# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Miao Du'
_publ_contact_author_email       DUMIAO@PUBLIC.TPT.TJ.CN

_publ_section_title              
;
Cocrystallization of a versatile building block
4-amino-3,5-bis(4-pyridyl)-1,2,4-triazole with R-isophthalic acids (R =
-H, -NH2, -SO3H, and -COOH): Polymorphism and substituent effect on
structural diversity
;
loop_
_publ_author_name
'Miao Du.'
'Hua Cai.'
'Xiu-Juan Jiang.'
'Xue Tan.'
'Zhi-Hui Zhang.'

data_1
_database_code_depnum_ccdc_archive 'CCDC 693289'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N6 O4'
_chemical_formula_weight         404.39

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.5354(9)
_cell_length_b                   6.5819(3)
_cell_length_c                   14.7391(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9870(10)
_cell_angle_gamma                90.00
_cell_volume                     1797.06(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3366
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.31

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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  'APEX II 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            8833
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.10
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3165
_reflns_number_gt                2584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker Apex II'
_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 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)+(0.0478P)²+0.4497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0060(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3165
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_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 0.35821(6) 0.88762(19) 0.62120(9) 0.0519(4) Uani 1 1 d . . .
O2 O 0.32241(6) 0.64876(19) 0.52272(9) 0.0483(3) Uani 1 1 d . . .
H2 H 0.3585 0.5910 0.5435 0.072 Uiso 1 1 calc R . .
O3 O 0.06795(6) 0.67717(18) 0.41019(10) 0.0528(4) Uani 1 1 d . . .
H3 H 0.0313 0.6372 0.3829 0.079 Uiso 1 1 calc R . .
O4 O 0.01521(6) 0.97903(19) 0.39120(9) 0.0515(3) Uani 1 1 d . . .
N1 N 0.43820(7) 0.4669(2) 0.58612(9) 0.0393(3) Uani 1 1 d . . .
N2 N 0.62087(7) -0.0649(2) 0.68097(11) 0.0464(4) Uani 1 1 d . . .
N3 N 0.68816(7) -0.1334(2) 0.70915(11) 0.0444(4) Uani 1 1 d . . .
N4 N 0.69231(6) 0.19795(18) 0.69896(8) 0.0306(3) Uani 1 1 d . . .
N5 N 0.72159(7) 0.3948(2) 0.69415(11) 0.0423(4) Uani 1 1 d . . .
H5A H 0.7112 0.4477 0.6352 0.063 Uiso 1 1 d R . .
H5B H 0.7008 0.4707 0.7415 0.063 Uiso 1 1 d R . .
N6 N 0.94637(7) -0.0573(2) 0.82122(10) 0.0412(4) Uani 1 1 d . . .
C1 C 0.55131(9) 0.4608(3) 0.66954(12) 0.0397(4) Uani 1 1 d . . .
H1 H 0.5856 0.5301 0.7052 0.048 Uiso 1 1 calc R . .
C2 C 0.48889(9) 0.5574(3) 0.63829(12) 0.0412(4) Uani 1 1 d . . .
H2A H 0.4820 0.6923 0.6545 0.049 Uiso 1 1 calc R . .
C3 C 0.44808(9) 0.2726(3) 0.56504(12) 0.0437(4) Uani 1 1 d . . .
H3A H 0.4131 0.2074 0.5289 0.052 Uiso 1 1 calc R . .
C4 C 0.50771(9) 0.1644(3) 0.59434(12) 0.0424(4) Uani 1 1 d . . .
H4 H 0.5120 0.0279 0.5792 0.051 Uiso 1 1 calc R . .
C5 C 0.56164(8) 0.2591(2) 0.64666(11) 0.0331(4) Uani 1 1 d . . .
C6 C 0.62421(8) 0.1343(2) 0.67546(11) 0.0340(4) Uani 1 1 d . . .
C7 C 0.73045(8) 0.0260(2) 0.71903(10) 0.0324(4) Uani 1 1 d . . .
C8 C 0.80661(8) 0.0091(2) 0.75051(10) 0.0320(4) Uani 1 1 d . . .
C9 C 0.84587(8) 0.1641(3) 0.79272(11) 0.0374(4) Uani 1 1 d . . .
H9 H 0.8260 0.2932 0.7980 0.045 Uiso 1 1 calc R . .
C10 C 0.91489(9) 0.1241(3) 0.82684(12) 0.0410(4) Uani 1 1 d . . .
H10 H 0.9406 0.2291 0.8551 0.049 Uiso 1 1 calc R . .
C11 C 0.90914(8) -0.2045(3) 0.77804(11) 0.0402(4) Uani 1 1 d . . .
H11 H 0.9310 -0.3307 0.7719 0.048 Uiso 1 1 calc R . .
C12 C 0.84019(8) -0.1790(2) 0.74232(11) 0.0362(4) Uani 1 1 d . . .
H12 H 0.8163 -0.2860 0.7131 0.043 Uiso 1 1 calc R . .
C13 C 0.25025(8) 0.9432(2) 0.53373(10) 0.0327(4) Uani 1 1 d . . .
C14 C 0.24727(9) 1.1475(2) 0.55625(11) 0.0385(4) Uani 1 1 d . . .
H14 H 0.2858 1.2077 0.5882 0.046 Uiso 1 1 calc R . .
C15 C 0.18720(9) 1.2622(3) 0.53136(12) 0.0423(4) Uani 1 1 d . . .
H15 H 0.1863 1.4003 0.5447 0.051 Uiso 1 1 calc R . .
C16 C 0.12882(9) 1.1726(3) 0.48697(11) 0.0387(4) Uani 1 1 d . . .
H16 H 0.0883 1.2499 0.4712 0.046 Uiso 1 1 calc R . .
C17 C 0.13033(8) 0.9674(2) 0.46575(10) 0.0329(4) Uani 1 1 d . . .
C18 C 0.19161(8) 0.8535(2) 0.48753(10) 0.0327(4) Uani 1 1 d . . .
H18 H 0.1935 0.7171 0.4712 0.039 Uiso 1 1 calc R . .
C19 C 0.31524(8) 0.8243(2) 0.56328(11) 0.0365(4) Uani 1 1 d . . .
C20 C 0.06527(8) 0.8759(3) 0.41891(11) 0.0369(4) 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
O1 C19 1.2206(18) . ?
O2 C19 1.310(2) . ?
O2 H2 0.8200 . ?
O3 C20 1.316(2) . ?
O3 H3 0.8200 . ?
O4 C20 1.2090(19) . ?
N1 C3 1.330(2) . ?
N1 C2 1.334(2) . ?
N2 C6 1.315(2) . ?
N2 N3 1.3766(18) . ?
N3 C7 1.314(2) . ?
N4 C7 1.3616(19) . ?
N4 C6 1.3632(19) . ?
N4 N5 1.4075(17) . ?
N5 H5A 0.9500 . ?
N5 H5B 0.9499 . ?
N6 C10 1.333(2) . ?
N6 C11 1.338(2) . ?
C1 C5 1.385(2) . ?
C1 C2 1.385(2) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.472(2) . ?
C7 C8 1.475(2) . ?
C8 C9 1.388(2) . ?
C8 C12 1.392(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.387(2) . ?
C13 C18 1.394(2) . ?
C13 C19 1.489(2) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(2) . ?
C17 C20 1.495(2) . ?
C18 H18 0.9300 . ?

