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

data_global

_publ_contact_author_email       LONPOBTY@SUPANET.COM

_publ_contact_author_name        'Dr Peter Critchley'
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?
_publ_contact_author_address     
;
Dr Peter Critchley
14 Ferndale Drive
Kenilworth
Warwickshire
CV8 2PF
UK
;

_publ_section_title              
;
Carbohydrate-protein interactions at interfaces:
comparison of the binding of Ricinus communis lectin to two series of
synthetic glycolipids using surface plasmon resonance studies
;

loop_
_publ_author_name
'Peter Critchley'
'G.J. Clarkson'

data_gc72
_database_code_CSD               213138

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H70 N2 O12'
_chemical_formula_weight         819.02

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   8.6168(8)
_cell_length_b                   9.3641(9)
_cell_length_c                   56.595(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4566.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6298
_cell_measurement_theta_min      3
_cell_measurement_theta_max      15

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
The temperature of the crystal was controlled using the Oxford Cryosystem
Cryostream Cooler (Cosier & Glazer, 1986).
The data collection nominally covered over a hemisphere of reciprocal
space, by a combination of three sets of exposures with
different φ angles for the crystal; each 10 s exposure covered 0.3° in ω.
The crystal-to-detector distance was 5.0 cm.  Coverage of the unique set
is over 97% complete to at least 26° in θ.
Crystal decay was found to be negligible by by repeating the initial frames at t
data collection and analyzing the duplicate reflections.

Hydrogen atoms were added at calculated positions and refined using a
riding model.  Anisotropic displacement parameters were used for all non-H atoms
H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for met
atoms) times the equivalent isotropic displacement parameter of the atom
to which they are attached. There was disorder in the aliphatic chain and this
was traced right back to the malonamide. The major component, 69% occupancy,
was allowed to refine isotropically. The minor component was refine isotropicall

;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens SMART diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        nil
_diffrn_reflns_number            24773
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_sigmaI/netI    0.1230
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         22.50
_reflns_number_total             5957
_reflns_number_gt                3502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Siemens, 1994)'
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'

_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)+(0.0443P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0136(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(17)
_refine_ls_number_reflns         5957
_refine_ls_number_parameters     670
