# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1041597'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: All of the authors have contribution in this research work.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
((1Z)-N-(benzylcarbamothioyl)ethanehydrazonoyl)ferrocene
;
_chemical_formula_moiety         'C20 H21 Fe N3 S'
_chemical_formula_sum            'C20 H21 Fe N3 S'
_chemical_formula_iupac          'C20 H21 Fe N3 S'
_chemical_formula_weight         391.31

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.0680(4)
_cell_length_b                   10.3127(5)
_cell_length_c                   14.2953(7)
_cell_angle_alpha                81.736(3)
_cell_angle_beta                 77.874(2)
_cell_angle_gamma                70.655(2)
_cell_volume                     958.11(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3224
_cell_measurement_theta_min      1.462
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  0.820
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.00
_diffrn_reflns_number            14116
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.462
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3744
_reflns_number_gt                3224
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.2810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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 0.28373(4) 0.04153(3) 0.25480(2) 0.04186(10) Uani 1 1 d . . . . .
S1 S 0.25089(8) 0.54457(5) 0.61447(4) 0.05592(16) Uani 1 1 d . . . . .
N1 N 0.2818(2) 0.23309(14) 0.47804(10) 0.0360(3) Uani 1 1 d . . . . .
N2 N 0.3315(2) 0.33731(14) 0.50856(10) 0.0381(3) Uani 1 1 d . . . . .
H2A H 0.4464 0.3513 0.4856 0.046 Uiso 1 1 calc R U . . .
N3 N 0.0217(2) 0.38631(15) 0.60673(10) 0.0419(4) Uani 1 1 d . . . . .
H3A H 0.0111 0.3154 0.5857 0.050 Uiso 1 1 calc R U . . .
C1 C 0.3153(6) 0.2097(3) 0.16664(17) 0.0893(10) Uani 1 1 d . . . . .
H1 H 0.3591 0.2787 0.1815 0.107 Uiso 1 1 calc R U . . .
C2 C 0.4402(6) 0.0887(3) 0.12518(17) 0.0943(10) Uani 1 1 d . . . . .
H2 H 0.5812 0.0625 0.1080 0.113 Uiso 1 1 calc R U . . .
C3 C 0.3142(7) 0.0142(3) 0.11435(16) 0.0970(11) Uani 1 1 d . . . . .
H3 H 0.3570 -0.0704 0.0881 0.116 Uiso 1 1 calc R U . . .
C4 C 0.1131(6) 0.0884(4) 0.1498(2) 0.1041(11) Uani 1 1 d . . . . .
H4 H -0.0013 0.0618 0.1516 0.125 Uiso 1 1 calc R U . . .
C5 C 0.1147(6) 0.2097(3) 0.1819(2) 0.0977(11) Uani 1 1 d . . . . .
H5 H 0.0012 0.2784 0.2087 0.117 Uiso 1 1 calc R U . . .
C6 C 0.4846(3) -0.07393(19) 0.34087(15) 0.0493(5) Uani 1 1 d . . . . .
H6 H 0.6257 -0.0985 0.3249 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3620(4) -0.15004(19) 0.32522(15) 0.0552(5) Uani 1 1 d . . . . .
H7 H 0.4086 -0.2339 0.2978 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1576(3) -0.0771(2) 0.35831(14) 0.0530(5) Uani 1 1 d . . . . .
H8 H 0.0457 -0.1043 0.3560 0.064 Uiso 1 1 calc R U . . .
C9 C 0.1501(3) 0.0448(2) 0.39587(12) 0.0420(4) Uani 1 1 d . . . . .
H9 H 0.0329 0.1112 0.4224 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3530(3) 0.04789(17) 0.38584(12) 0.0364(4) Uani 1 1 d . . . . .
C11 C 0.4143(3) 0.15543(17) 0.41661(13) 0.0378(4) Uani 1 1 d . . . . .
C12 C 0.6214(3) 0.1661(3) 0.3772(2) 0.0713(7) Uani 1 1 d . . . . .
H12A H 0.7018 0.0861 0.3437 0.107 Uiso 1 1 calc R U . . .
H12B H 0.6851 0.1719 0.4288 0.107 Uiso 1 1 calc R U . . .
H12C H 0.6108 0.2472 0.3336 0.107 Uiso 1 1 calc R U . . .
C13 C 0.1943(3) 0.41671(17) 0.57563(12) 0.0371(4) Uani 1 1 d . . . . .
C14 C -0.1506(3) 0.46369(19) 0.67354(13) 0.0450(4) Uani 1 1 d . . . . .
H14A H -0.2750 0.4722 0.6513 0.054 Uiso 1 1 calc R U . . .
H14B H -0.1423 0.5559 0.6725 0.054 Uiso 1 1 calc R U . . .
C15 C -0.1645(3) 0.40065(19) 0.77627(13) 0.0451(4) Uani 1 1 d . . . . .
C16 C -0.3537(3) 0.4109(2) 0.83134(15) 0.0558(5) Uani 1 1 d . . . . .
H16 H -0.4698 0.4518 0.8038 0.067 Uiso 1 1 calc R U . . .
C17 C -0.3731(5) 0.3612(3) 0.92717(17) 0.0765(8) Uani 1 1 d . . . . .
H17 H -0.5016 0.3694 0.9635 0.092 Uiso 1 1 calc R U . . .
C18 C -0.2040(6) 0.3002(3) 0.96818(19) 0.0943(9) Uani 1 1 d . . . . .
H18 H -0.2170 0.2668 1.0324 0.113 Uiso 1 1 calc R U . . .
C19 C -0.0151(5) 0.2884(3) 0.9146(2) 0.0985(10) Uani 1 1 d . . . . .
H19 H 0.1003 0.2473 0.9427 0.118 Uiso 1 1 calc R U . . .
C20 C 0.0053(4) 0.3376(3) 0.81830(17) 0.0734(7) Uani 1 1 d . . . . .
H20 H 0.1343 0.3278 0.7821 0.088 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 C3 2.024(2) . ?
Fe1 C4 2.027(3) . ?
Fe1 C2 2.032(2) . ?
Fe1 C8 2.032(2) . ?
Fe1 C6 2.035(2) . ?
Fe1 C5 2.038(3) . ?
Fe1 C1 2.039(2) . ?
Fe1 C9 2.0392(17) . ?
Fe1 C7 2.0398(19) . ?
Fe1 C10 2.0482(17) . ?
S1 C13 1.6912(17) . ?
N1 C11 1.284(2) . ?
N1 N2 1.3854(19) . ?
N2 C13 1.356(2) . ?
N2 H2A 0.8600 . ?
N3 C13 1.330(2) . ?
N3 C14 1.456(2) . ?
N3 H3A 0.8600 . ?
C1 C5 1.389(5) . ?
C1 C2 1.397(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.414(3) . ?
C6 C10 1.436(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.418(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.422(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.466(2) . ?
C11 C12 1.488(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.378(3) . ?
C15 C16 1.381(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(3) . ?
C19 H19 0.9300 . ?
C20 H20 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
C3 Fe1 C4 40.33(14) . . ?
C3 Fe1 C2 40.30(13) . . ?
C4 Fe1 C2 67.84(15) . . ?
C3 Fe1 C8 120.46(11) . . ?
C4 Fe1 C8 105.75(12) . . ?
C2 Fe1 C8 156.77(11) . . ?
C3 Fe1 C6 123.88(13) . . ?
C4 Fe1 C6 158.95(13) . . ?
C2 Fe1 C6 109.22(12) . . ?
C8 Fe1 C6 68.30(9) . . ?
C3 Fe1 C5 67.47(13) . . ?
C4 Fe1 C5 40.21(13) . . ?
C2 Fe1 C5 67.49(14) . . ?
C8 Fe1 C5 122.92(14) . . ?
C6 Fe1 C5 159.82(13) . . ?
C3 Fe1 C1 67.32(11) . . ?
C4 Fe1 C1 67.36(14) . . ?
C2 Fe1 C1 40.13(11) . . ?
C8 Fe1 C1 159.99(13) . . ?
C6 Fe1 C1 124.80(13) . . ?
C5 Fe1 C1 39.84(13) . . ?
C3 Fe1 C9 156.07(13) . . ?
C4 Fe1 C9 120.81(13) . . ?
C2 Fe1 C9 161.80(11) . . ?
C8 Fe1 C9 40.77(8) . . ?
C6 Fe1 C9 68.71(8) . . ?
C5 Fe1 C9 107.84(11) . . ?
C1 Fe1 C9 125.13(9) . . ?
C3 Fe1 C7 106.83(10) . . ?
C4 Fe1 C7 121.95(12) . . ?
C2 Fe1 C7 122.62(11) . . ?
C8 Fe1 C7 40.34(9) . . ?
C6 Fe1 C7 40.62(8) . . ?
C5 Fe1 C7 158.35(15) . . ?
C1 Fe1 C7 159.32(13) . . ?
C9 Fe1 C7 68.39(8) . . ?
C3 Fe1 C10 161.49(14) . . ?
C4 Fe1 C10 157.39(14) . . ?
C2 Fe1 C10 125.84(12) . . ?
C8 Fe1 C10 68.55(7) . . ?
C6 Fe1 C10 41.19(7) . . ?
C5 Fe1 C10 123.27(11) . . ?
C1 Fe1 C10 110.14(10) . . ?
C9 Fe1 C10 40.71(7) . . ?
C7 Fe1 C10 68.71(7) . . ?
C11 N1 N2 118.12(15) . . ?
C13 N2 N1 118.22(14) . . ?
C13 N2 H2A 120.9 . . ?
N1 N2 H2A 120.9 . . ?
C13 N3 C14 125.11(15) . . ?
C13 N3 H3A 117.4 . . ?
C14 N3 H3A 117.4 . . ?
C5 C1 C2 108.5(3) . . ?
C5 C1 Fe1 70.04(16) . . ?
C2 C1 Fe1 69.67(14) . . ?
C5 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
Fe1 C1 H1 126.1 . . ?
C1 C2 C3 107.4(3) . . ?
C1 C2 Fe1 70.20(14) . . ?
C3 C2 Fe1 69.56(15) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
Fe1 C2 H2 125.5 . . ?
C4 C3 C2 108.3(3) . . ?
C4 C3 Fe1 69.94(15) . . ?
C2 C3 Fe1 70.14(14) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
Fe1 C3 H3 125.7 . . ?
C3 C4 C5 107.7(3) . . ?
C3 C4 Fe1 69.73(17) . . ?
C5 C4 Fe1 70.31(17) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
Fe1 C4 H4 125.4 . . ?
C1 C5 C4 108.1(3) . . ?
C1 C5 Fe1 70.12(16) . . ?
C4 C5 Fe1 69.48(16) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 108.06(18) . . ?
C7 C6 Fe1 69.89(11) . . ?
C10 C6 Fe1 69.91(10) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 H6 126.0 . . ?
Fe1 C6 H6 125.8 . . ?
C8 C7 C6 108.19(17) . . ?
C8 C7 Fe1 69.54(11) . . ?
C6 C7 Fe1 69.49(11) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
Fe1 C7 H7 126.6 . . ?
C7 C8 C9 108.63(18) . . ?
C7 C8 Fe1 70.12(12) . . ?
C9 C8 Fe1 69.88(10) . . ?
C7 C8 H8 125.7 . . ?
C9 C8 H8 125.7 . . ?
Fe1 C8 H8 125.9 . . ?
C8 C9 C10 108.02(17) . . ?
C8 C9 Fe1 69.35(11) . . ?
C10 C9 Fe1 69.98(10) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 126.2 . . ?
C9 C10 C6 107.09(16) . . ?
C9 C10 C11 125.94(15) . . ?
C6 C10 C11 126.97(16) . . ?
C9 C10 Fe1 69.30(10) . . ?
C6 C10 Fe1 68.89(10) . . ?
C11 C10 Fe1 127.23(12) . . ?
N1 C11 C10 115.92(15) . . ?
N1 C11 C12 124.93(17) . . ?
C10 C11 C12 119.15(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 N2 116.16(15) . . ?
N3 C13 S1 124.51(13) . . ?
N2 C13 S1 119.33(13) . . ?
N3 C14 C15 114.75(15) . . ?
N3 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 118.4(2) . . ?
C20 C15 C14 122.28(18) . . ?
C16 C15 C14 119.27(19) . . ?
C15 C16 C17 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.4(3) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?