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
C19 O2 H2 109.5 . . ?
C20 O3 H3 109.5 . . ?
C3 N1 C2 117.63(14) . . ?
C6 N2 N3 107.50(13) . . ?
C7 N3 N2 107.64(13) . . ?
C7 N4 C6 105.61(12) . . ?
C7 N4 N5 125.30(12) . . ?
C6 N4 N5 128.71(12) . . ?
N4 N5 H5A 108.5 . . ?
N4 N5 H5B 106.3 . . ?
H5A N5 H5B 113.9 . . ?
C10 N6 C11 117.32(14) . . ?
C5 C1 C2 118.69(15) . . ?
C5 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
N1 C2 C1 123.42(16) . . ?
N1 C2 H2A 118.3 . . ?
C1 C2 H2A 118.3 . . ?
N1 C3 C4 122.78(16) . . ?
N1 C3 H3A 118.6 . . ?
C4 C3 H3A 118.6 . . ?
C3 C4 C5 119.90(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C1 C5 C4 117.54(14) . . ?
C1 C5 C6 125.39(14) . . ?
C4 C5 C6 117.04(14) . . ?
N2 C6 N4 109.62(13) . . ?
N2 C6 C5 122.41(14) . . ?
N4 C6 C5 127.97(14) . . ?
N3 C7 N4 109.63(13) . . ?
N3 C7 C8 122.36(14) . . ?
N4 C7 C8 127.98(14) . . ?
C9 C8 C12 117.61(14) . . ?
C9 C8 C7 124.51(14) . . ?
C12 C8 C7 117.76(14) . . ?
C10 C9 C8 119.12(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N6 C10 C9 123.32(16) . . ?
N6 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N6 C11 C12 123.39(16) . . ?
N6 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C8 119.19(15) . . ?
C11 C12 H12 120.4 . . ?
C8 C12 H12 120.4 . . ?
C14 C13 C18 119.41(14) . . ?
C14 C13 C19 118.56(14) . . ?
C18 C13 C19 121.98(14) . . ?
C15 C14 C13 120.26(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.23(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.17(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 119.76(15) . . ?
C16 C17 C20 118.29(14) . . ?
C18 C17 C20 121.95(14) . . ?
C17 C18 C13 120.11(15) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
O1 C19 O2 123.11(14) . . ?
O1 C19 C13 121.80(15) . . ?
O2 C19 C13 115.09(13) . . ?
O4 C20 O3 123.80(15) . . ?
O4 C20 C17 121.81(15) . . ?
O3 C20 C17 114.39(14) . . ?

