# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_exp_6679
_database_code_depnum_ccdc_archive 'CCDC 1509251'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cl Fe0.50 N2 O9'
_chemical_formula_weight         441.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   22.891(9)
_cell_length_b                   10.538(2)
_cell_length_c                   19.245(6)
_cell_angle_alpha                90
_cell_angle_beta                 127.27(5)
_cell_angle_gamma                90
_cell_volume                     3694(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1108
_cell_measurement_theta_min      4.7800
_cell_measurement_theta_max      58.1950

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    5.364
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.705
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11618
_diffrn_reflns_av_unetI/netI     0.1259
_diffrn_reflns_av_R_equivalents  0.1250
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.792
_diffrn_reflns_theta_max         66.957
_diffrn_reflns_theta_full        66.958
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3298
_reflns_number_gt                1394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1540P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     260
_refine_ls_number_restraints     732
_refine_ls_R_factor_all          0.1873
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_ref         0.3022
_refine_ls_wR_factor_gt          0.2364
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.962
_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
Fe1 Fe 0.5000 0.96609(17) 0.7500 0.0515(6) Uani 1 2 d S TU P . .
Cl1 Cl 0.28001(19) 0.5206(3) 0.3688(2) 0.0901(9) Uani 1 1 d . U . . .
N1 N 0.4241(4) 1.0509(7) 0.6222(4) 0.0569(16) Uani 1 1 d . U . . .
N2 N 0.5185(4) 0.8628(6) 0.6671(5) 0.0581(16) Uani 1 1 d . U . . .
O1 O 0.4275(3) 1.1377(6) 0.7515(4) 0.0676(17) Uani 1 1 d . U . . .
O2 O 0.3479(3) 1.2935(6) 0.6674(4) 0.0705(17) Uani 1 1 d . U . . .
O3 O 0.6578(4) 0.6509(6) 0.8139(5) 0.084(2) Uani 1 1 d . U . . .
O4 O 0.6047(4) 0.8103(6) 0.8341(4) 0.0742(18) Uani 1 1 d . U . . .
O5 O 0.2543(7) 0.4848(10) 0.4149(7) 0.149(4) Uani 1 1 d . U . . .
O6 O 0.2374(7) 0.6162(10) 0.3111(7) 0.164(4) Uani 1 1 d . U . . .
O7 O 0.3523(7) 0.5408(13) 0.4185(9) 0.202(5) Uani 1 1 d . U . . .
O8 O 0.2692(7) 0.4149(11) 0.3170(7) 0.177(5) Uani 1 1 d . U . . .
O9 O 0.4580(8) 0.4656(13) 0.6191(11) 0.272(7) Uani 1 1 d . U . . .
H9C H 0.4239 0.4746 0.5648 0.326 Uiso 1 1 d R U . . .
H9D H 0.4913 0.5195 0.6340 0.326 Uiso 1 1 d R U . . .
C1 C 0.3886(5) 1.1927(9) 0.6831(6) 0.062(2) Uani 1 1 d . U . . .
C2 C 0.3818(5) 1.1506(9) 0.6042(6) 0.062(2) Uani 1 1 d . U . . .
C3 C 0.3378(5) 1.2068(10) 0.5215(6) 0.072(2) Uani 1 1 d . U . . .
H3 H 0.3104 1.2793 0.5114 0.086 Uiso 1 1 calc R U . . .
C4 C 0.3362(6) 1.1521(11) 0.4561(7) 0.079(3) Uani 1 1 d . U . . .
H4 H 0.3070 1.1873 0.4004 0.095 Uiso 1 1 calc R U . . .
C5 C 0.3774(6) 1.0453(11) 0.4714(6) 0.075(2) Uani 1 1 d . U . . .
C6 C 0.4230(5) 0.9984(9) 0.5570(6) 0.064(2) Uani 1 1 d . U . . .
C7 C 0.4726(5) 0.8952(9) 0.5817(6) 0.0642(19) Uani 1 1 d . U . . .
C8 C 0.4738(6) 0.8279(10) 0.5169(6) 0.075(2) Uani 1 1 d . U . . .
C9 C 0.4242(6) 0.8786(11) 0.4296(6) 0.082(2) Uani 1 1 d . U . . .
H9 H 0.4228 0.8382 0.3856 0.098 Uiso 1 1 calc R U . . .
C10 C 0.3801(6) 0.9790(11) 0.4068(6) 0.082(3) Uani 1 1 d . U . . .
H10 H 0.3508 1.0067 0.3491 0.098 Uiso 1 1 calc R U . . .
C11 C 0.5220(6) 0.7308(11) 0.5471(7) 0.084(2) Uani 1 1 d . U . . .
H11 H 0.5228 0.6831 0.5071 0.101 Uiso 1 1 calc R U . . .
C12 C 0.5696(6) 0.6988(10) 0.6337(7) 0.081(2) Uani 1 1 d . U . . .
H12 H 0.6033 0.6331 0.6532 0.097 Uiso 1 1 calc R U . . .
C13 C 0.5648(6) 0.7695(9) 0.6904(7) 0.070(2) Uani 1 1 d . U . . .
C14 C 0.6118(6) 0.7474(9) 0.7874(7) 0.071(2) Uani 1 1 d . U . . .
C15 C 0.3506(6) 1.3389(9) 0.7434(7) 0.083(3) Uani 1 1 d . U . . .
H15A H 0.3278 1.2771 0.7566 0.125 Uiso 1 1 calc R U . . .
H15B H 0.3249 1.4181 0.7287 0.125 Uiso 1 1 calc R U . . .
H15C H 0.4008 1.3504 0.7933 0.125 Uiso 1 1 calc R U . . .
C16 C 0.7070(8) 0.6281(11) 0.9074(8) 0.123(5) Uani 1 1 d . U . . .
H16A H 0.7469 0.6875 0.9345 0.185 Uiso 1 1 calc R U . . .
H16B H 0.7259 0.5432 0.9183 0.185 Uiso 1 1 calc R U . . .
H16C H 0.6807 0.6385 0.9313 0.185 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 N1 2.166(7) 2_656 ?
Fe1 N1 2.166(7) . ?
Fe1 N2 2.173(7) 2_656 ?
Fe1 N2 2.173(7) . ?
Cl1 O7 1.335(13) . ?
Cl1 O6 1.374(10) . ?
Cl1 O5 1.381(9) . ?
Cl1 O8 1.413(11) . ?
N1 C2 1.325(11) . ?
N1 C6 1.356(10) . ?
N2 C13 1.311(11) . ?
N2 C7 1.354(11) . ?
O1 C1 1.201(10) . ?
O2 C1 1.322(10) . ?
O2 C15 1.504(11) . ?
O3 C14 1.324(11) . ?
O3 C16 1.453(13) . ?
O4 C14 1.203(10) . ?
C1 C2 1.497(12) . ?
C2 C3 1.399(12) . ?
C3 C4 1.365(13) . ?
C4 C5 1.380(14) . ?
C5 C6 1.402(13) . ?
C5 C10 1.461(14) . ?
C6 C7 1.430(13) . ?
C7 C8 1.449(12) . ?
C8 C11 1.351(14) . ?
C8 C9 1.445(14) . ?
C9 C10 1.340(15) . ?
C11 C12 1.371(14) . ?
C12 C13 1.378(12) . ?
C13 C14 1.506(13) . ?

