# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1043623'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_method           'APEX2 v2009.11-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Fe O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         416.24

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.68790(10)
_cell_length_b                   6.41630(10)
_cell_length_c                   34.7054(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.7760(10)
_cell_angle_gamma                90
_cell_volume                     1927.91(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.4722
_cell_measurement_theta_max      35.8087
_cell_measurement_temperature    90.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864

_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            29949
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         36.46
_diffrn_reflns_theta_full        36.46
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       57

_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.
;

_reflns_number_total             8888
_reflns_number_gt                7052
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0728
_refine_ls_goodness_of_fit_ref   2.394
_refine_ls_restrained_S_all      2.394
_refine_ls_number_reflns         8888
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.673
_refine_diff_density_min         -0.909
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2009, 11, 1, 0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe01 0.71062(2) 0.73034(3) 0.103624(5) 0.01693(5) Uani d . 1 . .
C C12 0.39363(12) 0.7738(2) 0.17319(4) 0.0179(2) Uani d . 1 . .
C C2 0.47023(12) 0.7780(2) 0.10349(4) 0.0189(2) Uani d . 1 . .
O O1 0.47727(10) 0.38976(14) 0.10439(3) 0.0280(2) Uani d . 1 . .
C C5 0.69058(12) 0.9004(2) 0.01557(4) 0.0173(2) Uani d . 1 . .
C C3 0.52938(13) 0.8982(2) 0.07417(4) 0.0186(2) Uani d . 1 . .
C C16 0.51781(14) 0.7662(2) 0.23748(4) 0.0234(2) Uani d . 1 . .
C C6 0.74094(13) 1.1061(2) 0.01885(4) 0.0203(2) Uani d . 1 . .
C C17 0.49672(13) 0.8628(2) 0.20165(4) 0.0198(2) Uani d . 1 . .
C C11 0.37180(16) 0.8704(2) 0.13344(4) 0.0236(2) Uani d . 1 . .
O O2 0.93316(10) 0.48444(14) 0.06406(3) 0.0285(2) Uani d . 1 . .
O O3 0.78498(10) 0.54786(16) 0.18029(3) 0.0296(2) Uani d . 1 . .
C C10 0.72366(13) 0.7877(2) -0.01690(4) 0.0204(2) Uani d . 1 . .
C C8 0.85756(13) 1.0782(2) -0.04133(4) 0.0231(2) Uani d . 1 . .
C C13 0.30880(13) 0.5971(2) 0.18202(4) 0.0210(2) Uani d . 1 . .
C C7 0.82409(14) 1.1939(2) -0.00961(4) 0.0227(2) Uani d . 1 . .
O O4 0.90220(11) 1.11253(16) 0.11795(3) 0.0322(2) Uani d . 1 . .
C C9 0.80663(14) 0.8763(2) -0.04535(4) 0.0237(2) Uani d . 1 . .
C C15 0.43999(14) 0.5878(2) 0.24630(4) 0.0241(2) Uani d . 1 . .
C C14 0.33405(14) 0.5073(2) 0.21826(4) 0.0238(2) Uani d . 1 . .
C C20 0.5835(2) 1.0610(2) 0.19476(6) 0.0304(4) Uani d . 1 . .
C C18 0.1863(2) 0.5072(2) 0.15342(5) 0.0358(4) Uani d . 1 . .
C C4 0.60488(13) 0.7971(2) 0.04502(4) 0.0183(2) Uani d . 1 . .
C C1 0.52604(13) 0.5641(2) 0.10257(4) 0.0202(2) Uani d . 1 . .
C C21 0.84637(13) 0.5774(2) 0.08018(4) 0.0208(2) Uani d . 1 . .
C C22 0.82730(14) 0.9695(2) 0.11166(4) 0.0211(2) Uani d . 1 . .
C C23 0.75504(13) 0.6266(2) 0.15111(4) 0.0205(2) Uani d . 1 . .
C C19 0.4659(2) 0.4837(4) 0.28499(5) 0.0425(5) Uani d . 1 . .
H H1 0.5694(13) 0.658(2) 0.0373(2) 0.017(3) Uiso d . 1 . .
H H2 0.5276(11) 1.047(2) 0.0756(2) 0.011(3) Uiso d . 1 . .
H H3 0.2638(15) 0.854(2) 0.1223(4) 0.026(4) Uiso d . 1 . .
H H4 0.3898(14) 1.015(2) 0.1344(4) 0.029(4) Uiso d . 1 . .
H H8 0.8292(13) 0.798(2) -0.0670(4) 0.025(4) Uiso d . 1 . .
H H7 0.9157(14) 1.138(2) -0.0615(4) 0.033(4) Uiso d . 1 . .
H H9 0.6874(13) 0.653(2) -0.0197(4) 0.019(4) Uiso d . 1 . .