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
C6 N2 N3 C7 -0.6(2) . . . . ?
C3 N1 C2 C1 1.4(3) . . . . ?
C5 C1 C2 N1 -0.8(3) . . . . ?
C2 N1 C3 C4 -0.3(3) . . . . ?
N1 C3 C4 C5 -1.5(3) . . . . ?
C2 C1 C5 C4 -0.9(2) . . . . ?
C2 C1 C5 C6 -178.99(16) . . . . ?
C3 C4 C5 C1 2.0(3) . . . . ?
C3 C4 C5 C6 -179.76(16) . . . . ?
N3 N2 C6 N4 0.3(2) . . . . ?
N3 N2 C6 C5 179.67(14) . . . . ?
C7 N4 C6 N2 0.10(19) . . . . ?
N5 N4 C6 N2 173.19(15) . . . . ?
C7 N4 C6 C5 -179.22(15) . . . . ?
N5 N4 C6 C5 -6.1(3) . . . . ?
C1 C5 C6 N2 154.88(18) . . . . ?
C4 C5 C6 N2 -23.2(2) . . . . ?
C1 C5 C6 N4 -25.9(3) . . . . ?
C4 C5 C6 N4 156.03(16) . . . . ?
N2 N3 C7 N4 0.68(19) . . . . ?
N2 N3 C7 C8 178.74(14) . . . . ?
C6 N4 C7 N3 -0.49(18) . . . . ?
N5 N4 C7 N3 -173.89(15) . . . . ?
C6 N4 C7 C8 -178.41(15) . . . . ?
N5 N4 C7 C8 8.2(3) . . . . ?
N3 C7 C8 C9 -155.71(16) . . . . ?
N4 C7 C8 C9 22.0(3) . . . . ?
N3 C7 C8 C12 20.2(2) . . . . ?
N4 C7 C8 C12 -162.08(15) . . . . ?
C12 C8 C9 C10 -2.0(2) . . . . ?
C7 C8 C9 C10 174.00(15) . . . . ?
C11 N6 C10 C9 1.8(3) . . . . ?
C8 C9 C10 N6 0.2(3) . . . . ?
C10 N6 C11 C12 -2.0(3) . . . . ?
N6 C11 C12 C8 0.3(3) . . . . ?
C9 C8 C12 C11 1.7(2) . . . . ?
C7 C8 C12 C11 -174.50(14) . . . . ?
C18 C13 C14 C15 -1.4(2) . . . . ?
C19 C13 C14 C15 -178.87(15) . . . . ?
C13 C14 C15 C16 2.4(3) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 -1.5(2) . . . . ?
C15 C16 C17 C20 179.01(15) . . . . ?
C16 C17 C18 C13 2.5(2) . . . . ?
C20 C17 C18 C13 -177.99(14) . . . . ?
C14 C13 C18 C17 -1.1(2) . . . . ?
C19 C13 C18 C17 176.33(14) . . . . ?
C14 C13 C19 O1 15.3(2) . . . . ?
C18 C13 C19 O1 -162.16(16) . . . . ?
C14 C13 C19 O2 -164.78(15) . . . . ?
C18 C13 C19 O2 17.8(2) . . . . ?
C16 C17 C20 O4 7.7(2) . . . . ?
C18 C17 C20 O4 -171.80(15) . . . . ?
C16 C17 C20 O3 -172.90(15) . . . . ?
C18 C17 C20 O3 7.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035

