# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2006

data_global

_journal_coden_Cambridge         440

_publ_requested_journal          'New Journal of Chemistry'

loop_
_publ_author_name
'Kenneth Lo'
'Jason Shing-Yip Lau'
'Nianyong Zhu'

_publ_contact_author_name        'Kenneth Lo'
_publ_contact_author_address     
;
Department of Biology and Chemistry
City University of Hong Kong
Tat Chee Avenue
Kowloon
Hong Kong
N.A.
CHINA
;

_publ_contact_author_email       BHKENLO@CITYU.EDU.HK

_publ_section_title              
;
Synthesis, Crystal Structures, Electrochemical and
Protein-Binding Properties of Ferrocene-Indole Conjugates
;

# Attachment 'B609052D_Fc1.cif'

data_mar810
_database_code_depnum_ccdc_archive 'CCDC 616828'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 Fe N2'
_chemical_formula_sum            'C21 H20 Fe N2'
_chemical_formula_weight         356.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.2320(14)
_cell_length_b                   9.890(2)
_cell_length_c                   24.259(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1735.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Marresearch Imaging Plate mar300'
_diffrn_measurement_method       Oscillation
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7098
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2730
_reflns_number_gt                2228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Marcontrol
_computing_cell_refinement       Scalepack
_computing_data_reduction        Denzo
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (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^)+(0.0000P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(16)
_refine_ls_number_reflns         2730
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0550
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_restrained_S_all      0.875
_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
Fe1 Fe 0.73849(4) -0.43298(3) 0.421951(12) 0.03736(11) Uani 1 1 d . . .
N1 N 0.9093(2) -0.2722(2) 0.28316(8) 0.0399(5) Uani 1 1 d . . .
N2 N 0.2687(3) -0.1451(2) 0.29908(7) 0.0420(5) Uani 1 1 d . . .
H2 H 0.1642 -0.1864 0.2981 0.050 Uiso 1 1 calc R . .
C1 C 0.8321(3) -0.3790(3) 0.30090(10) 0.0395(6) Uani 1 1 d . . .
H1 H 0.7353 -0.4155 0.2805 0.047 Uiso 1 1 calc R . .
C2 C 0.8330(3) -0.2097(3) 0.23334(10) 0.0490(7) Uani 1 1 d . . .
H2A H 0.7420 -0.2695 0.2169 0.059 Uiso 1 1 calc R . .
H2B H 0.9310 -0.1953 0.2067 0.059 Uiso 1 1 calc R . .
C3 C 0.7431(3) -0.0755(2) 0.24756(9) 0.0483(6) Uani 1 1 d . . .
H3A H 0.8283 -0.0237 0.2701 0.058 Uiso 1 1 calc R . .
H3B H 0.7232 -0.0253 0.2137 0.058 Uiso 1 1 calc R . .
C4 C 0.5613(3) -0.0868(3) 0.27774(10) 0.0409(6) Uani 1 1 d . . .
C5 C 0.4155(3) -0.1694(3) 0.26473(10) 0.0406(6) Uani 1 1 d . . .
H5 H 0.4161 -0.2330 0.2365 0.049 Uiso 1 1 calc R . .
C6 C 0.3158(3) -0.0441(3) 0.33514(10) 0.0408(6) Uani 1 1 d . . .
C7 C 0.5003(4) -0.0062(3) 0.32315(10) 0.0408(6) Uani 1 1 d . . .
C8 C 0.5845(4) 0.0932(3) 0.35580(11) 0.0536(7) Uani 1 1 d . . .
H8 H 0.7064 0.1185 0.3494 0.064 Uiso 1 1 calc R . .
C9 C 0.4841(4) 0.1527(3) 0.39747(13) 0.0719(10) Uani 1 1 d . . .
H9 H 0.5391 0.2186 0.4194 0.086 Uiso 1 1 calc R . .
C10 C 0.3001(4) 0.1152(3) 0.40727(12) 0.0714(10) Uani 1 1 d . . .
H10 H 0.2344 0.1580 0.4352 0.086 Uiso 1 1 calc R . .
C11 C 0.2150(4) 0.0172(3) 0.37667(11) 0.0571(8) Uani 1 1 d . . .
H11 H 0.0931 -0.0075 0.3836 0.068 Uiso 1 1 calc R . .
C12 C 0.8872(3) -0.4472(3) 0.35147(10) 0.0392(6) Uani 1 1 d . . .
C13 C 0.9985(3) -0.3957(3) 0.39442(11) 0.0475(8) Uani 1 1 d . . .
H13 H 1.0594 -0.3128 0.3944 0.057 Uiso 1 1 calc R . .
C14 C 1.0014(3) -0.4915(3) 0.43738(12) 0.0567(9) Uani 1 1 d . . .
H14 H 1.0633 -0.4819 0.4708 0.068 Uiso 1 1 calc R . .
C15 C 0.8952(3) -0.6043(3) 0.42145(12) 0.0543(7) Uani 1 1 d . . .
H15 H 0.8765 -0.6826 0.4419 0.065 Uiso 1 1 calc R . .
C16 C 0.8220(3) -0.5766(3) 0.36846(10) 0.0461(6) Uani 1 1 d . . .
H16 H 0.7448 -0.6332 0.3483 0.055 Uiso 1 1 calc R . .
C17 C 0.6286(5) -0.2522(4) 0.44460(16) 0.0776(10) Uani 1 1 d . . .
H17 H 0.6856 -0.1684 0.4409 0.093 Uiso 1 1 calc R . .
C18 C 0.6418(4) -0.3377(4) 0.49070(13) 0.0700(9) Uani 1 1 d . . .
H18 H 0.7086 -0.3209 0.5227 0.084 Uiso 1 1 calc R . .
C19 C 0.5349(3) -0.4539(4) 0.47942(12) 0.0630(9) Uani 1 1 d . . .
H19 H 0.5174 -0.5273 0.5028 0.076 Uiso 1 1 calc R . .
C20 C 0.4598(3) -0.4385(4) 0.42630(13) 0.0700(9) Uani 1 1 d . . .
H20 H 0.3852 -0.5011 0.4083 0.084 Uiso 1 1 calc R . .
C21 C 0.5152(4) -0.3143(4) 0.40506(13) 0.0692(11) Uani 1 1 d . . .
H21 H 0.4830 -0.2789 0.3709 0.083 Uiso 1 1 calc R . .