H H5 0.7210(11) 1.1843(18) 0.0400(2) 0.011(3) Uiso d . 1 . .
H H6 0.8586(13) 1.328(2) -0.0057(2) 0.015(4) Uiso d . 1 . .
H H12 0.1039(17) 0.604(2) 0.1472(4) 0.039(5) Uiso d . 1 . .
H H13 0.2256(15) 0.468(2) 0.1289(5) 0.042(5) Uiso d . 1 . .
H H20 0.6436(15) 1.050(2) 0.1724(4) 0.039(4) Uiso d . 1 . .
H H14 0.1478(16) 0.384(2) 0.1640(4) 0.046(5) Uiso d . 1 . .
H H18 0.5176(16) 1.173(2) 0.1906(4) 0.041(5) Uiso d . 1 . .
H H19 0.6550(17) 1.090(2) 0.2169(5) 0.051(5) Uiso d . 1 . .
H H16 0.516(2) 0.372(3) 0.2843(5) 0.072(7) Uiso d . 1 . .
H H15 0.372(2) 0.472(3) 0.2968(5) 0.066(6) Uiso d . 1 . .
H H17 0.534(2) 0.559(3) 0.3012(5) 0.082(8) Uiso d . 1 . .
H H21 0.5811(14) 0.823(2) 0.2541(4) 0.013(4) Uiso d . 1 . .
H H22 0.2787(13) 0.388(2) 0.2239(4) 0.021(4) Uiso d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe01 C21 . 1.7823(13) ?
Fe01 C23 . 1.7894(15) ?
Fe01 C22 . 1.8475(15) ?
Fe01 C1 . 1.9236(13) ?
Fe01 C3 . 2.1013(13) ?
Fe01 C2 . 2.1103(11) ?
Fe01 C4 . 2.2029(13) ?
C12 C17 . 1.3986(18) ?
C12 C13 . 1.4002(17) ?
C12 C11 . 1.5099(18) ?
C2 C3 . 1.4075(17) ?
C2 C1 . 1.4563(18) ?
C2 C11 . 1.5205(17) ?
O1 C1 . 1.1999(15) ?
C5 C6 . 1.3923(18) ?
C5 C10 . 1.3892(17) ?
C5 C4 . 1.4714(17) ?
C3 C4 . 1.4087(17) ?
C3 H2 . 0.957(11) ?
C16 C15 . 1.377(2) ?
C16 C17 . 1.388(2) ?
C16 H21 . 0.846(12) ?
C6 C7 . 1.3905(18) ?
C6 H5 . 0.918(12) ?
C17 C20 . 1.508(2) ?
C11 H3 . 0.991(13) ?
C11 H4 . 0.943(14) ?
O2 C21 . 1.1433(14) ?
O3 C23 . 1.1423(15) ?
C10 C9 . 1.3915(18) ?
C10 H9 . 0.921(13) ?
C8 C9 . 1.372(2) ?
C8 C7 . 1.379(2) ?
C8 H7 . 0.975(13) ?
C13 C14 . 1.384(2) ?
C13 C18 . 1.508(2) ?
C7 H6 . 0.919(12) ?
O4 C22 . 1.1356(15) ?
C9 H8 . 0.937(13) ?
C15 C14 . 1.383(2) ?
C15 C19 . 1.500(2) ?
C14 H22 . 0.934(12) ?
C20 H20 . 0.973(14) ?
C20 H18 . 0.920(15) ?
C20 H19 . 0.966(16) ?
C18 H12 . 0.960(15) ?
C18 H13 . 0.976(15) ?
C18 H14 . 0.944(16) ?
C4 H1 . 0.973(12) ?
C19 H16 . 0.839(18) ?
C19 H15 . 0.949(17) ?
C19 H17 . 0.92(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 Fe01 C23 . . 96.62(6) ?
C21 Fe01 C22 . . 98.67(6) ?
C23 Fe01 C22 . . 95.53(6) ?
C21 Fe01 C1 . . 105.56(6) ?
C23 Fe01 C1 . . 85.80(6) ?
C22 Fe01 C1 . . 155.42(6) ?
C21 Fe01 C3 . . 123.90(6) ?
C23 Fe01 C3 . . 137.23(5) ?
C22 Fe01 C3 . . 91.56(6) ?
C1 Fe01 C3 . . 71.65(6) ?
C21 Fe01 C2 . . 140.45(6) ?
C23 Fe01 C2 . . 101.16(5) ?
C22 Fe01 C2 . . 114.24(5) ?
C1 Fe01 C2 . . 42.01(5) ?
C3 Fe01 C2 . . 39.05(5) ?
C21 Fe01 C4 . . 85.79(5) ?
C23 Fe01 C4 . . 164.58(6) ?
C22 Fe01 C4 . . 99.16(5) ?
