# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Cl1 Fe O4'
_chemical_formula_weight         438.69

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   5.8525(14)
_cell_length_b                   7.4196(18)
_cell_length_c                   45.092(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1958.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1097
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14455
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         28.38
_reflns_number_total             4873
_reflns_number_gt                4467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.031(17)
_refine_ls_number_reflns         4873
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.935
_refine_ls_restrained_S_all      1.935
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.007

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 0.24286(6) 0.76946(4) 0.801400(6) 0.03267(9) Uani 1 1 d . . .
Cl1 Cl 1.08474(17) 1.11494(10) 1.034999(16) 0.0593(2) Uani 1 1 d . . .
O1 O 0.2050(3) 0.9464(3) 0.87952(4) 0.0551(5) Uani 1 1 d . . .
O2 O 0.5311(3) 0.7894(2) 0.87553(4) 0.0450(5) Uani 1 1 d . . .
O3 O 0.7935(4) 1.1940(2) 0.90096(4) 0.0535(5) Uani 1 1 d . . .
O4 O 0.6936(4) 1.1006(3) 0.85588(4) 0.0654(7) Uani 1 1 d . . .
C4 C 0.2313(5) 0.7054(3) 0.84480(5) 0.0360(5) Uani 1 1 d . . .
C5 C 0.7503(6) 0.9593(3) 1.00312(5) 0.0440(6) Uani 1 1 d . . .
H5A H 0.6722 0.9478 1.0210 0.053 Uiso 1 1 calc R . .
C05 C 1.0797(5) 1.0552(3) 0.97613(6) 0.0416(6) Uani 1 1 d . . .
H05A H 1.2240 1.1075 0.9760 0.050 Uiso 1 1 calc R . .
C6 C 0.7684(5) 0.9160(3) 0.95004(5) 0.0374(5) Uani 1 1 d . . .
C8 C 0.9828(5) 0.9936(4) 0.95002(5) 0.0409(6) Uani 1 1 d . . .
H8A H 1.0629 1.0046 0.9323 0.049 Uiso 1 1 calc R . .
C10 C 0.7087(5) 1.0763(3) 0.88194(5) 0.0431(7) Uani 1 1 d . . .
C12 C 0.3120(4) 0.8288(3) 0.86804(5) 0.0366(6) Uani 1 1 d . . .
C012 C 0.3766(11) 0.8165(5) 0.76095(8) 0.0954(17) Uani 1 1 d . . .
H01A H 0.4265 0.7264 0.7464 0.114 Uiso 1 1 calc R . .
C13 C 0.2170(5) 0.4979(3) 0.80761(5) 0.0452(7) Uani 1 1 d . . .
H13A H 0.2617 0.4056 0.7932 0.054 Uiso 1 1 calc R . .
C14 C 0.0068(5) 0.7075(4) 0.83258(5) 0.0414(6) Uani 1 1 d . . .
H14A H -0.1203 0.7840 0.8390 0.050 Uiso 1 1 calc R . .
C15 C 0.3740(7) 1.0200(4) 0.79808(7) 0.0594(9) Uani 1 1 d . . .
H15A H 0.4215 1.0964 0.8147 0.071 Uiso 1 1 calc R . .
C17 C 0.3609(5) 0.5741(3) 0.82900(5) 0.0388(6) Uani 1 1 d . . .
H17A H 0.5214 0.5431 0.8325 0.047 Uiso 1 1 calc R . .
C21 C 0.0005(5) 0.5774(4) 0.80965(5) 0.0428(7) Uani 1 1 d . . .
H21A H -0.1314 0.5498 0.7971 0.051 Uiso 1 1 calc R . .
C22 C 0.6533(5) 0.8441(4) 0.92358(6) 0.0430(6) Uani 1 1 d . . .
H22 H 0.5796 0.7348 0.9267 0.052 Uiso 1 1 calc R . .
C24 C 0.8896(8) 1.3570(4) 0.88867(7) 0.0763(12) Uani 1 1 d . . .
H24A H 0.7701 1.4461 0.8860 0.092 Uiso 1 1 calc R . .
H24B H 0.9571 1.3317 0.8695 0.092 Uiso 1 1 calc R . .
