# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global

_publ_contact_author_email       PAUL.V.MURPHY@UCD.IE

_publ_contact_author_name        'Dr Paul V Murphy'
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?
_publ_contact_author_address     
;
Department of Chemistry
University College Dublin
Belfield
Dublin 4
REPUBLIC OF IRELAND
;

_publ_section_title              
;
Synthesis and X-ray structure of a bivalent glycocluster
;

loop_
_publ_author_name
'Paul V. Murphy'
'Manuela Tosin'

data_mur01
_database_code_depnum_ccdc_archive 'CCDC 223648'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H38 N8 O16'
_chemical_formula_weight         790.70

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                   11.977(2)
_cell_length_b                   15.047(3)
_cell_length_c                   21.319(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3842.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8199
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_sigmaI/netI    0.1675
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         19.00
_reflns_number_total             3077
_reflns_number_gt                1815
_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^)+(0.1292P)^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   0.00
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0937
_refine_ls_wR_factor_ref         0.2455
_refine_ls_wR_factor_gt          0.2260
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.007
_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
O1 O 0.1917(7) 0.9381(6) 0.7542(5) 0.059(3) Uiso 1 1 d . . .
O2 O 0.3492(6) 1.0145(5) 0.8572(4) 0.037(2) Uiso 1 1 d . . .
O3 O 0.0522(6) 1.0538(5) 0.8424(4) 0.029(2) Uiso 1 1 d . . .
O4 O 0.0063(8) 1.1024(6) 0.7446(5) 0.064(3) Uiso 1 1 d . . .
O5 O 0.1617(6) 1.2342(5) 0.8383(4) 0.036(2) Uiso 1 1 d . . .
O6 O 0.0088(12) 1.2525(9) 0.8932(7) 0.123(5) Uiso 1 1 d . . .
O7 O 0.3311(7) 1.2295(5) 0.9364(4) 0.043(3) Uiso 1 1 d . . .
O8 O 0.4288(10) 1.3253(8) 0.8784(7) 0.100(4) Uiso 1 1 d . . .
O9 O 0.4387(7) 0.6604(6) 1.1502(5) 0.056(3) Uiso 1 1 d . . .
O10 O 0.4179(6) 0.8653(5) 1.0830(4) 0.038(2) Uiso 1 1 d . . .
O11 O 0.1987(7) 0.7602(5) 1.1787(4) 0.043(3) Uiso 1 1 d . . .
O12 O 0.1635(7) 0.6430(6) 1.1172(5) 0.055(3) Uiso 1 1 d . . .
O13 O 0.0910(7) 0.9144(5) 1.1264(4) 0.044(3) Uiso 1 1 d . . .
O14 O 0.0562(13) 0.9427(11) 1.2254(9) 0.154(6) Uiso 1 1 d . . .
O15 O 0.2415(7) 1.0561(6) 1.1070(4) 0.045(3) Uiso 1 1 d . . .
O16 O 0.1642(8) 1.0799(6) 1.0144(5) 0.068(3) Uiso 1 1 d . . .
N1 N 0.2337(8) 0.8360(7) 0.8262(5) 0.048(3) Uiso 1 1 d . . .
N2 N 0.4925(10) 1.0886(8) 0.9130(7) 0.059(4) Uiso 1 1 d . . .
N3 N 0.5451(12) 1.1017(9) 0.8672(8) 0.072(4) Uiso 1 1 d . . .
N4 N 0.5997(14) 1.1194(11) 0.8257(9) 0.111(6) Uiso 1 1 d . . .
N5 N 0.4139(8) 0.6865(6) 1.0467(5) 0.030(3) Uiso 1 1 d . . .
N6 N 0.4415(10) 1.0105(7) 1.0509(6) 0.052(3) Uiso 1 1 d . . .
N7 N 0.5404(13) 1.0066(8) 1.0498(7) 0.072(4) Uiso 1 1 d . . .
N8 N 0.6359(14) 1.0102(11) 1.0479(8) 0.111(6) Uiso 1 1 d . . .
C1 C 0.2777(9) 0.8061(8) 0.8865(6) 0.024(3) Uiso 1 1 d . . .
C2 C 0.2128(11) 0.7507(7) 0.9215(6) 0.033(4) Uiso 1 1 d . . .