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_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 -2.0096(15) 1.052(2) 0.1563(3) 0.129(6) Uani 0.694(4) 1 d P A 1
H1A H -2.0921 0.9877 0.1510 0.193 Uiso 0.694(4) 1 calc PR A 1
H1B H -1.9727 1.1094 0.1430 0.193 Uiso 0.694(4) 1 calc PR A 1
H1C H -2.0502 1.1152 0.1687 0.193 Uiso 0.694(4) 1 calc PR A 1
C2 C -1.8763(12) 0.9649(19) 0.1662(2) 0.128(5) Uani 0.694(4) 1 d P A 1
H2A H -1.9197 0.9035 0.1788 0.154 Uiso 0.694(4) 1 calc PR A 1
H2B H -1.8410 0.9003 0.1535 0.154 Uiso 0.694(4) 1 calc PR A 1
C3 C -1.7438(18) 1.030(2) 0.1755(4) 0.098(6) Uani 0.694(4) 1 d P A 1
H3A H -1.7803 1.0963 0.1880 0.118 Uiso 0.694(4) 1 calc PR A 1
H3B H -1.7007 1.0908 0.1628 0.118 Uiso 0.694(4) 1 calc PR A 1
C4 C -1.6134(9) 0.9517(14) 0.18552(15) 0.086(3) Uani 0.694(4) 1 d P A 1
H4A H -1.6549 0.8914 0.1984 0.103 Uiso 0.694(4) 1 calc PR A 1
H4B H -1.5751 0.8860 0.1731 0.103 Uiso 0.694(4) 1 calc PR A 1
C5 C -1.4800(15) 1.0269(18) 0.1948(3) 0.086(5) Uani 0.694(4) 1 d P A 1
H5A H -1.5181 1.0951 0.2069 0.103 Uiso 0.694(4) 1 calc PR A 1
H5B H -1.4353 1.0842 0.1818 0.103 Uiso 0.694(4) 1 calc PR A 1
C6 C -1.3522(8) 0.9443(11) 0.20559(15) 0.074(3) Uani 0.694(4) 1 d P A 1
H6A H -1.3055 0.8839 0.1931 0.089 Uiso 0.694(4) 1 calc PR A 1
H6B H -1.3978 0.8792 0.2175 0.089 Uiso 0.694(4) 1 calc PR A 1
C7 C -1.2248(14) 1.026(2) 0.2172(3) 0.066(4) Uani 0.694(4) 1 d P A 1
H7A H -1.2710 1.0818 0.2302 0.079 Uiso 0.694(4) 1 calc PR A 1
H7B H -1.1837 1.0947 0.2055 0.079 Uiso 0.694(4) 1 calc PR A 1
C8 C -1.0900(9) 0.9447(10) 0.22709(15) 0.067(3) Uani 0.694(4) 1 d P A 1
H8A H -1.0436 0.8878 0.2141 0.080 Uiso 0.694(4) 1 calc PR A 1
H8B H -1.1302 0.8765 0.2390 0.080 Uiso 0.694(4) 1 calc PR A 1
C9 C -0.9631(13) 1.0301(19) 0.2384(3) 0.061(4) Uani 0.694(4) 1 d P A 1
H9A H -0.9245 1.1002 0.2267 0.073 Uiso 0.694(4) 1 calc PR A 1
H9B H -1.0085 1.0848 0.2517 0.073 Uiso 0.694(4) 1 calc PR A 1
C10 C -0.8275(9) 0.9474(10) 0.24760(14) 0.067(2) Uani 0.694(4) 1 d P A 1
H10A H -0.7826 0.8922 0.2343 0.080 Uiso 0.694(4) 1 calc PR A 1
H10B H -0.8660 0.8779 0.2594 0.080 Uiso 0.694(4) 1 calc PR A 1
C11 C -0.6990(11) 1.0342(15) 0.2589(2) 0.058(3) Uani 0.694(4) 1 d P A 1
H11A H -0.6577 1.1015 0.2469 0.069 Uiso 0.694(4) 1 calc PR A 1
H11B H -0.7440 1.0917 0.2718 0.069 Uiso 0.694(4) 1 calc PR A 1
C12 C -0.5670(8) 0.9485(10) 0.26854(13) 0.061(2) Uani 0.694(4) 1 d P A 1
H12A H -0.5198 0.8936 0.2554 0.073 Uiso 0.694(4) 1 calc PR A 1
H12B H -0.6090 0.8789 0.2800 0.073 Uiso 0.694(4) 1 calc PR A 1
C13 C -0.4407(10) 1.0344(17) 0.2806(2) 0.058(3) Uani 0.694(4) 1 d P A 1
H13A H -0.4032 1.1069 0.2692 0.070 Uiso 0.694(4) 1 calc PR A 1
H13B H -0.4884 1.0865 0.2939 0.070 Uiso 0.694(4) 1 calc PR A 1
C14 C -0.3034(9) 0.9556(12) 0.28973(13) 0.065(3) Uani 0.694(4) 1 d P A 1
H14A H -0.2541 0.9044 0.2764 0.079 Uiso 0.694(4) 1 calc PR A 1
H14B H -0.3400 0.8828 0.3011 0.079 Uiso 0.694(4) 1 calc PR A 1
C15 C -0.1828(9) 1.0453(15) 0.30158(17) 0.062(3) Uani 0.694(4) 1 d P A 1
H15A H -0.2323 1.0950 0.3151 0.075 Uiso 0.694(4) 1 calc PR A 1