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
Fe1 0.02897(16) 0.0442(2) 0.03888(18) -0.00130(18) 0.00112(16) 0.00462(17)
N1 0.0304(10) 0.0446(14) 0.0448(13) -0.0030(12) 0.0058(8) -0.0043(9)
N2 0.0332(10) 0.0452(12) 0.0476(11) 0.0060(10) -0.0053(11) -0.0072(10)
C1 0.0323(12) 0.0442(18) 0.0420(16) -0.0127(13) 0.0081(10) -0.0024(11)
C2 0.0380(13) 0.063(2) 0.0459(17) 0.0021(15) 0.0101(11) -0.0092(13)
C3 0.0408(13) 0.0486(15) 0.0555(14) 0.0135(13) 0.0028(13) -0.0082(16)
C4 0.0395(13) 0.0383(17) 0.0450(16) 0.0124(14) -0.0013(10) -0.0012(12)
C5 0.0366(14) 0.0427(17) 0.0426(15) 0.0053(13) -0.0055(11) -0.0033(11)
C6 0.0405(14) 0.0377(18) 0.0442(16) 0.0119(13) 0.0011(10) -0.0009(10)
C7 0.0474(15) 0.0344(15) 0.0407(15) 0.0106(13) -0.0053(11) -0.0041(11)
C8 0.0569(16) 0.053(2) 0.0513(17) 0.0041(16) -0.0021(13) -0.0167(14)
C9 0.098(3) 0.059(2) 0.059(2) -0.0074(18) 0.0011(18) -0.0260(18)
C10 0.099(3) 0.059(2) 0.056(2) -0.0069(16) 0.0259(17) -0.0129(17)
C11 0.0587(19) 0.0550(18) 0.0576(18) 0.0103(15) 0.0136(14) -0.0056(13)
C12 0.0295(12) 0.0431(17) 0.0450(15) -0.0072(15) 0.0039(9) -0.0006(11)
C13 0.0318(13) 0.053(2) 0.0575(18) 0.0043(16) -0.0042(12) -0.0058(12)
C14 0.0358(15) 0.074(2) 0.060(2) 0.0074(17) -0.0036(12) 0.0075(14)
C15 0.0476(15) 0.0443(19) 0.0711(19) 0.0060(18) 0.0109(14) 0.0114(12)
C16 0.0497(14) 0.0365(17) 0.0521(17) -0.0058(15) 0.0044(11) -0.0011(12)
C17 0.086(3) 0.061(2) 0.085(3) -0.003(2) 0.032(2) 0.0221(19)
C18 0.071(2) 0.086(3) 0.054(2) -0.012(2) 0.0125(15) 0.0185(19)
C19 0.0460(17) 0.091(3) 0.0524(19) 0.0210(19) 0.0168(13) 0.0195(17)
C20 0.0281(14) 0.112(3) 0.070(2) 0.000(3) 0.0036(12) 0.0123(16)
C21 0.0539(19) 0.094(3) 0.060(2) 0.026(2) 0.0168(15) 0.0414(18)

