# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_namikoz45
_database_code_depnum_ccdc_archive 'CCDC 1001379'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cl Fe N3 O5 S'
_chemical_formula_sum            'C17 H17 Cl Fe N3 O5 S'
_chemical_formula_weight         466.69

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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.9857(8)
_cell_length_b                   7.8019(4)
_cell_length_c                   19.1976(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.655(5)
_cell_angle_gamma                90
_cell_volume                     1904.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    8456
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      27.77

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.077
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8081
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            13160
_diffrn_reflns_av_unetI/netI     0.1352
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.601
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_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             3751
_reflns_number_gt                1643
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia, 2012) and PLATON (Spek, 2009)'

_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)+(0.0399P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3751
_refine_ls_number_parameters     262
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1523
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_restrained_S_all      0.876
_refine_ls_shift/su_max          0.001
_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 0.72522(6) 0.40749(12) 0.55834(4) 0.0527(3) Uani 1 1 d . . . . .
Cl1 Cl 0.81609(13) 0.1731(2) 0.59416(8) 0.0716(5) Uani 1 1 d . . . . .
S1 S 0.61854(15) 0.2799(3) 0.32000(9) 0.0863(7) Uani 1 1 d . . . . .
O1 O 0.6015(3) 0.3929(6) 0.59865(17) 0.0558(10) Uani 1 1 d D . . . .
O2 O 0.2963(4) 0.1418(8) 0.6533(3) 0.0937(16) Uani 1 1 d . . . . .
H2A H 0.3253 0.1696 0.6937 0.141 Uiso 1 1 calc R U . . .
O3 O 0.7908(3) 0.5872(6) 0.61541(18) 0.0604(11) Uani 1 1 d . . . . .
O4 O 0.8763(3) 0.7552(6) 0.7306(2) 0.0658(12) Uani 1 1 d D . . . .
O5W O 0.6505(4) 0.6794(9) 0.7080(3) 0.1044(18) Uani 1 1 d D . . . .
N1 N 0.6302(4) 0.3394(7) 0.4613(2) 0.0552(13) Uani 1 1 d . . . . .
N2 N 0.7657(4) 0.4431(7) 0.4101(2) 0.0674(16) Uani 1 1 d . . . . .
N3 N 0.7989(4) 0.5025(7) 0.4797(2) 0.0581(14) Uani 1 1 d . . . . .
C1 C 0.5159(4) 0.3004(8) 0.5793(3) 0.0490(15) Uani 1 1 d . . . . .
C2 C 0.4533(4) 0.2685(8) 0.6284(3) 0.0549(16) Uani 1 1 d . . . . .
H2 H 0.4735 0.3086 0.6748 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3598(5) 0.1760(9) 0.6082(3) 0.0627(18) Uani 1 1 d . . . . .
C4 C 0.3277(5) 0.1173(9) 0.5389(3) 0.0664(18) Uani 1 1 d . . . . .
H4 H 0.2654 0.0558 0.5260 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3862(5) 0.1491(8) 0.4912(3) 0.0609(18) Uani 1 1 d . . . . .
H5 H 0.3631 0.1105 0.4448 0.073 Uiso 1 1 calc R U . . .
