# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Graeme Cooke'
'Anne-Marie Alexander'
'Marc Bria'
'Gunther Brunklaus'
'Stuart Caldwell'
'James F. Garety'
'Shanika Gunatilaka Hewage'
'Yann Hocquel'
'Niall McDonald'
'Gouher Rabani'
'Georgina Rosair'
'V. M. Rotello'
'Brian Smith'
'Hans Spiess'
'Patrice Woisel'

_publ_contact_author_name        'Graeme Cooke'
_publ_contact_author_address     
;
Department of Chemistry
University of Glasgow
Joseph Black Building
University Avenue
Glasgow
G12 8QQ
UNITED KINGDOM
;

_publ_contact_author_email       GRAEMEC@CHEM.GLA.AC.UK

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Probing the solvent-induced tautomerism of a
redox-active ureidopyrimidinone
;

data_x80469t
_database_code_depnum_ccdc_archive 'CCDC 638903'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 Fe N4 O2'
_chemical_formula_sum            'C23 H30 Fe N4 O2'
_chemical_formula_weight         450.36

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
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.8841(6)
_cell_length_b                   10.4063(10)
_cell_length_c                   16.1990(13)
_cell_angle_alpha                102.073(7)
_cell_angle_beta                 94.324(5)
_cell_angle_gamma                109.281(5)
_cell_volume                     1057.95(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3454
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.40

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8541
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            32280
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.68
_reflns_number_total             4424
_reflns_number_gt                3275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0265P)^2^+0.7687P] 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         4424
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 -0.3712(4) 0.2377(2) 0.51068(15) 0.0201(5) Uani 1 1 d . . .
O1 O -0.4942(3) 0.17074(18) 0.55942(11) 0.0230(4) Uani 1 1 d . . .
H1O H -0.572(4) 0.212(3) 0.5766(17) 0.028 Uiso 1 1 d . . .
N2 N -0.3888(3) 0.3562(2) 0.49700(12) 0.0189(4) Uani 1 1 d . . .
C3 C -0.2642(4) 0.4142(2) 0.44410(15) 0.0186(5) Uani 1 1 d . . .
N4 N -0.1242(3) 0.3701(2) 0.40727(12) 0.0195(4) Uani 1 1 d . . .
C5 C -0.1059(4) 0.2513(2) 0.42459(15) 0.0206(5) Uani 1 1 d . . .
C6 C -0.2292(4) 0.1812(2) 0.47577(15) 0.0202(5) Uani 1 1 d . . .
H6 H -0.2180 0.0976 0.4869 0.024 Uiso 1 1 calc R . .
N7 N -0.2923(3) 0.5334(2) 0.42860(13) 0.0199(4) Uani 1 1 d . . .
H7N H -0.386(4) 0.560(3) 0.4549(16) 0.024 Uiso 1 1 d . . .
C8 C -0.2057(4) 0.6137(3) 0.37370(15) 0.0209(5) Uani 1 1 d . . .
O8 O -0.2541(3) 0.71889(17) 0.37070(11) 0.0243(4) Uani 1 1 d . . .
N9 N -0.0742(3) 0.5786(2) 0.32539(13) 0.0225(5) Uani 1 1 d . . .
H9N H -0.047(4) 0.511(3) 0.3308(17) 0.027 Uiso 1 1 d . . .
C10 C 0.0202(4) 0.6642(3) 0.26822(16) 0.0255(6) Uani 1 1 d . . .
H10A H 0.0514 0.7644 0.2963 0.031 Uiso 1 1 calc R . .
H10B H -0.0811 0.6395 0.2156 0.031 Uiso 1 1 calc R . .
C11 C 0.2197(4) 0.6446(3) 0.24396(17) 0.0267(6) Uani 1 1 d . . .
H11A H 0.2974 0.7246 0.2211 0.032 Uiso 1 1 calc R . .
H11B H 0.3071 0.6484 0.2964 0.032 Uiso 1 1 calc R . .
C12 C 0.1897(4) 0.5089(3) 0.17856(16) 0.0248(6) Uani 1 1 d . . .
H12A H 0.1012 0.5035 0.1259 0.030 Uiso 1 1 calc R . .
H12B H 0.1162 0.4280 0.2015 0.030 Uiso 1 1 calc R . .
C13 C 0.3965(4) 0.4988(3) 0.15632(17) 0.0268(6) Uani 1 1 d . . .
H13A H 0.4670 0.5781 0.1316 0.032 Uiso 1 1 calc R . .
H13B H 0.4868 0.5088 0.2096 0.032 Uiso 1 1 calc R . .