H2 H 0.1402 0.7374 0.9091 0.040 Uiso 1 1 calc R . .
C3 C 0.2573(9) 0.7141(7) 0.9761(6) 0.024(3) Uiso 1 1 d . . .
H3 H 0.2132 0.6773 1.0009 0.029 Uiso 1 1 calc R . .
C4 C 0.3637(9) 0.7313(7) 0.9937(6) 0.023(3) Uiso 1 1 d . . .
C5 C 0.4298(10) 0.7875(8) 0.9581(6) 0.033(4) Uiso 1 1 d . . .
H5 H 0.5024 0.8006 0.9704 0.039 Uiso 1 1 calc R . .
C6 C 0.3844(10) 0.8247(8) 0.9025(7) 0.038(4) Uiso 1 1 d . . .
H6 H 0.4277 0.8615 0.8773 0.045 Uiso 1 1 calc R . .
C7 C 0.2163(12) 0.7645(10) 0.7786(7) 0.070(5) Uiso 1 1 d . . .
H7A H 0.2276 0.7075 0.7979 0.105 Uiso 1 1 calc R . .
H7B H 0.2686 0.7720 0.7449 0.105 Uiso 1 1 calc R . .
H7C H 0.1416 0.7680 0.7625 0.105 Uiso 1 1 calc R . .
C8 C 0.2218(10) 0.9182(9) 0.8099(7) 0.039(4) Uiso 1 1 d . . .
C9 C 0.2333(8) 0.9943(7) 0.8548(6) 0.023(3) Uiso 1 1 d . . .
H9 H 0.2079 0.9756 0.8965 0.028 Uiso 1 1 calc R . .
C10 C 0.1687(8) 1.0753(7) 0.8346(6) 0.023(3) Uiso 1 1 d . . .
H10 H 0.1836 1.0870 0.7902 0.028 Uiso 1 1 calc R . .
C11 C 0.1952(10) 1.1559(8) 0.8716(6) 0.034(4) Uiso 1 1 d . . .
H11 H 0.1549 1.1534 0.9116 0.041 Uiso 1 1 calc R . .
C12 C 0.3164(9) 1.1669(7) 0.8843(6) 0.032(4) Uiso 1 1 d . . .
H12 H 0.3536 1.1901 0.8468 0.038 Uiso 1 1 calc R . .
C13 C 0.3716(9) 1.0833(7) 0.9046(6) 0.028(4) Uiso 1 1 d . . .
H13 H 0.3382 1.0644 0.9444 0.034 Uiso 1 1 calc R . .
C14 C -0.0223(11) 1.0693(9) 0.7948(7) 0.044(4) Uiso 1 1 d . . .
C15 C -0.1365(10) 1.0479(9) 0.8138(7) 0.055(4) Uiso 1 1 d . . .
H15A H -0.1357 1.0226 0.8552 0.083 Uiso 1 1 calc R . .
H15B H -0.1680 1.0060 0.7849 0.083 Uiso 1 1 calc R . .
H15C H -0.1807 1.1011 0.8140 0.083 Uiso 1 1 calc R . .
C16 C 0.0715(13) 1.2763(10) 0.8534(9) 0.067(5) Uiso 1 1 d . . .
C17 C 0.0483(11) 1.3579(9) 0.8136(7) 0.060(5) Uiso 1 1 d . . .
H17A H 0.1081 1.3661 0.7841 0.090 Uiso 1 1 calc R . .
H17B H 0.0427 1.4092 0.8401 0.090 Uiso 1 1 calc R . .
H17C H -0.0206 1.3498 0.7912 0.090 Uiso 1 1 calc R . .
C18 C 0.3806(12) 1.3077(10) 0.9263(8) 0.057(5) Uiso 1 1 d . . .
C19 C 0.3900(13) 1.3606(11) 0.9863(8) 0.080(5) Uiso 1 1 d . . .
H19A H 0.3452 1.3332 1.0183 0.121 Uiso 1 1 calc R . .
H19B H 0.3643 1.4201 0.9792 0.121 Uiso 1 1 calc R . .
H19C H 0.4666 1.3619 0.9997 0.121 Uiso 1 1 calc R . .
C20 C 0.4050(11) 0.7131(9) 1.1075(7) 0.044(4) Uiso 1 1 d . . .
