#Supplementary Material (ESI) for Dalton Transactions
#This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'John Spencer'
_publ_contact_author_email       J.SPENCER@GRE.AC.UK

_publ_section_title              
;
Structural and Biological Investigation of
Ferrocene-Substituted 3-Methylidene-1,3-dihydro-2H-indol-2-ones
;
loop_
_publ_author_name
'John Spencer'
'Elizabeth Hillard'
'Mike Hursthouse'
'Gerard Jaouen'
'Arun K. Kotha'
'Louise Male'
;
A.P.Mendham
;
'Simon Richardson'
'Anne Vessieres'

# Attachment 'Ferrocenylmethylidene.cif'

data_(E)-3
_database_code_depnum_ccdc_archive 'CCDC 702095'

# EPSRC National Crystallography Service Code: 2008src0107

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-3-Ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
;
_chemical_name_common            
(E)-3-Ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Fe N O'
_chemical_formula_sum            'C19 H15 Fe N O'
_chemical_formula_weight         329.17

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   5.93060(10)
_cell_length_b                   13.5489(4)
_cell_length_c                   19.0452(5)
_cell_angle_alpha                73.8463(13)
_cell_angle_beta                 85.2798(15)
_cell_angle_gamma                86.0675(13)
_cell_volume                     1463.27(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    19855
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Slab
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_T_max  0.9040
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission from
SADABS: 0.6159 and 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30617
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6708
_reflns_number_gt                5216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    
;
Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R.,
2004)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP3 for Windows (Farrugia, (1997) &
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E.,
Shields, G. P., Taylor, R., Towler, M. and van de Streek, J., 2006
;
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.7880P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6708
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9169(4) 0.19495(17) 0.19069(11) 0.0171(4) Uani 1 1 d . . .
C2 C 1.1355(4) 0.18121(17) 0.22020(12) 0.0187(5) Uani 1 1 d . . .
H2 H 1.2603 0.1403 0.2074 0.022 Uiso 1 1 calc R . .
C3 C 1.1325(4) 0.23971(17) 0.27203(12) 0.0208(5) Uani 1 1 d . . .
H3 H 1.2559 0.2452 0.2993 0.025 Uiso 1 1 calc R . .
C4 C 0.9142(4) 0.28823(17) 0.27598(12) 0.0214(5) Uani 1 1 d . . .
H4 H 0.8663 0.3317 0.3064 0.026 Uiso 1 1 calc R . .
C5 C 0.7789(4) 0.26081(16) 0.22663(12) 0.0186(5) Uani 1 1 d . . .
H5 H 0.6249 0.2821 0.2187 0.022 Uiso 1 1 calc R . .
C6 C 0.7640(4) -0.01111(19) 0.32140(13) 0.0276(5) Uani 1 1 d . . .
H6 H 0.7277 -0.0428 0.2854 0.033 Uiso 1 1 calc R . .
C7 C 0.9775(4) -0.01920(18) 0.35213(13) 0.0254(5) Uani 1 1 d . . .
H7 H 1.1091 -0.0567 0.3400 0.030 Uiso 1 1 calc R . .
C8 C 0.9585(4) 0.03858(19) 0.40387(12) 0.0258(5) Uani 1 1 d . . .
H8 H 1.0755 0.0463 0.4329 0.031 Uiso 1 1 calc R . .
C9 C 0.7346(4) 0.0831(2) 0.40509(13) 0.0303(6) Uani 1 1 d . . .
H9 H 0.6756 0.1259 0.4349 0.036 Uiso 1 1 calc R . .
C10 C 0.6153(4) 0.0523(2) 0.35384(14) 0.0315(6) Uani 1 1 d . . .