_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 C16 2.017(3) . ?
Fe1 C20 2.019(2) . ?
Fe1 C14 2.023(2) . ?
Fe1 C12 2.025(2) . ?
Fe1 C13 2.030(2) . ?
Fe1 C17 2.032(3) . ?
Fe1 C21 2.038(3) . ?
Fe1 C19 2.038(2) . ?
Fe1 C15 2.039(2) . ?
Fe1 C18 2.039(3) . ?
N1 C1 1.270(3) . ?
N1 C2 1.465(3) . ?
N2 C6 1.370(3) . ?
N2 C5 1.371(3) . ?
C1 C12 1.456(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.509(3) . ?
C4 C5 1.370(3) . ?
C4 C7 1.430(4) . ?
C6 C11 1.384(3) . ?
C6 C7 1.416(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.377(4) . ?
C9 C10 1.402(4) . ?
C10 C11 1.367(4) . ?
C12 C13 1.412(3) . ?
C12 C16 1.425(3) . ?
C13 C14 1.409(4) . ?
C14 C15 1.409(4) . ?
C15 C16 1.417(3) . ?
C17 C21 1.403(5) . ?
C17 C18 1.405(4) . ?
C18 C19 1.411(5) . ?
C19 C20 1.407(4) . ?
C20 C21 1.391(4) . ?