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
C11 N1 N2 C13 -177.99(15) . . . . ?
C5 C1 C2 C3 0.4(3) . . . . ?
Fe1 C1 C2 C3 59.86(18) . . . . ?
C5 C1 C2 Fe1 -59.48(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
Fe1 C2 C3 C4 59.75(19) . . . . ?
C1 C2 C3 Fe1 -60.27(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
Fe1 C3 C4 C5 60.34(19) . . . . ?
C2 C3 C4 Fe1 -59.9(2) . . . . ?
C2 C1 C5 C4 -0.1(3) . . . . ?
Fe1 C1 C5 C4 -59.35(19) . . . . ?
C2 C1 C5 Fe1 59.25(19) . . . . ?
C3 C4 C5 C1 -0.2(3) . . . . ?
Fe1 C4 C5 C1 59.74(19) . . . . ?
C3 C4 C5 Fe1 -59.97(19) . . . . ?
C10 C6 C7 C8 0.8(2) . . . . ?
Fe1 C6 C7 C8 -58.95(14) . . . . ?
C10 C6 C7 Fe1 59.73(13) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
Fe1 C7 C8 C9 -59.47(13) . . . . ?
C6 C7 C8 Fe1 58.92(14) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
Fe1 C8 C9 C10 -59.52(12) . . . . ?
C7 C8 C9 Fe1 59.61(14) . . . . ?
C8 C9 C10 C6 0.4(2) . . . . ?
Fe1 C9 C10 C6 -58.75(13) . . . . ?
C8 C9 C10 C11 -179.21(16) . . . . ?
Fe1 C9 C10 C11 121.67(17) . . . . ?
C8 C9 C10 Fe1 59.12(13) . . . . ?
C7 C6 C10 C9 -0.7(2) . . . . ?
Fe1 C6 C10 C9 59.01(12) . . . . ?
C7 C6 C10 C11 178.87(17) . . . . ?
Fe1 C6 C10 C11 -121.41(18) . . . . ?
C7 C6 C10 Fe1 -59.72(14) . . . . ?
N2 N1 C11 C10 -179.27(14) . . . . ?
N2 N1 C11 C12 1.8(3) . . . . ?
C9 C10 C11 N1 18.3(3) . . . . ?
C6 C10 C11 N1 -161.16(18) . . . . ?
Fe1 C10 C11 N1 108.50(17) . . . . ?
C9 C10 C11 C12 -162.6(2) . . . . ?
C6 C10 C11 C12 17.9(3) . . . . ?
Fe1 C10 C11 C12 -72.5(2) . . . . ?
C14 N3 C13 N2 -175.79(15) . . . . ?
C14 N3 C13 S1 4.6(3) . . . . ?
N1 N2 C13 N3 0.2(2) . . . . ?
N1 N2 C13 S1 179.89(11) . . . . ?
C13 N3 C14 C15 -100.4(2) . . . . ?
N3 C14 C15 C20 38.3(3) . . . . ?
N3 C14 C15 C16 -144.27(18) . . . . ?
C20 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C17 -176.5(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C16 C15 C20 C19 -1.4(4) . . . . ?
C14 C15 C20 C19 176.1(3) . . . . ?
C18 C19 C20 C15 1.1(5) . . . . ?

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
N2 H2A S1 0.86 2.75 3.5878(16) 164.5 2_666
C12 H12C S1 0.96 2.88 3.415(2) 116.6 2_666

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.039

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1041598'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: All of the authors have contribution in this research work.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
((1Z)-N-((2-chlorobenzyl)carbamothioyl)ethanehydrazonoyl)ferrocene
;
_chemical_formula_moiety         'C20 H20 Cl Fe N3 S'
_chemical_formula_sum            'C20 H20 Cl Fe N3 S'
_chemical_formula_iupac          'C20 H20 Cl Fe N3 S'
_chemical_formula_weight         425.75

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'
S S 0.1246 0.1234 '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'