C14 C 0.3744(4) 0.3617(3) 0.09357(17) 0.0269(6) Uani 1 1 d . . .
H14A H 0.3122 0.2829 0.1200 0.032 Uiso 1 1 calc R . .
H14B H 0.2766 0.3487 0.0419 0.032 Uiso 1 1 calc R . .
C15 C 0.5781(4) 0.3539(3) 0.06648(17) 0.0265(6) Uani 1 1 d . . .
H15A H 0.6779 0.3693 0.1181 0.032 Uiso 1 1 calc R . .
H15B H 0.6385 0.4304 0.0381 0.032 Uiso 1 1 calc R . .
C16 C 0.5512(4) 0.2137(3) 0.00586(17) 0.0297(6) Uani 1 1 d . . .
H16A H 0.5053 0.1387 0.0365 0.036 Uiso 1 1 calc R . .
H16B H 0.4395 0.1935 -0.0424 0.036 Uiso 1 1 calc R . .
C17 C 0.7474(4) 0.2090(3) -0.02964(18) 0.0332(7) Uani 1 1 d . . .
H17A H 0.7945 0.2832 -0.0600 0.050 Uiso 1 1 calc R . .
H17B H 0.7176 0.1173 -0.0693 0.050 Uiso 1 1 calc R . .
H17C H 0.8567 0.2236 0.0174 0.050 Uiso 1 1 calc R . .
Fe1 Fe 0.01047(6) 0.08128(4) 0.26640(2) 0.01962(11) Uani 1 1 d . . .
C21 C 0.0551(4) 0.2058(2) 0.38697(15) 0.0209(5) Uani 1 1 d . . .
C22 C 0.0940(4) 0.0793(3) 0.38915(15) 0.0217(5) Uani 1 1 d . . .
H22 H 0.0190 0.0070 0.4191 0.026 Uiso 1 1 calc R . .
C23 C 0.2586(4) 0.0746(3) 0.34184(16) 0.0232(6) Uani 1 1 d . . .
H23 H 0.3180 -0.0020 0.3321 0.028 Uiso 1 1 calc R . .
C24 C 0.3215(4) 0.1965(3) 0.30947(16) 0.0239(6) Uani 1 1 d . . .
H24 H 0.4322 0.2201 0.2728 0.029 Uiso 1 1 calc R . .
C25 C 0.1972(4) 0.2776(2) 0.33663(15) 0.0205(5) Uani 1 1 d . . .
H25 H 0.2062 0.3685 0.3229 0.025 Uiso 1 1 calc R . .
C31 C -0.1811(4) 0.0998(3) 0.17000(16) 0.0278(6) Uani 1 1 d . . .
H31 H -0.1893 0.1896 0.1600 0.033 Uiso 1 1 calc R . .
C32 C -0.3000(4) 0.0189(3) 0.22181(16) 0.0257(6) Uani 1 1 d . . .
H32 H -0.4067 0.0419 0.2545 0.031 Uiso 1 1 calc R . .
C33 C -0.2408(4) -0.1003(3) 0.21900(16) 0.0235(6) Uani 1 1 d . . .
H33 H -0.2983 -0.1760 0.2492 0.028 Uiso 1 1 calc R . .
C34 C -0.0852(4) -0.0926(3) 0.16549(15) 0.0238(6) Uani 1 1 d . . .
H34 H -0.0131 -0.1618 0.1518 0.029 Uiso 1 1 calc R . .
C35 C -0.0493(4) 0.0302(3) 0.13505(16) 0.0260(6) Uani 1 1 d . . .