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
C16 Fe1 C20 108.28(12) . . ?
C16 Fe1 C14 68.64(11) . . ?
C20 Fe1 C14 157.10(15) . . ?
C16 Fe1 C12 41.29(9) . . ?
C20 Fe1 C12 124.92(11) . . ?
C14 Fe1 C12 68.72(10) . . ?
C16 Fe1 C13 68.82(11) . . ?
C20 Fe1 C13 161.28(13) . . ?
C14 Fe1 C13 40.69(10) . . ?
C12 Fe1 C13 40.77(9) . . ?
C16 Fe1 C17 155.63(13) . . ?
C20 Fe1 C17 67.62(15) . . ?
C14 Fe1 C17 124.70(14) . . ?
C12 Fe1 C17 119.81(13) . . ?
C13 Fe1 C17 106.93(13) . . ?
C16 Fe1 C21 120.91(13) . . ?
C20 Fe1 C21 40.09(12) . . ?
C14 Fe1 C21 161.25(15) . . ?
C12 Fe1 C21 106.92(11) . . ?
C13 Fe1 C21 124.29(13) . . ?
C17 Fe1 C21 40.35(13) . . ?
C16 Fe1 C19 125.81(13) . . ?
C20 Fe1 C19 40.58(11) . . ?
C14 Fe1 C19 121.56(11) . . ?
C12 Fe1 C19 162.60(12) . . ?
C13 Fe1 C19 155.91(12) . . ?
C17 Fe1 C19 67.78(14) . . ?
C21 Fe1 C19 67.89(12) . . ?
C16 Fe1 C15 40.89(10) . . ?
C20 Fe1 C15 122.21(14) . . ?
C14 Fe1 C15 40.59(11) . . ?
C12 Fe1 C15 69.02(11) . . ?
C13 Fe1 C15 68.53(11) . . ?
C17 Fe1 C15 161.85(15) . . ?
C21 Fe1 C15 156.64(14) . . ?
C19 Fe1 C15 108.74(13) . . ?
C16 Fe1 C18 162.64(13) . . ?
C20 Fe1 C18 68.12(13) . . ?
C14 Fe1 C18 107.66(13) . . ?
C12 Fe1 C18 154.81(13) . . ?
C13 Fe1 C18 120.19(13) . . ?
C17 Fe1 C18 40.38(12) . . ?
C21 Fe1 C18 68.07(13) . . ?
C19 Fe1 C18 40.51(13) . . ?
C15 Fe1 C18 125.42(13) . . ?
C1 N1 C2 117.7(2) . . ?
C6 N2 C5 108.9(2) . . ?
N1 C1 C12 123.4(2) . . ?
N1 C2 C3 110.0(2) . . ?
C4 C3 C2 114.7(2) . . ?
C5 C4 C7 105.8(2) . . ?
C5 C4 C3 127.1(2) . . ?
C7 C4 C3 127.0(2) . . ?
C4 C5 N2 110.6(2) . . ?
N2 C6 C11 130.8(2) . . ?
N2 C6 C7 107.2(2) . . ?
C11 C6 C7 122.0(2) . . ?
C8 C7 C6 118.6(3) . . ?
C8 C7 C4 133.8(3) . . ?
C6 C7 C4 107.5(2) . . ?
C9 C8 C7 119.1(3) . . ?
C8 C9 C10 120.8(3) . . ?
C11 C10 C9 121.5(3) . . ?
C10 C11 C6 117.9(3) . . ?
C13 C12 C16 107.4(2) . . ?
C13 C12 C1 127.6(2) . . ?
C16 C12 C1 124.7(2) . . ?
C13 C12 Fe1 69.80(14) . . ?
C16 C12 Fe1 69.05(14) . . ?
C1 C12 Fe1 122.28(15) . . ?
C14 C13 C12 108.1(2) . . ?
C14 C13 Fe1 69.40(14) . . ?
C12 C13 Fe1 69.43(13) . . ?
C15 C14 C13 108.8(2) . . ?
C15 C14 Fe1 70.31(14) . . ?
C13 C14 Fe1 69.91(14) . . ?
C14 C15 C16 107.4(3) . . ?
C14 C15 Fe1 69.10(15) . . ?
C16 C15 Fe1 68.72(15) . . ?
C15 C16 C12 108.2(2) . . ?
C15 C16 Fe1 70.38(14) . . ?
C12 C16 Fe1 69.66(14) . . ?
C21 C17 C18 108.7(3) . . ?
C21 C17 Fe1 70.1(2) . . ?
C18 C17 Fe1 70.08(19) . . ?
C17 C18 C19 107.4(3) . . ?
C17 C18 Fe1 69.53(17) . . ?
C19 C18 Fe1 69.70(17) . . ?
C20 C19 C18 107.5(3) . . ?
C20 C19 Fe1 69.00(14) . . ?
C18 C19 Fe1 69.79(17) . . ?
C21 C20 C19 108.9(3) . . ?
C21 C20 Fe1 70.67(16) . . ?
C19 C20 Fe1 70.42(15) . . ?
C20 C21 C17 107.6(3) . . ?
C20 C21 Fe1 69.24(15) . . ?
C17 C21 Fe1 69.60(18) . . ?