H10 H 0.4620 0.0710 0.3431 0.038 Uiso 1 1 calc R . .
C11 C 0.8514(4) 0.13941(17) 0.14120(11) 0.0167(4) Uani 1 1 d . . .
H11 H 0.9428 0.0792 0.1407 0.020 Uiso 1 1 calc R . .
C12 C 0.6809(4) 0.15984(16) 0.09581(11) 0.0157(4) Uani 1 1 d . . .
C13 C 0.6293(4) 0.08062(17) 0.05868(12) 0.0179(5) Uani 1 1 d . . .
C14 C 0.3615(4) 0.21196(16) 0.03035(11) 0.0161(4) Uani 1 1 d . . .
C15 C 0.5111(4) 0.24408(16) 0.07321(11) 0.0162(4) Uani 1 1 d . . .
C16 C 0.4791(4) 0.34325(17) 0.08117(12) 0.0222(5) Uani 1 1 d . . .
H16 H 0.5810 0.3685 0.1073 0.027 Uiso 1 1 calc R . .
C17 C 0.2961(4) 0.40461(19) 0.05029(14) 0.0287(6) Uani 1 1 d . . .
H17 H 0.2726 0.4721 0.0560 0.034 Uiso 1 1 calc R . .
C18 C 0.1462(4) 0.36952(19) 0.01115(13) 0.0272(5) Uani 1 1 d . . .
H18 H 0.0201 0.4126 -0.0083 0.033 Uiso 1 1 calc R . .
C19 C 0.1787(4) 0.27189(17) 0.00010(12) 0.0210(5) Uani 1 1 d . . .
H19 H 0.0786 0.2478 -0.0272 0.025 Uiso 1 1 calc R . .
N1 N 0.4345(3) 0.11402(14) 0.02427(10) 0.0180(4) Uani 1 1 d . . .
H1 H 0.3638 0.0786 0.0012 0.022 Uiso 1 1 calc R . .
O1 O 0.7387(3) -0.00037(12) 0.05932(9) 0.0228(4) Uani 1 1 d . . .
Fe1 Fe 0.89200(5) 0.13142(2) 0.301951(16) 0.01602(9) Uani 1 1 d . . .
C101 C 0.4615(4) 0.57816(16) 0.24520(11) 0.0169(4) Uani 1 1 d . . .
C102 C 0.5290(4) 0.62505(17) 0.16904(12) 0.0200(5) Uani 1 1 d . . .
H102 H 0.6734 0.6509 0.1506 0.024 Uiso 1 1 calc R . .
C103 C 0.3430(4) 0.62587(18) 0.12659(12) 0.0218(5) Uani 1 1 d . . .
H103 H 0.3419 0.6514 0.0748 0.026 Uiso 1 1 calc R . .
C104 C 0.1585(4) 0.58195(17) 0.17495(12) 0.0210(5) Uani 1 1 d . . .
H104 H 0.0129 0.5729 0.1610 0.025 Uiso 1 1 calc R . .
C105 C 0.2292(4) 0.55378(17) 0.24803(12) 0.0191(5) Uani 1 1 d . . .
H105 H 0.1378 0.5240 0.2911 0.023 Uiso 1 1 calc R . .
C106 C 0.3212(4) 0.81248(18) 0.25695(13) 0.0250(5) Uani 1 1 d . . .
H106 H 0.4322 0.8049 0.2915 0.030 Uiso 1 1 calc R . .
C107 C 0.3528(4) 0.85858(17) 0.18037(13) 0.0240(5) Uani 1 1 d . . .
H107 H 0.4881 0.8870 0.1548 0.029 Uiso 1 1 calc R . .
C108 C 0.1458(4) 0.85468(18) 0.14871(14) 0.0263(5) Uani 1 1 d . . .
H108 H 0.1186 0.8799 0.0982 0.032 Uiso 1 1 calc R . .
C109 C -0.0133(4) 0.80634(18) 0.20586(14) 0.0266(5) Uani 1 1 d . . .
H109 H -0.1657 0.7940 0.2002 0.032 Uiso 1 1 calc R . .
C110 C 0.0956(4) 0.77951(18) 0.27316(14) 0.0266(5) Uani 1 1 d . . .
H110 H 0.0295 0.7458 0.3202 0.032 Uiso 1 1 calc R . .
C111 C 0.6095(4) 0.56860(17) 0.30400(12) 0.0168(4) Uani 1 1 d . . .
H111 H 0.7235 0.6176 0.2931 0.020 Uiso 1 1 calc R . .
C112 C 0.6130(4) 0.50196(16) 0.37147(12) 0.0163(4) Uani 1 1 d . . .
C113 C 0.7925(4) 0.51185(17) 0.42029(12) 0.0180(5) Uani 1 1 d . . .
C114 C 0.5970(4) 0.37033(17) 0.47918(12) 0.0182(5) Uani 1 1 d . . .
C115 C 0.4918(4) 0.41027(17) 0.41275(12) 0.0175(4) Uani 1 1 d . . .
C116 C 0.3126(4) 0.35818(18) 0.39970(13) 0.0227(5) Uani 1 1 d . . .
H116 H 0.2381 0.3830 0.3554 0.027 Uiso 1 1 calc R . .
C117 C 0.2427(4) 0.26940(18) 0.45191(13) 0.0256(5) Uani 1 1 d . . .
H117 H 0.1195 0.2342 0.4430 0.031 Uiso 1 1 calc R . .
C118 C 0.3502(4) 0.23161(19) 0.51662(14) 0.0273(5) Uani 1 1 d . . .
H118 H 0.2999 0.1710 0.5515 0.033 Uiso 1 1 calc R . .
C119 C 0.5326(4) 0.28210(19) 0.53096(13) 0.0255(5) Uani 1 1 d . . .
H119 H 0.6089 0.2563 0.5748 0.031 Uiso 1 1 calc R . .
N101 N 0.7730(3) 0.43299(14) 0.48206(10) 0.0199(4) Uani 1 1 d . . .
H101 H 0.8594 0.4224 0.5191 0.024 Uiso 1 1 calc R . .