H35 H 0.0529 0.0628 0.0964 0.031 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
C1 0.0177(13) 0.0198(13) 0.0217(13) 0.0057(10) 0.0026(10) 0.0048(10)
O1 0.0234(10) 0.0220(9) 0.0297(10) 0.0101(8) 0.0110(8) 0.0122(8)
N2 0.0161(11) 0.0193(11) 0.0233(11) 0.0069(9) 0.0040(8) 0.0077(9)
C3 0.0170(13) 0.0174(12) 0.0209(12) 0.0041(10) 0.0001(10) 0.0063(10)
N4 0.0171(11) 0.0187(10) 0.0234(11) 0.0049(9) 0.0028(8) 0.0074(9)
C5 0.0182(13) 0.0198(13) 0.0226(13) 0.0020(10) -0.0007(10) 0.0080(10)
C6 0.0207(13) 0.0194(12) 0.0240(13) 0.0070(10) 0.0039(10) 0.0107(11)
N7 0.0186(11) 0.0198(11) 0.0255(11) 0.0082(9) 0.0082(9) 0.0094(9)
C8 0.0190(13) 0.0197(13) 0.0233(13) 0.0048(10) 0.0032(10) 0.0064(11)
O8 0.0259(10) 0.0227(9) 0.0326(10) 0.0131(8) 0.0115(8) 0.0137(8)
N9 0.0228(12) 0.0207(11) 0.0300(12) 0.0103(9) 0.0097(9) 0.0117(10)
C10 0.0258(15) 0.0227(13) 0.0310(14) 0.0092(11) 0.0108(11) 0.0097(11)
C11 0.0213(14) 0.0278(14) 0.0320(15) 0.0081(12) 0.0105(11) 0.0083(12)
C12 0.0215(14) 0.0256(14) 0.0291(14) 0.0094(11) 0.0068(11) 0.0083(11)
C13 0.0208(14) 0.0272(14) 0.0310(14) 0.0050(12) 0.0069(11) 0.0076(12)
C14 0.0219(14) 0.0252(14) 0.0321(15) 0.0049(11) 0.0057(11) 0.0072(11)
C15 0.0217(14) 0.0280(14) 0.0302(14) 0.0068(12) 0.0043(11) 0.0094(12)
C16 0.0243(15) 0.0320(15) 0.0332(15) 0.0052(12) 0.0029(12) 0.0127(13)
C17 0.0360(17) 0.0371(16) 0.0333(15) 0.0092(13) 0.0104(13) 0.0203(14)
Fe1 0.0168(2) 0.01956(19) 0.02367(19) 0.00548(14) 0.00381(14) 0.00779(15)
C21 0.0188(13) 0.0211(13) 0.0221(13) 0.0039(10) 0.0004(10) 0.0077(11)
C22 0.0187(13) 0.0234(13) 0.0245(13) 0.0065(11) 0.0016(10) 0.0095(11)
C23 0.0194(13) 0.0232(13) 0.0296(14) 0.0056(11) 0.0034(11) 0.0116(11)
C24 0.0173(13) 0.0253(13) 0.0286(14) 0.0039(11) 0.0059(11) 0.0080(11)
C25 0.0187(13) 0.0190(12) 0.0235(13) 0.0030(10) 0.0027(10) 0.0080(10)
C31 0.0279(15) 0.0238(14) 0.0311(14) 0.0076(11) -0.0042(12) 0.0098(12)
C32 0.0192(14) 0.0275(14) 0.0278(14) 0.0026(11) 0.0014(11) 0.0082(11)
C33 0.0193(13) 0.0208(13) 0.0266(13) 0.0051(11) 0.0015(11) 0.0032(11)
C34 0.0226(14) 0.0236(13) 0.0250(13) 0.0038(11) 0.0029(11) 0.0095(11)
C35 0.0247(14) 0.0267(14) 0.0223(13) 0.0071(11) 0.0016(11) 0.0035(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 O1 1.329(3) . ?
C1 N2 1.340(3) . ?
C1 C6 1.395(3) . ?
O1 H1O 0.82(3) . ?
N2 C3 1.349(3) . ?
C3 N4 1.326(3) . ?
C3 N7 1.386(3) . ?
N4 C5 1.366(3) . ?
C5 C6 1.375(3) . ?
C5 C21 1.467(3) . ?
C6 H6 0.9500 . ?
N7 C8 1.381(3) . ?
N7 H7N 0.88(3) . ?
C8 O8 1.254(3) . ?
C8 N9 1.331(3) . ?
N9 C10 1.459(3) . ?
N9 H9N 0.81(3) . ?
C10 C11 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.526(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.523(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
Fe1 C22 2.034(2) . ?
Fe1 C21 2.044(2) . ?
Fe1 C32 2.041(3) . ?
Fe1 C34 2.048(2) . ?
Fe1 C33 2.046(2) . ?
Fe1 C25 2.048(2) . ?
Fe1 C31 2.049(3) . ?
Fe1 C23 2.053(2) . ?
Fe1 C35 2.057(2) . ?
Fe1 C24 2.059(2) . ?
C21 C22 1.434(3) . ?
C21 C25 1.440(3) . ?
C22 C23 1.423(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.422(3) . ?
C23 H23 1.0000 . ?
C24 C25 1.419(3) . ?
C24 H24 1.0000 . ?
C25 H25 1.0000 . ?
C31 C35 1.417(4) . ?
C31 C32 1.424(4) . ?
C31 H31 1.0000 . ?
C32 C33 1.421(3) . ?
C32 H32 1.0000 . ?
C33 C34 1.420(3) . ?
C33 H33 1.0000 . ?
