# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global

_publ_contact_author_email       LKOZ@ICHO.EDU.PL

_publ_contact_author_name        'Prof Lech Kozerski'
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_publ_contact_author_address     
;
Institute of Organic Chemistry
Polish Academy of Sciences
Kasprzaka 44
Warsaw
01-224
POLAND
;

_publ_section_title              
;
Genistein complexes with amines. Evaluation of the
potential for biological function of the C-7, C-5, C-4'-OH groups
studied  in solution and solid state by 13C NMR and X-ray
;

loop_
_publ_author_name
'Lech Kozerski'
E.Bednarek
W.Bocian
P.E.Hansen
B.Kamienski
;
R.Kawecki
;
K.T.Nielsen
'Jerzy Sitkowski'
Z.Urbanczyk-Lipkowska
'K. Zakrzewska'

data_ok
_database_code_CSD               212666

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24.50 N2 O7.50'
_chemical_formula_weight         400.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   6.8220(10)
_cell_length_b                   23.501(5)
_cell_length_c                   23.730(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3804.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15
_cell_measurement_theta_min      17.1
_cell_measurement_theta_max      23.5

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1700
_exptl_absorpt_coefficient_mu    0.915
_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      150.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  MACH3
_diffrn_measurement_method       omega/2theta
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  3600s
_diffrn_standards_decay_%        26.1
_diffrn_reflns_number            3026
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         56.99
_reflns_number_total             1860
_reflns_number_gt                1705
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'EXPRESS, Nonius BV'
_computing_cell_refinement       'EXPRESS, Nonius BV'
_computing_data_reduction        'OpenMoleN, Nonius BV'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0423P)²+7.4402P] where P=(Fo²+2Fc²)/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         1860
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_restrained_S_all      1.257
_refine_ls_shift/su_max          0.090
_refine_ls_shift/su_mean         0.007