O101 O 0.9342(3) 0.57857(12) 0.40657(8) 0.0234(4) Uani 1 1 d . . .
Fe11 Fe 0.26330(5) 0.70791(2) 0.201825(16) 0.01685(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0192(11) 0.0191(11) 0.0140(10) -0.0056(9) -0.0018(9) -0.0032(9)
C2 0.0182(11) 0.0215(11) 0.0165(11) -0.0048(9) -0.0017(9) -0.0037(9)
C3 0.0233(12) 0.0237(12) 0.0170(11) -0.0059(9) -0.0041(9) -0.0081(10)
C4 0.0294(13) 0.0193(11) 0.0185(11) -0.0090(9) -0.0045(10) -0.0023(10)
C5 0.0203(11) 0.0168(11) 0.0187(11) -0.0044(9) -0.0040(9) -0.0005(9)
C6 0.0370(14) 0.0222(12) 0.0228(12) -0.0018(10) -0.0050(11) -0.0103(11)
C7 0.0296(13) 0.0205(12) 0.0231(12) -0.0021(10) 0.0007(10) 0.0000(10)
C8 0.0310(13) 0.0283(13) 0.0158(11) -0.0012(10) -0.0048(10) -0.0028(10)
C9 0.0350(14) 0.0304(14) 0.0211(12) -0.0032(11) 0.0087(11) 0.0004(11)
C10 0.0202(12) 0.0339(14) 0.0319(14) 0.0059(11) -0.0025(11) -0.0049(11)
C11 0.0192(11) 0.0174(11) 0.0143(10) -0.0055(9) -0.0007(8) -0.0027(9)
C12 0.0199(11) 0.0155(10) 0.0124(10) -0.0047(8) -0.0005(8) -0.0041(9)
C13 0.0215(11) 0.0179(11) 0.0148(10) -0.0042(9) -0.0035(9) -0.0031(9)
C14 0.0193(11) 0.0152(11) 0.0138(10) -0.0039(9) -0.0005(8) -0.0031(9)
C15 0.0200(11) 0.0172(11) 0.0113(10) -0.0027(8) -0.0016(8) -0.0030(9)
C16 0.0295(13) 0.0185(11) 0.0206(12) -0.0066(9) -0.0068(10) -0.0033(10)
C17 0.0409(15) 0.0187(12) 0.0297(13) -0.0108(10) -0.0134(11) 0.0076(11)
C18 0.0300(13) 0.0230(12) 0.0280(13) -0.0054(10) -0.0118(11) 0.0091(10)
C19 0.0230(12) 0.0203(12) 0.0206(11) -0.0060(9) -0.0048(9) -0.0004(9)
N1 0.0192(9) 0.0172(9) 0.0207(10) -0.0085(8) -0.0078(8) 0.0001(7)
O1 0.0266(9) 0.0194(8) 0.0263(9) -0.0118(7) -0.0105(7) 0.0042(7)
Fe1 0.01701(17) 0.01825(17) 0.01351(16) -0.00505(13) -0.00187(12) -0.00177(12)
C101 0.0188(11) 0.0171(11) 0.0155(11) -0.0050(9) -0.0060(9) 0.0015(9)
C102 0.0198(11) 0.0224(12) 0.0179(11) -0.0065(9) -0.0009(9) 0.0018(9)
C103 0.0261(12) 0.0245(12) 0.0153(11) -0.0062(9) -0.0043(9) 0.0011(10)
C104 0.0194(11) 0.0219(12) 0.0245(12) -0.0093(10) -0.0090(9) 0.0021(9)
C105 0.0195(11) 0.0184(11) 0.0186(11) -0.0041(9) -0.0006(9) -0.0011(9)
C106 0.0303(13) 0.0204(12) 0.0270(13) -0.0102(10) -0.0048(10) -0.0014(10)
C107 0.0260(12) 0.0178(11) 0.0262(12) -0.0029(10) -0.0005(10) -0.0023(10)
C108 0.0307(13) 0.0184(12) 0.0271(13) -0.0013(10) -0.0096(10) 0.0055(10)
C109 0.0185(12) 0.0219(12) 0.0400(15) -0.0100(11) -0.0045(10) 0.0044(10)
C110 0.0350(14) 0.0196(12) 0.0256(13) -0.0088(10) 0.0051(11) -0.0006(10)
C111 0.0159(10) 0.0176(11) 0.0176(11) -0.0055(9) -0.0017(8) -0.0018(9)
C112 0.0164(10) 0.0178(11) 0.0168(11) -0.0079(9) -0.0031(8) 0.0010(9)
C113 0.0172(11) 0.0223(12) 0.0155(11) -0.0067(9) -0.0024(9) 0.0012(9)
C114 0.0191(11) 0.0210(11) 0.0155(11) -0.0065(9) -0.0017(9) 0.0001(9)
C115 0.0195(11) 0.0179(11) 0.0161(11) -0.0071(9) -0.0009(9) 0.0008(9)
C116 0.0274(12) 0.0211(12) 0.0212(12) -0.0065(10) -0.0076(10) -0.0006(10)
C117 0.0274(13) 0.0218(12) 0.0294(13) -0.0087(10) -0.0042(10) -0.0048(10)
C118 0.0334(14) 0.0205(12) 0.0259(13) -0.0030(10) 0.0012(11) -0.0055(10)
C119 0.0313(13) 0.0266(13) 0.0188(12) -0.0054(10) -0.0053(10) -0.0016(10)
N101 0.0211(10) 0.0237(10) 0.0148(9) -0.0035(8) -0.0056(8) -0.0025(8)
O101 0.0230(8) 0.0281(9) 0.0182(8) -0.0024(7) -0.0057(7) -0.0073(7)
Fe11 0.01713(17) 0.01748(17) 0.01583(17) -0.00393(13) -0.00378(12) 0.00047(12)