C6 C 0.4815(4) 0.2389(8) 0.5082(3) 0.0516(15) Uani 1 1 d . . . . .
C7 C 0.5381(5) 0.2649(8) 0.4537(3) 0.0571(17) Uani 1 1 d . . . . .
H7 H 0.5076 0.2258 0.4085 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6773(5) 0.3595(9) 0.4026(3) 0.0593(18) Uani 1 1 d . . . . .
C9 C 0.8771(5) 0.6066(10) 0.4872(3) 0.0673(18) Uani 1 1 d . . . . .
H9 H 0.9059 0.6288 0.4476 0.081 Uiso 1 1 calc R U . . .
C10 C 0.9233(5) 0.6919(9) 0.5533(3) 0.0601(17) Uani 1 1 d . . . . .
C11 C 1.0114(5) 0.7960(10) 0.5553(4) 0.0716(19) Uani 1 1 d . . . . .
H11 H 1.0393 0.8085 0.5146 0.086 Uiso 1 1 calc R U . . .
C12 C 1.0568(5) 0.8788(10) 0.6156(4) 0.077(2) Uani 1 1 d . . . . .
H12 H 1.1171 0.9440 0.6167 0.092 Uiso 1 1 calc R U . . .
C13 C 1.0133(5) 0.8666(9) 0.6758(4) 0.071(2) Uani 1 1 d . . . . .
H13 H 1.0447 0.9248 0.7170 0.085 Uiso 1 1 calc R U . . .
C14 C 0.9257(5) 0.7709(8) 0.6757(3) 0.0544(16) Uani 1 1 d . . . . .
C15 C 0.8779(5) 0.6800(9) 0.6135(3) 0.0575(16) Uani 1 1 d . . . . .
C16 C 0.7069(6) 0.3452(15) 0.2660(3) 0.125(4) Uani 1 1 d . . . . .
H16A H 0.6833 0.4514 0.2430 0.187 Uiso 1 1 calc R U . . .
H16B H 0.7098 0.2590 0.2308 0.187 Uiso 1 1 calc R U . . .
H16C H 0.7757 0.3606 0.2951 0.187 Uiso 1 1 calc R U . . .
C17 C 0.9212(5) 0.8388(11) 0.7960(3) 0.089(2) Uani 1 1 d . . . . .
H17A H 0.9890 0.7902 0.8150 0.133 Uiso 1 1 calc R U . . .
H17B H 0.8760 0.8234 0.8294 0.133 Uiso 1 1 calc R U . . .
H17C H 0.9287 0.9590 0.7874 0.133 Uiso 1 1 calc R U . . .
H5A H 0.7137(19) 0.690(9) 0.702(3) 0.133 Uiso 1 1 d D U . . .
H5B H 0.622(4) 0.595(8) 0.682(4) 0.133 Uiso 1 1 d D 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 O3 1.874(4) . ?
Fe1 O1 1.923(4) . ?
Fe1 N3 2.080(5) . ?
Fe1 N1 2.085(4) . ?
Fe1 Cl1 2.2093(19) . ?
S1 C8 1.730(6) . ?
S1 C16 1.769(7) . ?
O1 C1 1.314(7) . ?
O2 C3 1.338(7) . ?
O2 H2A 0.8200 . ?
O3 C15 1.350(7) . ?
O4 C14 1.346(7) . ?
O4 C17 1.430(6) . ?
O5W H5A 0.856(18) . ?
O5W H5B 0.858(16) . ?
N1 C7 1.311(7) . ?
N1 C8 1.395(7) . ?
N2 C8 1.304(8) . ?
N2 N3 1.399(6) . ?
N3 C9 1.285(8) . ?
C1 C2 1.386(7) . ?
C1 C6 1.431(7) . ?
C2 C3 1.399(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(8) . ?
C4 C5 1.326(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(8) . ?
C7 H7 0.9300 . ?
C9 C10 1.452(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(9) . ?
C10 C15 1.402(8) . ?
C11 C12 1.353(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.420(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O3 Fe1 O1 97.27(17) . . ?
O3 Fe1 N3 86.35(19) . . ?
O1 Fe1 N3 149.05(18) . . ?
O3 Fe1 N1 146.07(19) . . ?
O1 Fe1 N1 87.28(17) . . ?
N3 Fe1 N1 73.7(2) . . ?
O3 Fe1 Cl1 106.63(14) . . ?
O1 Fe1 Cl1 105.25(14) . . ?
N3 Fe1 Cl1 103.05(15) . . ?
N1 Fe1 Cl1 104.47(15) . . ?
C8 S1 C16 102.4(3) . . ?
C1 O1 Fe1 130.2(4) . . ?
C3 O2 H2A 109.5 . . ?
C15 O3 Fe1 132.0(4) . . ?
C14 O4 C17 118.1(5) . . ?
H5A O5W H5B 108(3) . . ?
C7 N1 C8 120.0(5) . . ?
C7 N1 Fe1 125.0(4) . . ?
C8 N1 Fe1 114.6(4) . . ?
C8 N2 N3 111.4(5) . . ?
C9 N3 N2 113.6(5) . . ?
C9 N3 Fe1 127.8(4) . . ?
N2 N3 Fe1 118.5(4) . . ?
O1 C1 C2 119.0(5) . . ?