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
O3 O 0.1237(17) 0.0083(4) 0.5045(5) 0.068(3) Uani 0.50 1 d PD . .
H5 H 0.875(10) 0.313(2) 0.267(2) 0.046(19) Uiso 1 1 d . . .
H18 H 0.873(11) 0.386(3) -0.082(3) 0.05(2) Uiso 1 1 d . . .
H19 H 0.443(11) 0.869(3) 0.365(3) 0.06(2) Uiso 1 1 d . . .
H20' H 0.491(10) 1.057(3) 0.355(2) 0.04(2) Uiso 1 1 d . . .
H20 H 0.301(15) 1.034(3) 0.356(4) 0.09(3) Uiso 1 1 d . . .
H20A H 0.052(14) 0.120(4) 0.670(4) 0.10(3) Uiso 1 1 d . . .
H20B H 0.231(12) 0.098(3) 0.650(3) 0.06(2) Uiso 1 1 d . . .
H21A H 0.479(14) 0.990(4) 0.158(3) 0.09(3) Uiso 1 1 d . . .
H21B H 0.415(15) 1.050(4) 0.149(4) 0.11(3) Uiso 1 1 d . . .
H31 H 0.160(15) 0.033(3) 0.475(3) 0.01(3) Uiso 0.50 1 d PD . .
C1' C 0.8460(8) 0.2807(2) 0.0806(2) 0.0183(13) Uani 1 1 d . . .
C2 C 0.7663(8) 0.1876(2) 0.1238(2) 0.0173(12) Uani 1 1 d . . .
H7 H 0.7527 0.1745 0.0870 0.021 Uiso 1 1 calc R . .
C2' C 0.7049(8) 0.2860(2) 0.0380(2) 0.0176(13) Uani 1 1 d . . .
H13 H 0.5900 0.2648 0.0402 0.021 Uiso 1 1 calc R . .
C2" C 0.3957(10) 0.9355(2) 0.4119(2) 0.0373(16) Uani 1 1 d . . .
H94A H 0.4345 0.9169 0.4467 0.045 Uiso 1 1 calc R . .
H94B H 0.2537 0.9366 0.4104 0.045 Uiso 1 1 calc R . .
C3' C 0.7331(8) 0.3222(2) -0.0075(2) 0.0198(13) Uani 1 1 d . . .
H14 H 0.6380 0.3251 -0.0355 0.024 Uiso 1 1 calc R . .
C3 C 0.8140(7) 0.2428(2) 0.1309(2) 0.0172(13) Uani 1 1 d . . .
C3" C 0.4779(10) 0.9956(2) 0.4100(2) 0.0318(15) Uani 1 1 d . . .
H95A H 0.4248 1.0175 0.4411 0.038 Uiso 1 1 calc R . .
H95B H 0.6193 0.9943 0.4142 0.038 Uiso 1 1 calc R . .
C4 C 0.8378(7) 0.2644(2) 0.1883(2) 0.0145(12) Uani 1 1 d . . .
C4' C 0.9067(9) 0.3543(2) -0.0110(2) 0.0207(13) Uani 1 1 d . . .
C5" C 0.4825(8) 0.9893(2) 0.3056(2) 0.0232(14) Uani 1 1 d . . .
H97A H 0.6241 0.9884 0.3020 0.028 Uiso 1 1 calc R . .
H97B H 0.4293 1.0070 0.2720 0.028 Uiso 1 1 calc R . .
C5 C 0.8217(7) 0.2388(2) 0.2911(2) 0.0127(12) Uani 1 1 d . . .
C5' C 1.0508(8) 0.3485(2) 0.0307(2) 0.0202(13) Uani 1 1 d . . .
H16 H 1.1669 0.3691 0.0280 0.024 Uiso 1 1 calc R . .
C6' C 1.0209(8) 0.3122(2) 0.0757(2) 0.0187(13) Uani 1 1 d . . .
H17 H 1.1175 0.3085 0.1031 0.022 Uiso 1 1 calc R . .
C6" C 0.4043(9) 0.9288(2) 0.3107(2) 0.0276(14) Uani 1 1 d . . .
H98A H 0.2621 0.9293 0.3103 0.033 Uiso 1 1 calc R . .
H98B H 0.4491 0.9062 0.2790 0.033 Uiso 1 1 calc R . .
C6 C 0.7916(7) 0.1995(2) 0.3332(2) 0.0136(12) Uani 1 1 d . . .
H3 H 0.8056 0.2102 0.3707 0.016 Uiso 1 1 calc R . .
C7 C 0.7390(7) 0.1426(2) 0.3195(2) 0.0150(12) Uani 1 1 d . . .
C8 C 0.7185(7) 0.1278(2) 0.2623(2) 0.0151(12) Uani 1 1 d . . .
H1 H 0.6814 0.0911 0.2525 0.018 Uiso 1 1 calc R . .
C9 C 0.7531(8) 0.1674(2) 0.22113(19) 0.0140(11) Uiso 1 1 d . . .
C10 C 0.8049(8) 0.2245(2) 0.23335(19) 0.0141(12) Uiso 1 1 d . . .
N1" N 0.4733(8) 0.9037(2) 0.3630(2) 0.0332(13) Uani 1 1 d . . .
N4" N 0.4276(8) 1.0238(2) 0.3560(2) 0.0238(12) Uani 1 1 d . . .
O1 O 0.7365(5) 0.14943(13) 0.16596(13) 0.0157(8) Uani 1 1 d . . .
O4' O 0.9424(6) 0.39262(16) -0.05312(16) 0.0303(11) Uani 1 1 d . . .
O4 O 0.8824(5) 0.31574(14) 0.19833(14) 0.0212(9) Uani 1 1 d . . .
O5 O 0.8730(5) 0.29324(14) 0.30586(15) 0.0196(9) Uani 1 1 d . . .
O7 O 0.7115(5) 0.10440(13) 0.36006(13) 0.0186(9) Uani 1 1 d . . .
O2 O 0.1191(7) 0.08619(17) 0.66601(19) 0.0319(11) Uani 1 1 d . . .
O6 O 0.5209(6) 1.02367(19) 0.16364(18) 0.0280(10) Uani 1 1 d . . .