_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
C1 C2 1.435(3) . ?
C1 C5 1.443(3) . ?
C1 C11 1.449(3) . ?
C1 Fe1 2.050(2) . ?
C2 C3 1.426(3) . ?
C2 Fe1 2.036(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.417(3) . ?
C3 Fe1 2.049(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(3) . ?
C4 Fe1 2.054(2) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.044(2) . ?
C5 H5 0.9500 . ?
C6 C10 1.414(4) . ?
C6 C7 1.423(3) . ?
C6 Fe1 2.049(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(3) . ?
C7 Fe1 2.046(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.422(4) . ?
C8 Fe1 2.051(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(4) . ?
C9 Fe1 2.055(2) . ?
C9 H9 0.9500 . ?
C10 Fe1 2.050(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.349(3) . ?
C11 H11 0.9500 . ?
C12 C15 1.464(3) . ?
C12 C13 1.500(3) . ?
C13 O1 1.234(3) . ?
C13 N1 1.362(3) . ?
C14 C19 1.374(3) . ?
C14 N1 1.400(3) . ?
C14 C15 1.419(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 H1 0.8800 . ?
C101 C105 1.432(3) . ?
C101 C102 1.447(3) . ?
C101 C111 1.452(3) . ?
C101 Fe11 2.055(2) . ?
C102 C103 1.418(3) . ?
C102 Fe11 2.030(2) . ?
C102 H102 0.9500 . ?
C103 C104 1.420(3) . ?
C103 Fe11 2.053(2) . ?
C103 H103 0.9500 . ?
C104 C105 1.427(3) . ?
C104 Fe11 2.060(2) . ?
C104 H104 0.9500 . ?
C105 Fe11 2.045(2) . ?
C105 H105 0.9500 . ?
C106 C107 1.420(3) . ?
C106 C110 1.422(3) . ?
C106 Fe11 2.045(2) . ?
C106 H106 0.9500 . ?
C107 C108 1.422(3) . ?
C107 Fe11 2.065(2) . ?
C107 H107 0.9500 . ?
C108 C109 1.423(4) . ?
C108 Fe11 2.066(2) . ?
C108 H108 0.9500 . ?
C109 C110 1.427(3) . ?
C109 Fe11 2.052(2) . ?
C109 H109 0.9500 . ?
C110 Fe11 2.038(2) . ?
C110 H110 0.9500 . ?
C111 C112 1.350(3) . ?
C111 H111 0.9500 . ?
C112 C115 1.471(3) . ?
C112 C113 1.506(3) . ?
C113 O101 1.236(3) . ?
C113 N101 1.354(3) . ?
C114 C119 1.375(3) . ?
C114 N101 1.404(3) . ?
C114 C115 1.409(3) . ?
C115 C116 1.391(3) . ?
C116 C117 1.394(3) . ?
C116 H116 0.9500 . ?
C117 C118 1.386(3) . ?
C117 H117 0.9500 . ?
C118 C119 1.403(3) . ?
C118 H118 0.9500 . ?
C119 H119 0.9500 . ?
N101 H101 0.8800 . ?