_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                   19.7141(14)
_cell_length_b                   7.0263(4)
_cell_length_c                   28.099(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.386(2)
_cell_angle_gamma                90
_cell_volume                     3892.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2799
_cell_measurement_theta_min      1.449
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.822
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.00
_diffrn_reflns_number            14496
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.449
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3821
_reflns_number_gt                2799
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_number_reflns         3821
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0381P)²+2.1934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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 0.01310(2) 0.69450(5) 0.12089(2) 0.03764(12) Uani 1 1 d . . . . .
Cl1 Cl 0.11766(6) 0.91693(18) -0.23216(4) 0.1149(4) Uani 1 1 d . . . . .
S1 S 0.27503(4) 1.06262(10) -0.05718(3) 0.0557(2) Uani 1 1 d . . . . .
N1 N 0.11336(9) 0.8885(3) 0.00949(7) 0.0345(5) Uani 1 1 d . . . . .
N2 N 0.16598(10) 1.0011(3) -0.00640(7) 0.0369(5) Uani 1 1 d . . . . .
H2A H 0.1707 1.1156 0.0039 0.044 Uiso 1 1 calc R U . . .
N3 N 0.19773(10) 0.7510(3) -0.05237(7) 0.0395(5) Uani 1 1 d . . . . .
H3A H 0.1611 0.6983 -0.0424 0.047 Uiso 1 1 calc R U . . .
C1 C 0.09431(15) 0.7639(6) 0.16249(11) 0.0714(10) Uani 1 1 d . . . . .
H1 H 0.1287 0.8485 0.1546 0.086 Uiso 1 1 calc R U . . .
C2 C 0.09412(19) 0.5688(7) 0.15341(12) 0.0786(11) Uani 1 1 d . . . . .
H2 H 0.1280 0.5003 0.1381 0.094 Uiso 1 1 calc R U . . .
C3 C 0.0335(2) 0.4948(6) 0.17153(12) 0.0816(11) Uani 1 1 d . . . . .
H3 H 0.0202 0.3679 0.1706 0.098 Uiso 1 1 calc R U . . .
C4 C -0.00335(18) 0.6440(6) 0.19109(11) 0.0765(11) Uani 1 1 d . . . . .
H4 H -0.0456 0.6340 0.2054 0.092 Uiso 1 1 calc R U . . .
C5 C 0.03368(17) 0.8106(6) 0.18554(11) 0.0720(10) Uani 1 1 d . . . . .
H5 H 0.0206 0.9315 0.1954 0.086 Uiso 1 1 calc R U . . .
C6 C -0.04079(12) 0.8864(4) 0.08202(10) 0.0481(7) Uani 1 1 d . . . . .
H6 H -0.0519 1.0092 0.0915 0.058 Uiso 1 1 calc R U . . .
C7 C -0.08008(13) 0.7210(5) 0.08991(11) 0.0560(8) Uani 1 1 d . . . . .
H7 H -0.1217 0.7162 0.1053 0.067 Uiso 1 1 calc R U . . .
C8 C -0.04510(14) 0.5648(4) 0.07040(10) 0.0529(8) Uani 1 1 d . . . . .
H8 H -0.0596 0.4389 0.0707 0.064 Uiso 1 1 calc R U . . .
C9 C 0.01574(13) 0.6322(4) 0.05034(8) 0.0396(6) Uani 1 1 d . . . . .
H9 H 0.0483 0.5582 0.0353 0.048 Uiso 1 1 calc R U . . .
C10 C 0.01868(11) 0.8325(3) 0.05705(8) 0.0347(5) Uani 1 1 d . . . . .
C11 C 0.07352(11) 0.9573(3) 0.04088(9) 0.0347(5) Uani 1 1 d . . . . .
C12 C 0.07832(16) 1.1541(4) 0.06091(12) 0.0662(10) Uani 1 1 d . . . . .
H12A H 0.1207 1.1684 0.0776 0.099 Uiso 1 1 calc R U . . .
H12B H 0.0415 1.1750 0.0825 0.099 Uiso 1 1 calc R U . . .
H12C H 0.0758 1.2451 0.0355 0.099 Uiso 1 1 calc R U . . .
C13 C 0.20985(12) 0.9290(3) -0.03837(8) 0.0357(6) Uani 1 1 d . . . . .
C14 C 0.24085(13) 0.6387(4) -0.08296(9) 0.0444(6) Uani 1 1 d . . . . .
H14A H 0.2458 0.5130 -0.0691 0.053 Uiso 1 1 calc R U . . .
H14B H 0.2855 0.6968 -0.0835 0.053 Uiso 1 1 calc R U . . .
C15 C 0.21595(12) 0.6171(4) -0.13343(9) 0.0383(6) Uani 1 1 d . . . . .
C16 C 0.18129(14) 0.7609(4) -0.15671(10) 0.0506(7) Uani 1 1 d . . . . .
H16 H 0.1719 0.8745 -0.1411 0.061 Uiso 1 1 calc R U . . .
C17 C 0.16077(15) 0.7346(5) -0.20313(11) 0.0604(8) Uani 1 1 d . . . . .
C18 C 0.17391(16) 0.5701(5) -0.22737(11) 0.0681(9) Uani 1 1 d . . . . .
H18 H 0.1595 0.5550 -0.2587 0.082 Uiso 1 1 calc R U . . .
C19 C 0.20877(17) 0.4275(5) -0.20441(12) 0.0653(9) Uani 1 1 d . . . . .
H19 H 0.2184 0.3149 -0.2204 0.078 Uiso 1 1 calc R U . . .
C20 C 0.22954(14) 0.4505(4) -0.15795(10) 0.0513(7) Uani 1 1 d . . . . .
H20 H 0.2530 0.3528 -0.1428 0.062 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 C5 2.030(3) . ?
Fe1 C6 2.031(3) . ?
Fe1 C9 2.031(2) . ?
Fe1 C4 2.032(3) . ?
Fe1 C8 2.034(3) . ?
Fe1 C1 2.035(3) . ?
Fe1 C7 2.036(3) . ?
Fe1 C3 2.036(3) . ?
Fe1 C2 2.036(3) . ?
Fe1 C10 2.043(2) . ?
Cl1 C17 1.737(3) . ?
S1 C13 1.680(2) . ?
N1 C11 1.280(3) . ?
N1 N2 1.381(3) . ?
N2 C13 1.350(3) . ?
N2 H2A 0.8600 . ?
N3 C13 1.332(3) . ?
N3 C14 1.447(3) . ?
N3 H3A 0.8600 . ?
C1 C2 1.395(5) . ?
C1 C5 1.402(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.415(4) . ?
C6 C10 1.422(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.409(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.421(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.466(3) . ?
C11 C12 1.495(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.505(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.382(4) . ?
C15 C20 1.386(4) . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(5) . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 H20 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
C5 Fe1 C6 108.37(14) . . ?
C5 Fe1 C9 162.52(12) . . ?
C6 Fe1 C9 68.59(11) . . ?
C5 Fe1 C4 39.98(14) . . ?
C6 Fe1 C4 123.47(14) . . ?
C9 Fe1 C4 156.20(14) . . ?
C5 Fe1 C8 155.88(13) . . ?
C6 Fe1 C8 68.40(12) . . ?
C9 Fe1 C8 40.60(10) . . ?
C4 Fe1 C8 120.39(13) . . ?
C5 Fe1 C1 40.36(13) . . ?
C6 Fe1 C1 123.81(14) . . ?
C9 Fe1 C1 125.94(12) . . ?
C4 Fe1 C1 67.32(13) . . ?
C8 Fe1 C1 161.04(15) . . ?
C5 Fe1 C7 121.35(14) . . ?
C6 Fe1 C7 40.72(11) . . ?
C9 Fe1 C7 68.37(12) . . ?
C4 Fe1 C7 106.35(13) . . ?
C8 Fe1 C7 40.52(12) . . ?
C1 Fe1 C7 158.07(16) . . ?
C5 Fe1 C3 67.32(16) . . ?
C6 Fe1 C3 158.95(15) . . ?
C9 Fe1 C3 121.81(14) . . ?
C4 Fe1 C3 39.97(15) . . ?
C8 Fe1 C3 106.64(14) . . ?
C1 Fe1 C3 67.24(16) . . ?
C7 Fe1 C3 122.33(14) . . ?
C5 Fe1 C2 67.75(15) . . ?
C6 Fe1 C2 159.27(15) . . ?
C9 Fe1 C2 108.61(13) . . ?
C4 Fe1 C2 67.58(15) . . ?
C8 Fe1 C2 123.75(15) . . ?
C1 Fe1 C2 40.06(15) . . ?
C7 Fe1 C2 159.10(16) . . ?
C3 Fe1 C2 40.29(14) . . ?
C5 Fe1 C10 125.70(13) . . ?
C6 Fe1 C10 40.85(10) . . ?
C9 Fe1 C10 40.84(9) . . ?
C4 Fe1 C10 160.91(14) . . ?
C8 Fe1 C10 68.51(10) . . ?
C1 Fe1 C10 110.11(12) . . ?
C7 Fe1 C10 68.58(10) . . ?
C3 Fe1 C10 158.30(15) . . ?
C2 Fe1 C10 123.59(13) . . ?
C11 N1 N2 118.2(2) . . ?
C13 N2 N1 119.1(2) . . ?
C13 N2 H2A 120.5 . . ?
N1 N2 H2A 120.5 . . ?
C13 N3 C14 125.6(2) . . ?
C13 N3 H3A 117.2 . . ?
C14 N3 H3A 117.2 . . ?
C2 C1 C5 108.3(3) . . ?
C2 C1 Fe1 70.01(19) . . ?
C5 C1 Fe1 69.61(17) . . ?
C2 C1 H1 125.9 . . ?
C5 C1 H1 125.9 . . ?
Fe1 C1 H1 126.1 . . ?
C1 C2 C3 107.4(3) . . ?
C1 C2 Fe1 69.93(19) . . ?
C3 C2 Fe1 69.85(19) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
Fe1 C2 H2 125.5 . . ?
C4 C3 C2 108.2(4) . . ?
C4 C3 Fe1 69.9(2) . . ?
C2 C3 Fe1 69.86(19) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.0 . . ?
C5 C4 C3 108.4(3) . . ?
C5 C4 Fe1 69.91(18) . . ?
C3 C4 Fe1 70.17(18) . . ?
C5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
Fe1 C4 H4 125.7 . . ?
C4 C5 C1 107.8(3) . . ?
C4 C5 Fe1 70.10(18) . . ?
C1 C5 Fe1 70.03(17) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 126.1 . . ?
Fe1 C5 H5 125.3 . . ?
C7 C6 C10 108.2(3) . . ?
C7 C6 Fe1 69.83(16) . . ?
C10 C6 Fe1 70.03(14) . . ?
C7 C6 H6 125.9 . . ?
C10 C6 H6 125.9 . . ?
Fe1 C6 H6 125.8 . . ?
C8 C7 C6 108.0(2) . . ?
C8 C7 Fe1 69.68(15) . . ?
C6 C7 Fe1 69.45(15) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe1 C7 H7 126.4 . . ?
C7 C8 C9 108.3(2) . . ?
C7 C8 Fe1 69.81(16) . . ?
C9 C8 Fe1 69.59(14) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
Fe1 C8 H8 126.3 . . ?
C8 C9 C10 108.3(2) . . ?
C8 C9 Fe1 69.81(15) . . ?
C10 C9 Fe1 70.02(14) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe1 C9 H9 125.9 . . ?
C9 C10 C6 107.2(2) . . ?
C9 C10 C11 125.5(2) . . ?
C6 C10 C11 127.3(2) . . ?
C9 C10 Fe1 69.14(13) . . ?
C6 C10 Fe1 69.12(15) . . ?
C11 C10 Fe1 126.86(17) . . ?
N1 C11 C10 116.4(2) . . ?
N1 C11 C12 124.8(2) . . ?
C10 C11 C12 118.8(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 N2 115.8(2) . . ?
N3 C13 S1 124.60(19) . . ?
N2 C13 S1 119.64(19) . . ?
N3 C14 C15 115.2(2) . . ?
N3 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
N3 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C20 118.6(3) . . ?
C16 C15 C14 122.0(2) . . ?
C20 C15 C14 119.4(2) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 Cl1 118.9(3) . . ?
C16 C17 Cl1 119.1(3) . . ?
C17 C18 C19 118.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?

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
C11 N1 N2 C13 177.9(2) . . . . ?
C5 C1 C2 C3 -0.8(4) . . . . ?
Fe1 C1 C2 C3 -60.1(2) . . . . ?
C5 C1 C2 Fe1 59.3(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
Fe1 C2 C3 C4 -59.5(2) . . . . ?
C1 C2 C3 Fe1 60.1(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
Fe1 C3 C4 C5 -59.7(2) . . . . ?
C2 C3 C4 Fe1 59.5(2) . . . . ?
C3 C4 C5 C1 -0.3(4) . . . . ?
Fe1 C4 C5 C1 -60.2(2) . . . . ?
C3 C4 C5 Fe1 59.9(2) . . . . ?
C2 C1 C5 C4 0.7(4) . . . . ?
Fe1 C1 C5 C4 60.2(2) . . . . ?
C2 C1 C5 Fe1 -59.6(2) . . . . ?
C10 C6 C7 C8 0.5(3) . . . . ?
Fe1 C6 C7 C8 -59.22(19) . . . . ?
C10 C6 C7 Fe1 59.74(18) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
Fe1 C7 C8 C9 -59.14(18) . . . . ?
C6 C7 C8 Fe1 59.08(19) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
Fe1 C8 C9 C10 -59.69(17) . . . . ?
C7 C8 C9 Fe1 59.28(19) . . . . ?
C8 C9 C10 C6 0.7(3) . . . . ?
Fe1 C9 C10 C6 -58.84(18) . . . . ?
C8 C9 C10 C11 -179.3(2) . . . . ?
Fe1 C9 C10 C11 121.1(2) . . . . ?
C8 C9 C10 Fe1 59.56(18) . . . . ?
C7 C6 C10 C9 -0.8(3) . . . . ?
Fe1 C6 C10 C9 58.85(17) . . . . ?
C7 C6 C10 C11 179.3(2) . . . . ?
Fe1 C6 C10 C11 -121.1(2) . . . . ?
C7 C6 C10 Fe1 -59.61(19) . . . . ?
N2 N1 C11 C10 -179.54(19) . . . . ?
N2 N1 C11 C12 1.8(4) . . . . ?
C9 C10 C11 N1 16.6(4) . . . . ?
C6 C10 C11 N1 -163.5(2) . . . . ?
Fe1 C10 C11 N1 105.9(2) . . . . ?
C9 C10 C11 C12 -164.7(3) . . . . ?
C6 C10 C11 C12 15.2(4) . . . . ?
Fe1 C10 C11 C12 -75.4(3) . . . . ?
C14 N3 C13 N2 -174.3(2) . . . . ?
C14 N3 C13 S1 4.9(3) . . . . ?
N1 N2 C13 N3 0.5(3) . . . . ?
N1 N2 C13 S1 -178.74(16) . . . . ?
C13 N3 C14 C15 -104.3(3) . . . . ?
N3 C14 C15 C16 34.4(3) . . . . ?
N3 C14 C15 C20 -147.3(2) . . . . ?
C20 C15 C16 C17 0.6(4) . . . . ?
C14 C15 C16 C17 178.8(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C15 C16 C17 Cl1 -179.6(2) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
Cl1 C17 C18 C19 179.2(2) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 -0.3(4) . . . . ?
C14 C15 C20 C19 -178.7(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
N2 H2A S1 0.86 2.91 3.730(2) 159.8 7_575
C12 H12A S1 0.96 2.85 3.512(3) 126.6 7_575