H15B H -0.1486 1.1195 0.2903 0.075 Uiso 0.694(4) 1 calc PR A 1
C16 C -0.0415(9) 0.9694(13) 0.31058(14) 0.062(3) Uani 0.694(4) 1 d P A 1
H16A H -0.0749 0.8961 0.3221 0.074 Uiso 0.694(4) 1 calc PR A 1
H16B H 0.0081 0.9191 0.2972 0.074 Uiso 0.694(4) 1 calc PR A 1
C17 C 0.0774(9) 1.0625(12) 0.32212(14) 0.065(3) Uani 0.694(4) 1 d P A 1
H17A H 0.0273 1.1133 0.3354 0.078 Uiso 0.694(4) 1 calc PR A 1
H17B H 0.1108 1.1356 0.3105 0.078 Uiso 0.694(4) 1 calc PR A 1
C18 C 0.2210(15) 0.9878(19) 0.3314(3) 0.057(5) Uani 0.694(4) 1 d P A 1
H18A H 0.1929 0.9191 0.3440 0.068 Uiso 0.694(4) 1 calc PR A 1
H18B H 0.2743 0.9355 0.3186 0.068 Uiso 0.694(4) 1 calc PR A 1
O19 O 0.3175(7) 1.0963(5) 0.34052(9) 0.0629(17) Uani 0.694(4) 1 d P A 1
C20 C 0.4596(12) 1.0550(11) 0.35053(17) 0.047(3) Uani 0.694(4) 1 d P A 1
C21 C 0.5107(13) 0.9142(10) 0.35257(16) 0.050(3) Uani 0.694(4) 1 d P A 1
H21A H 0.4504 0.8363 0.3470 0.060 Uiso 0.694(4) 1 calc PR A 1
C22 C 0.6547(12) 0.8939(11) 0.36320(15) 0.055(3) Uani 0.694(4) 1 d P A 1
H22A H 0.6921 0.7989 0.3647 0.066 Uiso 0.694(4) 1 calc PR A 1
C23 C 0.7448(12) 1.001(2) 0.3715(2) 0.046(9) Uani 0.694(4) 1 d P A 1
C24 C 0.6906(13) 1.1403(13) 0.3692(2) 0.056(3) Uani 0.694(4) 1 d P A 1
H24A H 0.7514 1.2176 0.3749 0.068 Uiso 0.694(4) 1 calc PR A 1
C25 C 0.5490(10) 1.1669(9) 0.35868(14) 0.058(2) Uani 0.694(4) 1 d P A 1
H25A H 0.5130 1.2623 0.3571 0.069 Uiso 0.694(4) 1 calc PR A 1
C26 C 0.896(2) 0.974(2) 0.3839(5) 0.047(4) Uani 0.694(4) 1 d P A 1
H26A H 0.9664 1.0552 0.3806 0.056 Uiso 0.694(4) 1 calc PR A 1
H26B H 0.9436 0.8874 0.3771 0.056 Uiso 0.694(4) 1 calc PR A 1
C27 C 0.886(2) 0.954(2) 0.4113(4) 0.047(4) Uani 0.694(4) 1 d P A 1
C28 C 0.825(2) 1.116(2) 0.4216(4) 0.034(4) Uani 0.694(4) 1 d P A 1
O28 O 0.9025(12) 1.2217(13) 0.4181(2) 0.040(2) Uani 0.694(4) 1 d P A 1
N29 N 0.6895(13) 1.1080(11) 0.43342(16) 0.044(3) Uani 0.694(4) 1 d P A 1
H29A H 0.6533 1.0284 0.4396 0.053 Uiso 0.694(4) 1 calc PR A 1
C30 C 0.6105(13) 1.2421(12) 0.43485(19) 0.053(3) Uani 0.694(4) 1 d P A 1
H30A H 0.5164 1.2312 0.4444 0.079 Uiso 0.694(4) 1 calc PR A 1
H30B H 0.5822 1.2740 0.4189 0.079 Uiso 0.694(4) 1 calc PR A 1
H30C H 0.6788 1.3130 0.4422 0.079 Uiso 0.694(4) 1 calc PR A 1
C31 C 0.7864(18) 0.8187(15) 0.4172(3) 0.041(5) Uani 0.694(4) 1 d P A 1
O31 O 0.6565(12) 0.8328(11) 0.42589(16) 0.042(2) Uani 0.694(4) 1 d P A 1
N32 N 0.8586(15) 0.7013(13) 0.4135(3) 0.031(3) Uani 0.694(4) 1 d P A 1
H32A H 0.9580 0.7025 0.4099 0.037 Uiso 0.694(4) 1 calc PR A 1
C33 C 0.773(3) 0.561(3) 0.4152(4) 0.065(7) Uani 0.694(4) 1 d P A 1
H33A H 0.8447 0.4865 0.4206 0.097 Uiso 0.694(4) 1 calc PR A 1
H33B H 0.7320 0.5352 0.3997 0.097 Uiso 0.694(4) 1 calc PR A 1
H33C H 0.6874 0.5702 0.4265 0.097 Uiso 0.694(4) 1 calc PR A 1
C34 C 1.0536(16) 0.9424(18) 0.4195(3) 0.043(4) Uani 0.694(4) 1 d P A 1
H34 H 1.1079 1.0343 0.4159 0.052 Uiso 0.694(4) 1 calc PR A 1
C35 C 1.063(2) 0.9148(18) 0.4459(4) 0.065(7) Uani 0.694(4) 1 d P A 1
H35 H 0.9966 0.8314 0.4504 0.078 Uiso 0.694(4) 1 calc PR A 1
O52 O 1.1244(11) 0.8368(16) 0.4076(2) 0.051(4) Uani 0.694(4) 1 d P A 1