_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
O3 O3 1.74(2) 5_556 ?
O3 H31 0.93(2) . ?
C1' C2' 1.402(7) . ?
C1' C6' 1.409(8) . ?
C1' C3 1.506(7) . ?
C2 C3 1.349(7) . ?
C2 O1 1.358(6) . ?
C2 H7 0.9300 . ?
C2' C3' 1.387(7) . ?
C2' H13 0.9300 . ?
C2" N1" 1.477(8) . ?
C2" C3" 1.521(8) . ?
C2" H94A 0.9700 . ?
C2" H94B 0.9700 . ?
C3' C4' 1.408(8) . ?
C3' H14 0.9300 . ?
C3 C4 1.462(7) . ?
C3" N4" 1.483(7) . ?
C3" H95A 0.9700 . ?
C3" H95B 0.9700 . ?
C4 O4 1.268(6) . ?
C4 C10 1.439(7) . ?
C4' O4' 1.366(6) . ?
C4' C5' 1.402(7) . ?
C5" N4" 1.491(7) . ?
C5" C6" 1.525(8) . ?
C5" H97A 0.9700 . ?
C5" H97B 0.9700 . ?
C5 O5 1.372(6) . ?
C5 C6 1.375(7) . ?
C5 C10 1.416(7) . ?
C5' C6' 1.383(7) . ?
C5' H16 0.9300 . ?
C6' H17 0.9300 . ?
C6" N1" 1.452(7) . ?
C6" H98A 0.9700 . ?
C6" H98B 0.9700 . ?
C6 C7 1.421(7) . ?
C6 H3 0.9300 . ?
C7 O7 1.330(6) . ?
C7 C8 1.408(7) . ?
C8 C9 1.369(7) . ?
C8 H1 0.9300 . ?
C9 O1 1.380(6) . ?
C9 C10 1.419(7) . ?
N1" H19 0.85(7) . ?
N4" H20' 0.90(7) . ?
N4" H20 0.90(10) . ?
O4' H18 0.84(7) . ?
O5 H5 1.03(6) . ?
O2 H20A 0.93(9) . ?
O2 H20B 0.90(8) . ?
O6 H21A 0.86(9) . ?
O6 H21B 1.02(10) . ?