C34 C35 1.417(3) . ?
C34 H34 1.0000 . ?
C35 H35 1.0000 . ?

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
O1 C1 N2 118.8(2) . . ?
O1 C1 C6 118.5(2) . . ?
N2 C1 C6 122.7(2) . . ?
C1 O1 H1O 110.9(19) . . ?
C1 N2 C3 114.9(2) . . ?
N4 C3 N2 127.6(2) . . ?
N4 C3 N7 118.9(2) . . ?
N2 C3 N7 113.4(2) . . ?
C3 N4 C5 115.9(2) . . ?
N4 C5 C6 121.4(2) . . ?
N4 C5 C21 116.0(2) . . ?
C6 C5 C21 122.5(2) . . ?
C5 C6 C1 117.3(2) . . ?
C5 C6 H6 121.3 . . ?
C1 C6 H6 121.3 . . ?
C8 N7 C3 129.9(2) . . ?
C8 N7 H7N 113.8(16) . . ?
C3 N7 H7N 116.2(16) . . ?
O8 C8 N9 121.5(2) . . ?
O8 C8 N7 118.6(2) . . ?
N9 C8 N7 119.9(2) . . ?
C8 N9 C10 120.2(2) . . ?
C8 N9 H9N 117.2(19) . . ?
C10 N9 H9N 122.6(19) . . ?
N9 C10 C11 112.9(2) . . ?
N9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 115.4(2) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 112.1(2) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 113.9(2) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 114.4(2) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 113.0(2) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 113.9(2) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 Fe1 C21 41.19(9) . . ?
C22 Fe1 C32 117.62(10) . . ?
C21 Fe1 C32 105.81(10) . . ?
C22 Fe1 C34 124.14(10) . . ?
C21 Fe1 C34 161.02(10) . . ?
C32 Fe1 C34 68.22(10) . . ?
C22 Fe1 C33 104.76(10) . . ?
C21 Fe1 C33 123.29(10) . . ?
C32 Fe1 C33 40.69(10) . . ?
C34 Fe1 C33 40.60(10) . . ?
C22 Fe1 C25 68.99(10) . . ?
C21 Fe1 C25 41.21(9) . . ?
C32 Fe1 C25 126.10(10) . . ?
C34 Fe1 C25 156.54(10) . . ?
C33 Fe1 C25 162.15(9) . . ?
C22 Fe1 C31 153.66(10) . . ?
C21 Fe1 C31 119.89(10) . . ?
C32 Fe1 C31 40.75(10) . . ?
C34 Fe1 C31 68.14(10) . . ?
C33 Fe1 C31 68.49(10) . . ?
C25 Fe1 C31 109.28(10) . . ?
C22 Fe1 C23 40.75(9) . . ?
C21 Fe1 C23 68.83(9) . . ?
C32 Fe1 C23 152.76(10) . . ?
C34 Fe1 C23 107.75(10) . . ?
C33 Fe1 C23 118.51(10) . . ?
C25 Fe1 C23 68.35(10) . . ?
C31 Fe1 C23 164.97(10) . . ?
C22 Fe1 C35 162.61(10) . . ?
C21 Fe1 C35 155.95(10) . . ?
C32 Fe1 C35 68.14(10) . . ?
C34 Fe1 C35 40.41(10) . . ?
C33 Fe1 C35 68.20(10) . . ?
C25 Fe1 C35 122.39(10) . . ?
C31 Fe1 C35 40.39(10) . . ?
C23 Fe1 C35 127.29(10) . . ?
C22 Fe1 C24 68.52(10) . . ?
C21 Fe1 C24 68.73(10) . . ?
C32 Fe1 C24 164.47(10) . . ?
C34 Fe1 C24 121.59(10) . . ?
C33 Fe1 C24 154.48(10) . . ?
C25 Fe1 C24 40.44(9) . . ?
C31 Fe1 C24 128.24(10) . . ?
C23 Fe1 C24 40.47(10) . . ?
C35 Fe1 C24 110.57(10) . . ?
C22 C21 C25 107.1(2) . . ?
C22 C21 C5 127.0(2) . . ?
C25 C21 C5 125.8(2) . . ?
C22 C21 Fe1 69.06(14) . . ?
C25 C21 Fe1 69.54(13) . . ?
C5 C21 Fe1 124.07(17) . . ?
C23 C22 C21 108.3(2) . . ?
C23 C22 Fe1 70.34(14) . . ?
C21 C22 Fe1 69.75(13) . . ?
C23 C22 H22 125.9 . . ?
C21 C22 H22 125.9 . . ?