C1A C -1.994(3) 0.988(3) 0.1511(6) 0.073(10) Uiso 0.306(4) 1 d PD A 2
H1AA H -2.0858 1.0458 0.1474 0.110 Uiso 0.306(4) 1 calc PR A 2
H1AB H -2.0267 0.9017 0.1596 0.110 Uiso 0.306(4) 1 calc PR A 2
H1AC H -1.9417 0.9606 0.1364 0.110 Uiso 0.306(4) 1 calc PR A 2
C2A C -1.882(2) 1.076(2) 0.1668(4) 0.065(8) Uiso 0.306(4) 1 d PD A 2
H2AA H -1.8548 1.1662 0.1588 0.078 Uiso 0.306(4) 1 calc PR A 2
H2AB H -1.9328 1.0992 0.1820 0.078 Uiso 0.306(4) 1 calc PR A 2
C3A C -1.732(4) 0.988(4) 0.1715(10) 0.068(13) Uiso 0.306(4) 1 d PD A 2
H3AA H -1.7595 0.9001 0.1803 0.082 Uiso 0.306(4) 1 calc PR A 2
H3AB H -1.6856 0.9596 0.1563 0.082 Uiso 0.306(4) 1 calc PR A 2
C4A C -1.6140(19) 1.074(2) 0.1858(3) 0.059(6) Uiso 0.306(4) 1 d PD A 2
H4AA H -1.6676 1.1216 0.1992 0.071 Uiso 0.306(4) 1 calc PR A 2
H4AB H -1.5695 1.1500 0.1756 0.071 Uiso 0.306(4) 1 calc PR A 2
C5A C -1.481(3) 0.981(3) 0.1955(6) 0.043(10) Uiso 0.306(4) 1 d PD A 2
H5AA H -1.4354 0.9244 0.1825 0.052 Uiso 0.306(4) 1 calc PR A 2
H5AB H -1.5235 0.9130 0.2073 0.052 Uiso 0.306(4) 1 calc PR A 2
C6A C -1.3545(16) 1.0741(19) 0.2071(3) 0.046(5) Uiso 0.306(4) 1 d PD A 2
H6AA H -1.4001 1.1289 0.2204 0.056 Uiso 0.306(4) 1 calc PR A 2
H6AB H -1.3140 1.1431 0.1954 0.056 Uiso 0.306(4) 1 calc PR A 2
C7A C -1.220(4) 0.980(3) 0.2164(9) 0.071(17) Uiso 0.306(4) 1 d PD A 2
H7AA H -1.2610 0.9099 0.2279 0.086 Uiso 0.306(4) 1 calc PR A 2
H7AB H -1.1732 0.9268 0.2031 0.086 Uiso 0.306(4) 1 calc PR A 2
C8A C -1.0931(15) 1.0706(17) 0.2285(3) 0.036(4) Uiso 0.306(4) 1 d PD A 2
H8AA H -1.0477 1.1369 0.2168 0.043 Uiso 0.306(4) 1 calc PR A 2
H8AB H -1.1410 1.1286 0.2412 0.043 Uiso 0.306(4) 1 calc PR A 2
C9A C -0.964(3) 0.979(2) 0.2391(7) 0.057(14) Uiso 0.306(4) 1 d PD A 2
H9AA H -1.0083 0.9156 0.2514 0.068 Uiso 0.306(4) 1 calc PR A 2
H9AB H -0.9186 0.9180 0.2266 0.068 Uiso 0.306(4) 1 calc PR A 2
C10A C -0.8353(14) 1.0695(18) 0.2501(3) 0.038(4) Uiso 0.306(4) 1 d PD A 2
H10C H -0.8809 1.1323 0.2624 0.046 Uiso 0.306(4) 1 calc PR A 2
H10D H -0.7891 1.1313 0.2378 0.046 Uiso 0.306(4) 1 calc PR A 2
C11A C -0.707(2) 0.978(2) 0.2613(5) 0.037(9) Uiso 0.306(4) 1 d PD A 2
H11C H -0.6666 0.9107 0.2493 0.044 Uiso 0.306(4) 1 calc PR A 2
H11D H -0.7521 0.9211 0.2744 0.044 Uiso 0.306(4) 1 calc PR A 2
C12A C -0.5703(14) 1.0679(18) 0.2712(3) 0.038(5) Uiso 0.306(4) 1 d PD A 2
H12C H -0.5268 1.1272 0.2583 0.046 Uiso 0.306(4) 1 calc PR A 2
H12D H -0.6097 1.1330 0.2836 0.046 Uiso 0.306(4) 1 calc PR A 2
C13A C -0.442(2) 0.975(2) 0.2815(6) 0.053(12) Uiso 0.306(4) 1 d PD A 2
H13C H -0.4018 0.9110 0.2690 0.064 Uiso 0.306(4) 1 calc PR A 2
H13D H -0.4855 0.9157 0.2943 0.064 Uiso 0.306(4) 1 calc PR A 2
C14A C -0.3071(15) 1.0671(19) 0.2914(3) 0.044(5) Uiso 0.306(4) 1 d PD A 2
H14C H -0.2632 1.1268 0.2786 0.053 Uiso 0.306(4) 1 calc PR A 2
H14D H -0.3469 1.1315 0.3039 0.053 Uiso 0.306(4) 1 calc PR A 2
C15A C -0.1813(18) 0.9722(18) 0.3015(4) 0.033(8) Uiso 0.306(4) 1 d PD A 2
H15C H -0.1396 0.9100 0.2889 0.040 Uiso 0.306(4) 1 calc PR A 2
H15D H -0.2265 0.9101 0.3139 0.040 Uiso 0.306(4) 1 calc PR A 2
C16A C -0.0479(18) 1.061(2) 0.3123(4) 0.054(8) Uiso 0.306(4) 1 d PD A 2