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.877
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044

# Attachment 'B609052D_Fc2.cif'

data_mar959
_database_code_depnum_ccdc_archive 'CCDC 616829'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Fe N2'
_chemical_formula_sum            'C21 H22 Fe N2'
_chemical_formula_weight         358.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   6.9070(14)
_cell_length_b                   13.826(3)
_cell_length_c                   17.936(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.36(3)
_cell_angle_gamma                90.00
_cell_volume                     1712.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'marresearch IPDS mar300'
_diffrn_measurement_method       Oscillation
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9717
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.44
_reflns_number_total             2946
_reflns_number_gt                2309
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Marcontrol
_computing_cell_refinement       Scalepack
_computing_data_reduction        Denzo
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (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^)+(0.0487P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2946
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Fe1 Fe 0.03695(4) 0.19308(2) 0.557669(17) 0.02901(13) Uani 1 1 d . . .
N1 N -0.0994(3) 0.29761(13) 0.73260(10) 0.0322(4) Uani 1 1 d . . .
N2 N 0.5442(3) 0.40522(15) 0.73927(11) 0.0402(5) Uani 1 1 d . . .
C1 C -0.1776(3) 0.17945(15) 0.63400(12) 0.0317(5) Uani 1 1 d . . .
C2 C -0.1409(3) 0.08920(16) 0.59884(13) 0.0350(5) Uani 1 1 d . . .
H2A H -0.1015 0.0326 0.6228 0.042 Uiso 1 1 calc R . .
C3 C -0.1750(3) 0.10053(17) 0.52068(13) 0.0362(5) Uani 1 1 d . . .
H3 H -0.1621 0.0526 0.4847 0.043 Uiso 1 1 calc R . .
C4 C -0.2321(3) 0.19742(16) 0.50732(13) 0.0357(5) Uani 1 1 d . . .
H4 H -0.2630 0.2245 0.4611 0.043 Uiso 1 1 calc R . .
C5 C -0.2336(3) 0.24605(17) 0.57722(12) 0.0330(5) Uani 1 1 d . . .
H5 H -0.2658 0.3106 0.5845 0.040 Uiso 1 1 calc R . .
C6 C 0.3143(3) 0.1479(2) 0.57773(15) 0.0460(6) Uani 1 1 d . . .
H6 H 0.3501 0.0904 0.6012 0.055 Uiso 1 1 calc R . .
C7 C 0.2802(3) 0.16060(19) 0.50022(14) 0.0439(6) Uani 1 1 d . . .
H7 H 0.2906 0.1132 0.4637 0.053 Uiso 1 1 calc R . .
C8 C 0.2275(3) 0.25804(19) 0.48814(14) 0.0434(6) Uani 1 1 d . . .
H8 H 0.1966 0.2862 0.4423 0.052 Uiso 1 1 calc R . .
C9 C 0.2299(3) 0.30534(18) 0.55795(15) 0.0459(6) Uani 1 1 d . . .
H9 H 0.2004 0.3701 0.5660 0.055 Uiso 1 1 calc R . .
C10 C 0.2845(3) 0.2377(2) 0.61315(14) 0.0475(7) Uani 1 1 d . . .
H10 H 0.2985 0.2500 0.6640 0.057 Uiso 1 1 calc R . .
C11 C -0.1599(4) 0.19795(16) 0.71598(13) 0.0395(6) Uani 1 1 d . . .
H11A H -0.2837 0.1857 0.7386 0.047 Uiso 1 1 calc R . .
H11B H -0.0661 0.1535 0.7379 0.047 Uiso 1 1 calc R . .
C12 C -0.0334(3) 0.30911(17) 0.81023(12) 0.0402(6) Uani 1 1 d . . .