#===END

data_2
_database_code_depnum_ccdc_archive 'CCDC 693290'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N6 O4'
_chemical_formula_weight         404.39

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.255(2)
_cell_length_b                   7.187(2)
_cell_length_c                   20.272(4)
_cell_angle_alpha                83.78(3)
_cell_angle_beta                 86.62(3)
_cell_angle_gamma                79.03(2)
_cell_volume                     888.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    457
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      26.56

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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  'APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4675
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.1930
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.01
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3073
_reflns_number_gt                1237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_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 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)+(0.0261P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3073
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_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 0.2222(4) 0.1792(4) 0.76837(12) 0.0528(9) Uani 1 1 d . . .
H1 H 0.1768 0.1716 0.7318 0.079 Uiso 1 1 calc R . .
O2 O 0.5319(4) 0.0352(4) 0.72196(12) 0.0576(9) Uani 1 1 d . . .
O3 O 0.5041(4) 0.2938(4) 1.05453(12) 0.0636(10) Uani 1 1 d . . .
O4 O 0.1981(4) 0.3393(4) 1.00011(12) 0.0552(9) Uani 1 1 d . . .
H4 H 0.1439 0.3722 1.0358 0.083 Uiso 1 1 calc R . .
N1 N 0.0471(6) 0.3989(5) 0.12637(15) 0.0484(10) Uani 1 1 d . . .
N2 N -0.3186(5) 0.3860(4) 0.35837(15) 0.0481(10) Uani 1 1 d . . .
N3 N -0.3130(5) 0.3586(4) 0.42752(15) 0.0443(9) Uani 1 1 d . . .
N4 N 0.0211(5) 0.2884(4) 0.38511(14) 0.0370(9) Uani 1 1 d . . .
N5 N 0.2486(5) 0.2109(5) 0.38198(14) 0.0463(10) Uani 1 1 d . . .
H5A H 0.2843 0.1637 0.3426 0.059(12) Uiso 1 1 d R . .
H5B H 0.3317 0.2988 0.3851 0.16(3) Uiso 1 1 d R . .
N6 N 0.0663(6) 0.1880(4) 0.64605(15) 0.0498(10) Uani 1 1 d . . .
C1 C -0.1973(6) 0.3286(5) 0.21783(18) 0.0456(12) Uani 1 1 d . . .
H1A H -0.3280 0.2913 0.2323 0.055 Uiso 1 1 calc R . .
C2 C -0.1392(7) 0.3516(6) 0.1501(2) 0.0514(14) Uani 1 1 d . . .
H2 H -0.2374 0.3325 0.1199 0.062 Uiso 1 1 calc R . .
C3 C 0.1847(6) 0.4298(5) 0.16984(19) 0.0485(12) Uani 1 1 d . . .
H3 H 0.3154 0.4648 0.1540 0.058 Uiso 1 1 calc R . .
C4 C 0.1401(7) 0.4117(5) 0.23855(18) 0.0439(12) Uani 1 1 d . . .
H4A H 0.2412 0.4322 0.2675 0.053 Uiso 1 1 calc R . .
C5 C -0.0533(6) 0.3635(5) 0.26280(18) 0.0398(12) Uani 1 1 d . . .
C6 C -0.1162(6) 0.3434(5) 0.33447(18) 0.0382(11) Uani 1 1 d . . .