H16C H -0.0862 1.1164 0.3260 0.065 Uiso 0.306(4) 1 calc PR A 2
H16D H -0.0069 1.1287 0.3004 0.065 Uiso 0.306(4) 1 calc PR A 2
C17A C 0.0815(17) 0.957(2) 0.3202(3) 0.045(6) Uiso 0.306(4) 1 d PD A 2
H17C H 0.0357 0.8838 0.3308 0.053 Uiso 0.306(4) 1 calc PR A 2
H17D H 0.1226 0.9066 0.3061 0.053 Uiso 0.306(4) 1 calc PR A 2
C18A C 0.215(3) 1.029(3) 0.3329(7) 0.040(12) Uiso 0.306(4) 1 d PD A 2
H18C H 0.2592 1.1066 0.3231 0.049 Uiso 0.306(4) 1 calc PR A 2
H18D H 0.1801 1.0693 0.3482 0.049 Uiso 0.306(4) 1 calc PR A 2
O19A O 0.3304(12) 0.9133(11) 0.33665(17) 0.044(3) Uiso 0.306(4) 1 d P A 2
C20A C 0.4701(14) 0.949(2) 0.3471(3) 0.026(7) Uiso 0.306(4) 1 d PG A 2
C21A C 0.5676(16) 0.8318(16) 0.3502(2) 0.059(7) Uiso 0.306(4) 1 d PG A 2
H21B H 0.5386 0.7408 0.3443 0.071 Uiso 0.306(4) 1 calc PR A 2
C22A C 0.7075(16) 0.8482(16) 0.3622(3) 0.038(7) Uiso 0.306(4) 1 d PG A 2
H22B H 0.7741 0.7684 0.3643 0.046 Uiso 0.306(4) 1 calc PR A 2
C23A C 0.7499(17) 0.981(2) 0.3709(4) 0.04(2) Uiso 0.306(4) 1 d PG A 2
C24A C 0.652(2) 1.0980(16) 0.3677(4) 0.036(9) Uiso 0.306(4) 1 d PG A 2
H24B H 0.6814 1.1889 0.3737 0.043 Uiso 0.306(4) 1 calc PR A 2
C25A C 0.513(2) 1.0816(17) 0.3558(4) 0.048(11) Uiso 0.306(4) 1 d PG A 2
H25B H 0.4459 1.1614 0.3536 0.058 Uiso 0.306(4) 1 calc PR A 2
C26A C 0.914(5) 0.994(6) 0.3834(9) 0.033(9) Uiso 0.306(4) 1 d P A 2
H26C H 0.9844 0.9195 0.3773 0.039 Uiso 0.306(4) 1 calc PR A 2
H26D H 0.9603 1.0886 0.3797 0.039 Uiso 0.306(4) 1 calc PR A 2
C27A C 0.897(4) 0.978(4) 0.4107(5) 0.008(7) Uiso 0.306(4) 1 d P A 2
C28A C 0.825(6) 1.093(5) 0.4162(7) 0.024(12) Uiso 0.306(4) 1 d P A 2
O28A O 0.895(3) 1.210(4) 0.4108(4) 0.038(8) Uiso 0.306(4) 1 d P A 2
N29A N 0.689(3) 1.108(2) 0.4252(3) 0.013(6) Uiso 0.306(4) 1 d P A 2
H29B H 0.6217 1.0417 0.4209 0.016 Uiso 0.306(4) 1 calc PR A 2
C30A C 0.614(4) 1.239(3) 0.4449(4) 0.042(8) Uiso 0.306(4) 1 d P A 2
H30D H 0.5462 1.1934 0.4566 0.063 Uiso 0.306(4) 1 calc PR A 2
H30E H 0.5541 1.3100 0.4359 0.063 Uiso 0.306(4) 1 calc PR A 2
H30F H 0.6999 1.2869 0.4530 0.063 Uiso 0.306(4) 1 calc PR A 2
C31A C 0.803(4) 0.851(3) 0.4146(5) 0.009(8) Uiso 0.306(4) 1 d P A 2
O31A O 0.656(3) 0.836(2) 0.4182(3) 0.016(5) Uiso 0.306(4) 1 d P A 2
N32A N 0.856(5) 0.709(4) 0.4066(6) 0.049(12) Uiso 0.306(4) 1 d P A 2
H32B H 0.9399 0.7056 0.3979 0.059 Uiso 0.306(4) 1 calc PR A 2
C33A C 0.783(5) 0.578(6) 0.4118(7) 0.018(8) Uiso 0.306(4) 1 d P A 2
H33D H 0.8606 0.5016 0.4116 0.027 Uiso 0.306(4) 1 calc PR A 2
H33E H 0.7034 0.5585 0.3999 0.027 Uiso 0.306(4) 1 calc PR A 2
H33F H 0.7348 0.5834 0.4274 0.027 Uiso 0.306(4) 1 calc PR A 2
C34A C 1.069(3) 0.973(3) 0.4236(6) 0.009(7) Uiso 0.306(4) 1 d P A 2
H34A H 1.1269 1.0635 0.4206 0.011 Uiso 0.306(4) 1 calc PR A 2
C35A C 1.073(4) 0.936(4) 0.4494(5) 0.004(6) Uiso 0.306(4) 1 d P A 2
H35A H 1.0031 0.8525 0.4523 0.005 Uiso 0.306(4) 1 calc PR A 2
O52A O 1.156(3) 0.837(3) 0.4099(5) 0.026(6) Uiso 0.306(4) 1 d P A 2
O36 O 1.0137(4) 1.0494(4) 0.45955(6) 0.0526(10) Uani 1 1 d . . .
C37 C 0.9053(7) 1.0366(8) 0.47718(11) 0.0723(18) Uani 1 1 d . A .