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
C2 C1 C5 107.24(18) . . ?
C2 C1 C11 123.3(2) . . ?
C5 C1 C11 129.0(2) . . ?
C2 C1 Fe1 68.89(12) . . ?
C5 C1 Fe1 69.14(12) . . ?
C11 C1 Fe1 121.11(15) . . ?
C3 C2 C1 107.98(19) . . ?
C3 C2 Fe1 70.08(12) . . ?
C1 C2 Fe1 69.98(12) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 125.5 . . ?
C4 C3 C2 108.45(19) . . ?
C4 C3 Fe1 69.97(13) . . ?
C2 C3 Fe1 69.06(12) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
Fe1 C3 H3 126.8 . . ?
C3 C4 C5 108.38(19) . . ?
C3 C4 Fe1 69.61(13) . . ?
C5 C4 Fe1 69.32(13) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 126.8 . . ?
C4 C5 C1 107.9(2) . . ?
C4 C5 Fe1 70.05(13) . . ?
C1 C5 Fe1 69.59(12) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 125.9 . . ?
C10 C6 C7 108.1(2) . . ?
C10 C6 Fe1 69.86(14) . . ?
C7 C6 Fe1 69.56(13) . . ?
C10 C6 H6 126.0 . . ?
C7 C6 H6 126.0 . . ?
Fe1 C6 H6 126.2 . . ?
C8 C7 C6 107.7(2) . . ?
C8 C7 Fe1 70.00(14) . . ?
C6 C7 Fe1 69.78(14) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 125.7 . . ?
C7 C8 C9 108.3(2) . . ?
C7 C8 Fe1 69.67(13) . . ?
C9 C8 Fe1 69.92(14) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 126.1 . . ?
C10 C9 C8 107.7(2) . . ?
C10 C9 Fe1 69.60(14) . . ?
C8 C9 Fe1 69.56(13) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
Fe1 C9 H9 126.3 . . ?
C6 C10 C9 108.2(2) . . ?
C6 C10 Fe1 69.78(14) . . ?
C9 C10 Fe1 70.01(14) . . ?
C6 C10 H10 125.9 . . ?
C9 C10 H10 125.9 . . ?
Fe1 C10 H10 125.9 . . ?
C12 C11 C1 130.1(2) . . ?
C12 C11 H11 115.0 . . ?
C1 C11 H11 115.0 . . ?
C11 C12 C15 135.49(19) . . ?
C11 C12 C13 118.88(19) . . ?
C15 C12 C13 105.56(17) . . ?
O1 C13 N1 125.7(2) . . ?
O1 C13 C12 127.3(2) . . ?
N1 C13 C12 107.01(18) . . ?
C19 C14 N1 127.9(2) . . ?
C19 C14 C15 123.0(2) . . ?
N1 C14 C15 109.11(18) . . ?
C16 C15 C14 118.4(2) . . ?
C16 C15 C12 134.7(2) . . ?
C14 C15 C12 106.81(18) . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 121.5(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 117.3(2) . . ?
C14 C19 H19 121.4 . . ?
C18 C19 H19 121.4 . . ?
C13 N1 C14 111.24(17) . . ?
C13 N1 H1 124.4 . . ?
C14 N1 H1 124.4 . . ?
C2 Fe1 C5 69.22(9) . . ?
C2 Fe1 C7 106.73(9) . . ?
C5 Fe1 C7 161.44(9) . . ?
C2 Fe1 C6 121.10(10) . . ?
C5 Fe1 C6 124.78(9) . . ?
C7 Fe1 C6 40.66(10) . . ?
C2 Fe1 C3 40.86(8) . . ?
C5 Fe1 C3 68.48(9) . . ?
C7 Fe1 C3 121.04(10) . . ?
C6 Fe1 C3 156.66(10) . . ?
C2 Fe1 C10 156.81(10) . . ?
C5 Fe1 C10 107.99(10) . . ?
C7 Fe1 C10 68.19(10) . . ?
C6 Fe1 C10 40.36(10) . . ?
C3 Fe1 C10 161.31(10) . . ?
C2 Fe1 C1 41.13(8) . . ?
C5 Fe1 C1 41.27(8) . . ?
C7 Fe1 C1 123.94(9) . . ?
C6 Fe1 C1 107.45(9) . . ?
C3 Fe1 C1 68.74(8) . . ?
C10 Fe1 C1 121.56(10) . . ?
C2 Fe1 C8 123.73(9) . . ?
C5 Fe1 C8 156.84(9) . . ?
C7 Fe1 C8 40.34(9) . . ?
C6 Fe1 C8 67.91(10) . . ?
C3 Fe1 C8 107.61(9) . . ?
C10 Fe1 C8 67.98(10) . . ?
C1 Fe1 C8 160.60(9) . . ?
C2 Fe1 C4 68.67(9) . . ?
C5 Fe1 C4 40.63(9) . . ?
C7 Fe1 C4 156.38(10) . . ?
C6 Fe1 C4 161.62(10) . . ?
C3 Fe1 C4 40.42(9) . . ?
C10 Fe1 C4 125.10(10) . . ?
C1 Fe1 C4 68.76(9) . . ?
C8 Fe1 C4 121.63(9) . . ?
C2 Fe1 C9 160.76(10) . . ?
C5 Fe1 C9 121.57(10) . . ?
C7 Fe1 C9 68.13(10) . . ?
C6 Fe1 C9 67.92(10) . . ?
C3 Fe1 C9 124.55(10) . . ?
C10 Fe1 C9 40.39(11) . . ?
C1 Fe1 C9 157.11(10) . . ?
C8 Fe1 C9 40.52(10) . . ?
C4 Fe1 C9 108.16(10) . . ?
C105 C101 C102 106.84(19) . . ?
C105 C101 C111 130.2(2) . . ?
C102 C101 C111 122.79(19) . . ?
C105 C101 Fe11 69.19(12) . . ?
C102 C101 Fe11 68.31(12) . . ?
C111 C101 Fe11 123.79(15) . . ?
C103 C102 C101 108.4(2) . . ?
C103 C102 Fe11 70.56(13) . . ?
C101 C102 Fe11 70.19(12) . . ?
C103 C102 H102 125.8 . . ?
C101 C102 H102 125.8 . . ?
Fe11 C102 H102 125.0 . . ?