H12A H 0.0598 0.2588 0.8226 0.048 Uiso 1 1 calc R . .
H12B H -0.1428 0.3017 0.8427 0.048 Uiso 1 1 calc R . .
C13 C 0.0590(3) 0.40728(18) 0.82360(12) 0.0397(6) Uani 1 1 d . . .
H13A H -0.0337 0.4573 0.8100 0.048 Uiso 1 1 calc R . .
H13B H 0.0905 0.4142 0.8763 0.048 Uiso 1 1 calc R . .
C14 C 0.2401(3) 0.42163(17) 0.77975(12) 0.0349(5) Uani 1 1 d . . .
C15 C 0.2595(3) 0.47822(16) 0.71359(12) 0.0343(5) Uani 1 1 d . . .
C16 C 0.1331(3) 0.53599(18) 0.67104(14) 0.0449(6) Uani 1 1 d . . .
H16 H 0.0060 0.5452 0.6856 0.054 Uiso 1 1 calc R . .
C17 C 0.1994(4) 0.57913(19) 0.60718(16) 0.0542(7) Uani 1 1 d . . .
H17 H 0.1158 0.6174 0.5785 0.065 Uiso 1 1 calc R . .
C18 C 0.3903(4) 0.56628(18) 0.58485(15) 0.0504(7) Uani 1 1 d . . .
H18 H 0.4312 0.5966 0.5417 0.060 Uiso 1 1 calc R . .
C19 C 0.5191(3) 0.50985(17) 0.62520(14) 0.0426(6) Uani 1 1 d . . .
H19 H 0.6459 0.5013 0.6102 0.051 Uiso 1 1 calc R . .
C20 C 0.4517(3) 0.46601(16) 0.68952(13) 0.0354(5) Uani 1 1 d . . .
C21 C 0.4155(3) 0.37841(18) 0.79224(13) 0.0388(6) Uani 1 1 d . . .
H21 H 0.4437 0.3364 0.8315 0.047 Uiso 1 1 calc R . .
H1 H -0.010(3) 0.3102(14) 0.7062(13) 0.028(6) Uiso 1 1 d . . .
H2 H 0.658(4) 0.3803(19) 0.7331(14) 0.058(8) Uiso 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
Fe1 0.0253(2) 0.0289(2) 0.0329(2) -0.00181(14) 0.00330(12) -0.00231(12)
N1 0.0292(11) 0.0409(12) 0.0266(10) 0.0017(8) 0.0053(8) -0.0030(8)
N2 0.0276(12) 0.0486(14) 0.0443(12) -0.0041(10) -0.0021(8) 0.0032(9)
C1 0.0261(12) 0.0326(14) 0.0366(13) 0.0017(10) 0.0061(9) -0.0035(8)
C2 0.0338(12) 0.0276(13) 0.0438(14) 0.0029(10) 0.0022(9) -0.0044(9)
C3 0.0315(12) 0.0341(14) 0.0429(14) -0.0077(10) -0.0008(9) -0.0060(9)
C4 0.0313(12) 0.0387(14) 0.0368(13) 0.0010(11) -0.0029(9) -0.0014(9)
C5 0.0273(11) 0.0312(13) 0.0406(14) -0.0017(10) 0.0002(9) 0.0010(9)
C6 0.0263(13) 0.0485(17) 0.0635(18) 0.0029(14) 0.0049(11) 0.0017(10)
C7 0.0361(13) 0.0425(15) 0.0540(17) -0.0110(12) 0.0181(11) -0.0034(10)
C8 0.0426(14) 0.0414(15) 0.0470(15) 0.0011(12) 0.0162(10) -0.0065(11)
C9 0.0339(14) 0.0373(15) 0.0671(18) -0.0120(13) 0.0146(11) -0.0089(10)
C10 0.0250(12) 0.0676(19) 0.0500(16) -0.0149(14) 0.0022(10) -0.0082(11)
C11 0.0446(14) 0.0387(15) 0.0357(14) 0.0041(11) 0.0092(10) -0.0061(10)
C12 0.0410(14) 0.0520(16) 0.0278(13) 0.0031(11) 0.0036(9) -0.0012(10)
C13 0.0382(13) 0.0514(16) 0.0296(13) -0.0050(11) 0.0005(9) 0.0009(10)
C14 0.0346(13) 0.0384(14) 0.0317(12) -0.0073(10) -0.0018(9) -0.0003(9)
C15 0.0337(13) 0.0301(13) 0.0391(13) -0.0061(10) -0.0002(9) 0.0000(9)
C16 0.0388(14) 0.0389(15) 0.0570(16) 0.0014(12) 0.0021(11) 0.0068(10)
C17 0.0593(17) 0.0391(16) 0.0639(18) 0.0129(14) -0.0051(13) 0.0078(12)
C18 0.0630(17) 0.0377(16) 0.0508(17) 0.0074(12) 0.0083(12) -0.0069(12)
C19 0.0408(14) 0.0360(15) 0.0513(16) -0.0067(12) 0.0076(11) -0.0061(10)
C20 0.0362(12) 0.0315(13) 0.0383(13) -0.0067(10) -0.0017(9) -0.0017(9)
C21 0.0372(13) 0.0454(16) 0.0336(13) -0.0009(11) -0.0041(9) 0.0023(10)