O37 O 0.8471(5) 0.9255(5) 0.48197(9) 0.1089(17) Uani 1 1 d . . .
C38 C 0.8702(8) 1.1777(7) 0.48800(11) 0.100(2) Uani 1 1 d . . .
H38A H 0.7623 1.1789 0.4935 0.150 Uiso 1 1 calc R A .
H38B H 0.8853 1.2531 0.4762 0.150 Uiso 1 1 calc R . .
H38C H 0.9398 1.1940 0.5014 0.150 Uiso 1 1 calc R . .
C39 C 1.2315(6) 0.8952(6) 0.45526(11) 0.0569(16) Uani 1 1 d . . .
H39A H 1.2933 0.9840 0.4525 0.068 Uiso 1 1 calc R A 1
O40 O 1.2276(4) 0.8626(4) 0.47990(8) 0.0732(12) Uani 1 1 d . A .
O41 O 1.4146(6) 1.0205(6) 0.48706(10) 0.140(2) Uani 1 1 d . A .
C41 C 1.3209(8) 0.9367(8) 0.49447(14) 0.086(2) Uani 1 1 d . . .
C42 C 1.2821(8) 0.9028(7) 0.52004(12) 0.108(3) Uani 1 1 d . A .
H42A H 1.3640 0.9403 0.5303 0.163 Uiso 1 1 calc R . .
H42B H 1.2745 0.7992 0.5221 0.163 Uiso 1 1 calc R . .
H42C H 1.1828 0.9472 0.5242 0.163 Uiso 1 1 calc R . .
C43 C 1.3001(6) 0.7716(5) 0.44128(11) 0.0525(15) Uani 1 1 d . A .
H43A H 1.4102 0.7546 0.4461 0.063 Uiso 1 1 calc R . .
O44 O 1.2065(3) 0.6485(3) 0.44655(6) 0.0512(9) Uani 1 1 d . . .
C45 C 1.2826(6) 0.5245(6) 0.45071(9) 0.0504(14) Uani 1 1 d . A .
O45 O 1.4204(4) 0.5126(4) 0.45027(6) 0.0695(12) Uani 1 1 d . . .
C46 C 1.1678(6) 0.4099(5) 0.45660(9) 0.0649(17) Uani 1 1 d . . .
H46A H 1.2211 0.3175 0.4573 0.097 Uiso 1 1 calc R A .
H46B H 1.0874 0.4065 0.4444 0.097 Uiso 1 1 calc R . .
H46C H 1.1200 0.4306 0.4719 0.097 Uiso 1 1 calc R . .
C47 C 1.2918(6) 0.8096(6) 0.41563(12) 0.0575(17) Uani 1 1 d . . .
H47A H 1.3515 0.9000 0.4133 0.069 Uiso 1 1 calc R A 1
C48 C 1.3522(5) 0.7011(6) 0.39799(11) 0.0601(16) Uani 1 1 d . A .
H48A H 1.3444 0.7402 0.3818 0.072 Uiso 1 1 calc R . .
H48B H 1.4628 0.6802 0.4013 0.072 Uiso 1 1 calc R . .
O49 O 1.2614(3) 0.5709(4) 0.39979(6) 0.0529(10) Uani 1 1 d . . .
O50 O 1.4257(5) 0.4750(5) 0.37396(8) 0.1055(16) Uani 1 1 d . . .
C50 C 1.3171(6) 0.4654(8) 0.38688(11) 0.0675(17) Uani 1 1 d . A .
C51 C 1.2258(7) 0.3290(6) 0.39042(11) 0.088(2) Uani 1 1 d . . .
H51A H 1.2243 0.2745 0.3756 0.131 Uiso 1 1 calc R A .
H51B H 1.1193 0.3524 0.3951 0.131 Uiso 1 1 calc R . .
H51C H 1.2748 0.2717 0.4028 0.131 Uiso 1 1 calc R . .


_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 1.516(16) . ?
C2 C3 1.398(17) . ?
C3 C4 1.459(14) . ?
C4 C5 1.447(14) . ?
C5 C6 1.477(13) . ?
C6 C7 1.489(14) . ?
C7 C8 1.495(13) . ?
C8 C9 1.499(12) . ?
C9 C10 1.495(12) . ?
C10 C11 1.514(12) . ?
C11 C12 1.496(12) . ?
C12 C13 1.514(11) . ?
C13 C14 1.488(13) . ?
C14 C15 1.495(11) . ?
C15 C16 1.499(12) . ?
C16 C17 1.495(11) . ?
C17 C18 1.516(15) . ?
C18 O19 1.410(12) . ?
O19 C20 1.403(11) . ?
C20 C25 1.380(14) . ?
C20 C21 1.394(12) . ?
C21 C22 1.392(14) . ?
C22 C23 1.353(13) . ?
C23 C24 1.390(17) . ?
C23 C26 1.50(2) . ?
C24 C25 1.381(11) . ?
C26 C27 1.57(2) . ?
C27 C34 1.52(2) . ?