C102 C103 C104 108.1(2) . . ?
C102 C103 Fe11 68.79(12) . . ?
C104 C103 Fe11 70.08(13) . . ?
C102 C103 H103 126.0 . . ?
C104 C103 H103 126.0 . . ?
Fe11 C103 H103 126.8 . . ?
C103 C104 C105 108.4(2) . . ?
C103 C104 Fe11 69.52(13) . . ?
C105 C104 Fe11 69.09(12) . . ?
C103 C104 H104 125.8 . . ?
C105 C104 H104 125.8 . . ?
Fe11 C104 H104 127.2 . . ?
C104 C105 C101 108.21(19) . . ?
C104 C105 Fe11 70.23(13) . . ?
C101 C105 Fe11 69.92(12) . . ?
C104 C105 H105 125.9 . . ?
C101 C105 H105 125.9 . . ?
Fe11 C105 H105 125.5 . . ?
C107 C106 C110 108.6(2) . . ?
C107 C106 Fe11 70.56(13) . . ?
C110 C106 Fe11 69.38(13) . . ?
C107 C106 H106 125.7 . . ?
C110 C106 H106 125.7 . . ?
Fe11 C106 H106 125.9 . . ?
C106 C107 C108 107.8(2) . . ?
C106 C107 Fe11 69.01(13) . . ?
C108 C107 Fe11 69.92(13) . . ?
C106 C107 H107 126.1 . . ?
C108 C107 H107 126.1 . . ?
Fe11 C107 H107 126.5 . . ?
C107 C108 C109 108.0(2) . . ?
C107 C108 Fe11 69.82(13) . . ?
C109 C108 Fe11 69.27(13) . . ?
C107 C108 H108 126.0 . . ?
C109 C108 H108 126.0 . . ?
Fe11 C108 H108 126.5 . . ?
C108 C109 C110 108.2(2) . . ?
C108 C109 Fe11 70.32(13) . . ?
C110 C109 Fe11 69.06(13) . . ?
C108 C109 H109 125.9 . . ?
C110 C109 H109 125.9 . . ?
Fe11 C109 H109 126.3 . . ?
C106 C110 C109 107.4(2) . . ?
C106 C110 Fe11 69.85(13) . . ?
C109 C110 Fe11 70.11(13) . . ?
C106 C110 H110 126.3 . . ?
C109 C110 H110 126.3 . . ?
Fe11 C110 H110 125.3 . . ?
C112 C111 C101 131.0(2) . . ?
C112 C111 H111 114.5 . . ?
C101 C111 H111 114.5 . . ?
C111 C112 C115 136.6(2) . . ?
C111 C112 C113 118.1(2) . . ?
C115 C112 C113 105.08(18) . . ?
O101 C113 N101 125.9(2) . . ?
O101 C113 C112 126.7(2) . . ?
N101 C113 C112 107.41(19) . . ?
C119 C114 N101 127.3(2) . . ?
C119 C114 C115 123.2(2) . . ?
N101 C114 C115 109.51(19) . . ?
C116 C115 C114 118.0(2) . . ?
C116 C115 C112 135.1(2) . . ?
C114 C115 C112 106.90(18) . . ?
C115 C116 C117 119.7(2) . . ?
C115 C116 H116 120.2 . . ?
C117 C116 H116 120.2 . . ?
C118 C117 C116 121.0(2) . . ?
C118 C117 H117 119.5 . . ?
C116 C117 H117 119.5 . . ?
C117 C118 C119 120.5(2) . . ?
C117 C118 H118 119.7 . . ?
C119 C118 H118 119.7 . . ?
C114 C119 C118 117.5(2) . . ?
C114 C119 H119 121.2 . . ?
C118 C119 H119 121.2 . . ?
C113 N101 C114 111.10(18) . . ?
C113 N101 H101 124.5 . . ?
C114 N101 H101 124.5 . . ?
C102 Fe11 C110 153.09(10) . . ?
C102 Fe11 C106 119.35(10) . . ?
C110 Fe11 C106 40.77(10) . . ?
C102 Fe11 C105 69.14(9) . . ?
C110 Fe11 C105 105.96(9) . . ?
C106 Fe11 C105 125.51(9) . . ?
C102 Fe11 C109 164.90(10) . . ?
C110 Fe11 C109 40.83(10) . . ?
C106 Fe11 C109 68.19(10) . . ?
C105 Fe11 C109 118.56(9) . . ?
C102 Fe11 C103 40.65(9) . . ?
C110 Fe11 C103 164.09(10) . . ?
C106 Fe11 C103 154.42(10) . . ?
C105 Fe11 C103 68.62(9) . . ?
C109 Fe11 C103 127.38(10) . . ?
C102 Fe11 C101 41.50(9) . . ?
C110 Fe11 C101 117.47(9) . . ?
C106 Fe11 C101 106.74(9) . . ?
C105 Fe11 C101 40.88(8) . . ?
C109 Fe11 C101 152.45(10) . . ?
C103 Fe11 C101 68.91(9) . . ?
C102 Fe11 C104 68.37(9) . . ?
C110 Fe11 C104 126.00(10) . . ?
C106 Fe11 C104 163.42(10) . . ?
C105 Fe11 C104 40.68(9) . . ?
C109 Fe11 C104 108.22(9) . . ?
C103 Fe11 C104 40.40(9) . . ?
C101 Fe11 C104 68.51(8) . . ?
C102 Fe11 C107 108.47(10) . . ?
C110 Fe11 C107 68.43(10) . . ?
C106 Fe11 C107 40.43(9) . . ?
C105 Fe11 C107 163.62(9) . . ?
C109 Fe11 C107 67.97(10) . . ?
C103 Fe11 C107 120.84(9) . . ?
C101 Fe11 C107 126.71(9) . . ?
C104 Fe11 C107 154.86(9) . . ?
C102 Fe11 C108 127.54(10) . . ?
C110 Fe11 C108 68.42(10) . . ?
C106 Fe11 C108 67.92(10) . . ?
C105 Fe11 C108 153.70(10) . . ?
C109 Fe11 C108 40.41(10) . . ?
C103 Fe11 C108 109.41(10) . . ?
C101 Fe11 C108 164.90(10) . . ?
C104 Fe11 C108 120.61(9) . . ?
C107 Fe11 C108 40.26(10) . . ?