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1041599'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: All of the authors have contribution in this research work.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
((1Z)-N-((4-methoxybenzyl)carbamothioyl)ethanehydrazonoyl)ferrocene
;
_chemical_formula_moiety         'C21 H23 Fe N3 O S'
_chemical_formula_sum            'C21 H23 Fe N3 O S'
_chemical_formula_iupac          'C21 H23 Fe N3 O S'
_chemical_formula_weight         421.33

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.1685(3)
_cell_length_b                   10.3397(4)
_cell_length_c                   14.5960(6)
_cell_angle_alpha                80.533(2)
_cell_angle_beta                 81.1130(10)
_cell_angle_gamma                70.067(2)
_cell_volume                     997.53(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3195
_cell_measurement_theta_min      1.485
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_T_max  0.859
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.00
_diffrn_reflns_number            14909
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.422
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3911
_reflns_number_gt                3195
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+0.2659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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 0.26301(4) 0.05767(3) 0.25858(2) 0.04489(11) Uani 1 1 d . . . . .
S1 S 0.26901(9) 0.53273(6) 0.61357(4) 0.05813(17) Uani 1 1 d . . . . .
O1 O -0.4961(3) 0.3469(2) 0.96158(12) 0.0920(6) Uani 1 1 d . . . . .
N1 N 0.2888(2) 0.23382(15) 0.47602(10) 0.0365(3) Uani 1 1 d . . . . .
N2 N 0.3401(2) 0.33465(15) 0.50779(10) 0.0381(3) Uani 1 1 d . . . . .
H2A H 0.4512 0.3491 0.4871 0.046 Uiso 1 1 calc R U . . .
N3 N 0.0433(2) 0.37954(16) 0.59853(11) 0.0431(4) Uani 1 1 d . . . . .
H3A H 0.0309 0.3122 0.5751 0.052 Uiso 1 1 calc R U . . .
C1 C 0.2659(7) 0.2355(3) 0.17561(19) 0.0936(11) Uani 1 1 d . . . . .
H1 H 0.3026 0.3063 0.1915 0.112 Uiso 1 1 calc R U . . .
C2 C 0.3936(6) 0.1203(3) 0.13334(19) 0.0976(10) Uani 1 1 d . . . . .
H2 H 0.5301 0.1005 0.1168 0.117 Uiso 1 1 calc R U . . .
C3 C 0.2810(7) 0.0415(3) 0.12076(18) 0.1013(12) Uani 1 1 d . . . . .
H3 H 0.3289 -0.0405 0.0936 0.122 Uiso 1 1 calc R U . . .
C4 C 0.0861(7) 0.1039(5) 0.1548(3) 0.1144(13) Uani 1 1 d . . . . .
H4 H -0.0195 0.0710 0.1548 0.137 Uiso 1 1 calc R U . . .
C5 C 0.0735(6) 0.2257(4) 0.1898(2) 0.1064(12) Uani 1 1 d . . . . .
H5 H -0.0406 0.2877 0.2170 0.128 Uiso 1 1 calc R U . . .
C6 C 0.4758(3) -0.06301(19) 0.34130(15) 0.0489(5) Uani 1 1 d . . . . .
H6 H 0.6129 -0.0857 0.3255 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3555(4) -0.1386(2) 0.32532(16) 0.0559(6) Uani 1 1 d . . . . .
H7 H 0.3998 -0.2202 0.2977 0.067 Uiso 1 1 calc R U . . .
C8 C 0.1579(4) -0.0697(2) 0.35823(15) 0.0564(6) Uani 1 1 d . . . . .
H8 H 0.0484 -0.0975 0.3559 0.068 Uiso 1 1 calc R U . . .
C9 C 0.1527(3) 0.0493(2) 0.39570(13) 0.0452(5) Uani 1 1 d . . . . .
H9 H 0.0396 0.1133 0.4221 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3505(3) 0.05424(18) 0.38591(12) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.4133(3) 0.15924(18) 0.41699(13) 0.0370(4) Uani 1 1 d . . . . .
C12 C 0.6144(3) 0.1698(3) 0.38115(19) 0.0687(7) Uani 1 1 d . . . . .
H12A H 0.6847 0.1668 0.4327 0.103 Uiso 1 1 calc R U . . .
H12B H 0.6000 0.2556 0.3414 0.103 Uiso 1 1 calc R U . . .
H12C H 0.6879 0.0938 0.3462 0.103 Uiso 1 1 calc R U . . .
C13 C 0.2112(3) 0.40999(18) 0.57223(12) 0.0387(4) Uani 1 1 d . . . . .
C14 C -0.1207(3) 0.4501(2) 0.66336(13) 0.0466(5) Uani 1 1 d . . . . .
H14A H -0.2452 0.4637 0.6389 0.056 Uiso 1 1 calc R U . . .
H14B H -0.1124 0.5409 0.6665 0.056 Uiso 1 1 calc R U . . .
C15 C -0.1257(3) 0.37472(19) 0.76112(13) 0.0402(4) Uani 1 1 d . . . . .
C16 C -0.3099(3) 0.3960(2) 0.81388(13) 0.0455(5) Uani 1 1 d . . . . .
H16 H -0.4254 0.4529 0.7881 0.055 Uiso 1 1 calc R U . . .
C17 C -0.3216(4) 0.3329(3) 0.90447(15) 0.0591(6) Uani 1 1 d . . . . .
C18 C -0.1511(5) 0.2483(3) 0.94273(17) 0.0747(7) Uani 1 1 d . . . . .
H18 H -0.1592 0.2058 1.0038 0.090 Uiso 1 1 calc R U . . .
C19 C 0.0299(4) 0.2270(3) 0.89087(18) 0.0713(7) Uani 1 1 d . . . . .
H19 H 0.1447 0.1696 0.9170 0.086 Uiso 1 1 calc R U . . .
C20 C 0.0449(3) 0.2898(2) 0.79967(15) 0.0558(5) Uani 1 1 d . . . . .
H20 H 0.1690 0.2748 0.7649 0.067 Uiso 1 1 calc R U . . .
C21 C -0.6740(4) 0.4416(4) 0.9288(2) 0.1020(11) Uani 1 1 d . . . . .
H21A H -0.6612 0.5324 0.9145 0.153 Uiso 1 1 calc R U . . .
H21B H -0.7836 0.4437 0.9762 0.153 Uiso 1 1 calc R U . . .
H21C H -0.6981 0.4132 0.8736 0.153 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 C4 2.018(3) . ?
Fe1 C3 2.026(3) . ?
Fe1 C5 2.027(3) . ?
Fe1 C6 2.029(2) . ?
Fe1 C8 2.031(2) . ?
Fe1 C2 2.033(3) . ?
Fe1 C1 2.033(2) . ?
Fe1 C9 2.034(2) . ?
Fe1 C7 2.035(2) . ?
Fe1 C10 2.0427(18) . ?
S1 C13 1.6837(19) . ?
O1 C17 1.369(3) . ?
O1 C21 1.413(4) . ?
N1 C11 1.282(2) . ?
N1 N2 1.382(2) . ?
N2 C13 1.352(2) . ?
N2 H2A 0.8600 . ?
N3 C13 1.330(2) . ?
N3 C14 1.452(2) . ?
N3 H3A 0.8600 . ?
C1 C5 1.398(5) . ?
C1 C2 1.401(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.411(3) . ?
C6 C10 1.427(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.400(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.421(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.464(2) . ?
C11 C12 1.490(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.379(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(4) . ?