O1 C1 C6 122.6(5) . . ?
C2 C1 C6 118.4(6) . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
O2 C3 C4 116.7(6) . . ?
O2 C3 C2 122.6(6) . . ?
C4 C3 C2 120.7(6) . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.3(6) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 117.9(5) . . ?
C5 C6 C1 118.7(5) . . ?
C7 C6 C1 123.3(6) . . ?
N1 C7 C6 125.7(5) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N2 C8 N1 119.2(5) . . ?
N2 C8 S1 119.7(4) . . ?
N1 C8 S1 121.1(5) . . ?
N3 C9 C10 124.4(6) . . ?
N3 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
C11 C10 C15 119.7(6) . . ?
C11 C10 C9 118.8(6) . . ?
C15 C10 C9 121.4(6) . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.0(7) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O4 C14 C13 125.4(6) . . ?
O4 C14 C15 114.6(5) . . ?
C13 C14 C15 120.0(6) . . ?
O3 C15 C10 123.6(6) . . ?
O3 C15 C14 118.1(5) . . ?
C10 C15 C14 118.3(6) . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 Fe1 O3 C15 -172.7(5) . . . . ?
N3 Fe1 O3 C15 -23.6(5) . . . . ?
N1 Fe1 O3 C15 -76.8(6) . . . . ?
Cl1 Fe1 O3 C15 78.9(5) . . . . ?
C8 N2 N3 C9 -170.3(6) . . . . ?
C8 N2 N3 Fe1 12.8(7) . . . . ?
Fe1 O1 C1 C2 159.2(4) . . . . ?
Fe1 O1 C1 C6 -24.4(8) . . . . ?
O1 C1 C2 C3 177.5(5) . . . . ?
C6 C1 C2 C3 0.9(9) . . . . ?
C1 C2 C3 O2 -179.8(6) . . . . ?
C1 C2 C3 C4 -0.9(9) . . . . ?
O2 C3 C4 C5 178.9(6) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C3 C4 C5 C6 1.0(10) . . . . ?
C4 C5 C6 C7 179.5(6) . . . . ?
C4 C5 C6 C1 -1.0(9) . . . . ?
O1 C1 C6 C5 -176.5(5) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
O1 C1 C6 C7 3.0(9) . . . . ?
C2 C1 C6 C7 179.5(6) . . . . ?
C8 N1 C7 C6 -179.0(6) . . . . ?
Fe1 N1 C7 C6 9.1(9) . . . . ?
C5 C6 C7 N1 -177.0(5) . . . . ?
C1 C6 C7 N1 3.5(10) . . . . ?
N3 N2 C8 N1 -0.6(8) . . . . ?
N3 N2 C8 S1 177.8(4) . . . . ?
C7 N1 C8 N2 175.9(6) . . . . ?
Fe1 N1 C8 N2 -11.4(7) . . . . ?
C7 N1 C8 S1 -2.5(8) . . . . ?
Fe1 N1 C8 S1 170.2(3) . . . . ?
C16 S1 C8 N2 -0.2(7) . . . . ?
C16 S1 C8 N1 178.2(6) . . . . ?
N2 N3 C9 C10 177.3(6) . . . . ?
Fe1 N3 C9 C10 -6.2(10) . . . . ?
N3 C9 C10 C11 177.0(6) . . . . ?
N3 C9 C10 C15 -6.8(10) . . . . ?
C15 C10 C11 C12 3.3(10) . . . . ?
C9 C10 C11 C12 179.6(6) . . . . ?
C10 C11 C12 C13 -2.6(11) . . . . ?
C11 C12 C13 C14 0.6(11) . . . . ?
C17 O4 C14 C13 -3.0(9) . . . . ?
C17 O4 C14 C15 178.2(6) . . . . ?
C12 C13 C14 O4 -178.0(6) . . . . ?
C12 C13 C14 C15 0.7(10) . . . . ?
Fe1 O3 C15 C10 19.2(9) . . . . ?
Fe1 O3 C15 C14 -161.0(4) . . . . ?
C11 C10 C15 O3 177.7(6) . . . . ?
C9 C10 C15 O3 1.6(10) . . . . ?
C11 C10 C15 C14 -2.0(9) . . . . ?
C9 C10 C15 C14 -178.2(6) . . . . ?
O4 C14 C15 O3 -0.9(8) . . . . ?
C13 C14 C15 O3 -179.7(5) . . . . ?
O4 C14 C15 C10 178.9(5) . . . . ?
C13 C14 C15 C10 0.1(9) . . . . ?

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 H2A O5W 0.82 1.85 2.628(7) 157.8 2_646
O5W H5B O1 0.858(16) 2.232(18) 3.044(6) 158(4) .
O5W H5A O4 0.856(18) 2.133(17) 2.936(6) 156(5) .
O5W H5A O3 0.856(18) 2.25(5) 2.881(6) 130(4) .

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.079