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
N1 H1 O1 0.88 1.92 2.795(2) 169.5 2_655
N101 H101 O101 0.88 1.94 2.815(2) 170.7 2_766

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.111

#==============================================================================

data_(Z)-3
_database_code_depnum_ccdc_archive 'CCDC 702096'

# EPSRC National Crystallography Service Code: 2008src0011r

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(Z)-3-Ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
;
_chemical_name_common            
(Z)-3-Ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Fe N O'
_chemical_formula_sum            'C19 H15 Fe N O'
_chemical_formula_weight         329.17

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.1939(14)
_cell_length_b                   6.1825(6)
_cell_length_c                   15.4621(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.168(5)
_cell_angle_gamma                90.00
_cell_volume                     1450.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    29087
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9402
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Parameter refinement on 8606 reflections reduced R(int) from 0.1781 to 0.1014
Ratio of minimum to maximum apparent transmission: 0.712024
The given Tmin and Tmax were generated using the SHELX SIZE command.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10819
_diffrn_reflns_av_R_equivalents  0.1211
_diffrn_reflns_av_sigmaI/netI    0.1067
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2563
_reflns_number_gt                1752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    
;
Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R.,
2004)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP3 for Windows (Farrugia, (1997) &
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E.,
Shields, G. P., Taylor, R., Towler, M. and van de Streek, J., 2006
;
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The diffraction data were rather weak, especially at higher angle which has
led to a slightly high value of Rint. This was the best crystal and the
best quality dataset that could be obtained.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+23.9414P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2563
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.1877
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3017(6) 0.1441(15) 0.4624(6) 0.028(2) Uani 1 1 d . . .
C2 C 0.2601(5) -0.0124(15) 0.5160(5) 0.025(2) Uani 1 1 d . . .
H2 H 0.2794 -0.1567 0.5264 0.030 Uiso 1 1 calc R . .
C3 C 0.1863(5) 0.0856(16) 0.5501(5) 0.027(2) Uani 1 1 d . . .
H3 H 0.1469 0.0172 0.5871 0.033 Uiso 1 1 calc R . .
C4 C 0.1794(6) 0.3037(16) 0.5205(6) 0.032(2) Uani 1 1 d . . .
H4 H 0.1361 0.4063 0.5351 0.039 Uiso 1 1 calc R . .
C5 C 0.2492(5) 0.3381(15) 0.4656(6) 0.027(2) Uani 1 1 d . . .
H5 H 0.2599 0.4685 0.4355 0.033 Uiso 1 1 calc R . .
C6 C 0.1693(6) -0.0289(19) 0.2946(7) 0.044(3) Uani 1 1 d . . .
H6 H 0.2189 -0.0550 0.2613 0.053 Uiso 1 1 calc R . .
C7 C 0.1308(7) -0.1772(17) 0.3511(7) 0.040(3) Uani 1 1 d . . .
H7 H 0.1500 -0.3210 0.3629 0.048 Uiso 1 1 calc R . .
C8 C 0.0586(6) -0.0722(18) 0.3868(6) 0.038(2) Uani 1 1 d . . .
H8 H 0.0207 -0.1341 0.4270 0.045 Uiso 1 1 calc R . .
C9 C 0.0519(6) 0.1370(18) 0.3535(7) 0.040(3) Uani 1 1 d . . .
H9 H 0.0088 0.2416 0.3666 0.048 Uiso 1 1 calc R . .
C10 C 0.1204(7) 0.1655(18) 0.2969(6) 0.042(3) Uani 1 1 d . . .
H10 H 0.1318 0.2937 0.2656 0.051 Uiso 1 1 calc R . .
C11 C 0.3767(5) 0.1328(13) 0.4091(5) 0.0219(19) Uani 1 1 d . . .
H11 H 0.3839 0.2573 0.3741 0.026 Uiso 1 1 calc R . .
C12 C 0.4386(5) -0.0212(12) 0.3994(5) 0.0176(18) Uani 1 1 d . . .
C13 C 0.4483(5) -0.2376(14) 0.4421(6) 0.0217(19) Uani 1 1 d . . .
C14 C 0.5609(6) -0.2013(14) 0.3483(5) 0.024(2) Uani 1 1 d . . .
C15 C 0.5136(6) -0.0071(14) 0.3417(6) 0.025(2) Uani 1 1 d . . .
C16 C 0.5423(6) 0.1516(14) 0.2875(5) 0.025(2) Uani 1 1 d . . .
H16 H 0.5121 0.2859 0.2827 0.030 Uiso 1 1 calc R . .
C17 C 0.6153(6) 0.1144(15) 0.2403(5) 0.027(2) Uani 1 1 d . . .
H17 H 0.6355 0.2235 0.2030 0.033 Uiso 1 1 calc R . .
C18 C 0.6594(6) -0.0832(16) 0.2473(6) 0.030(2) Uani 1 1 d . . .
H18 H 0.7091 -0.1079 0.2140 0.036 Uiso 1 1 calc R . .
C19 C 0.6320(5) -0.2436(16) 0.3020(6) 0.029(2) Uani 1 1 d . . .
H19 H 0.6619 -0.3783 0.3069 0.035 Uiso 1 1 calc R . .
N1 N 0.5196(4) -0.3355(11) 0.4072(5) 0.0232(16) Uani 1 1 d . . .
H1 H 0.5374 -0.4676 0.4203 0.028 Uiso 1 1 calc R . .
O1 O 0.4049(4) -0.3204(9) 0.4976(4) 0.0247(14) Uani 1 1 d . . .
Fe1 Fe 0.17228(8) 0.0904(2) 0.41818(8) 0.0239(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.023(4) 0.034(5) 0.026(5) -0.001(4) 0.000(4) -0.001(4)
C2 0.014(4) 0.036(5) 0.024(5) 0.000(4) -0.003(4) 0.004(4)
C3 0.022(4) 0.038(5) 0.023(5) -0.007(5) -0.001(4) 0.002(4)
C4 0.026(5) 0.029(5) 0.042(6) -0.014(5) -0.004(4) 0.003(4)
C5 0.023(4) 0.027(5) 0.032(5) -0.004(4) -0.002(4) 0.004(4)
C6 0.021(5) 0.073(8) 0.038(6) -0.024(6) -0.007(4) 0.003(5)
C7 0.041(6) 0.028(5) 0.049(7) -0.007(5) -0.017(5) 0.004(5)
C8 0.026(5) 0.050(6) 0.036(6) -0.009(5) -0.003(4) -0.006(5)
C9 0.024(5) 0.047(7) 0.048(7) -0.009(5) -0.012(5) 0.006(5)
C10 0.045(6) 0.048(7) 0.031(6) 0.010(5) -0.023(5) -0.006(5)
C11 0.021(4) 0.020(5) 0.024(5) 0.003(4) -0.004(4) 0.001(4)
C12 0.029(5) 0.012(4) 0.011(4) -0.002(3) -0.005(3) -0.002(3)
C13 0.018(4) 0.020(4) 0.026(5) -0.002(4) -0.005(4) 0.005(4)
C14 0.036(5) 0.023(5) 0.012(4) -0.002(4) -0.002(4) 0.009(4)
C15 0.027(5) 0.028(5) 0.019(5) -0.001(4) -0.007(4) -0.003(4)
C16 0.030(5) 0.026(5) 0.018(4) 0.006(4) -0.006(4) -0.004(4)
C17 0.031(5) 0.030(5) 0.022(5) 0.011(4) 0.001(4) -0.011(4)
C18 0.028(5) 0.035(5) 0.028(5) -0.003(5) 0.010(4) -0.002(5)
C19 0.016(4) 0.040(6) 0.031(5) -0.004(4) -0.006(4) 0.004(4)
N1 0.024(4) 0.017(4) 0.029(4) 0.000(3) 0.001(3) 0.006(3)
O1 0.019(3) 0.023(3) 0.032(4) 0.007(3) 0.004(3) -0.005(3)
Fe1 0.0199(6) 0.0267(7) 0.0246(7) -0.0039(6) -0.0037(5) 0.0029(6)

_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
C1 C2 1.442(13) . ?
C1 C5 1.443(12) . ?
C1 C11 1.445(12) . ?
C1 Fe1 2.073(8) . ?
C2 C3 1.403(12) . ?
C2 Fe1 2.061(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(14) . ?
C3 Fe1 2.039(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(13) . ?
C4 Fe1 2.058(9) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.038(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(15) . ?
C6 C10 1.415(15) . ?
C6 Fe1 2.046(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(14) . ?
C7 Fe1 2.034(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(15) . ?
C8 Fe1 2.034(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.407(15) . ?
C9 Fe1 2.056(9) . ?
C9 H9 0.9500 . ?
C10 Fe1 2.046(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.353(11) . ?
C11 H11 0.9500 . ?
C12 C15 1.488(12) . ?
C12 C13 1.495(11) . ?
C13 O1 1.222(10) . ?
C13 N1 1.378(11) . ?
C14 C19 1.355(12) . ?
C14 C15 1.400(12) . ?
C14 N1 1.404(11) . ?
C15 C16 1.376(12) . ?
C16 C17 1.381(12) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(13) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 H1 0.8800 . ?