C27 C31 1.57(3) . ?
C27 C28 1.71(3) . ?
C28 O28 1.21(2) . ?
C28 N29 1.34(2) . ?
N29 C30 1.431(14) . ?
C31 O31 1.229(19) . ?
C31 N32 1.28(2) . ?
N32 C33 1.51(3) . ?
C34 O52 1.343(18) . ?
C34 C35 1.52(3) . ?
C35 O36 1.540(18) . ?
C35 C39 1.559(19) . ?
O52 C47 1.534(12) . ?
C1A C2A 1.551(19) . ?
C2A C3A 1.549(19) . ?
C3A C4A 1.533(19) . ?
C4A C5A 1.542(18) . ?
C5A C6A 1.547(18) . ?
C6A C7A 1.550(18) . ?
C7A C8A 1.540(18) . ?
C8A C9A 1.529(17) . ?
C9A C10A 1.527(17) . ?
C10A C11A 1.536(16) . ?
C11A C12A 1.549(16) . ?
C12A C13A 1.519(17) . ?
C13A C14A 1.551(17) . ?
C14A C15A 1.515(16) . ?
C15A C16A 1.543(17) . ?
C16A C17A 1.550(16) . ?
C17A C18A 1.515(18) . ?
C18A O19A 1.49(3) . ?
O19A C20A 1.380(15) . ?
C20A C21A 1.3900 . ?
C20A C25A 1.3900 . ?
C21A C22A 1.3900 . ?
C22A C23A 1.3900 . ?
C23A C24A 1.3900 . ?
C23A C26A 1.59(4) . ?
C24A C25A 1.3900 . ?
C26A C27A 1.56(4) . ?
C27A C28A 1.28(5) . ?
C27A C31A 1.45(5) . ?
C27A C34A 1.66(4) . ?
C28A N29A 1.28(6) . ?
C28A O28A 1.29(6) . ?
N29A C30A 1.78(3) . ?
C31A O31A 1.29(5) . ?
C31A N32A 1.48(5) . ?
N32A C33A 1.40(7) . ?
C34A C35A 1.50(5) . ?
C34A O52A 1.66(4) . ?
C35A O36 1.31(4) . ?
C35A C39 1.45(3) . ?
O52A C47 1.24(3) . ?
O36 C37 1.372(6) . ?
C37 O37 1.187(6) . ?
C37 C38 1.487(8) . ?
C39 O40 1.428(6) . ?
C39 C43 1.521(7) . ?
O40 C41 1.345(7) . ?
O41 C41 1.202(7) . ?
C41 C42 1.518(9) . ?
C43 O44 1.438(5) . ?
C43 C47 1.496(7) . ?
O44 C45 1.354(5) . ?
C45 O45 1.193(5) . ?
C45 C46 1.497(6) . ?
C47 C48 1.517(7) . ?
C48 O49 1.452(5) . ?
O49 C50 1.319(6) . ?
O50 C50 1.191(6) . ?
C50 C51 1.513(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 121.4(17) . . ?
C2 C3 C4 123.6(17) . . ?
C5 C4 C3 120.5(14) . . ?
C4 C5 C6 119.2(14) . . ?
C5 C6 C7 117.7(12) . . ?
C6 C7 C8 118.6(15) . . ?
C7 C8 C9 117.2(11) . . ?
C10 C9 C8 116.2(13) . . ?
C9 C10 C11 116.1(10) . . ?
C12 C11 C10 115.0(11) . . ?
C11 C12 C13 115.2(10) . . ?
C14 C13 C12 117.7(12) . . ?
C13 C14 C15 115.5(11) . . ?
C14 C15 C16 116.8(11) . . ?
C17 C16 C15 115.4(11) . . ?
C16 C17 C18 116.2(10) . . ?
O19 C18 C17 106.0(12) . . ?
C20 O19 C18 117.6(8) . . ?
C25 C20 C21 120.9(10) . . ?
C25 C20 O19 114.3(8) . . ?
C21 C20 O19 124.7(12) . . ?
C22 C21 C20 116.5(10) . . ?
C23 C22 C21 124.1(10) . . ?
C22 C23 C24 118.0(10) . . ?
C22 C23 C26 122.4(17) . . ?
C24 C23 C26 119.5(15) . . ?
C25 C24 C23 120.4(11) . . ?
C20 C25 C24 120.0(9) . . ?
C23 C26 C27 115.8(12) . . ?
C34 C27 C26 104.9(15) . . ?
C34 C27 C31 113.3(16) . . ?
C26 C27 C31 109.8(13) . . ?
C34 C27 C28 104.8(14) . . ?
C26 C27 C28 104.5(14) . . ?
C31 C27 C28 118.5(16) . . ?
O28 C28 N29 127.4(16) . . ?
O28 C28 C27 119.9(16) . . ?
N29 C28 C27 112.7(16) . . ?
C28 N29 C30 113.0(12) . . ?
O31 C31 N32 126.9(12) . . ?
O31 C31 C27 119.7(15) . . ?