C18 C19 1.364(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C4 Fe1 C3 39.76(14) . . ?
C4 Fe1 C5 40.64(14) . . ?
C3 Fe1 C5 67.62(14) . . ?
C4 Fe1 C6 156.64(15) . . ?
C3 Fe1 C6 122.94(14) . . ?
C5 Fe1 C6 161.89(15) . . ?
C4 Fe1 C8 105.50(13) . . ?
C3 Fe1 C8 121.65(12) . . ?
C5 Fe1 C8 120.93(15) . . ?
C6 Fe1 C8 68.24(9) . . ?
C4 Fe1 C2 67.09(16) . . ?
C3 Fe1 C2 39.60(13) . . ?
C5 Fe1 C2 67.86(15) . . ?
C6 Fe1 C2 109.86(13) . . ?
C8 Fe1 C2 158.05(12) . . ?
C4 Fe1 C1 67.44(15) . . ?
C3 Fe1 C1 67.06(12) . . ?
C5 Fe1 C1 40.28(14) . . ?
C6 Fe1 C1 126.36(14) . . ?
C8 Fe1 C1 158.12(14) . . ?
C2 Fe1 C1 40.31(12) . . ?
C4 Fe1 C9 122.22(16) . . ?
C3 Fe1 C9 157.66(14) . . ?
C5 Fe1 C9 107.28(12) . . ?
C6 Fe1 C9 68.61(8) . . ?
C8 Fe1 C9 40.71(8) . . ?
C2 Fe1 C9 160.76(12) . . ?
C1 Fe1 C9 124.07(11) . . ?
C4 Fe1 C7 120.18(13) . . ?
C3 Fe1 C7 106.99(11) . . ?
C5 Fe1 C7 155.92(16) . . ?
C6 Fe1 C7 40.64(8) . . ?
C8 Fe1 C7 40.27(9) . . ?
C2 Fe1 C7 123.93(12) . . ?
C1 Fe1 C7 161.33(14) . . ?
C9 Fe1 C7 68.28(9) . . ?
C4 Fe1 C10 159.68(16) . . ?
C3 Fe1 C10 159.86(15) . . ?
C5 Fe1 C10 124.45(12) . . ?
C6 Fe1 C10 41.03(7) . . ?
C8 Fe1 C10 68.54(8) . . ?
C2 Fe1 C10 125.41(12) . . ?
C1 Fe1 C10 110.46(10) . . ?
C9 Fe1 C10 40.78(7) . . ?
C7 Fe1 C10 68.62(8) . . ?
C17 O1 C21 118.0(2) . . ?
C11 N1 N2 118.54(15) . . ?
C13 N2 N1 118.30(15) . . ?
C13 N2 H2A 120.9 . . ?
N1 N2 H2A 120.9 . . ?
C13 N3 C14 125.69(16) . . ?
C13 N3 H3A 117.2 . . ?
C14 N3 H3A 117.2 . . ?
C5 C1 C2 108.1(3) . . ?
C5 C1 Fe1 69.63(16) . . ?
C2 C1 Fe1 69.83(15) . . ?
C5 C1 H1 125.9 . . ?
C2 C1 H1 125.9 . . ?
Fe1 C1 H1 126.2 . . ?
C3 C2 C1 107.8(3) . . ?
C3 C2 Fe1 69.95(17) . . ?
C1 C2 Fe1 69.87(16) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
Fe1 C2 H2 125.6 . . ?
C2 C3 C4 108.9(3) . . ?
C2 C3 Fe1 70.45(16) . . ?
C4 C3 Fe1 69.78(17) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
Fe1 C3 H3 125.8 . . ?
C3 C4 C5 108.5(4) . . ?
C3 C4 Fe1 70.46(18) . . ?
C5 C4 Fe1 70.05(17) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 125.3 . . ?
C1 C5 C4 106.7(3) . . ?
C1 C5 Fe1 70.09(17) . . ?
C4 C5 Fe1 69.31(17) . . ?
C1 C5 H5 126.6 . . ?
C4 C5 H5 126.6 . . ?
Fe1 C5 H5 125.5 . . ?
C7 C6 C10 108.13(19) . . ?
C7 C6 Fe1 69.88(12) . . ?
C10 C6 Fe1 69.99(11) . . ?
C7 C6 H6 125.9 . . ?
C10 C6 H6 125.9 . . ?
Fe1 C6 H6 125.8 . . ?
C8 C7 C6 108.25(18) . . ?
C8 C7 Fe1 69.74(12) . . ?
C6 C7 Fe1 69.47(11) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
Fe1 C7 H7 126.5 . . ?
C7 C8 C9 108.49(18) . . ?
C7 C8 Fe1 69.99(12) . . ?
C9 C8 Fe1 69.77(11) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 126.1 . . ?
C8 C9 C10 108.05(18) . . ?
C8 C9 Fe1 69.52(12) . . ?
C10 C9 Fe1 69.92(11) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 126.2 . . ?
C9 C10 C6 107.07(16) . . ?
C9 C10 C11 126.18(17) . . ?
C6 C10 C11 126.74(17) . . ?
C9 C10 Fe1 69.30(10) . . ?
C6 C10 Fe1 68.97(11) . . ?
C11 C10 Fe1 127.37(13) . . ?
N1 C11 C10 116.01(16) . . ?
N1 C11 C12 124.92(17) . . ?
C10 C11 C12 119.04(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 N2 115.65(16) . . ?
N3 C13 S1 124.55(14) . . ?
N2 C13 S1 119.80(14) . . ?
N3 C14 C15 114.61(16) . . ?
N3 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 119.68(19) . . ?
C20 C15 C14 122.44(18) . . ?
C16 C15 C14 117.86(17) . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O1 C17 C18 115.6(2) . . ?
O1 C17 C16 124.2(2) . . ?
C18 C17 C16 120.2(2) . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.4(2) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C11 N1 N2 C13 -177.93(16) . . . . ?
C5 C1 C2 C3 0.6(3) . . . . ?
Fe1 C1 C2 C3 59.9(2) . . . . ?
C5 C1 C2 Fe1 -59.3(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
Fe1 C2 C3 C4 59.4(2) . . . . ?
C1 C2 C3 Fe1 -59.9(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
Fe1 C3 C4 C5 60.0(2) . . . . ?
C2 C3 C4 Fe1 -59.8(2) . . . . ?
C2 C1 C5 C4 -0.5(3) . . . . ?
Fe1 C1 C5 C4 -59.9(2) . . . . ?
C2 C1 C5 Fe1 59.4(2) . . . . ?
C3 C4 C5 C1 0.2(3) . . . . ?
Fe1 C4 C5 C1 60.4(2) . . . . ?
C3 C4 C5 Fe1 -60.2(2) . . . . ?
C10 C6 C7 C8 0.6(2) . . . . ?
Fe1 C6 C7 C8 -59.14(15) . . . . ?
C10 C6 C7 Fe1 59.78(14) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
Fe1 C7 C8 C9 -59.35(14) . . . . ?
C6 C7 C8 Fe1 58.98(15) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
Fe1 C8 C9 C10 -59.53(13) . . . . ?
C7 C8 C9 Fe1 59.49(15) . . . . ?
C8 C9 C10 C6 0.4(2) . . . . ?
Fe1 C9 C10 C6 -58.85(13) . . . . ?
C8 C9 C10 C11 -178.88(17) . . . . ?
Fe1 C9 C10 C11 121.84(18) . . . . ?
C8 C9 C10 Fe1 59.28(14) . . . . ?
C7 C6 C10 C9 -0.7(2) . . . . ?
Fe1 C6 C10 C9 59.06(13) . . . . ?
C7 C6 C10 C11 178.65(18) . . . . ?
Fe1 C6 C10 C11 -121.64(18) . . . . ?
C7 C6 C10 Fe1 -59.71(14) . . . . ?
N2 N1 C11 C10 -179.99(14) . . . . ?
N2 N1 C11 C12 1.8(3) . . . . ?
C9 C10 C11 N1 16.7(3) . . . . ?
C6 C10 C11 N1 -162.49(18) . . . . ?
Fe1 C10 C11 N1 107.12(18) . . . . ?
C9 C10 C11 C12 -165.0(2) . . . . ?
C6 C10 C11 C12 15.8(3) . . . . ?
Fe1 C10 C11 C12 -74.6(2) . . . . ?
C14 N3 C13 N2 -177.13(16) . . . . ?
C14 N3 C13 S1 2.9(3) . . . . ?
N1 N2 C13 N3 -0.6(2) . . . . ?
N1 N2 C13 S1 179.38(12) . . . . ?
C13 N3 C14 C15 -100.9(2) . . . . ?
N3 C14 C15 C20 30.1(3) . . . . ?
N3 C14 C15 C16 -151.67(17) . . . . ?
C20 C15 C16 C17 0.2(3) . . . . ?
C14 C15 C16 C17 -178.05(19) . . . . ?
C21 O1 C17 C18 174.7(2) . . . . ?
C21 O1 C17 C16 -5.9(4) . . . . ?
C15 C16 C17 O1 -179.6(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
O1 C17 C18 C19 179.4(2) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C14 C15 C20 C19 178.1(2) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?

