A 2
C4B C 0.7212(8) -0.055(3) 0.6572(14) 0.079(3) Uani 0.378(5) 1 d . U P A 2
H4B H 0.7319 -0.1268 0.7226 0.094 Uiso 0.378(5) 1 calc R U P A 2
C5B C 0.6697(7) 0.145(3) 0.6478(12) 0.068(2) Uani 0.378(5) 1 d . U P A 2
C6B C 0.6281(7) 0.262(3) 0.7196(12) 0.063(2) Uani 0.378(5) 1 d . U P A 2
C7B C 0.5790(16) 0.458(5) 0.679(3) 0.058(2) Uani 0.378(5) 1 d . U P A 2
C8B C 0.5359(4) 0.5905(18) 0.7371(6) 0.061(2) Uani 0.378(5) 1 d . U P A 2
C9B C 0.4849(4) 0.7975(18) 0.7010(6) 0.062(2) Uani 0.378(5) 1 d R U P A 2
C10B C 0.4525(4) 0.9499(18) 0.7776(6) 0.072(3) Uani 0.378(5) 1 d R U P A 2
H10B H 0.4616 0.9185 0.8485 0.086 Uiso 0.378(5) 1 calc R U P A 2
C11B C 0.4064(4) 1.1490(18) 0.7484(6) 0.076(3) Uani 0.378(5) 1 d R U P A 2
H11B H 0.3846 1.2510 0.7997 0.092 Uiso 0.378(5) 1 calc R U P A 2
C12B C 0.3927(4) 1.1959(18) 0.6425(6) 0.073(3) Uani 0.378(5) 1 d R U P A 2
H12B H 0.3619 1.3292 0.6230 0.087 Uiso 0.378(5) 1 calc R U P A 2
C13B C 0.4252(4) 1.0435(18) 0.5659(6) 0.068(3) Uani 0.378(5) 1 d R U P A 2
H13B H 0.4161 1.0749 0.4951 0.082 Uiso 0.378(5) 1 calc R U P A 2
C14B C 0.4713(4) 0.8443(18) 0.5951(6) 0.063(3) Uani 0.378(5) 1 d R U P A 2
H14B H 0.4930 0.7424 0.5438 0.076 Uiso 0.378(5) 1 calc R U P A 2
C15B C 0.5972(5) 0.4502(19) 0.5618(8) 0.061(2) Uani 0.378(5) 1 d . U P A 2
H15C H 0.5557 0.4026 0.5203 0.073 Uiso 0.378(5) 1 calc R U P A 2
H15D H 0.6147 0.6175 0.5379 0.073 Uiso 0.378(5) 1 calc R U P A 2
C16B C 0.6537(8) 0.250(3) 0.5537(13) 0.073(2) Uani 0.378(5) 1 d . U P A 2






_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








































O1 C6 1.274(14) . ?
O2 C8 1.437(19) . ?
C1 C2 1.388(11) . ?
C1 C16 1.390(10) . ?
C2 C3 1.358(11) . ?
C3 C4 1.386(11) . ?
C4 C5 1.411(10) . ?
C5 C16 1.354(9) . ?
C5 C6 1.438(10) . ?
C6 C7 1.455(14) . ?
C7 C8 1.315(14) . ?
C7 C15 1.508(19) . ?
C8 C9 1.5344 . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C15 C16 1.516(10) . ?
O1B C6B 1.16(3) . ?
O2B C8B 1.35(2) . ?
C1B C2B 1.431(18) . ?
C1B C16B 1.465(19) . ?
C2B C3B 1.35(2) . ?
C3B C4B 1.28(2) . ?
C4B C5B 1.416(17) . ?
C5B C6B 1.340(15) . ?
C5B C16B 1.345(17) . ?
C6B C7B 1.46(3) . ?
C7B C8B 1.29(2) . ?
C7B C15B 1.53(3) . ?
C8B C9B 1.5008 . ?
C9B C14B 1.3900 . ?
C9B C10B 1.3900 . ?
C10B C11B 1.3900 . ?
C11B C12B 1.3900 . ?
C12B C13B 1.3900 . ?
C13B C14B 1.3900 . ?
C15B C16B 1.480(18) . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag
























