C25 C 0.6552(5) 0.8969(3) 0.97717(6) 0.0422(6) Uani 1 1 d . . .
H25A H 0.5131 0.8409 0.9777 0.051 Uiso 1 1 calc R . .
C27 C 0.9608(5) 1.0383(3) 1.00224(5) 0.0389(6) Uani 1 1 d . . .
C28 C 0.5113(6) 0.8989(6) 0.78317(10) 0.0803(13) Uani 1 1 d . . .
H28A H 0.6730 0.8749 0.7872 0.096 Uiso 1 1 calc R . .
C29 C 0.1647(6) 1.0175(5) 0.78562(8) 0.0626(9) Uani 1 1 d . . .
H29A H 0.0345 1.0908 0.7921 0.075 Uiso 1 1 calc R . .
C30 C 0.1593(7) 0.8943(5) 0.76331(7) 0.0702(12) Uani 1 1 d . . .
H30A H 0.0271 0.8664 0.7508 0.084 Uiso 1 1 calc R . .
C33 C 0.6346(5) 0.9053(4) 0.89614(6) 0.0400(6) Uani 1 1 d . . .
C34 C 1.0631(8) 1.4270(5) 0.90868(8) 0.0906(13) Uani 1 1 d . . .
H34A H 1.1250 1.5365 0.9007 0.136 Uiso 1 1 calc R . .
H34B H 1.1830 1.3397 0.9109 0.136 Uiso 1 1 calc R . .
H34C H 0.9958 1.4509 0.9277 0.136 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 C012 2.015(3) . ?
Fe1 C28 2.016(3) . ?
Fe1 C4 2.015(2) . ?
Fe1 C30 2.012(3) . ?
Fe1 C15 2.017(3) . ?
Fe1 C14 2.024(3) . ?
Fe1 C29 2.026(3) . ?
Fe1 C17 2.031(2) . ?
Fe1 C13 2.040(2) . ?
Fe1 C21 2.045(3) . ?
Cl1 C27 1.741(3) . ?
O1 C12 1.192(3) . ?
O2 C12 1.358(3) . ?
O2 C33 1.403(3) . ?
O3 C10 1.321(3) . ?
O3 C24 1.444(4) . ?
O4 C10 1.192(3) . ?
C4 C14 1.425(4) . ?
C4 C17 1.425(3) . ?
C4 C12 1.470(3) . ?
C5 C27 1.365(4) . ?
C5 C25 1.376(4) . ?
C05 C27 1.373(4) . ?
C05 C8 1.384(4) . ?
C6 C8 1.381(4) . ?
C6 C25 1.398(3) . ?
C6 C22 1.470(3) . ?
C10 C33 1.486(4) . ?
C012 C30 1.401(6) . ?
C012 C28 1.414(6) . ?
C13 C17 1.399(4) . ?
C13 C21 1.401(4) . ?
C14 C21 1.415(4) . ?
C15 C29 1.348(5) . ?
C15 C28 1.380(5) . ?
C22 C33 1.322(3) . ?
C24 C34 1.454(5) . ?
C29 C30 1.360(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
C012 Fe1 C28 41.05(18) . . ?
C012 Fe1 C4 158.9(2) . . ?
C28 Fe1 C4 122.30(15) . . ?
C012 Fe1 C30 40.71(18) . . ?
C28 Fe1 C30 67.79(16) . . ?
C4 Fe1 C30 158.38(15) . . ?
C012 Fe1 C15 67.99(15) . . ?
C28 Fe1 C15 40.02(16) . . ?
C4 Fe1 C15 107.60(12) . . ?
C30 Fe1 C15 66.71(14) . . ?
C012 Fe1 C14 158.9(2) . . ?
C28 Fe1 C14 157.39(17) . . ?
C4 Fe1 C14 41.31(11) . . ?
C30 Fe1 C14 122.13(15) . . ?
C15 Fe1 C14 121.39(14) . . ?
C012 Fe1 C29 67.20(16) . . ?
C28 Fe1 C29 66.43(15) . . ?
C4 Fe1 C29 123.23(13) . . ?
C30 Fe1 C29 39.36(15) . . ?
C15 Fe1 C29 38.96(14) . . ?
C14 Fe1 C29 107.24(14) . . ?
C012 Fe1 C17 123.09(17) . . ?