Fe1 C22 H22 125.9 . . ?
C24 C23 C22 108.2(2) . . ?
C24 C23 Fe1 69.97(14) . . ?
C22 C23 Fe1 68.91(14) . . ?
C24 C23 H23 125.9 . . ?
C22 C23 H23 125.9 . . ?
Fe1 C23 H23 125.9 . . ?
C25 C24 C23 108.3(2) . . ?
C25 C24 Fe1 69.36(14) . . ?
C23 C24 Fe1 69.56(14) . . ?
C25 C24 H24 125.8 . . ?
C23 C24 H24 125.8 . . ?
Fe1 C24 H24 125.8 . . ?
C24 C25 C21 108.2(2) . . ?
C24 C25 Fe1 70.20(14) . . ?
C21 C25 Fe1 69.25(14) . . ?
C24 C25 H25 125.9 . . ?
C21 C25 H25 125.9 . . ?
Fe1 C25 H25 125.9 . . ?
C35 C31 C32 107.8(2) . . ?
C35 C31 Fe1 70.10(14) . . ?
C32 C31 Fe1 69.33(14) . . ?
C35 C31 H31 126.1 . . ?
C32 C31 H31 126.1 . . ?
Fe1 C31 H31 126.1 . . ?
C31 C32 C33 108.2(2) . . ?
C31 C32 Fe1 69.93(14) . . ?
C33 C32 Fe1 69.85(14) . . ?
C31 C32 H32 125.9 . . ?
C33 C32 H32 125.9 . . ?
Fe1 C32 H32 125.9 . . ?
C34 C33 C32 107.6(2) . . ?
C34 C33 Fe1 69.76(14) . . ?
C32 C33 Fe1 69.46(14) . . ?
C34 C33 H33 126.2 . . ?
C32 C33 H33 126.2 . . ?
Fe1 C33 H33 126.2 . . ?
C35 C34 C33 108.3(2) . . ?
C35 C34 Fe1 70.14(14) . . ?
C33 C34 Fe1 69.64(14) . . ?
C35 C34 H34 125.8 . . ?
C33 C34 H34 125.8 . . ?
Fe1 C34 H34 125.8 . . ?
C34 C35 C31 108.1(2) . . ?
C34 C35 Fe1 69.45(14) . . ?
C31 C35 Fe1 69.51(14) . . ?
C34 C35 H35 125.9 . . ?
C31 C35 H35 125.9 . . ?
Fe1 C35 H35 125.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 C3 -177.4(2) . . . . ?
C6 C1 N2 C3 2.4(3) . . . . ?
C1 N2 C3 N4 -2.4(4) . . . . ?
C1 N2 C3 N7 177.5(2) . . . . ?
N2 C3 N4 C5 0.6(4) . . . . ?
N7 C3 N4 C5 -179.4(2) . . . . ?
C3 N4 C5 C6 1.3(3) . . . . ?
C3 N4 C5 C21 -177.4(2) . . . . ?
N4 C5 C6 C1 -1.1(4) . . . . ?
C21 C5 C6 C1 177.4(2) . . . . ?
O1 C1 C6 C5 179.1(2) . . . . ?
N2 C1 C6 C5 -0.8(4) . . . . ?
N4 C3 N7 C8 5.4(4) . . . . ?
N2 C3 N7 C8 -174.6(2) . . . . ?
C3 N7 C8 O8 -179.7(2) . . . . ?
C3 N7 C8 N9 0.4(4) . . . . ?
O8 C8 N9 C10 1.0(4) . . . . ?
N7 C8 N9 C10 -179.1(2) . . . . ?
C8 N9 C10 C11 158.5(2) . . . . ?
N9 C10 C11 C12 75.7(3) . . . . ?
C10 C11 C12 C13 178.8(2) . . . . ?
C11 C12 C13 C14 177.7(2) . . . . ?
C12 C13 C14 C15 176.3(2) . . . . ?
C13 C14 C15 C16 178.2(2) . . . . ?
C14 C15 C16 C17 173.7(2) . . . . ?
N4 C5 C21 C22 -174.3(2) . . . . ?
C6 C5 C21 C22 7.1(4) . . . . ?
N4 C5 C21 C25 2.2(4) . . . . ?
C6 C5 C21 C25 -176.5(2) . . . . ?
N4 C5 C21 Fe1 -86.0(2) . . . . ?
C6 C5 C21 Fe1 95.4(3) . . . . ?
C32 Fe1 C21 C22 114.09(15) . . . . ?
C34 Fe1 C21 C22 45.4(4) . . . . ?
C33 Fe1 C21 C22 73.28(17) . . . . ?