_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 C6 2.039(2) . ?
Fe1 C2 2.040(2) . ?
Fe1 C7 2.042(2) . ?
Fe1 C8 2.042(2) . ?
Fe1 C3 2.043(2) . ?
Fe1 C5 2.045(2) . ?
Fe1 C9 2.045(2) . ?
Fe1 C4 2.047(2) . ?
Fe1 C1 2.050(2) . ?
Fe1 C10 2.053(2) . ?
N1 C12 1.463(3) . ?
N1 C11 1.468(3) . ?
N2 C21 1.368(3) . ?
N2 C20 1.372(3) . ?
C1 C5 1.420(3) . ?
C1 C2 1.424(3) . ?
C1 C11 1.495(3) . ?
C2 C3 1.425(3) . ?
C3 C4 1.415(3) . ?
C4 C5 1.423(3) . ?
C6 C10 1.412(4) . ?
C6 C7 1.416(3) . ?
C7 C8 1.411(4) . ?
C8 C9 1.412(3) . ?
C9 C10 1.407(4) . ?
C12 C13 1.517(3) . ?
C13 C14 1.506(3) . ?
C14 C21 1.365(3) . ?
C14 C15 1.430(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.415(3) . ?
C16 C17 1.379(4) . ?
C17 C18 1.399(4) . ?
C18 C19 1.376(4) . ?
C19 C20 1.393(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Fe1 C2 106.95(10) . . ?
C6 Fe1 C7 40.60(10) . . ?
C2 Fe1 C7 122.53(9) . . ?
C6 Fe1 C8 68.06(11) . . ?
C2 Fe1 C8 158.91(10) . . ?
C7 Fe1 C8 40.42(10) . . ?
C6 Fe1 C3 121.89(10) . . ?
C2 Fe1 C3 40.84(9) . . ?
C7 Fe1 C3 106.87(10) . . ?
C8 Fe1 C3 122.97(10) . . ?
C6 Fe1 C5 159.72(10) . . ?
C2 Fe1 C5 68.25(9) . . ?
C7 Fe1 C5 158.67(10) . . ?
C8 Fe1 C5 123.49(10) . . ?
C3 Fe1 C5 68.24(9) . . ?
C6 Fe1 C9 67.85(10) . . ?
C2 Fe1 C9 158.64(10) . . ?
C7 Fe1 C9 67.94(10) . . ?
C8 Fe1 C9 40.43(10) . . ?
C3 Fe1 C9 159.67(10) . . ?
C5 Fe1 C9 109.01(9) . . ?
C6 Fe1 C4 157.79(10) . . ?
C2 Fe1 C4 68.42(9) . . ?
C7 Fe1 C4 122.20(10) . . ?
C8 Fe1 C4 107.99(10) . . ?
C3 Fe1 C4 40.48(8) . . ?
C5 Fe1 C4 40.70(9) . . ?
C9 Fe1 C4 124.28(10) . . ?
C6 Fe1 C1 123.03(10) . . ?
C2 Fe1 C1 40.74(9) . . ?
C7 Fe1 C1 158.98(10) . . ?
C8 Fe1 C1 159.18(9) . . ?
C3 Fe1 C1 68.62(9) . . ?
C5 Fe1 C1 40.57(9) . . ?
C9 Fe1 C1 123.32(9) . . ?
C4 Fe1 C1 68.55(9) . . ?