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
N2 H2A S1 0.86 2.80 3.6273(16) 161.6 2_666
C12 H12B S1 0.96 2.86 3.467(2) 122.2 2_666

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1041600'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: All of the authors have contribution in this research work.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
((1Z)-N-((2-fluorobenzyl)carbamothioyl)ethanehydrazonoyl)ferrocene
;
_chemical_formula_moiety         'C20 H20 F Fe N3 S'
_chemical_formula_sum            'C20 H20 F Fe N3 S'
_chemical_formula_iupac          'C20 H20 F Fe N3 S'
_chemical_formula_weight         409.30

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'
F F 0.0171 0.0103 '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'
Fe Fe 0.3463 0.8444 '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                   18.8634(13)
_cell_length_b                   7.1602(5)
_cell_length_c                   27.7613(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.830(4)
_cell_angle_gamma                90
_cell_volume                     3745.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2682
_cell_measurement_theta_min      1.469
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_T_max  0.864
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.00
_diffrn_reflns_number            13585
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.469
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3682
_reflns_number_gt                2678
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         3682
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0323P)²+2.3946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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 0.01155(2) 0.69231(5) 0.12211(2) 0.03808(12) Uani 1 1 d . . . . .
S1 S 0.28097(3) 1.07159(10) -0.05419(3) 0.0515(2) Uani 1 1 d . . . . .
F1 F 0.23984(13) 0.4009(3) -0.16164(7) 0.0958(7) Uani 1 1 d . . . . .
N1 N 0.11713(9) 0.8865(3) 0.01217(6) 0.0320(4) Uani 1 1 d . . . . .
N2 N 0.17203(9) 0.9999(3) -0.00141(6) 0.0339(4) Uani 1 1 d . . . . .
H2A H 0.1795 1.1066 0.0121 0.041 Uiso 1 1 calc R U . . .
N3 N 0.19677(10) 0.7726(3) -0.05514(7) 0.0383(5) Uani 1 1 d . . . . .
H3A H 0.1598 0.7179 -0.0450 0.046 Uiso 1 1 calc R U . . .
C1 C 0.09415(16) 0.7721(6) 0.16754(10) 0.0751(11) Uani 1 1 d . . . . .
H1 H 0.1295 0.8571 0.1606 0.090 Uiso 1 1 calc R U . . .
C2 C 0.09684(19) 0.5810(7) 0.15983(12) 0.0842(12) Uani 1 1 d . . . . .
H2 H 0.1339 0.5154 0.1468 0.101 Uiso 1 1 calc R U . . .
C3 C 0.0329(2) 0.5045(6) 0.17541(12) 0.0864(11) Uani 1 1 d . . . . .
H3 H 0.0204 0.3789 0.1747 0.104 Uiso 1 1 calc R U . . .
C4 C -0.00844(18) 0.6511(6) 0.19215(10) 0.0793(11) Uani 1 1 d . . . . .
H4 H -0.0533 0.6401 0.2043 0.095 Uiso 1 1 calc R U . . .
C5 C 0.02953(18) 0.8161(6) 0.18745(10) 0.0746(10) Uani 1 1 d . . . . .
H5 H 0.0146 0.9348 0.1960 0.090 Uiso 1 1 calc R U . . .
C6 C -0.04557(12) 0.8689(4) 0.07862(9) 0.0424(6) Uani 1 1 d . . . . .
H6 H -0.0597 0.9887 0.0869 0.051 Uiso 1 1 calc R U . . .
C7 C -0.08415(12) 0.7043(4) 0.08524(9) 0.0479(7) Uani 1 1 d . . . . .
H7 H -0.1285 0.6962 0.0982 0.057 Uiso 1 1 calc R U . . .
C8 C -0.04423(13) 0.5537(4) 0.06885(9) 0.0463(6) Uani 1 1 d . . . . .
H8 H -0.0576 0.4287 0.0693 0.056 Uiso 1 1 calc R U . . .
C9 C 0.01981(12) 0.6244(3) 0.05142(8) 0.0370(6) Uani 1 1 d . . . . .
H9 H 0.0558 0.5542 0.0386 0.044 Uiso 1 1 calc R U . . .
C10 C 0.01916(11) 0.8211(3) 0.05707(7) 0.0318(5) Uani 1 1 d . . . . .
C11 C 0.07513(11) 0.9493(3) 0.04347(8) 0.0324(5) Uani 1 1 d . . . . .
C12 C 0.07964(15) 1.1391(4) 0.06544(11) 0.0619(9) Uani 1 1 d . . . . .
H12A H 0.1236 1.1511 0.0842 0.093 Uiso 1 1 calc R U . . .
H12B H 0.0407 1.1569 0.0859 0.093 Uiso 1 1 calc R U . . .
H12C H 0.0776 1.2317 0.0404 0.093 Uiso 1 1 calc R U . . .
C13 C 0.21363(11) 0.9392(3) -0.03648(8) 0.0327(5) Uani 1 1 d . . . . .
C14 C 0.23617(12) 0.6764(4) -0.09136(8) 0.0424(6) Uani 1 1 d . . . . .
H14A H 0.2365 0.5438 -0.0843 0.051 Uiso 1 1 calc R U . . .
H14B H 0.2850 0.7196 -0.0892 0.051 Uiso 1 1 calc R U . . .
C15 C 0.20642(12) 0.7053(4) -0.14235(9) 0.0436(6) Uani 1 1 d . . . . .
C16 C 0.21018(15) 0.5660(4) -0.17616(11) 0.0580(8) Uani 1 1 d . . . . .
C17 C 0.18670(19) 0.5847(6) -0.22348(12) 0.0788(11) Uani 1 1 d . . . . .
H17 H 0.1903 0.4862 -0.2451 0.095 Uiso 1 1 calc R U . . .
C18 C 0.15800(19) 0.7512(7) -0.23807(12) 0.0881(12) Uani 1 1 d . . . . .
H18 H 0.1419 0.7673 -0.2700 0.106 Uiso 1 1 calc R U . . .
C19 C 0.15280(18) 0.8950(6) -0.20586(12) 0.0842(11) Uani 1 1 d . . . . .
H19 H 0.1330 1.0082 -0.2159 0.101 Uiso 1 1 calc R U . . .
C20 C 0.17697(15) 0.8716(5) -0.15851(11) 0.0636(8) Uani 1 1 d . . . . .
H20 H 0.1733 0.9702 -0.1370 0.076 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 C4 2.020(3) . ?
Fe1 C6 2.022(2) . ?
Fe1 C3 2.025(3) . ?
Fe1 C8 2.031(3) . ?
Fe1 C5 2.032(3) . ?
Fe1 C7 2.033(2) . ?
Fe1 C9 2.035(2) . ?
Fe1 C1 2.037(3) . ?
Fe1 C2 2.038(3) . ?
Fe1 C10 2.039(2) . ?
S1 C13 1.678(2) . ?
F1 C16 1.360(4) . ?
N1 C11 1.286(3) . ?
N1 N2 1.383(2) . ?
N2 C13 1.352(3) . ?
N2 H2A 0.8600 . ?
N3 C13 1.333(3) . ?
N3 C14 1.453(3) . ?
N3 H3A 0.8600 . ?
C1 C2 1.386(5) . ?
C1 C5 1.399(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.413(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.402(3) . ?
C6 C10 1.428(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.418(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.462(3) . ?
C11 C12 1.491(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.374(4) . ?
C15 C20 1.379(4) . ?
C16 C17 1.372(4) . ?
C17 C18 1.363(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 H20 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
C4 Fe1 C6 123.13(14) . . ?
C4 Fe1 C3 40.50(14) . . ?
C6 Fe1 C3 158.78(14) . . ?
C4 Fe1 C8 120.97(13) . . ?
C6 Fe1 C8 68.24(11) . . ?
C3 Fe1 C8 106.53(14) . . ?
C4 Fe1 C5 40.14(13) . . ?
C6 Fe1 C5 108.71(13) . . ?
C3 Fe1 C5 67.60(16) . . ?
C8 Fe1 C5 157.01(12) . . ?
C4 Fe1 C7 106.71(12) . . ?
C6 Fe1 C7 40.46(10) . . ?
C3 Fe1 C7 122.37(14) . . ?
C8 Fe1 C7 40.42(10) . . ?
C5 Fe1 C7 122.42(12) . . ?
C4 Fe1 C9 156.90(14) . . ?
C6 Fe1 C9 68.75(10) . . ?
C3 Fe1 C9 121.61(14) . . ?
C8 Fe1 C9 40.78(9) . . ?
C5 Fe1 C9 161.36(12) . . ?
C7 Fe1 C9 68.46(10) . . ?
C4 Fe1 C1 67.57(13) . . ?
C6 Fe1 C1 124.27(15) . . ?
C3 Fe1 C1 67.39(15) . . ?
C8 Fe1 C1 160.15(14) . . ?
C5 Fe1 C1 40.21(12) . . ?
C7 Fe1 C1 158.91(15) . . ?
C9 Fe1 C1 124.85(11) . . ?
C4 Fe1 C2 68.20(14) . . ?
C6 Fe1 C2 159.24(15) . . ?
C3 Fe1 C2 40.69(14) . . ?
C8 Fe1 C2 123.40(16) . . ?
C5 Fe1 C2 67.61(16) . . ?
C7 Fe1 C2 159.10(17) . . ?
C9 Fe1 C2 107.81(13) . . ?
C1 Fe1 C2 39.76(14) . . ?
C4 Fe1 C10 160.54(15) . . ?
C6 Fe1 C10 41.16(9) . . ?
C3 Fe1 C10 158.04(15) . . ?
C8 Fe1 C10 68.47(10) . . ?
C5 Fe1 C10 125.25(13) . . ?
C7 Fe1 C10 68.56(9) . . ?
C9 Fe1 C10 40.72(9) . . ?
C1 Fe1 C10 109.65(12) . . ?
C2 Fe1 C10 122.92(12) . . ?
C11 N1 N2 118.25(18) . . ?
C13 N2 N1 118.44(18) . . ?
C13 N2 H2A 120.8 . . ?
N1 N2 H2A 120.8 . . ?
C13 N3 C14 124.94(19) . . ?
C13 N3 H3A 117.5 . . ?
C14 N3 H3A 117.5 . . ?
C2 C1 C5 108.8(3) . . ?
C2 C1 Fe1 70.1(2) . . ?
C5 C1 Fe1 69.70(17) . . ?
C2 C1 H1 125.6 . . ?
C5 C1 H1 125.6 . . ?
Fe1 C1 H1 126.1 . . ?
C1 C2 C3 107.3(3) . . ?
C1 C2 Fe1 70.10(19) . . ?
C3 C2 Fe1 69.15(18) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
Fe1 C2 H2 126.0 . . ?
C4 C3 C2 108.0(4) . . ?
C4 C3 Fe1 69.58(19) . . ?
C2 C3 Fe1 70.16(18) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 125.8 . . ?
C5 C4 C3 107.9(3) . . ?
C5 C4 Fe1 70.39(17) . . ?
C3 C4 Fe1 69.92(17) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe1 C4 H4 125.2 . . ?
C4 C5 C1 108.0(3) . . ?
C4 C5 Fe1 69.47(18) . . ?
C1 C5 Fe1 70.08(17) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 108.3(2) . . ?
C7 C6 Fe1 70.17(14) . . ?
C10 C6 Fe1 70.05(13) . . ?
C7 C6 H6 125.9 . . ?
C10 C6 H6 125.9 . . ?
Fe1 C6 H6 125.5 . . ?
C6 C7 C8 108.3(2) . . ?
C6 C7 Fe1 69.37(14) . . ?
C8 C7 Fe1 69.74(14) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
Fe1 C7 H7 126.6 . . ?
C7 C8 C9 108.4(2) . . ?
C7 C8 Fe1 69.85(14) . . ?
C9 C8 Fe1 69.77(14) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 126.2 . . ?
C8 C9 C10 107.8(2) . . ?
C8 C9 Fe1 69.45(14) . . ?
C10 C9 Fe1 69.77(13) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
Fe1 C9 H9 126.2 . . ?
C9 C10 C6 107.3(2) . . ?
C9 C10 C11 125.8(2) . . ?
C6 C10 C11 127.0(2) . . ?
C9 C10 Fe1 69.51(13) . . ?
C6 C10 Fe1 68.79(13) . . ?
C11 C10 Fe1 126.57(15) . . ?
N1 C11 C10 115.6(2) . . ?
N1 C11 C12 124.8(2) . . ?
C10 C11 C12 119.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 N2 115.58(19) . . ?
N3 C13 S1 124.15(17) . . ?
N2 C13 S1 120.27(17) . . ?
N3 C14 C15 113.8(2) . . ?
N3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C20 116.0(3) . . ?
C16 C15 C14 120.7(3) . . ?
C20 C15 C14 123.2(2) . . ?
F1 C16 C17 118.5(3) . . ?
F1 C16 C15 117.6(3) . . ?
C17 C16 C15 123.9(3) . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 121.6(3) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?