C2 C1 C16 118.3(8) . . ?
C3 C2 C1 121.3(8) . . ?
C2 C3 C4 120.8(8) . . ?
C3 C4 C5 117.9(8) . . ?
C16 C5 C4 120.8(8) . . ?
C16 C5 C6 109.2(7) . . ?
C4 C5 C6 130.0(8) . . ?
O1 C6 C5 127.6(9) . . ?
O1 C6 C7 122.3(11) . . ?
C5 C6 C7 109.9(10) . . ?
C8 C7 C6 118.8(13) . . ?
C8 C7 C15 135.1(10) . . ?
C6 C7 C15 106.1(9) . . ?
C7 C8 O2 123.0(13) . . ?
C7 C8 C9 126.4(7) . . ?
O2 C8 C9 110.5(10) . . ?
C10 C9 C14 120.0 . . ?
C10 C9 C8 116.5 . . ?
C14 C9 C8 123.5 . . ?
C11 C10 C9 120.0 . . ?
C10 C11 C12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C14 C9 120.0 . . ?
C7 C15 C16 103.9(6) . . ?
C5 C16 C1 120.8(7) . . ?
C5 C16 C15 110.8(7) . . ?
C1 C16 C15 128.3(7) . . ?
C2B C1B C16B 114.2(15) . . ?
C3B C2B C1B 120.6(16) . . ?
C4B C3B C2B 125.0(14) . . ?
C3B C4B C5B 118.6(15) . . ?
C6B C5B C16B 107.2(12) . . ?
C6B C5B C4B 131.6(13) . . ?
C16B C5B C4B 121.2(14) . . ?
O1B C6B C5B 128(2) . . ?
O1B C6B C7B 115(3) . . ?
C5B C6B C7B 115.7(15) . . ?
C8B C7B C6B 124(3) . . ?
C8B C7B C15B 136(2) . . ?
C6B C7B C15B 100.8(15) . . ?
C7B C8B O2B 124.7(19) . . ?
C7B C8B C9B 126.6(15) . . ?
O2B C8B C9B 108.6(13) . . ?
C14B C9B C10B 120.0 . . ?
C14B C9B C8B 122.4 . . ?
C10B C9B C8B 117.6 . . ?
C11B C10B C9B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C11B C12B C13B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C9B C14B C13B 120.0 . . ?
C16B C15B C7B 104.2(12) . . ?
C5B C16B C1B 120.3(14) . . ?
C5B C16B C15B 112.1(13) . . ?
C1B C16B C15B 127.6(13) . . ?



loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A


O2 H21 O1 0.90(7) 1.71(8) 2.50(3) 144(10) .
O2B H21B O1B 0.90(7) 1.78(15) 2.55(5) 141(18) .



_refine_diff_density_max         0.114

_refine_diff_density_min         -0.097

_refine_diff_density_rms         0.026



_shelxl_version_number           2013-2
_database_code_depnum_ccdc_archive 'CCDC 992714'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_4a



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         
'C51 H39 Fe O9'

_chemical_formula_sum            
'C51 H39 Fe O9'

_chemical_formula_weight         851.67



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source








C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'



_symmetry_cell_setting           hexagonal

_symmetry_space_group_name_H-M   'R -3'

_symmetry_space_group_name_Hall  '-R 3'



loop_

_symmetry_equiv_pos_as_xyz


















'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'



_cell_length_a                   14.6288(14)

_cell_length_b                   14.6288(14)

_cell_length_c                   33.985(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                120.00

_cell_volume                     6298.4(10)

_cell_formula_units_Z            6

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    1387

_cell_measurement_theta_min      2.78

_cell_measurement_theta_max      23.57



_exptl_crystal_description       octahedron

_exptl_crystal_colour            red

_exptl_crystal_size_min          0.136

_exptl_crystal_size_mid          0.221

_exptl_crystal_size_max          0.237

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.347

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             2658

_exptl_absorpt_coefficient_mu    0.419

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6139

_exptl_absorpt_correction_T_max  0.7452

_exptl_absorpt_process_details   '(Sheldrick, 2008)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'

_diffrn_measurement_method       ω-scans

_diffrn_detector_area_resol_mean 8.333

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        0

_diffrn_reflns_number            5901

_diffrn_reflns_av_R_equivalents  0.0521

_diffrn_reflns_av_sigmaI/netI    0.0896

_diffrn_reflns_limit_h_min       -16

_diffrn_reflns_limit_h_max       13

_diffrn_reflns_limit_k_min       -16

_diffrn_reflns_limit_k_max       16

_diffrn_reflns_limit_l_min       -14

_diffrn_reflns_limit_l_max       40

_diffrn_reflns_theta_min         1.72

_diffrn_reflns_theta_max         25.36

_reflns_number_total             2565

_reflns_number_gt                1367

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'

_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'

_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'

_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'



_refine_special_details          
; 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 

 goodness of fit S are based on F², conventional R-factors R are based 

 on F, with F set to zero for negative F². The threshold expression of 

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F² are statistically about twice as large as those based on F, and R- 

 factors based on ALL data will be even larger. 