C6 Fe1 C10 40.39(11) . . ?
C2 Fe1 C10 122.55(10) . . ?
C7 Fe1 C10 67.97(10) . . ?
C8 Fe1 C10 67.82(10) . . ?
C3 Fe1 C10 158.10(11) . . ?
C5 Fe1 C10 124.28(10) . . ?
C9 Fe1 C10 40.16(11) . . ?
C4 Fe1 C10 160.36(11) . . ?
C1 Fe1 C10 108.12(10) . . ?
C12 N1 C11 112.08(18) . . ?
C21 N2 C20 108.50(19) . . ?
C5 C1 C2 107.4(2) . . ?
C5 C1 C11 127.5(2) . . ?
C2 C1 C11 125.1(2) . . ?
C5 C1 Fe1 69.51(12) . . ?
C2 C1 Fe1 69.23(12) . . ?
C11 C1 Fe1 126.69(15) . . ?
C1 C2 C3 108.2(2) . . ?
C1 C2 Fe1 70.03(12) . . ?
C3 C2 Fe1 69.72(12) . . ?
C4 C3 C2 108.0(2) . . ?
C4 C3 Fe1 69.91(13) . . ?
C2 C3 Fe1 69.44(12) . . ?
C3 C4 C5 107.8(2) . . ?
C3 C4 Fe1 69.61(13) . . ?
C5 C4 Fe1 69.55(12) . . ?
C1 C5 C4 108.5(2) . . ?
C1 C5 Fe1 69.92(12) . . ?
C4 C5 Fe1 69.75(12) . . ?
C10 C6 C7 108.0(2) . . ?
C10 C6 Fe1 70.33(13) . . ?
C7 C6 Fe1 69.80(13) . . ?
C8 C7 C6 107.8(2) . . ?
C8 C7 Fe1 69.82(12) . . ?
C6 C7 Fe1 69.60(13) . . ?
C7 C8 C9 108.0(2) . . ?
C7 C8 Fe1 69.76(13) . . ?
C9 C8 Fe1 69.91(13) . . ?
C10 C9 C8 108.3(2) . . ?
C10 C9 Fe1 70.20(14) . . ?
C8 C9 Fe1 69.67(13) . . ?
C9 C10 C6 107.9(2) . . ?
C9 C10 Fe1 69.65(14) . . ?
C6 C10 Fe1 69.29(13) . . ?
N1 C11 C1 112.12(18) . . ?
N1 C12 C13 111.60(19) . . ?
C14 C13 C12 112.76(19) . . ?
C21 C14 C15 106.0(2) . . ?
C21 C14 C13 127.0(2) . . ?
C15 C14 C13 126.9(2) . . ?
C16 C15 C20 118.7(2) . . ?
C16 C15 C14 134.1(2) . . ?
C20 C15 C14 107.15(19) . . ?
C17 C16 C15 119.0(2) . . ?
C16 C17 C18 121.1(3) . . ?
C19 C18 C17 121.6(2) . . ?
C18 C19 C20 117.3(2) . . ?
N2 C20 C19 130.2(2) . . ?
N2 C20 C15 107.5(2) . . ?
C19 C20 C15 122.3(2) . . ?
C14 C21 N2 110.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        25.44
_diffrn_measured_fraction_theta_full 0.925
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054