# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 950008'
_audit_update_record             
;
2013-07-12 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cl Fe N4 O3'
_chemical_formula_weight         423.62

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9901(7)
_cell_length_b                   10.9240(11)
_cell_length_c                   12.1442(13)
_cell_angle_alpha                97.445(2)
_cell_angle_beta                 98.875(2)
_cell_angle_gamma                105.900(2)
_cell_volume                     866.64(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4427
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_type   ?
_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         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10846
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.60
_reflns_number_total             3948
_reflns_number_gt                3331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0532P)²+0.1172P] 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         3948
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.68391(4) 0.14721(2) 0.37899(2) 0.02897(10) Uani 1 1 d . . .
Cl1 Cl 0.97621(8) 0.21021(6) 0.30746(5) 0.04868(15) Uani 1 1 d . . .
O1 O 0.8098(2) 0.13408(13) 0.52626(11) 0.0359(3) Uani 1 1 d . . .
O2 O 0.5795(2) -0.02563(13) 0.30327(11) 0.0380(3) Uani 1 1 d . . .
O3 O 0.3990(2) 0.11436(13) 0.44376(12) 0.0393(3) Uani 1 1 d . . .
H3A H 0.3799 0.1745 0.4839 0.059 Uiso 1 1 d R . .
H3B H 0.3258 0.0397 0.4362 0.059 Uiso 1 1 d R . .
N1 N 0.6302(3) 0.64089(17) 0.41688(16) 0.0421(4) Uani 1 1 d . . .
N2 N 0.3245(4) 0.4166(2) 0.10777(18) 0.0617(6) Uani 1 1 d . . .
N3 N 0.7093(2) 0.34298(14) 0.44241(12) 0.0274(3) Uani 1 1 d . . .
N4 N 0.5033(2) 0.19776(14) 0.24455(12) 0.0292(3) Uani 1 1 d . . .
C1 C 0.8981(3) 0.22101(18) 0.61917(15) 0.0301(4) Uani 1 1 d . . .
C2 C 0.9984(3) 0.1821(2) 0.71139(17) 0.0378(4) Uani 1 1 d . . .
H2 H 1.0025 0.0972 0.7052 0.045 Uiso 1 1 calc R . .
C3 C 1.0901(3) 0.2678(2) 0.81042(17) 0.0429(5) Uani 1 1 d . . .
H3 H 1.1553 0.2399 0.8705 0.051 Uiso 1 1 calc R . .
C4 C 1.0878(3) 0.3963(2) 0.82297(17) 0.0457(5) Uani 1 1 d . . .
H4 H 1.1510 0.4534 0.8907 0.055 Uiso 1 1 calc R . .
C5 C 0.9918(3) 0.4372(2) 0.73459(16) 0.0375(4) Uani 1 1 d . . .
H5 H 0.9893 0.5225 0.7430 0.045 Uiso 1 1 calc R . .
C6 C 0.8960(3) 0.35199(18) 0.63046(15) 0.0302(4) Uani 1 1 d . . .
C7 C 0.8040(3) 0.40589(17) 0.54430(15) 0.0289(4) Uani 1 1 d . . .
H7 H 0.8114 0.4928 0.5615 0.035 Uiso 1 1 calc R . .
C8 C 0.6152(3) 0.40153(17) 0.36469(15) 0.0282(4) Uani 1 1 d . . .
C9 C 0.6239(3) 0.53546(18) 0.39165(16) 0.0312(4) Uani 1 1 d . . .
C10 C 0.5086(3) 0.32690(18) 0.26331(15) 0.0298(4) Uani 1 1 d . . .
C11 C 0.4070(3) 0.3796(2) 0.17853(18) 0.0391(4) Uani 1 1 d . . .
C12 C 0.3925(3) 0.11819(19) 0.15320(16) 0.0333(4) Uani 1 1 d . . .
H12 H 0.3207 0.1520 0.1002 0.040 Uiso 1 1 calc R . .
C13 C 0.3727(3) -0.01521(19) 0.12831(16) 0.0336(4) Uani 1 1 d . . .
C14 C 0.2524(3) -0.0861(2) 0.02256(17) 0.0417(5) Uani 1 1 d . . .
H14 H 0.1891 -0.0436 -0.0262 0.050 Uiso 1 1 calc R . .
C15 C 0.2267(4) -0.2144(2) -0.00961(18) 0.0493(6) Uani 1 1 d . . .
H15 H 0.1484 -0.2588 -0.0798 0.059 Uiso 1 1 calc R . .