N32 C31 C27 113.2(15) . . ?
C31 N32 C33 120.0(14) . . ?
O52 C34 C35 110.1(15) . . ?
O52 C34 C27 109.5(12) . . ?
C35 C34 C27 111.1(15) . . ?
C34 C35 O36 110.0(15) . . ?
C34 C35 C39 113.9(14) . . ?
O36 C35 C39 100.4(10) . . ?
C34 O52 C47 113.6(12) . . ?
C3A C2A C1A 109.8(16) . . ?
C4A C3A C2A 111.4(18) . . ?
C3A C4A C5A 112.4(16) . . ?
C4A C5A C6A 110.6(16) . . ?
C5A C6A C7A 110.7(15) . . ?
C8A C7A C6A 111.7(17) . . ?
C9A C8A C7A 112.5(15) . . ?
C10A C9A C8A 112.2(15) . . ?
C9A C10A C11A 112.4(13) . . ?
C10A C11A C12A 113.1(14) . . ?
C13A C12A C11A 112.4(13) . . ?
C12A C13A C14A 111.7(14) . . ?
C15A C14A C13A 110.5(14) . . ?
C14A C15A C16A 111.5(13) . . ?
C15A C16A C17A 108.1(14) . . ?
C18A C17A C16A 113.7(15) . . ?
O19A C18A C17A 104.5(19) . . ?
C20A O19A C18A 118.1(14) . . ?
O19A C20A C21A 113.2(13) . . ?
O19A C20A C25A 126.5(13) . . ?
C21A C20A C25A 120.0 . . ?
C20A C21A C22A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C24A C23A C22A 120.0 . . ?
C24A C23A C26A 122(2) . . ?
C22A C23A C26A 118(2) . . ?
C23A C24A C25A 120.0 . . ?
C24A C25A C20A 120.0 . . ?
C27A C26A C23A 110(2) . . ?
C28A C27A C31A 113(4) . . ?
C28A C27A C26A 102(3) . . ?
C31A C27A C26A 107(2) . . ?
C28A C27A C34A 111(3) . . ?
C31A C27A C34A 114(3) . . ?
C26A C27A C34A 111(2) . . ?
C27A C28A N29A 129(4) . . ?
C27A C28A O28A 116(4) . . ?
N29A C28A O28A 116(4) . . ?
C28A N29A C30A 131(3) . . ?
O31A C31A C27A 131(3) . . ?
O31A C31A N32A 105(3) . . ?
C27A C31A N32A 122(3) . . ?
C33A N32A C31A 126(4) . . ?
C35A C34A C27A 117(3) . . ?
C35A C34A O52A 106(3) . . ?
C27A C34A O52A 103(2) . . ?
O36 C35A C39 119(2) . . ?
O36 C35A C34A 103(2) . . ?
C39 C35A C34A 108(2) . . ?
C47 O52A C34A 117(2) . . ?
C35A O36 C37 120.8(13) . . ?
C35A O36 C35 8(2) . . ?
C37 O36 C35 118.8(8) . . ?
O37 C37 O36 122.0(6) . . ?
O37 C37 C38 126.8(6) . . ?
O36 C37 C38 111.1(6) . . ?
O40 C39 C35A 104.8(12) . . ?
O40 C39 C43 110.8(4) . . ?
C35A C39 C43 116.4(14) . . ?
O40 C39 C35 109.7(9) . . ?
C35A C39 C35 10.6(19) . . ?
C43 C39 C35 105.9(8) . . ?
C41 O40 C39 118.4(5) . . ?
O41 C41 O40 121.6(8) . . ?
O41 C41 C42 128.1(7) . . ?
O40 C41 C42 110.2(7) . . ?
O44 C43 C47 111.4(4) . . ?
O44 C43 C39 106.5(4) . . ?
C47 C43 C39 107.8(4) . . ?
C45 O44 C43 116.8(4) . . ?
O45 C45 O44 124.0(5) . . ?
O45 C45 C46 126.5(5) . . ?
O44 C45 C46 109.5(4) . . ?
O52A C47 C43 110.5(13) . . ?
O52A C47 C48 106.9(15) . . ?
C43 C47 C48 117.6(5) . . ?
O52A C47 O52 3(2) . . ?
C43 C47 O52 111.9(6) . . ?
C48 C47 O52 103.8(7) . . ?
O49 C48 C47 109.3(4) . . ?
C50 O49 C48 113.2(4) . . ?
O50 C50 O49 124.7(6) . . ?
O50 C50 C51 123.6(6) . . ?
O49 C50 C51 111.7(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N29 H29A O31 0.88 1.99 2.627(15) 128.3 .
N32 H32A O52 0.88 1.91 2.640(17) 138.9 .
N32 H32A O49 0.88 2.95 3.761(13) 154.6 .
N29A H29B O31A 0.88 1.95 2.59(3) 127.7 .
N32A H32B O52A 0.88 2.34 2.86(5) 118.5 .
N32A H32B O49 0.88 3.05 3.75(4) 138.2 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        22.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034



