# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_gczx219
_database_code_depnum_ccdc_archive 'CCDC 1439981'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-03-29 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            'C18 H18 Fe S'
_chemical_formula_weight         322.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Fe Fe 0.3463 0.8444 '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'
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'

_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                   19.1342(5)
_cell_length_b                   7.59440(10)
_cell_length_c                   10.3523(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.834(2)
_cell_angle_gamma                90
_cell_volume                     1502.48(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9028
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      25.9

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    1.129
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'Enhance sealed-tube, fine-focus MoX-ray sources'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23151
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.886
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2958
_reflns_number_gt                2607
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX

_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)+(0.0197P)²+0.9502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct menthods'
_atom_sites_solution_secondary   'F map'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0582
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.37380(2) 0.47732(3) 0.84141(2) 0.01726(8) Uani 1 1 d . . . . .
S2 S 0.20218(3) 0.89121(7) 0.92332(5) 0.03246(13) Uani 1 1 d . . . . .
C1 C 0.45102(10) 0.3418(3) 0.75550(18) 0.0313(4) Uani 1 1 d . . . . .
H1 H 0.4999 0.3575 0.7716 0.038 Uiso 1 1 calc R U . . .
C2 C 0.40922(12) 0.4304(2) 0.66185(17) 0.0333(5) Uani 1 1 d . . . . .
H2 H 0.4249 0.5165 0.6033 0.040 Uiso 1 1 calc R U . . .
C3 C 0.33988(11) 0.3702(3) 0.66913(18) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.3007 0.4085 0.6166 0.042 Uiso 1 1 calc R U . . .
C4 C 0.33899(11) 0.2422(2) 0.76906(19) 0.0328(5) Uani 1 1 d . . . . .
H4 H 0.2992 0.1795 0.7957 0.039 Uiso 1 1 calc R U . . .
C5 C 0.40832(11) 0.2258(2) 0.82145(17) 0.0305(4) Uani 1 1 d . . . . .
H5 H 0.4234 0.1491 0.8898 0.037 Uiso 1 1 calc R U . . .
C6 C 0.36952(9) 0.7426(2) 0.86819(16) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.3773 0.8308 0.8054 0.025 Uiso 1 1 calc R U . . .
C7 C 0.42144(9) 0.6669(2) 0.95438(15) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.4699 0.6949 0.9590 0.025 Uiso 1 1 calc R U . . .
C8 C 0.38784(9) 0.5419(2) 1.03204(15) 0.0210(4) Uani 1 1 d . . . . .
H8 H 0.4100 0.4714 1.0978 0.025 Uiso 1 1 calc R U . . .
C9 C 0.31535(9) 0.5402(2) 0.99474(16) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.2806 0.4694 1.0316 0.025 Uiso 1 1 calc R U . . .
C10 C 0.30400(9) 0.6639(2) 0.89207(15) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.23550(9) 0.7119(2) 0.82359(17) 0.0241(4) Uani 1 1 d . . . . .
H11 H 0.2450 0.7598 0.7362 0.029 Uiso 1 1 calc R U . . .
C12 C 0.13250(9) 0.9843(2) 0.82713(19) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.08118(11) 1.0712(3) 0.8926(2) 0.0419(5) Uani 1 1 d . . . . .
H13 H 0.0830 1.0721 0.9845 0.050 Uiso 1 1 calc R U . . .
C14 C 0.02724(12) 1.1569(3) 0.8236(3) 0.0522(6) Uani 1 1 d . . . . .
H14 H -0.0076 1.2170 0.8687 0.063 Uiso 1 1 calc R U . . .
C15 C 0.02374(11) 1.1555(3) 0.6910(3) 0.0478(6) Uani 1 1 d . . . . .
H15 H -0.0130 1.2158 0.6444 0.057 Uiso 1 1 calc R U . . .
C16 C 0.07372(11) 1.0662(3) 0.6255(2) 0.0442(5) Uani 1 1 d . . . . .
H16 H 0.0708 1.0628 0.5337 0.053 Uiso 1 1 calc R U . . .
C17 C 0.12834(10) 0.9813(3) 0.6932(2) 0.0373(5) Uani 1 1 d . . . . .
H17 H 0.1629 0.9209 0.6475 0.045 Uiso 1 1 calc R U . . .
C18 C 0.18344(10) 0.5628(3) 0.8076(2) 0.0356(5) Uani 1 1 d . . . . .
H18A H 0.2025 0.4711 0.7528 0.053 Uiso 1 1 calc R U . . .
H18B H 0.1396 0.6075 0.7672 0.053 Uiso 1 1 calc R U . . .
H18C H 0.1745 0.5132 0.8926 0.053 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 C10 2.0337(16) . ?
S2 C12 1.7712(19) . ?
S2 C11 1.8417(17) . ?
C1 C2 1.399(3) . ?
C1 C5 1.402(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.420(3) . ?
C4 C5 1.414(3) . ?
C6 C10 1.422(2) . ?
C6 C7 1.424(2) . ?
C7 C8 1.418(2) . ?
C8 C9 1.421(2) . ?
C9 C10 1.427(2) . ?
C10 C11 1.504(2) . ?
C11 C18 1.512(3) . ?
C12 C17 1.385(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.372(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.388(3) . ?

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
C12 S2 C11 104.58(8) . . ?
C2 C1 C5 108.25(17) . . ?
C1 C2 C3 108.32(17) . . ?
C2 C3 C4 107.84(17) . . ?
C5 C4 C3 107.17(17) . . ?
C1 C5 C4 108.42(17) . . ?
C10 C6 C7 108.37(14) . . ?
C8 C7 C6 107.69(15) . . ?
C7 C8 C9 108.41(15) . . ?
C8 C9 C10 107.88(15) . . ?
C6 C10 C9 107.65(15) . . ?
C6 C10 C11 124.86(15) . . ?
C9 C10 C11 127.42(16) . . ?
C6 C10 Fe1 69.64(9) . . ?
C9 C10 Fe1 69.87(9) . . ?
C11 C10 Fe1 127.99(12) . . ?
C10 C11 C18 115.10(15) . . ?
C10 C11 S2 103.46(11) . . ?
C18 C11 S2 111.74(13) . . ?
C17 C12 C13 119.32(18) . . ?
C17 C12 S2 124.10(14) . . ?
C13 C12 S2 116.52(16) . . ?
C14 C13 C12 119.9(2) . . ?
C15 C14 C13 120.6(2) . . ?
C14 C15 C16 119.7(2) . . ?
C15 C16 C17 120.3(2) . . ?
C12 C17 C16 120.1(2) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.048