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
C11 N1 N2 C13 -175.9(2) . . . . ?
C5 C1 C2 C3 -0.3(4) . . . . ?
Fe1 C1 C2 C3 -59.4(2) . . . . ?
C5 C1 C2 Fe1 59.1(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
Fe1 C2 C3 C4 -59.5(2) . . . . ?
C1 C2 C3 Fe1 60.0(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
Fe1 C3 C4 C5 -60.4(2) . . . . ?
C2 C3 C4 Fe1 59.9(2) . . . . ?
C3 C4 C5 C1 0.4(4) . . . . ?
Fe1 C4 C5 C1 -59.7(2) . . . . ?
C3 C4 C5 Fe1 60.1(2) . . . . ?
C2 C1 C5 C4 -0.1(4) . . . . ?
Fe1 C1 C5 C4 59.4(2) . . . . ?
C2 C1 C5 Fe1 -59.4(2) . . . . ?
C10 C6 C7 C8 0.9(3) . . . . ?
Fe1 C6 C7 C8 -59.08(18) . . . . ?
C10 C6 C7 Fe1 59.93(16) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
Fe1 C7 C8 C9 -59.29(17) . . . . ?
C6 C7 C8 Fe1 58.85(18) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
Fe1 C8 C9 C10 -59.48(16) . . . . ?
C7 C8 C9 Fe1 59.34(18) . . . . ?
C8 C9 C10 C6 0.6(3) . . . . ?
Fe1 C9 C10 C6 -58.63(16) . . . . ?
C8 C9 C10 C11 -179.7(2) . . . . ?
Fe1 C9 C10 C11 121.0(2) . . . . ?
C8 C9 C10 Fe1 59.28(16) . . . . ?
C7 C6 C10 C9 -0.9(3) . . . . ?
Fe1 C6 C10 C9 59.08(16) . . . . ?
C7 C6 C10 C11 179.5(2) . . . . ?
Fe1 C6 C10 C11 -120.5(2) . . . . ?
C7 C6 C10 Fe1 -60.01(17) . . . . ?
N2 N1 C11 C10 -178.72(17) . . . . ?
N2 N1 C11 C12 2.0(3) . . . . ?
C9 C10 C11 N1 20.8(3) . . . . ?
C6 C10 C11 N1 -159.7(2) . . . . ?
Fe1 C10 C11 N1 110.7(2) . . . . ?
C9 C10 C11 C12 -159.8(2) . . . . ?
C6 C10 C11 C12 19.7(4) . . . . ?
Fe1 C10 C11 C12 -70.0(3) . . . . ?
C14 N3 C13 N2 -176.8(2) . . . . ?
C14 N3 C13 S1 3.7(3) . . . . ?
N1 N2 C13 N3 0.5(3) . . . . ?
N1 N2 C13 S1 -179.92(15) . . . . ?
C13 N3 C14 C15 -96.2(3) . . . . ?
N3 C14 C15 C16 -146.5(2) . . . . ?
N3 C14 C15 C20 36.2(3) . . . . ?
C20 C15 C16 F1 179.1(2) . . . . ?
C14 C15 C16 F1 1.7(4) . . . . ?
C20 C15 C16 C17 -0.1(4) . . . . ?
C14 C15 C16 C17 -177.5(3) . . . . ?
F1 C16 C17 C18 -179.0(3) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C16 C15 C20 C19 0.1(4) . . . . ?
C14 C15 C20 C19 177.5(3) . . . . ?
C18 C19 C20 C15 -0.2(5) . . . . ?

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
N2 H2A S1 0.86 2.67 3.528(2) 173.3 7_575
C12 H12A S1 0.96 2.83 3.374(3) 116.6 7_575

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1041601'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: All of the authors have contribution in this research work.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
((1Z)-N-((4-flourobenzyl)carbamothioyl)ethanehydrazonoyl)ferrocene
;
_chemical_formula_moiety         'C20 H20 F Fe N3 S'
_chemical_formula_sum            'C20 H20 F Fe N3 S'
_chemical_formula_iupac          'C20 H20 F Fe N3 S'
_chemical_formula_weight         409.30