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
C2 C1 C5 106.1(8) . . ?
C2 C1 C11 132.9(8) . . ?
C5 C1 C11 121.0(8) . . ?
C2 C1 Fe1 69.2(5) . . ?
C5 C1 Fe1 68.2(5) . . ?
C11 C1 Fe1 124.6(6) . . ?
C3 C2 C1 108.1(8) . . ?
C3 C2 Fe1 69.1(5) . . ?
C1 C2 Fe1 70.0(5) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 126.5 . . ?
C2 C3 C4 109.5(8) . . ?
C2 C3 Fe1 70.8(5) . . ?
C4 C3 Fe1 70.4(5) . . ?
C2 C3 H3 125.3 . . ?
C4 C3 H3 125.3 . . ?
Fe1 C3 H3 125.1 . . ?
C5 C4 C3 106.9(8) . . ?
C5 C4 Fe1 69.1(5) . . ?
C3 C4 Fe1 68.9(5) . . ?
C5 C4 H4 126.5 . . ?
C3 C4 H4 126.5 . . ?
Fe1 C4 H4 127.0 . . ?
C4 C5 C1 109.3(8) . . ?
C4 C5 Fe1 70.6(5) . . ?
C1 C5 Fe1 70.8(5) . . ?
C4 C5 H5 125.3 . . ?
C1 C5 H5 125.3 . . ?
Fe1 C5 H5 124.9 . . ?
C7 C6 C10 107.4(9) . . ?
C7 C6 Fe1 69.3(6) . . ?
C10 C6 Fe1 69.8(6) . . ?
C7 C6 H6 126.3 . . ?
C10 C6 H6 126.3 . . ?
Fe1 C6 H6 126.2 . . ?
C6 C7 C8 107.5(9) . . ?
C6 C7 Fe1 70.2(6) . . ?
C8 C7 Fe1 69.7(6) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
Fe1 C7 H7 125.5 . . ?
C9 C8 C7 108.9(10) . . ?
C9 C8 Fe1 70.9(6) . . ?
C7 C8 Fe1 69.7(5) . . ?
C9 C8 H8 125.5 . . ?
C7 C8 H8 125.5 . . ?
Fe1 C8 H8 125.4 . . ?
C8 C9 C10 107.7(9) . . ?
C8 C9 Fe1 69.2(5) . . ?
C10 C9 Fe1 69.6(5) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
Fe1 C9 H9 126.6 . . ?
C9 C10 C6 108.5(10) . . ?
C9 C10 Fe1 70.3(6) . . ?
C6 C10 Fe1 69.8(6) . . ?
C9 C10 H10 125.7 . . ?
C6 C10 H10 125.7 . . ?
Fe1 C10 H10 125.8 . . ?
C12 C11 C1 132.2(8) . . ?
C12 C11 H11 113.9 . . ?
C1 C11 H11 113.9 . . ?
C11 C12 C15 125.8(8) . . ?
C11 C12 C13 129.3(8) . . ?
C15 C12 C13 104.9(7) . . ?
O1 C13 N1 123.9(8) . . ?
O1 C13 C12 129.8(8) . . ?
N1 C13 C12 106.3(7) . . ?
C19 C14 C15 123.2(9) . . ?
C19 C14 N1 128.8(8) . . ?
C15 C14 N1 108.0(7) . . ?
C16 C15 C14 118.5(8) . . ?
C16 C15 C12 133.3(8) . . ?
C14 C15 C12 108.2(7) . . ?
C15 C16 C17 119.6(8) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.1(8) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 121.1(8) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C14 C19 C18 117.4(9) . . ?
C14 C19 H19 121.3 . . ?
C18 C19 H19 121.3 . . ?
C13 N1 C14 112.5(7) . . ?
C13 N1 H1 123.7 . . ?
C14 N1 H1 123.7 . . ?
C8 Fe1 C7 40.7(4) . . ?
C8 Fe1 C5 156.9(4) . . ?
C7 Fe1 C5 161.8(4) . . ?
C8 Fe1 C3 105.8(4) . . ?
C7 Fe1 C3 120.7(4) . . ?
C5 Fe1 C3 68.0(4) . . ?
C8 Fe1 C10 67.3(4) . . ?
C7 Fe1 C10 67.9(4) . . ?
C5 Fe1 C10 110.1(4) . . ?
C3 Fe1 C10 158.9(4) . . ?
C8 Fe1 C6 68.0(4) . . ?
C7 Fe1 C6 40.6(4) . . ?
C5 Fe1 C6 126.1(4) . . ?
C3 Fe1 C6 157.6(5) . . ?
C10 Fe1 C6 40.5(4) . . ?
C8 Fe1 C9 39.8(4) . . ?
C7 Fe1 C9 67.9(4) . . ?
C5 Fe1 C9 123.2(4) . . ?
C3 Fe1 C9 122.0(4) . . ?
C10 Fe1 C9 40.1(4) . . ?
C6 Fe1 C9 67.9(4) . . ?
C8 Fe1 C4 120.5(4) . . ?
C7 Fe1 C4 156.2(4) . . ?
C5 Fe1 C4 40.3(4) . . ?
C3 Fe1 C4 40.7(4) . . ?
C10 Fe1 C4 124.1(4) . . ?
C6 Fe1 C4 161.2(5) . . ?
C9 Fe1 C4 107.0(4) . . ?
C8 Fe1 C2 122.0(4) . . ?
C7 Fe1 C2 107.0(4) . . ?
C5 Fe1 C2 68.4(4) . . ?
C3 Fe1 C2 40.0(3) . . ?
C10 Fe1 C2 160.6(4) . . ?
C6 Fe1 C2 123.6(4) . . ?
C9 Fe1 C2 157.3(4) . . ?
C4 Fe1 C2 68.2(4) . . ?
C8 Fe1 C1 159.3(4) . . ?
C7 Fe1 C1 124.1(4) . . ?
C5 Fe1 C1 41.1(3) . . ?
C3 Fe1 C1 68.1(3) . . ?
C10 Fe1 C1 125.2(4) . . ?
C6 Fe1 C1 109.7(4) . . ?
C9 Fe1 C1 160.1(4) . . ?
C4 Fe1 C1 68.6(4) . . ?
C2 Fe1 C1 40.8(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
N1 H1 O1 0.88 1.99 2.797(9) 151.0 3_646

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.502
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.145