C1 Fe01 C4 . . 78.89(5) ?
C3 Fe01 C4 . . 38.12(5) ?
C2 Fe01 C4 . . 68.48(5) ?
C17 C12 C13 . . 119.60(12) ?
C17 C12 C11 . . 120.13(12) ?
C13 C12 C11 . . 120.26(13) ?
C3 C2 C1 . . 110.99(11) ?
C3 C2 C11 . . 122.71(12) ?
C1 C2 C11 . . 126.13(12) ?
C3 C2 Fe01 . . 70.13(7) ?
C1 C2 Fe01 . . 62.12(7) ?
C11 C2 Fe01 . . 131.89(10) ?
C6 C5 C10 . . 118.37(12) ?
C6 C5 C4 . . 122.96(12) ?
C10 C5 C4 . . 118.68(12) ?
C2 C3 C4 . . 119.12(13) ?
C2 C3 Fe01 . . 70.82(7) ?
C4 C3 Fe01 . . 74.85(8) ?
C2 C3 H2 . . 120.1(7) ?
C4 C3 H2 . . 120.5(7) ?
Fe01 C3 H2 . . 120.1(7) ?
C15 C16 C17 . . 122.68(14) ?
C15 C16 H21 . . 120.8(9) ?
C17 C16 H21 . . 116.6(9) ?
C7 C6 C5 . . 120.30(13) ?
C7 C6 H5 . . 119.4(7) ?
C5 C6 H5 . . 120.3(7) ?
C16 C17 C12 . . 118.65(13) ?
C16 C17 C20 . . 119.24(14) ?
C12 C17 C20 . . 122.10(14) ?
C12 C11 C2 . . 115.44(11) ?
C12 C11 H3 . . 110.8(7) ?
C2 C11 H3 . . 105.0(7) ?
C12 C11 H4 . . 111.4(9) ?
C2 C11 H4 . . 107.9(8) ?
H3 C11 H4 . . 105.7(11) ?
C9 C10 C5 . . 121.13(14) ?
C9 C10 H9 . . 120.1(8) ?
C5 C10 H9 . . 118.7(8) ?
C9 C8 C7 . . 120.13(13) ?
C9 C8 H7 . . 118.5(8) ?
C7 C8 H7 . . 121.3(8) ?
C14 C13 C12 . . 119.29(13) ?
C14 C13 C18 . . 119.24(13) ?
C12 C13 C18 . . 121.42(14) ?
C8 C7 C6 . . 120.36(14) ?
C8 C7 H6 . . 122.4(8) ?
C6 C7 H6 . . 117.2(8) ?
C8 C9 C10 . . 119.71(14) ?
C8 C9 H8 . . 119.9(8) ?
C10 C9 H8 . . 120.4(8) ?
C14 C15 C16 . . 117.68(13) ?
C14 C15 C19 . . 120.34(16) ?
C16 C15 C19 . . 121.98(16) ?
C15 C14 C13 . . 122.00(13) ?
C15 C14 H22 . . 118.9(8) ?
C13 C14 H22 . . 119.1(8) ?
C17 C20 H20 . . 112.1(8) ?
C17 C20 H18 . . 111.7(9) ?
H20 C20 H18 . . 107.3(12) ?
C17 C20 H19 . . 109.6(9) ?
H20 C20 H19 . . 107.2(12) ?
H18 C20 H19 . . 108.9(13) ?
C13 C18 H12 . . 111.8(9) ?
C13 C18 H13 . . 113.2(8) ?
H12 C18 H13 . . 106.1(12) ?
C13 C18 H14 . . 108.4(10) ?
H12 C18 H14 . . 110.4(12) ?
H13 C18 H14 . . 106.7(13) ?
C3 C4 C5 . . 125.76(13) ?
C3 C4 Fe01 . . 67.03(7) ?
C5 C4 Fe01 . . 122.19(9) ?
C3 C4 H1 . . 117.6(7) ?
C5 C4 H1 . . 112.8(7) ?
Fe01 C4 H1 . . 100.1(7) ?
O1 C1 C2 . . 139.25(12) ?
O1 C1 Fe01 . . 144.43(11) ?
C2 C1 Fe01 . . 75.87(8) ?
O2 C21 Fe01 . . 177.48(12) ?
O4 C22 Fe01 . . 177.06(13) ?
O3 C23 Fe01 . . 175.45(12) ?
C15 C19 H16 . . 113.3(13) ?
C15 C19 H15 . . 110.6(11) ?
H16 C19 H15 . . 114.5(16) ?
C15 C19 H17 . . 110.7(12) ?
H16 C19 H17 . . 98.7(17) ?
H15 C19 H17 . . 108.4(16) ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane, Ethyl acetate'
_chemical_properties_physical    Photo-sensitive