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'
F F 0.0171 0.0103 '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'
Fe Fe 0.3463 0.8444 '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                   19.0887(9)
_cell_length_b                   7.2037(3)
_cell_length_c                   27.4267(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.056(2)
_cell_angle_gamma                90
_cell_volume                     3770.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2950
_cell_measurement_theta_min      1.485
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  0.818
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.00
_diffrn_reflns_number            14970
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.485
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3704
_reflns_number_gt                2950
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         3704
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0354P)²+2.0033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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 0.00546(2) 0.69857(4) 0.12220(2) 0.03898(10) Uani 1 1 d . . . . .
S1 S 0.28141(3) 1.07621(9) -0.05654(2) 0.05934(19) Uani 1 1 d . . . . .
F1 F 0.14262(12) 0.7877(3) -0.28698(6) 0.1097(7) Uani 1 1 d . . . . .
N1 N 0.11884(8) 0.8868(2) 0.01224(6) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.17371(8) 0.9999(2) -0.00129(6) 0.0385(4) Uani 1 1 d . . . . .
H2A H 0.1811 1.1047 0.0129 0.046 Uiso 1 1 calc R U . . .
N3 N 0.20022(9) 0.7745(2) -0.05603(6) 0.0449(4) Uani 1 1 d . . . . .
H3A H 0.1646 0.7173 -0.0446 0.054 Uiso 1 1 calc R U . . .
C1 C 0.08473(14) 0.7808(5) 0.16821(9) 0.0711(8) Uani 1 1 d . . . . .
H1 H 0.1206 0.8629 0.1608 0.085 Uiso 1 1 calc R U . . .
C2 C 0.08664(16) 0.5883(5) 0.16207(9) 0.0792(9) Uani 1 1 d . . . . .
H2 H 0.1236 0.5196 0.1497 0.095 Uiso 1 1 calc R U . . .
C3 C 0.02221(19) 0.5175(5) 0.17805(10) 0.0841(9) Uani 1 1 d . . . . .
H3 H 0.0094 0.3929 0.1785 0.101 Uiso 1 1 calc R U . . .
C4 C -0.01945(16) 0.6666(5) 0.19325(8) 0.0757(8) Uani 1 1 d . . . . .
H4 H -0.0647 0.6587 0.2051 0.091 Uiso 1 1 calc R U . . .
C5 C 0.01968(15) 0.8291(4) 0.18737(8) 0.0713(8) Uani 1 1 d . . . . .
H5 H 0.0050 0.9487 0.1949 0.086 Uiso 1 1 calc R U . . .
C6 C 0.01988(11) 0.6257(3) 0.05136(7) 0.0401(5) Uani 1 1 d . . . . .
H6 H 0.0567 0.5556 0.0394 0.048 Uiso 1 1 calc R U . . .
C7 C -0.04473(12) 0.5557(3) 0.06805(8) 0.0505(5) Uani 1 1 d . . . . .
H7 H -0.0577 0.4313 0.0689 0.061 Uiso 1 1 calc R U . . .
C8 C -0.08621(11) 0.7063(3) 0.08323(8) 0.0513(6) Uani 1 1 d . . . . .
H8 H -0.1312 0.6984 0.0955 0.062 Uiso 1 1 calc R U . . .
C9 C -0.04759(10) 0.8710(3) 0.07656(7) 0.0425(5) Uani 1 1 d . . . . .
H9 H -0.0625 0.9904 0.0841 0.051 Uiso 1 1 calc R U . . .
C10 C 0.01848(10) 0.8226(3) 0.05622(6) 0.0347(4) Uani 1 1 d . . . . .
C11 C 0.07490(10) 0.9495(3) 0.04315(7) 0.0358(4) Uani 1 1 d . . . . .
C12 C 0.07669(13) 1.1396(3) 0.06494(10) 0.0622(7) Uani 1 1 d . . . . .
H12A H 0.1180 1.1527 0.0851 0.093 Uiso 1 1 calc R U . . .
H12B H 0.0359 1.1576 0.0844 0.093 Uiso 1 1 calc R U . . .
H12C H 0.0773 1.2305 0.0394 0.093 Uiso 1 1 calc R U . . .
C13 C 0.21548(10) 0.9414(3) -0.03752(7) 0.0398(5) Uani 1 1 d . . . . .
C14 C 0.23919(11) 0.6819(3) -0.09408(8) 0.0498(5) Uani 1 1 d . . . . .
H14A H 0.2406 0.5500 -0.0871 0.060 Uiso 1 1 calc R U . . .
H14B H 0.2870 0.7273 -0.0931 0.060 Uiso 1 1 calc R U . . .
C15 C 0.20948(11) 0.7092(3) -0.14493(8) 0.0476(5) Uani 1 1 d . . . . .
C16 C 0.18072(14) 0.8755(4) -0.15998(9) 0.0657(7) Uani 1 1 d . . . . .
H16 H 0.1768 0.9720 -0.1377 0.079 Uiso 1 1 calc R U . . .
C17 C 0.15746(15) 0.9024(4) -0.20756(10) 0.0763(8) Uani 1 1 d . . . . .
H17 H 0.1379 1.0151 -0.2172 0.092 Uiso 1 1 calc R U . . .
C18 C 0.16381(16) 0.7609(4) -0.23989(10) 0.0722(8) Uani 1 1 d . . . . .
C19 C 0.19073(16) 0.5932(4) -0.22664(10) 0.0756(8) Uani 1 1 d . . . . .
H19 H 0.1938 0.4976 -0.2493 0.091 Uiso 1 1 calc R U . . .
C20 C 0.21361(13) 0.5671(4) -0.17887(9) 0.0633(7) Uani 1 1 d . . . . .
H20 H 0.2320 0.4527 -0.1695 0.076 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 C9 2.022(2) . ?
Fe1 C4 2.028(2) . ?
Fe1 C7 2.032(2) . ?
Fe1 C3 2.033(3) . ?
Fe1 C5 2.033(2) . ?
Fe1 C8 2.034(2) . ?
Fe1 C6 2.0364(19) . ?
Fe1 C10 2.0374(18) . ?
Fe1 C1 2.040(2) . ?
Fe1 C2 2.041(3) . ?
S1 C13 1.680(2) . ?
F1 C18 1.360(3) . ?
N1 C11 1.286(2) . ?
N1 N2 1.383(2) . ?
N2 C13 1.353(2) . ?
N2 H2A 0.8600 . ?
N3 C13 1.335(3) . ?
N3 C14 1.454(3) . ?
N3 H3A 0.8600 . ?
C1 C2 1.398(4) . ?
C1 C5 1.401(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.409(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.416(3) . ?
C6 C10 1.425(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.410(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.432(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.463(3) . ?
C11 C12 1.494(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.378(3) . ?
C15 C20 1.387(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 H20 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
C9 Fe1 C4 122.76(11) . . ?
C9 Fe1 C7 68.57(9) . . ?
C4 Fe1 C7 121.94(11) . . ?
C9 Fe1 C3 158.55(12) . . ?
C4 Fe1 C3 40.46(12) . . ?
C7 Fe1 C3 106.94(12) . . ?
C9 Fe1 C5 108.50(11) . . ?
C4 Fe1 C5 40.33(11) . . ?
C7 Fe1 C5 158.44(10) . . ?
C3 Fe1 C5 67.53(13) . . ?
C9 Fe1 C8 40.69(9) . . ?
C4 Fe1 C8 107.06(11) . . ?
C7 Fe1 C8 40.58(9) . . ?
C3 Fe1 C8 122.37(12) . . ?
C5 Fe1 C8 123.28(11) . . ?
C9 Fe1 C6 69.07(8) . . ?
C4 Fe1 C6 157.81(12) . . ?
C7 Fe1 C6 40.73(8) . . ?
C3 Fe1 C6 122.10(12) . . ?
C5 Fe1 C6 160.02(10) . . ?
C8 Fe1 C6 68.64(9) . . ?
C9 Fe1 C10 41.30(7) . . ?
C4 Fe1 C10 159.74(11) . . ?
C7 Fe1 C10 68.68(8) . . ?
C3 Fe1 C10 158.53(12) . . ?
C5 Fe1 C10 124.16(11) . . ?
C8 Fe1 C10 68.85(8) . . ?
C6 Fe1 C10 40.95(8) . . ?
C9 Fe1 C1 124.19(11) . . ?
C4 Fe1 C1 67.85(11) . . ?
C7 Fe1 C1 158.96(11) . . ?
C3 Fe1 C1 67.39(13) . . ?
C5 Fe1 C1 40.24(11) . . ?
C8 Fe1 C1 159.72(12) . . ?
C6 Fe1 C1 123.60(10) . . ?
C10 Fe1 C1 108.72(10) . . ?
C9 Fe1 C2 159.63(12) . . ?
C4 Fe1 C2 68.29(12) . . ?
C7 Fe1 C2 122.51(13) . . ?
C3 Fe1 C2 40.46(12) . . ?
C5 Fe1 C2 67.76(13) . . ?
C8 Fe1 C2 158.33(13) . . ?
C6 Fe1 C2 107.23(10) . . ?
C10 Fe1 C2 122.87(10) . . ?
C1 Fe1 C2 40.05(12) . . ?
C11 N1 N2 118.44(16) . . ?
C13 N2 N1 118.22(16) . . ?
C13 N2 H2A 120.9 . . ?
N1 N2 H2A 120.9 . . ?
C13 N3 C14 125.08(18) . . ?
C13 N3 H3A 117.5 . . ?
C14 N3 H3A 117.5 . . ?
C2 C1 C5 108.5(3) . . ?
C2 C1 Fe1 70.01(16) . . ?
C5 C1 Fe1 69.63(14) . . ?
C2 C1 H1 125.8 . . ?
C5 C1 H1 125.8 . . ?
Fe1 C1 H1 126.2 . . ?
C1 C2 C3 107.3(3) . . ?
C1 C2 Fe1 69.93(15) . . ?
C3 C2 Fe1 69.46(15) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
Fe1 C2 H2 125.8 . . ?
C4 C3 C2 108.6(3) . . ?
C4 C3 Fe1 69.57(15) . . ?
C2 C3 Fe1 70.08(15) . . ?
C4 C3 H3 125.7 . . ?
C2 C3 H3 125.7 . . ?
Fe1 C3 H3 126.2 . . ?
C5 C4 C3 107.4(3) . . ?
C5 C4 Fe1 70.06(13) . . ?
C3 C4 Fe1 69.97(14) . . ?
C5 C4 H4 126.3 . . ?
C3 C4 H4 126.3 . . ?
Fe1 C4 H4 125.3 . . ?
C4 C5 C1 108.3(3) . . ?
C4 C5 Fe1 69.61(15) . . ?
C1 C5 Fe1 70.13(14) . . ?
C4 C5 H5 125.9 . . ?
C1 C5 H5 125.9 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 107.81(18) . . ?
C7 C6 Fe1 69.48(12) . . ?
C10 C6 Fe1 69.56(10) . . ?
C7 C6 H6 126.1 . . ?
C10 C6 H6 126.1 . . ?
Fe1 C6 H6 126.4 . . ?
C8 C7 C6 108.60(19) . . ?
C8 C7 Fe1 69.79(12) . . ?
C6 C7 Fe1 69.79(12) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
Fe1 C7 H7 126.3 . . ?
C7 C8 C9 108.12(18) . . ?
C7 C8 Fe1 69.63(12) . . ?
C9 C8 Fe1 69.19(12) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
Fe1 C8 H8 126.8 . . ?
C8 C9 C10 108.16(19) . . ?
C8 C9 Fe1 70.12(12) . . ?
C10 C9 Fe1 69.92(11) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe1 C9 H9 125.6 . . ?
C6 C10 C9 107.30(17) . . ?
C6 C10 C11 125.76(17) . . ?
C9 C10 C11 126.95(17) . . ?
C6 C10 Fe1 69.49(10) . . ?
C9 C10 Fe1 68.78(11) . . ?
C11 C10 Fe1 126.46(13) . . ?
N1 C11 C10 115.73(17) . . ?
N1 C11 C12 125.14(18) . . ?
C10 C11 C12 119.11(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 N2 115.63(17) . . ?
N3 C13 S1 124.18(15) . . ?
N2 C13 S1 120.19(15) . . ?
N3 C14 C15 114.52(18) . . ?
N3 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C20 117.9(2) . . ?
C16 C15 C14 122.1(2) . . ?
C20 C15 C14 120.0(2) . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 118.7(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 122.0(3) . . ?
C17 C18 F1 119.0(3) . . ?
C19 C18 F1 118.9(3) . . ?
C18 C19 C20 119.0(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?

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
C11 N1 N2 C13 -173.18(18) . . . . ?
C5 C1 C2 C3 -0.5(3) . . . . ?
Fe1 C1 C2 C3 -59.69(18) . . . . ?
C5 C1 C2 Fe1 59.19(17) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
Fe1 C2 C3 C4 -59.12(19) . . . . ?
C1 C2 C3 Fe1 59.99(18) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
Fe1 C3 C4 C5 -60.35(18) . . . . ?
C2 C3 C4 Fe1 59.44(18) . . . . ?
C3 C4 C5 C1 0.6(3) . . . . ?
Fe1 C4 C5 C1 -59.69(17) . . . . ?
C3 C4 C5 Fe1 60.29(18) . . . . ?
C2 C1 C5 C4 -0.1(3) . . . . ?
Fe1 C1 C5 C4 59.36(18) . . . . ?
C2 C1 C5 Fe1 -59.43(18) . . . . ?
C10 C6 C7 C8 0.0(2) . . . . ?
Fe1 C6 C7 C8 59.18(15) . . . . ?
C10 C6 C7 Fe1 -59.21(13) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
Fe1 C7 C8 C9 58.64(15) . . . . ?
C6 C7 C8 Fe1 -59.18(15) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
Fe1 C8 C9 C10 59.81(13) . . . . ?
C7 C8 C9 Fe1 -58.92(15) . . . . ?
C7 C6 C10 C9 0.6(2) . . . . ?
Fe1 C6 C10 C9 -58.58(13) . . . . ?
C7 C6 C10 C11 179.99(18) . . . . ?
Fe1 C6 C10 C11 120.83(18) . . . . ?
C7 C6 C10 Fe1 59.16(14) . . . . ?
C8 C9 C10 C6 -0.9(2) . . . . ?
Fe1 C9 C10 C6 59.03(13) . . . . ?
C8 C9 C10 C11 179.69(18) . . . . ?
Fe1 C9 C10 C11 -120.37(19) . . . . ?
C8 C9 C10 Fe1 -59.94(14) . . . . ?
N2 N1 C11 C10 -179.53(15) . . . . ?
N2 N1 C11 C12 2.1(3) . . . . ?
C6 C10 C11 N1 21.8(3) . . . . ?
C9 C10 C11 N1 -158.94(19) . . . . ?
Fe1 C10 C11 N1 111.49(18) . . . . ?
C6 C10 C11 C12 -159.7(2) . . . . ?
C9 C10 C11 C12 19.6(3) . . . . ?
Fe1 C10 C11 C12 -70.0(2) . . . . ?
C14 N3 C13 N2 -178.12(19) . . . . ?
C14 N3 C13 S1 2.0(3) . . . . ?
N1 N2 C13 N3 -1.7(3) . . . . ?
N1 N2 C13 S1 178.17(13) . . . . ?
C13 N3 C14 C15 -95.5(2) . . . . ?
N3 C14 C15 C16 37.7(3) . . . . ?
N3 C14 C15 C20 -145.4(2) . . . . ?
C20 C15 C16 C17 -0.9(4) . . . . ?
C14 C15 C16 C17 176.1(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 1.5(5) . . . . ?
C16 C17 C18 F1 -178.4(3) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
F1 C18 C19 C20 178.7(2) . . . . ?
C18 C19 C20 C15 -0.2(4) . . . . ?
C16 C15 C20 C19 1.2(4) . . . . ?
C14 C15 C20 C19 -175.8(2) . . . . ?

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
N2 H2A S1 0.86 2.68 3.5388(17) 173.9 7_575
C12 H12A S1 0.96 2.86 3.407(2) 117.3 7_575

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6