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
N1 Fe1 N1 131.3(4) 2_656 . ?
N1 Fe1 N2 75.6(3) 2_656 2_656 ?
N1 Fe1 N2 131.4(3) . 2_656 ?
N1 Fe1 N2 131.4(3) 2_656 . ?
N1 Fe1 N2 75.6(3) . . ?
N2 Fe1 N2 119.9(4) 2_656 . ?
O7 Cl1 O6 115.3(9) . . ?
O7 Cl1 O5 114.1(9) . . ?
O6 Cl1 O5 110.5(7) . . ?
O7 Cl1 O8 104.0(8) . . ?
O6 Cl1 O8 105.8(7) . . ?
O5 Cl1 O8 106.1(8) . . ?
C2 N1 C6 118.7(8) . . ?
C2 N1 Fe1 125.5(6) . . ?
C6 N1 Fe1 115.8(6) . . ?
C13 N2 C7 118.4(8) . . ?
C13 N2 Fe1 127.0(6) . . ?
C7 N2 Fe1 114.4(6) . . ?
C1 O2 C15 115.2(7) . . ?
C14 O3 C16 116.3(8) . . ?
O1 C1 O2 126.2(9) . . ?
O1 C1 C2 121.4(9) . . ?
O2 C1 C2 112.4(8) . . ?
N1 C2 C3 122.9(9) . . ?
N1 C2 C1 111.1(8) . . ?
C3 C2 C1 126.0(9) . . ?
C4 C3 C2 117.9(10) . . ?
C3 C4 C5 120.9(10) . . ?
C4 C5 C6 117.7(10) . . ?
C4 C5 C10 125.7(10) . . ?
C6 C5 C10 116.5(11) . . ?
N1 C6 C5 121.7(10) . . ?
N1 C6 C7 115.9(8) . . ?
C5 C6 C7 122.3(9) . . ?
N2 C7 C6 118.0(8) . . ?
N2 C7 C8 121.2(10) . . ?
C6 C7 C8 120.8(9) . . ?
C11 C8 C9 130.0(10) . . ?
C11 C8 C7 115.9(10) . . ?
C9 C8 C7 114.1(10) . . ?
C10 C9 C8 125.3(10) . . ?
C9 C10 C5 120.8(10) . . ?
C8 C11 C12 123.4(10) . . ?
C11 C12 C13 116.3(11) . . ?
N2 C13 C12 124.8(10) . . ?
N2 C13 C14 111.2(8) . . ?
C12 C13 C14 124.0(10) . . ?
O4 C14 O3 124.8(10) . . ?
O4 C14 C13 121.6(10) . . ?
O3 C14 C13 113.6(9) . . ?

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.093