C21 C 0.3679(9) 0.8012(8) 1.1269(6) 0.035(4) Uiso 1 1 d . . .
H21 H 0.3959 0.8133 1.1693 0.042 Uiso 1 1 calc R . .
C22 C 0.2421(9) 0.8113(8) 1.1267(6) 0.030(4) Uiso 1 1 d . . .
H22 H 0.2111 0.7895 1.0870 0.036 Uiso 1 1 calc R . .
C23 C 0.2062(9) 0.9064(8) 1.1379(6) 0.032(4) Uiso 1 1 d . . .
H23 H 0.2226 0.9234 1.1813 0.039 Uiso 1 1 calc R . .
C24 C 0.2655(10) 0.9680(8) 1.0934(7) 0.031(4) Uiso 1 1 d . . .
H24 H 0.2415 0.9549 1.0505 0.037 Uiso 1 1 calc R . .
C25 C 0.3888(10) 0.9525(8) 1.0987(7) 0.047(4) Uiso 1 1 d . . .
H25 H 0.4156 0.9675 1.1409 0.056 Uiso 1 1 calc R . .
C26 C 0.1629(11) 0.6776(9) 1.1658(8) 0.046(4) Uiso 1 1 d . . .
C27 C 0.1204(12) 0.6349(11) 1.2260(8) 0.073(5) Uiso 1 1 d . . .
H27A H 0.1284 0.6760 1.2601 0.109 Uiso 1 1 calc R . .
H27B H 0.1628 0.5822 1.2346 0.109 Uiso 1 1 calc R . .
H27C H 0.0430 0.6196 1.2211 0.109 Uiso 1 1 calc R . .
C28 C 0.0159(14) 0.9342(11) 1.1738(10) 0.079(6) Uiso 1 1 d . . .
C29 C -0.1007(10) 0.9409(9) 1.1545(7) 0.054(4) Uiso 1 1 d . . .
H29A H -0.1066 0.9289 1.1104 0.081 Uiso 1 1 calc R . .
H29B H -0.1277 0.9998 1.1630 0.081 Uiso 1 1 calc R . .
H29C H -0.1445 0.8985 1.1774 0.081 Uiso 1 1 calc R . .
C30 C 0.1957(12) 1.1113(10) 1.0628(8) 0.055(4) Uiso 1 1 d . . .
C31 C 0.1925(13) 1.2030(10) 1.0851(8) 0.075(5) Uiso 1 1 d . . .
H31A H 0.2236 1.2059 1.1266 0.113 Uiso 1 1 calc R . .
H31B H 0.1166 1.2234 1.0861 0.113 Uiso 1 1 calc R . .
H31C H 0.2353 1.2400 1.0574 0.113 Uiso 1 1 calc R . .
C32 C 0.4557(12) 0.5970(9) 1.0325(7) 0.059(5) Uiso 1 1 d . . .
H32A H 0.4575 0.5886 0.9879 0.088 Uiso 1 1 calc R . .
H32B H 0.4073 0.5536 1.0512 0.088 Uiso 1 1 calc R . .
H32C H 0.5297 0.5904 1.0493 0.088 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
O1 C8 1.278(14) . ?
O2 C9 1.422(12) . ?
O2 C13 1.472(13) . ?
O3 C14 1.372(15) . ?
O3 C10 1.442(12) . ?
O4 C14 1.228(15) . ?
O5 C16 1.292(16) . ?
O5 C11 1.432(13) . ?
O6 C16 1.188(18) . ?
O7 C18 1.335(16) . ?
O7 C12 1.467(13) . ?
O8 C18 1.202(17) . ?
O9 C20 1.273(15) . ?
O10 C25 1.398(14) . ?
O10 C21 1.472(14) . ?
O11 C26 1.343(14) . ?
O11 C22 1.446(13) . ?
O12 C26 1.161(15) . ?
O13 C28 1.385(18) . ?
O13 C23 1.407(13) . ?
O14 C28 1.21(2) . ?
O15 C30 1.371(16) . ?
O15 C24 1.386(13) . ?
O16 C30 1.195(15) . ?
N1 C8 1.292(15) . ?
N1 C1 1.460(15) . ?
N1 C7 1.492(16) . ?
N2 N3 1.178(16) . ?