C25 Fe1 C21 C22 -118.6(2) . . . . ?
C31 Fe1 C21 C22 155.89(14) . . . . ?
C23 Fe1 C21 C22 -37.71(14) . . . . ?
C35 Fe1 C21 C22 -174.3(2) . . . . ?
C24 Fe1 C21 C22 -81.26(15) . . . . ?
C22 Fe1 C21 C25 118.6(2) . . . . ?
C32 Fe1 C21 C25 -127.32(14) . . . . ?
C34 Fe1 C21 C25 164.0(3) . . . . ?
C33 Fe1 C21 C25 -168.13(14) . . . . ?
C31 Fe1 C21 C25 -85.51(16) . . . . ?
C23 Fe1 C21 C25 80.89(15) . . . . ?
C35 Fe1 C21 C25 -55.7(3) . . . . ?
C24 Fe1 C21 C25 37.33(14) . . . . ?
C22 Fe1 C21 C5 -121.3(3) . . . . ?
C32 Fe1 C21 C5 -7.2(2) . . . . ?
C34 Fe1 C21 C5 -76.0(4) . . . . ?
C33 Fe1 C21 C5 -48.1(2) . . . . ?
C25 Fe1 C21 C5 120.1(3) . . . . ?
C31 Fe1 C21 C5 34.6(2) . . . . ?
C23 Fe1 C21 C5 -159.0(2) . . . . ?
C35 Fe1 C21 C5 64.4(3) . . . . ?
C24 Fe1 C21 C5 157.4(2) . . . . ?
C25 C21 C22 C23 0.7(3) . . . . ?
C5 C21 C22 C23 177.6(2) . . . . ?
Fe1 C21 C22 C23 60.05(17) . . . . ?
C25 C21 C22 Fe1 -59.39(16) . . . . ?
C5 C21 C22 Fe1 117.6(2) . . . . ?
C21 Fe1 C22 C23 -119.1(2) . . . . ?
C32 Fe1 C22 C23 158.44(14) . . . . ?
C34 Fe1 C22 C23 77.14(17) . . . . ?
C33 Fe1 C22 C23 116.78(15) . . . . ?
C25 Fe1 C22 C23 -80.81(15) . . . . ?
C31 Fe1 C22 C23 -172.0(2) . . . . ?
C35 Fe1 C22 C23 53.1(4) . . . . ?
C24 Fe1 C22 C23 -37.28(14) . . . . ?
C32 Fe1 C22 C21 -82.47(16) . . . . ?
C34 Fe1 C22 C21 -163.76(14) . . . . ?
C33 Fe1 C22 C21 -124.13(15) . . . . ?
C25 Fe1 C22 C21 38.29(14) . . . . ?
C31 Fe1 C22 C21 -52.9(3) . . . . ?
C23 Fe1 C22 C21 119.1(2) . . . . ?
C35 Fe1 C22 C21 172.2(3) . . . . ?
C24 Fe1 C22 C21 81.82(15) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
Fe1 C22 C23 C24 59.15(17) . . . . ?
C21 C22 C23 Fe1 -59.68(16) . . . . ?
C22 Fe1 C23 C24 -119.7(2) . . . . ?
C21 Fe1 C23 C24 -81.64(15) . . . . ?
C32 Fe1 C23 C24 -165.1(2) . . . . ?
C34 Fe1 C23 C24 118.18(15) . . . . ?
C33 Fe1 C23 C24 161.01(14) . . . . ?
C25 Fe1 C23 C24 -37.22(14) . . . . ?
C31 Fe1 C23 C24 46.6(4) . . . . ?
C35 Fe1 C23 C24 77.75(17) . . . . ?
C21 Fe1 C23 C22 38.10(14) . . . . ?
C32 Fe1 C23 C22 -45.4(3) . . . . ?
C34 Fe1 C23 C22 -122.08(15) . . . . ?
C33 Fe1 C23 C22 -79.26(16) . . . . ?
C25 Fe1 C23 C22 82.52(15) . . . . ?
C31 Fe1 C23 C22 166.3(4) . . . . ?
C35 Fe1 C23 C22 -162.51(14) . . . . ?
C24 Fe1 C23 C22 119.7(2) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
Fe1 C23 C24 C25 58.69(17) . . . . ?
C22 C23 C24 Fe1 -58.49(17) . . . . ?
C22 Fe1 C24 C25 -82.40(15) . . . . ?
C21 Fe1 C24 C25 -38.02(14) . . . . ?
C32 Fe1 C24 C25 34.0(4) . . . . ?
C34 Fe1 C24 C25 159.83(14) . . . . ?