C16 C 0.3197(4) -0.2789(2) 0.06433(19) 0.0464(5) Uani 1 1 d . . .
H16 H 0.3022 -0.3667 0.0428 0.056 Uiso 1 1 calc R . .
C17 C 0.4365(3) -0.21455(19) 0.16817(17) 0.0382(4) Uani 1 1 d . . .
H17 H 0.4963 -0.2596 0.2159 0.046 Uiso 1 1 calc R . .
C18 C 0.4667(3) -0.08255(18) 0.20325(15) 0.0312(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
Fe1 O2 1.8791(14) . ?
Fe1 O1 1.9086(13) . ?
Fe1 N3 2.1263(15) . ?
Fe1 N4 2.1317(15) . ?
Fe1 O3 2.2086(13) . ?
Fe1 Cl1 2.3098(6) . ?
O1 C1 1.320(2) . ?
O2 C18 1.313(2) . ?
O3 H3A 0.8200 . ?
O3 H3B 0.8200 . ?
N1 C9 1.140(3) . ?
N2 C11 1.140(3) . ?
N3 C7 1.311(2) . ?
N3 C8 1.389(2) . ?
N4 C12 1.305(2) . ?
N4 C10 1.389(2) . ?
C1 C2 1.404(3) . ?
C1 C6 1.424(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.420(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.364(3) . ?
C8 C9 1.439(3) . ?
C10 C11 1.431(3) . ?
C12 C13 1.413(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.417(3) . ?
C13 C18 1.434(3) . ?
C14 C15 1.360(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(3) . ?
C17 H17 0.9300 . ?

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
O2 Fe1 O1 103.59(6) . . ?
O2 Fe1 N3 162.05(6) . . ?
O1 Fe1 N3 88.82(6) . . ?
O2 Fe1 N4 87.98(6) . . ?
O1 Fe1 N4 162.52(6) . . ?
N3 Fe1 N4 77.20(6) . . ?
O2 Fe1 O3 86.39(6) . . ?
O1 Fe1 O3 86.53(6) . . ?
N3 Fe1 O3 81.40(5) . . ?
N4 Fe1 O3 81.10(6) . . ?
O2 Fe1 Cl1 99.76(5) . . ?
O1 Fe1 Cl1 97.32(5) . . ?
N3 Fe1 Cl1 91.31(4) . . ?
N4 Fe1 Cl1 93.48(4) . . ?
O3 Fe1 Cl1 171.71(4) . . ?
C1 O1 Fe1 132.37(12) . . ?
C18 O2 Fe1 134.02(12) . . ?
Fe1 O3 H3A 119.1 . . ?
Fe1 O3 H3B 118.2 . . ?
H3A O3 H3B 121.8 . . ?
C7 N3 C8 121.54(16) . . ?
C7 N3 Fe1 124.90(12) . . ?
C8 N3 Fe1 113.56(11) . . ?
C12 N4 C10 121.14(16) . . ?
C12 N4 Fe1 125.38(13) . . ?
C10 N4 Fe1 113.46(11) . . ?
O1 C1 C2 118.29(18) . . ?
O1 C1 C6 123.21(17) . . ?
C2 C1 C6 118.50(17) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.28(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 116.18(18) . . ?
C5 C6 C1 118.87(17) . . ?
C7 C6 C1 124.94(17) . . ?
N3 C7 C6 125.21(17) . . ?
N3 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
C10 C8 N3 117.80(16) . . ?
C10 C8 C9 121.03(16) . . ?
N3 C8 C9 121.13(16) . . ?
N1 C9 C8 177.5(2) . . ?
C8 C10 N4 117.67(16) . . ?
C8 C10 C11 121.39(17) . . ?
N4 C10 C11 120.94(17) . . ?
N2 C11 C10 177.0(2) . . ?
N4 C12 C13 125.23(17) . . ?
N4 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
C12 C13 C14 117.60(18) . . ?
C12 C13 C18 124.03(17) . . ?
C14 C13 C18 118.37(18) . . ?
C15 C14 C13 121.9(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
O2 C18 C17 118.69(18) . . ?
O2 C18 C13 122.87(17) . . ?
C17 C18 C13 118.43(17) . . ?

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
O2 Fe1 O1 C1 -175.32(16) . . . . ?
N3 Fe1 O1 C1 -8.43(17) . . . . ?
N4 Fe1 O1 C1 -45.0(3) . . . . ?