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
O3 O3 H31 108(7) 5_556 . ?
C2' C1' C6' 118.4(5) . . ?
C2' C1' C3 121.7(5) . . ?
C6' C1' C3 119.9(5) . . ?
C3 C2 O1 125.4(5) . . ?
C3 C2 H7 117.3 . . ?
O1 C2 H7 117.3 . . ?
C3' C2' C1' 121.4(5) . . ?
C3' C2' H13 119.3 . . ?
C1' C2' H13 119.3 . . ?
N1" C2" C3" 108.3(5) . . ?
N1" C2" H94A 110.0 . . ?
C3" C2" H94A 110.0 . . ?
N1" C2" H94B 110.0 . . ?
C3" C2" H94B 110.0 . . ?
H94A C2" H94B 108.4 . . ?
C2' C3' C4' 119.4(5) . . ?
C2' C3' H14 120.3 . . ?
C4' C3' H14 120.3 . . ?
C2 C3 C4 118.5(5) . . ?
C2 C3 C1' 120.3(5) . . ?
C4 C3 C1' 121.1(4) . . ?
N4" C3" C2" 110.8(5) . . ?
N4" C3" H95A 109.5 . . ?
C2" C3" H95A 109.5 . . ?
N4" C3" H95B 109.5 . . ?
C2" C3" H95B 109.5 . . ?
H95A C3" H95B 108.1 . . ?
O4 C4 C10 121.2(5) . . ?
O4 C4 C3 122.1(5) . . ?
C10 C4 C3 116.7(4) . . ?
O4' C4' C5' 117.1(5) . . ?
O4' C4' C3' 123.2(5) . . ?
C5' C4' C3' 119.7(5) . . ?
N4" C5" C6" 110.8(5) . . ?
N4" C5" H97A 109.5 . . ?
C6" C5" H97A 109.5 . . ?
N4" C5" H97B 109.5 . . ?
C6" C5" H97B 109.5 . . ?
H97A C5" H97B 108.1 . . ?
O5 C5 C6 118.6(4) . . ?
O5 C5 C10 119.3(5) . . ?
C6 C5 C10 122.1(4) . . ?
C6' C5' C4' 120.2(5) . . ?
C6' C5' H16 119.9 . . ?
C4' C5' H16 119.9 . . ?
C5' C6' C1' 120.8(5) . . ?
C5' C6' H17 119.6 . . ?
C1' C6' H17 119.6 . . ?
N1" C6" C5" 109.5(5) . . ?
N1" C6" H98A 109.8 . . ?
C5" C6" H98A 109.8 . . ?
N1" C6" H98B 109.8 . . ?
C5" C6" H98B 109.8 . . ?
H98A C6" H98B 108.2 . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H3 119.9 . . ?
C7 C6 H3 119.9 . . ?
O7 C7 C8 121.1(5) . . ?
O7 C7 C6 120.4(4) . . ?
C8 C7 C6 118.5(4) . . ?
C9 C8 C7 120.2(5) . . ?
C9 C8 H1 119.9 . . ?
C7 C8 H1 119.9 . . ?
C8 C9 O1 117.1(4) . . ?
C8 C9 C10 122.7(4) . . ?
O1 C9 C10 120.2(4) . . ?
C5 C10 C9 116.3(4) . . ?
C5 C10 C4 123.5(5) . . ?
C9 C10 C4 120.2(4) . . ?
C6" N1" C2" 110.5(5) . . ?
C6" N1" H19 111(5) . . ?
C2" N1" H19 111(5) . . ?
C3" N4" C5" 113.1(4) . . ?
C3" N4" H20' 107(4) . . ?
C5" N4" H20' 110(4) . . ?
C3" N4" H20 110(5) . . ?
C5" N4" H20 113(6) . . ?
H20' N4" H20 102(6) . . ?
C2 O1 C9 119.0(4) . . ?
C4' O4' H18 112(5) . . ?
C5 O5 H5 101(3) . . ?
H20A O2 H20B 101(7) . . ?
H21A O6 H21B 107(8) . . ?

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
O5 H5 O4 1.03(6) 1.64(6) 2.607(5) 156(5) .
O4' H18 O7 0.84(7) 1.78(7) 2.594(5) 162(7) 7_565
N1" H19 O5 0.85(7) 2.58(7) 3.112(6) 121(6) 8_765
N4" H20' O7 0.90(7) 1.87(7) 2.711(6) 154(6) 1_565
N4" H20 O6 0.90(10) 1.98(10) 2.814(7) 153(7) 6_556
O2 H20A O4 0.93(9) 2.01(10) 2.917(6) 165(8) 7_466
O2 H20B N1" 0.90(8) 2.04(9) 2.875(7) 153(6) 5_666
O6 H21A O2 0.86(9) 1.91(9) 2.753(6) 166(8) 2_564
O6 H21B O7 1.02(10) 1.89(10) 2.893(5) 167(7) 6_566
O3 H31 O4' 0.93(2) 2.40(9) 2.970(12) 120(8) 7_466

_diffrn_measured_fraction_theta_max 0.725
_diffrn_reflns_theta_full        56.99
_diffrn_measured_fraction_theta_full 0.725
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.068