C33 Fe1 C24 C25 -161.5(2) . . . . ?
C31 Fe1 C24 C25 73.95(18) . . . . ?
C23 Fe1 C24 C25 -119.9(2) . . . . ?
C35 Fe1 C24 C25 116.22(15) . . . . ?
C22 Fe1 C24 C23 37.52(14) . . . . ?
C21 Fe1 C24 C23 81.91(15) . . . . ?
C32 Fe1 C24 C23 153.9(3) . . . . ?
C34 Fe1 C24 C23 -80.25(16) . . . . ?
C33 Fe1 C24 C23 -41.6(3) . . . . ?
C25 Fe1 C24 C23 119.9(2) . . . . ?
C31 Fe1 C24 C23 -166.13(15) . . . . ?
C35 Fe1 C24 C23 -123.86(15) . . . . ?
C23 C24 C25 C21 0.2(3) . . . . ?
Fe1 C24 C25 C21 59.03(17) . . . . ?
C23 C24 C25 Fe1 -58.82(17) . . . . ?
C22 C21 C25 C24 -0.5(3) . . . . ?
C5 C21 C25 C24 -177.5(2) . . . . ?
Fe1 C21 C25 C24 -59.63(17) . . . . ?
C22 C21 C25 Fe1 59.09(16) . . . . ?
C5 C21 C25 Fe1 -117.9(2) . . . . ?
C22 Fe1 C25 C24 81.13(15) . . . . ?
C21 Fe1 C25 C24 119.4(2) . . . . ?
C32 Fe1 C25 C24 -169.32(15) . . . . ?
C34 Fe1 C25 C24 -47.5(3) . . . . ?
C33 Fe1 C25 C24 153.5(3) . . . . ?
C31 Fe1 C25 C24 -126.91(15) . . . . ?
C23 Fe1 C25 C24 37.24(14) . . . . ?
C35 Fe1 C25 C24 -84.10(17) . . . . ?
C22 Fe1 C25 C21 -38.27(14) . . . . ?
C32 Fe1 C25 C21 71.28(17) . . . . ?
C34 Fe1 C25 C21 -166.9(2) . . . . ?
C33 Fe1 C25 C21 34.1(4) . . . . ?
C31 Fe1 C25 C21 113.69(15) . . . . ?
C23 Fe1 C25 C21 -82.16(15) . . . . ?
C35 Fe1 C25 C21 156.50(14) . . . . ?
C24 Fe1 C25 C21 -119.4(2) . . . . ?
C22 Fe1 C31 C35 -160.9(2) . . . . ?
C21 Fe1 C31 C35 161.78(14) . . . . ?
C32 Fe1 C31 C35 -118.9(2) . . . . ?
C34 Fe1 C31 C35 -37.38(15) . . . . ?
C33 Fe1 C31 C35 -81.22(16) . . . . ?
C25 Fe1 C31 C35 117.69(15) . . . . ?
C23 Fe1 C31 C35 39.5(5) . . . . ?
C24 Fe1 C31 C35 76.36(18) . . . . ?
C22 Fe1 C31 C32 -42.0(3) . . . . ?
C21 Fe1 C31 C32 -79.30(17) . . . . ?
C34 Fe1 C31 C32 81.55(16) . . . . ?
C33 Fe1 C31 C32 37.71(15) . . . . ?
C25 Fe1 C31 C32 -123.39(15) . . . . ?
C23 Fe1 C31 C32 158.4(4) . . . . ?
C35 Fe1 C31 C32 118.9(2) . . . . ?
C24 Fe1 C31 C32 -164.72(14) . . . . ?
C35 C31 C32 C33 0.2(3) . . . . ?
Fe1 C31 C32 C33 -59.59(17) . . . . ?
C35 C31 C32 Fe1 59.80(17) . . . . ?
C22 Fe1 C32 C31 160.42(15) . . . . ?
C21 Fe1 C32 C31 117.70(15) . . . . ?
C34 Fe1 C32 C31 -81.35(16) . . . . ?
C33 Fe1 C32 C31 -119.2(2) . . . . ?
C25 Fe1 C32 C31 77.28(18) . . . . ?
C23 Fe1 C32 C31 -168.0(2) . . . . ?
C35 Fe1 C32 C31 -37.67(15) . . . . ?
C24 Fe1 C32 C31 50.6(4) . . . . ?
C22 Fe1 C32 C33 -80.35(17) . . . . ?
C21 Fe1 C32 C33 -123.08(15) . . . . ?
C34 Fe1 C32 C33 37.87(15) . . . . ?