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²] 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         2565

_refine_ls_number_parameters     185

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1346

_refine_ls_R_factor_gt           0.0601

_refine_ls_wR_factor_ref         0.1614

_refine_ls_wR_factor_gt          0.1289

_refine_ls_goodness_of_fit_ref   1.012

_refine_ls_restrained_S_all      1.012

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group


































Fe1 Fe 0.6667 0.3333 0.01166(3) 0.0478(4) Uani 1 3 d S . .
O2 O 0.5387(2) 0.2433(2) 0.04421(8) 0.0547(7) Uani 1 1 d . . .
C3 C 0.4570(3) 0.1596(3) 0.03175(12) 0.0491(10) Uani 1 1 d . . .
C4 C 0.3576(3) 0.1110(3) 0.05359(14) 0.0554(11) Uani 1 1 d . . .
C5 C 0.3348(4) 0.1383(4) 0.08995(15) 0.0745(14) Uani 1 1 d . . .
H5 H 0.3864 0.1943 0.1044 0.089 Uiso 1 1 calc R . .
C6 C 0.2336(5) 0.0799(4) 0.10370(18) 0.0978(18) Uani 1 1 d . . .
H6 H 0.2165 0.0955 0.1282 0.117 Uiso 1 1 calc R . .
C7 C 0.1575(4) -0.0005(5) 0.0821(2) 0.102(2) Uani 1 1 d . . .
H7 H 0.0887 -0.0363 0.0916 0.123 Uiso 1 1 calc R . .
C8 C 0.1794(4) -0.0305(4) 0.04652(18) 0.0915(17) Uani 1 1 d . . .
H8 H 0.1271 -0.0872 0.0325 0.110 Uiso 1 1 calc R . .
C9 C 0.2816(3) 0.0262(3) 0.03217(14) 0.0634(12) Uani 1 1 d . . .
C10 C 0.3313(3) 0.0107(3) -0.00398(14) 0.0658(13) Uani 1 1 d . . .
H10A H 0.2958 0.0140 -0.0276 0.079 Uiso 1 1 calc R . .
H10B H 0.3290 -0.0567 -0.0032 0.079 Uiso 1 1 calc R . .
C11 C 0.4445(3) 0.1017(3) -0.00263(13) 0.0503(10) Uani 1 1 d . . .
C12 C 0.5268(3) 0.1282(3) -0.02931(13) 0.0499(10) Uani 1 1 d . . .
C13 C 0.5195(3) 0.0729(3) -0.06653(12) 0.0515(10) Uani 1 1 d . . .
C14 C 0.4465(3) -0.0318(3) -0.07419(12) 0.0545(11) Uani 1 1 d . . .
H14 H 0.3967 -0.0712 -0.0551 0.065 Uiso 1 1 calc R . .
C15 C 0.4458(3) -0.0795(3) -0.10949(13) 0.0637(12) Uani 1 1 d . . .
H15 H 0.3976 -0.1506 -0.1136 0.076 Uiso 1 1 calc R . .
C16 C 0.5184(4) -0.0197(4) -0.13888(14) 0.0666(13) Uani 1 1 d . . .
C17 C 0.5911(4) 0.0844(4) -0.13176(15) 0.0792(15) Uani 1 1 d . . .
H17 H 0.6399 0.1249 -0.1510 0.095 Uiso 1 1 calc R . .
C18 C 0.5908(3) 0.1283(4) -0.09590(14) 0.0698(13) Uani 1 1 d . . .
H18 H 0.6411 0.1985 -0.0913 0.084 Uiso 1 1 calc R . .
O19 O 0.6199(2) 0.2086(2) -0.02293(8) 0.0556(7) Uani 1 1 d . . .
O20 O 0.5101(3) -0.0710(3) -0.17319(11) 0.0939(11) Uani 1 1 d . . .
C21 C 0.5786(5) -0.0092(5) -0.20454(17) 0.119(2) Uani 1 1 d . . .
H21A H 0.5683 -0.0538 -0.2268 0.179 Uiso 1 1 calc R . .
H21B H 0.6507 0.0230 -0.1959 0.179 Uiso 1 1 calc R . .
H21C H 0.5628 0.0448 -0.2119 0.179 Uiso 1 1 calc R . .