N2 C13 1.461(15) . ?
N3 N4 1.132(18) . ?
N5 C20 1.359(16) . ?
N5 C4 1.448(15) . ?
N5 C32 1.468(15) . ?
N6 N7 1.186(14) . ?
N6 C25 1.484(16) . ?
N7 N8 1.146(17) . ?
C1 C6 1.352(15) . ?
C1 C2 1.363(15) . ?
C2 C3 1.394(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(15) . ?
C5 C6 1.419(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.498(17) . ?
C9 C10 1.507(15) . ?
C9 H9 0.9800 . ?
C10 C11 1.481(15) . ?
C10 H10 0.9800 . ?
C11 C12 1.486(16) . ?
C11 H11 0.9800 . ?
C12 C13 1.486(15) . ?
C12 H12 0.9800 . ?
C13 H13 0.9800 . ?
C14 C15 1.463(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.519(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.51(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.459(17) . ?
C21 C22 1.514(16) . ?
C21 H21 0.9800 . ?
C22 C23 1.513(16) . ?
C22 H22 0.9800 . ?
C23 C24 1.504(16) . ?
C23 H23 0.9800 . ?
C24 C25 1.500(16) . ?
C24 H24 0.9800 . ?
C25 H25 0.9800 . ?
C26 C27 1.522(19) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.460(19) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.460(19) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
C9 O2 C13 110.7(8) . . ?
C14 O3 C10 120.4(10) . . ?
C16 O5 C11 120.9(11) . . ?
C18 O7 C12 119.8(11) . . ?
C25 O10 C21 111.1(9) . . ?
C26 O11 C22 116.8(11) . . ?
C28 O13 C23 121.8(12) . . ?
C30 O15 C24 121.3(11) . . ?
C8 N1 C1 124.7(12) . . ?
C8 N1 C7 119.5(12) . . ?
C1 N1 C7 115.3(10) . . ?
N3 N2 C13 116.0(13) . . ?
N4 N3 N2 174.7(18) . . ?
C20 N5 C4 125.1(10) . . ?
C20 N5 C32 119.5(12) . . ?
C4 N5 C32 114.1(11) . . ?
N7 N6 C25 114.2(13) . . ?
N8 N7 N6 174.4(18) . . ?
C6 C1 C2 121.8(13) . . ?
C6 C1 N1 120.0(12) . . ?
C2 C1 N1 117.7(11) . . ?
C1 C2 C3 118.7(12) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.1(12) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.2(12) . . ?
C3 C4 N5 121.2(11) . . ?
C5 C4 N5 118.3(10) . . ?
C4 C5 C6 118.7(12) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.4(13) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 120.3(13) . . ?
O1 C8 C9 116.1(11) . . ?
N1 C8 C9 123.4(13) . . ?
O2 C9 C8 106.0(9) . . ?
O2 C9 C10 109.8(9) . . ?
C8 C9 C10 112.9(10) . . ?
O2 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
O3 C10 C11 109.2(9) . . ?
O3 C10 C9 106.4(8) . . ?
C11 C10 C9 113.7(9) . . ?
O3 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
O5 C11 C10 110.5(9) . . ?
O5 C11 C12 105.8(10) . . ?
C10 C11 C12 113.4(10) . . ?
O5 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
O7 C12 C11 109.1(9) . . ?
O7 C12 C13 105.7(9) . . ?
C11 C12 C13 113.2(10) . . ?
O7 C12 H12 109.6 . . ?
C11 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
N2 C13 O2 107.7(9) . . ?
N2 C13 C12 115.5(10) . . ?
O2 C13 C12 108.4(9) . . ?
N2 C13 H13 108.4 . . ?
O2 C13 H13 108.4 . . ?
C12 C13 H13 108.4 . . ?
O4 C14 O3 122.2(12) . . ?
O4 C14 C15 126.3(13) . . ?
O3 C14 C15 111.4(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 O5 123.9(16) . . ?
O6 C16 C17 121.8(16) . . ?
O5 C16 C17 114.1(14) . . ?
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 . . ?
O8 C18 O7 123.0(16) . . ?
O8 C18 C19 124.6(15) . . ?
O7 C18 C19 111.1(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O9 C20 N5 118.3(12) . . ?
O9 C20 C21 117.3(13) . . ?