C25 Fe1 C32 C33 -163.50(14) . . . . ?
C31 Fe1 C32 C33 119.2(2) . . . . ?
C23 Fe1 C32 C33 -48.7(3) . . . . ?
C35 Fe1 C32 C33 81.55(16) . . . . ?
C24 Fe1 C32 C33 169.8(3) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
Fe1 C32 C33 C34 -59.57(17) . . . . ?
C31 C32 C33 Fe1 59.64(18) . . . . ?
C22 Fe1 C33 C34 -125.76(15) . . . . ?
C21 Fe1 C33 C34 -166.46(14) . . . . ?
C32 Fe1 C33 C34 118.8(2) . . . . ?
C25 Fe1 C33 C34 167.3(3) . . . . ?
C31 Fe1 C33 C34 81.08(16) . . . . ?
C23 Fe1 C33 C34 -84.22(16) . . . . ?
C35 Fe1 C33 C34 37.47(15) . . . . ?
C24 Fe1 C33 C34 -54.9(3) . . . . ?
C22 Fe1 C33 C32 115.40(15) . . . . ?
C21 Fe1 C33 C32 74.70(17) . . . . ?
C34 Fe1 C33 C32 -118.8(2) . . . . ?
C25 Fe1 C33 C32 48.5(4) . . . . ?
C31 Fe1 C33 C32 -37.76(15) . . . . ?
C23 Fe1 C33 C32 156.94(15) . . . . ?
C35 Fe1 C33 C32 -81.37(16) . . . . ?
C24 Fe1 C33 C32 -173.7(2) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
Fe1 C33 C34 C35 -59.70(17) . . . . ?
C32 C33 C34 Fe1 59.38(17) . . . . ?
C22 Fe1 C34 C35 -169.18(15) . . . . ?
C21 Fe1 C34 C35 156.3(3) . . . . ?
C32 Fe1 C34 C35 81.42(16) . . . . ?
C33 Fe1 C34 C35 119.4(2) . . . . ?
C25 Fe1 C34 C35 -50.9(3) . . . . ?
C31 Fe1 C34 C35 37.37(15) . . . . ?
C23 Fe1 C34 C35 -127.26(15) . . . . ?
C24 Fe1 C34 C35 -85.06(17) . . . . ?
C22 Fe1 C34 C33 71.45(17) . . . . ?
C21 Fe1 C34 C33 37.0(4) . . . . ?
C32 Fe1 C34 C33 -37.96(15) . . . . ?
C25 Fe1 C34 C33 -170.3(2) . . . . ?
C31 Fe1 C34 C33 -82.01(16) . . . . ?
C23 Fe1 C34 C33 113.37(15) . . . . ?
C35 Fe1 C34 C33 -119.4(2) . . . . ?
C24 Fe1 C34 C33 155.56(15) . . . . ?
C33 C34 C35 C31 0.4(3) . . . . ?
Fe1 C34 C35 C31 -58.94(17) . . . . ?
C33 C34 C35 Fe1 59.39(17) . . . . ?
C32 C31 C35 C34 -0.4(3) . . . . ?
Fe1 C31 C35 C34 58.91(17) . . . . ?
C32 C31 C35 Fe1 -59.31(18) . . . . ?
C22 Fe1 C35 C34 31.3(4) . . . . ?
C21 Fe1 C35 C34 -161.3(2) . . . . ?
C32 Fe1 C35 C34 -81.63(16) . . . . ?
C33 Fe1 C35 C34 -37.64(15) . . . . ?
C25 Fe1 C35 C34 158.55(14) . . . . ?
C31 Fe1 C35 C34 -119.6(2) . . . . ?
C23 Fe1 C35 C34 72.34(18) . . . . ?
C24 Fe1 C35 C34 114.98(15) . . . . ?
C22 Fe1 C35 C31 151.0(3) . . . . ?
C21 Fe1 C35 C31 -41.7(3) . . . . ?
C32 Fe1 C35 C31 37.99(15) . . . . ?
C34 Fe1 C35 C31 119.6(2) . . . . ?
C33 Fe1 C35 C31 81.99(16) . . . . ?
C25 Fe1 C35 C31 -81.83(17) . . . . ?
C23 Fe1 C35 C31 -168.04(15) . . . . ?
C24 Fe1 C35 C31 -125.39(15) . . . . ?

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
O1 H1O O8 0.82(3) 1.77(3) 2.583(2) 168(3) 2_466
N9 H9N N4 0.81(3) 2.07(3) 2.713(3) 136(2) .
N7 H7N N2 0.88(3) 2.14(3) 3.013(3) 171(2) 2_466

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.070