O3 Fe1 O1 C1 -89.89(17) . . . . ?
Cl1 Fe1 O1 C1 82.74(16) . . . . ?
O1 Fe1 O2 C18 174.90(17) . . . . ?
N3 Fe1 O2 C18 42.2(3) . . . . ?
N4 Fe1 O2 C18 8.14(18) . . . . ?
O3 Fe1 O2 C18 89.35(18) . . . . ?
Cl1 Fe1 O2 C18 -85.04(18) . . . . ?
O2 Fe1 N3 C7 140.40(19) . . . . ?
O1 Fe1 N3 C7 6.05(15) . . . . ?
N4 Fe1 N3 C7 175.48(15) . . . . ?
O3 Fe1 N3 C7 92.72(14) . . . . ?
Cl1 Fe1 N3 C7 -91.25(14) . . . . ?
O2 Fe1 N3 C8 -39.8(2) . . . . ?
O1 Fe1 N3 C8 -174.19(12) . . . . ?
N4 Fe1 N3 C8 -4.76(11) . . . . ?
O3 Fe1 N3 C8 -87.52(12) . . . . ?
Cl1 Fe1 N3 C8 88.51(11) . . . . ?
O2 Fe1 N4 C12 -4.24(16) . . . . ?
O1 Fe1 N4 C12 -136.39(19) . . . . ?
N3 Fe1 N4 C12 -174.03(16) . . . . ?
O3 Fe1 N4 C12 -90.89(16) . . . . ?
Cl1 Fe1 N4 C12 95.42(15) . . . . ?
O2 Fe1 N4 C10 174.26(12) . . . . ?
O1 Fe1 N4 C10 42.1(3) . . . . ?
N3 Fe1 N4 C10 4.47(12) . . . . ?
O3 Fe1 N4 C10 87.60(12) . . . . ?
Cl1 Fe1 N4 C10 -86.08(12) . . . . ?
Fe1 O1 C1 C2 -172.62(13) . . . . ?
Fe1 O1 C1 C6 7.6(3) . . . . ?
O1 C1 C2 C3 -179.07(18) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 -179.04(18) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
O1 C1 C6 C5 178.71(17) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
O1 C1 C6 C7 -1.3(3) . . . . ?
C2 C1 C6 C7 178.94(17) . . . . ?
C8 N3 C7 C6 176.98(16) . . . . ?
Fe1 N3 C7 C6 -3.3(3) . . . . ?
C5 C6 C7 N3 179.62(17) . . . . ?
C1 C6 C7 N3 -0.4(3) . . . . ?
C7 N3 C8 C10 -175.72(16) . . . . ?
Fe1 N3 C8 C10 4.5(2) . . . . ?
C7 N3 C8 C9 2.2(3) . . . . ?
Fe1 N3 C8 C9 -177.56(13) . . . . ?
C10 C8 C9 N1 140(5) . . . . ?
N3 C8 C9 N1 -38(5) . . . . ?
N3 C8 C10 N4 -0.6(3) . . . . ?
C9 C8 C10 N4 -178.51(15) . . . . ?
N3 C8 C10 C11 179.99(16) . . . . ?
C9 C8 C10 C11 2.1(3) . . . . ?
C12 N4 C10 C8 174.93(17) . . . . ?
Fe1 N4 C10 C8 -3.6(2) . . . . ?
C12 N4 C10 C11 -5.6(3) . . . . ?
Fe1 N4 C10 C11 175.80(14) . . . . ?
C8 C10 C11 N2 171(5) . . . . ?
N4 C10 C11 N2 -8(5) . . . . ?
C10 N4 C12 C13 -178.04(17) . . . . ?
Fe1 N4 C12 C13 0.4(3) . . . . ?
N4 C12 C13 C14 -177.34(18) . . . . ?
N4 C12 C13 C18 2.6(3) . . . . ?
C12 C13 C14 C15 179.1(2) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
Fe1 O2 C18 C17 172.35(14) . . . . ?
Fe1 O2 C18 C13 -7.7(3) . . . . ?
C16 C17 C18 O2 179.98(19) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C12 C13 C18 O2 0.6(3) . . . . ?
C14 C13 C18 O2 -179.44(18) . . . . ?
C12 C13 C18 C17 -179.52(18) . . . . ?
C14 C13 C18 C17 0.5(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
O3 H3A N1 0.82 2.24 3.047(2) 170.6 2_666
O3 H3B O1 0.82 2.02 2.8068(19) 160.5 2_656

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.057