C28 Fe1 C17 108.94(13) . . ?
C4 Fe1 C17 41.24(10) . . ?
C30 Fe1 C17 159.11(14) . . ?
C15 Fe1 C17 125.01(13) . . ?
C14 Fe1 C17 69.16(11) . . ?
C29 Fe1 C17 160.10(14) . . ?
C012 Fe1 C13 108.92(13) . . ?
C28 Fe1 C13 125.74(15) . . ?
C4 Fe1 C13 68.35(10) . . ?
C30 Fe1 C13 123.65(13) . . ?
C15 Fe1 C13 161.60(15) . . ?
C14 Fe1 C13 68.25(12) . . ?
C29 Fe1 C13 158.28(14) . . ?
C17 Fe1 C13 40.21(10) . . ?
C012 Fe1 C21 123.70(16) . . ?
C28 Fe1 C21 161.18(16) . . ?
C4 Fe1 C21 68.63(10) . . ?
C30 Fe1 C21 107.92(13) . . ?
C15 Fe1 C21 156.92(15) . . ?
C14 Fe1 C21 40.69(10) . . ?
C29 Fe1 C21 122.72(14) . . ?
C17 Fe1 C21 68.11(11) . . ?
C13 Fe1 C21 40.11(12) . . ?
C12 O2 C33 116.1(2) . . ?
C10 O3 C24 116.8(2) . . ?
C14 C4 C17 107.7(2) . . ?
C14 C4 C12 124.4(2) . . ?
C17 C4 C12 127.7(3) . . ?
C14 C4 Fe1 69.68(13) . . ?
C17 C4 Fe1 69.99(13) . . ?
C12 C4 Fe1 122.32(17) . . ?
C27 C5 C25 119.0(3) . . ?
C27 C05 C8 119.5(3) . . ?
C8 C6 C25 118.3(2) . . ?
C8 C6 C22 124.5(2) . . ?
C25 C6 C22 117.1(3) . . ?
C05 C8 C6 120.6(3) . . ?
O4 C10 O3 124.6(3) . . ?
O4 C10 C33 122.2(2) . . ?
O3 C10 C33 113.2(2) . . ?
O1 C12 O2 123.1(2) . . ?
O1 C12 C4 126.6(3) . . ?
O2 C12 C4 110.3(2) . . ?
C30 C012 C28 105.9(3) . . ?
C30 C012 Fe1 69.51(19) . . ?
C28 C012 Fe1 69.52(19) . . ?
C17 C13 C21 109.2(2) . . ?
C17 C13 Fe1 69.57(14) . . ?
C21 C13 Fe1 70.14(15) . . ?
C21 C14 C4 107.4(2) . . ?
C21 C14 Fe1 70.43(15) . . ?
C4 C14 Fe1 69.01(14) . . ?
C29 C15 C28 108.5(3) . . ?
C29 C15 Fe1 70.9(2) . . ?
C28 C15 Fe1 69.97(19) . . ?
C13 C17 C4 107.5(3) . . ?
C13 C17 Fe1 70.21(15) . . ?
C4 C17 Fe1 68.77(14) . . ?
C13 C21 C14 108.1(2) . . ?
C13 C21 Fe1 69.75(15) . . ?
C14 C21 Fe1 68.87(15) . . ?
C33 C22 C6 132.3(3) . . ?
O3 C24 C34 109.4(3) . . ?
C5 C25 C6 121.2(3) . . ?
C5 C27 C05 121.4(2) . . ?
C5 C27 Cl1 119.5(2) . . ?
C05 C27 Cl1 119.1(2) . . ?
C15 C28 C012 107.6(3) . . ?
C15 C28 Fe1 70.01(19) . . ?
C012 C28 Fe1 69.4(2) . . ?
C30 C29 C15 109.8(4) . . ?
C30 C29 Fe1 69.8(2) . . ?
C15 C29 Fe1 70.2(2) . . ?
C29 C30 C012 108.2(3) . . ?
C29 C30 Fe1 70.88(18) . . ?
C012 C30 Fe1 69.8(2) . . ?
C22 C33 O2 116.4(2) . . ?
C22 C33 C10 132.2(2) . . ?
O2 C33 C10 111.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 883909'