_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 O19 1.983(3) . ?
Fe1 O19 1.983(3) 2_655 ?
Fe1 O19 1.983(3) 3_665 ?
Fe1 O2 1.999(3) . ?
Fe1 O2 1.999(3) 2_655 ?
Fe1 O2 1.999(3) 3_665 ?
O2 C3 1.281(4) . ?
C3 C11 1.401(5) . ?
C3 C4 1.462(5) . ?
C4 C9 1.388(6) . ?
C4 C5 1.390(6) . ?
C5 C6 1.369(6) . ?
C6 C7 1.361(7) . ?
C7 C8 1.377(7) . ?
C8 C9 1.386(6) . ?
C9 C10 1.501(6) . ?
C10 C11 1.520(5) . ?
C11 C12 1.399(5) . ?
C12 O19 1.297(4) . ?
C12 C13 1.476(6) . ?
C13 C18 1.377(5) . ?
C13 C14 1.385(5) . ?
C14 C15 1.385(5) . ?
C15 C16 1.401(6) . ?
C16 O20 1.359(5) . ?
C16 C17 1.375(6) . ?
C17 C18 1.378(6) . ?
O20 C21 1.432(6) . ?



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
















































O19 Fe1 O19 88.45(11) . 2_655 ?
O19 Fe1 O19 88.45(11) . 3_665 ?
O19 Fe1 O19 88.45(11) 2_655 3_665 ?
O19 Fe1 O2 86.75(11) . . ?
O19 Fe1 O2 175.08(11) 2_655 . ?
O19 Fe1 O2 92.53(10) 3_665 . ?
O19 Fe1 O2 92.53(10) . 2_655 ?
O19 Fe1 O2 86.75(11) 2_655 2_655 ?
O19 Fe1 O2 175.07(11) 3_665 2_655 ?
O2 Fe1 O2 92.35(11) . 2_655 ?
O19 Fe1 O2 175.07(11) . 3_665 ?
O19 Fe1 O2 92.53(10) 2_655 3_665 ?
O19 Fe1 O2 86.75(11) 3_665 3_665 ?
O2 Fe1 O2 92.34(11) . 3_665 ?
O2 Fe1 O2 92.35(11) 2_655 3_665 ?
C3 O2 Fe1 124.4(3) . . ?
O2 C3 C11 129.1(4) . . ?
O2 C3 C4 121.5(4) . . ?
C11 C3 C4 109.4(4) . . ?
C9 C4 C5 121.6(4) . . ?
C9 C4 C3 109.0(4) . . ?
C5 C4 C3 129.4(4) . . ?
C6 C5 C4 117.6(5) . . ?
C7 C6 C5 121.1(5) . . ?
C6 C7 C8 121.9(5) . . ?
C7 C8 C9 118.1(5) . . ?
C8 C9 C4 119.5(5) . . ?
C8 C9 C10 131.1(5) . . ?
C4 C9 C10 109.4(4) . . ?
C9 C10 C11 104.0(4) . . ?
C12 C11 C3 122.6(4) . . ?
C12 C11 C10 129.3(4) . . ?
C3 C11 C10 108.1(4) . . ?
O19 C12 C11 120.7(4) . . ?
O19 C12 C13 113.3(4) . . ?
C11 C12 C13 125.9(4) . . ?
C18 C13 C14 116.9(4) . . ?
C18 C13 C12 118.2(4) . . ?
C14 C13 C12 124.9(4) . . ?
C13 C14 C15 121.8(4) . . ?
C14 C15 C16 119.3(4) . . ?
O20 C16 C17 124.7(5) . . ?
O20 C16 C15 115.9(4) . . ?
C17 C16 C15 119.5(4) . . ?
C16 C17 C18 119.4(4) . . ?
C13 C18 C17 123.0(4) . . ?
C12 O19 Fe1 131.0(3) . . ?
C16 O20 C21 116.6(4) . . ?



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.36

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.355

_refine_diff_density_min         -0.300

_refine_diff_density_rms         0.055








_database_code_depnum_ccdc_archive 'CCDC 992715'