N5 C20 C21 124.2(13) . . ?
C20 C21 O10 106.9(10) . . ?
C20 C21 C22 113.2(11) . . ?
O10 C21 C22 109.7(10) . . ?
C20 C21 H21 109.0 . . ?
O10 C21 H21 109.0 . . ?
C22 C21 H21 109.0 . . ?
O11 C22 C23 106.2(10) . . ?
O11 C22 C21 107.6(10) . . ?
C23 C22 C21 112.2(10) . . ?
O11 C22 H22 110.3 . . ?
C23 C22 H22 110.3 . . ?
C21 C22 H22 110.3 . . ?
O13 C23 C24 107.4(10) . . ?
O13 C23 C22 109.4(10) . . ?
C24 C23 C22 110.4(10) . . ?
O13 C23 H23 109.9 . . ?
C24 C23 H23 109.9 . . ?
C22 C23 H23 109.9 . . ?
O15 C24 C25 109.7(10) . . ?
O15 C24 C23 111.1(10) . . ?
C25 C24 C23 108.7(11) . . ?
O15 C24 H24 109.1 . . ?
C25 C24 H24 109.1 . . ?
C23 C24 H24 109.1 . . ?
O10 C25 N6 106.3(11) . . ?
O10 C25 C24 112.0(11) . . ?
N6 C25 C24 106.0(11) . . ?
O10 C25 H25 110.8 . . ?
N6 C25 H25 110.8 . . ?
C24 C25 H25 110.8 . . ?
O12 C26 O11 126.5(14) . . ?
O12 C26 C27 124.5(14) . . ?
O11 C26 C27 109.0(14) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O14 C28 O13 115.4(17) . . ?
O14 C28 C29 129(2) . . ?
O13 C28 C29 115.5(16) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O16 C30 O15 118.6(14) . . ?
O16 C30 C31 130.3(16) . . ?
O15 C30 C31 111.1(14) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

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
C13 N2 N3 N4 130(19) . . . . ?
C25 N6 N7 N8 -141(20) . . . . ?
C8 N1 C1 C6 -64.1(16) . . . . ?
C7 N1 C1 C6 107.8(13) . . . . ?
C8 N1 C1 C2 123.8(14) . . . . ?
C7 N1 C1 C2 -64.3(14) . . . . ?
C6 C1 C2 C3 1.7(18) . . . . ?
N1 C1 C2 C3 173.6(10) . . . . ?
C1 C2 C3 C4 -1.5(17) . . . . ?
C2 C3 C4 C5 1.4(17) . . . . ?
C2 C3 C4 N5 -173.6(10) . . . . ?
C20 N5 C4 C3 -85.8(15) . . . . ?
C32 N5 C4 C3 80.9(14) . . . . ?
C20 N5 C4 C5 99.1(14) . . . . ?
C32 N5 C4 C5 -94.2(13) . . . . ?
C3 C4 C5 C6 -1.4(17) . . . . ?
N5 C4 C5 C6 173.8(10) . . . . ?
C2 C1 C6 C5 -1.7(19) . . . . ?
N1 C1 C6 C5 -173.4(11) . . . . ?
C4 C5 C6 C1 1.5(18) . . . . ?
C1 N1 C8 O1 173.9(11) . . . . ?
C7 N1 C8 O1 2.3(18) . . . . ?
C1 N1 C8 C9 -10.8(19) . . . . ?
C7 N1 C8 C9 177.6(10) . . . . ?
C13 O2 C9 C8 -174.7(9) . . . . ?
C13 O2 C9 C10 63.0(13) . . . . ?
O1 C8 C9 O2 -99.2(12) . . . . ?
N1 C8 C9 O2 85.4(14) . . . . ?
O1 C8 C9 C10 21.1(15) . . . . ?
N1 C8 C9 C10 -154.4(12) . . . . ?
C14 O3 C10 C11 106.2(12) . . . . ?
C14 O3 C10 C9 -130.7(11) . . . . ?
O2 C9 C10 O3 -171.6(10) . . . . ?
C8 C9 C10 O3 70.4(12) . . . . ?
O2 C9 C10 C11 -51.3(14) . . . . ?
C8 C9 C10 C11 -169.3(10) . . . . ?
C16 O5 C11 C10 102.6(13) . . . . ?
C16 O5 C11 C12 -134.2(12) . . . . ?
O3 C10 C11 O5 -80.5(12) . . . . ?
C9 C10 C11 O5 160.8(10) . . . . ?
O3 C10 C11 C12 160.8(10) . . . . ?
C9 C10 C11 C12 42.1(14) . . . . ?
C18 O7 C12 C11 -114.4(12) . . . . ?
C18 O7 C12 C13 123.5(12) . . . . ?
O5 C11 C12 O7 76.7(12) . . . . ?
C10 C11 C12 O7 -161.9(10) . . . . ?
O5 C11 C12 C13 -165.9(10) . . . . ?
C10 C11 C12 C13 -44.6(15) . . . . ?
N3 N2 C13 O2 55.4(15) . . . . ?
N3 N2 C13 C12 -65.8(17) . . . . ?
C9 O2 C13 N2 169.4(10) . . . . ?
C9 O2 C13 C12 -65.0(12) . . . . ?
O7 C12 C13 N2 -65.3(14) . . . . ?
C11 C12 C13 N2 175.3(11) . . . . ?
O7 C12 C13 O2 173.9(8) . . . . ?
C11 C12 C13 O2 54.5(14) . . . . ?
C10 O3 C14 O4 -0.8(18) . . . . ?
C10 O3 C14 C15 -176.5(9) . . . . ?
C11 O5 C16 O6 -3(2) . . . . ?
C11 O5 C16 C17 180.0(11) . . . . ?
C12 O7 C18 O8 -11(2) . . . . ?
C12 O7 C18 C19 -178.5(10) . . . . ?
C4 N5 C20 O9 169.4(11) . . . . ?
C32 N5 C20 O9 3.3(18) . . . . ?
C4 N5 C20 C21 -15.9(19) . . . . ?
C32 N5 C20 C21 178.1(11) . . . . ?
O9 C20 C21 O10 135.0(11) . . . . ?
N5 C20 C21 O10 -39.8(16) . . . . ?
O9 C20 C21 C22 -104.1(15) . . . . ?
N5 C20 C21 C22 81.1(16) . . . . ?
C25 O10 C21 C20 -178.8(11) . . . . ?
C25 O10 C21 C22 58.2(13) . . . . ?
C26 O11 C22 C23 143.7(10) . . . . ?
C26 O11 C22 C21 -96.1(12) . . . . ?
C20 C21 C22 O11 71.7(15) . . . . ?
O10 C21 C22 O11 -169.0(9) . . . . ?
C20 C21 C22 C23 -171.8(12) . . . . ?
O10 C21 C22 C23 -52.5(15) . . . . ?
C28 O13 C23 C24 -125.9(13) . . . . ?
C28 O13 C23 C22 114.2(14) . . . . ?
O11 C22 C23 O13 -73.0(13) . . . . ?
C21 C22 C23 O13 169.8(11) . . . . ?
O11 C22 C23 C24 169.0(10) . . . . ?
C21 C22 C23 C24 51.8(15) . . . . ?
C30 O15 C24 C25 117.0(13) . . . . ?
C30 O15 C24 C23 -122.7(12) . . . . ?
O13 C23 C24 O15 66.4(13) . . . . ?
C22 C23 C24 O15 -174.4(10) . . . . ?
O13 C23 C24 C25 -172.7(11) . . . . ?
C22 C23 C24 C25 -53.5(15) . . . . ?
C21 O10 C25 N6 -178.8(10) . . . . ?
C21 O10 C25 C24 -63.5(14) . . . . ?
N7 N6 C25 O10 -61.7(16) . . . . ?
N7 N6 C25 C24 179.0(12) . . . . ?
O15 C24 C25 O10 -177.6(11) . . . . ?
C23 C24 C25 O10 60.7(15) . . . . ?
O15 C24 C25 N6 -62.1(15) . . . . ?
C23 C24 C25 N6 176.2(10) . . . . ?
C22 O11 C26 O12 0.2(19) . . . . ?
C22 O11 C26 C27 -179.9(10) . . . . ?
C23 O13 C28 O14 -1(2) . . . . ?
C23 O13 C28 C29 179.6(11) . . . . ?
C24 O15 C30 O16 8.8(19) . . . . ?
C24 O15 C30 C31 -172.1(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        19.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.079