C7 C -0.1058(6) 0.2983(5) 0.44214(19) 0.0395(12) Uani 1 1 d . . .
C8 C -0.0385(6) 0.2561(5) 0.51151(18) 0.0405(12) Uani 1 1 d . . .
C9 C 0.1717(6) 0.1842(5) 0.52964(18) 0.0526(13) Uani 1 1 d . . .
H9 H 0.2830 0.1571 0.4977 0.063 Uiso 1 1 calc R . .
C10 C 0.2139(7) 0.1527(6) 0.5971(2) 0.0609(14) Uani 1 1 d . . .
H10 H 0.3567 0.1032 0.6087 0.073 Uiso 1 1 calc R . .
C11 C -0.1362(7) 0.2569(6) 0.62735(19) 0.0536(13) Uani 1 1 d . . .
H11 H -0.2450 0.2807 0.6603 0.064 Uiso 1 1 calc R . .
C12 C -0.1948(6) 0.2953(5) 0.56183(19) 0.0456(12) Uani 1 1 d . . .
H12 H -0.3383 0.3471 0.5517 0.055 Uiso 1 1 calc R . .
C13 C 0.4326(7) 0.1087(5) 0.76907(19) 0.0433(12) Uani 1 1 d . . .
C14 C 0.5360(6) 0.1270(5) 0.83114(17) 0.0366(11) Uani 1 1 d . . .
C15 C 0.7602(7) 0.0672(5) 0.83403(19) 0.0478(12) Uani 1 1 d . . .
H15 H 0.8398 0.0188 0.7975 0.057 Uiso 1 1 calc R . .
C16 C 0.8659(6) 0.0794(5) 0.89115(19) 0.0515(13) Uani 1 1 d . . .
H16 H 1.0158 0.0380 0.8930 0.062 Uiso 1 1 calc R . .
C17 C 0.7494(6) 0.1527(5) 0.94527(19) 0.0467(12) Uani 1 1 d . . .
H17 H 0.8208 0.1611 0.9835 0.056 Uiso 1 1 calc R . .
C18 C 0.5249(6) 0.2143(5) 0.94276(18) 0.0383(11) Uani 1 1 d . . .
C19 C 0.4104(7) 0.2856(5) 1.00484(19) 0.0424(11) Uani 1 1 d . . .
C20 C 0.4190(6) 0.2013(5) 0.88600(17) 0.0423(12) Uani 1 1 d . . .
H20 H 0.2690 0.2423 0.8844 0.051 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 C13 1.317(4) . ?
O1 H1 0.8200 . ?
O2 C13 1.221(4) . ?
O3 C19 1.207(4) . ?
O4 C19 1.317(4) . ?
O4 H4 0.8200 . ?
N1 C2 1.325(5) . ?
N1 C3 1.331(4) . ?
N2 C6 1.320(4) . ?
N2 N3 1.396(4) . ?
N3 C7 1.326(4) . ?
N4 C6 1.355(4) . ?
N4 C7 1.364(4) . ?
N4 N5 1.426(4) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.9000 . ?
N6 C10 1.326(4) . ?
N6 C11 1.331(5) . ?
C1 C5 1.392(4) . ?
C1 C2 1.400(5) . ?
C1 H1A 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.482(5) . ?
C7 C8 1.475(5) . ?
C8 C9 1.374(5) . ?
C8 C12 1.384(5) . ?
C9 C10 1.394(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.478(5) . ?
C14 C15 1.389(5) . ?
C14 C20 1.393(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9300 . ?
C18 C20 1.381(4) . ?
C18 C19 1.501(5) . ?
C20 H20 0.9300 . ?

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
C13 O1 H1 109.5 . . ?
C19 O4 H4 109.5 . . ?
C2 N1 C3 117.6(4) . . ?
C6 N2 N3 107.6(3) . . ?
C7 N3 N2 106.7(3) . . ?
C6 N4 C7 106.2(3) . . ?
C6 N4 N5 128.5(3) . . ?
C7 N4 N5 124.8(3) . . ?
N4 N5 H5A 109.3 . . ?
N4 N5 H5B 112.7 . . ?
H5A N5 H5B 106.9 . . ?
C10 N6 C11 115.5(4) . . ?
C5 C1 C2 117.9(4) . . ?
C5 C1 H1A 121.1 . . ?
C2 C1 H1A 121.1 . . ?
N1 C2 C1 124.0(3) . . ?
N1 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?
N1 C3 C4 122.5(4) . . ?
N1 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C1 118.3(4) . . ?
C4 C5 C6 123.6(3) . . ?
C1 C5 C6 118.1(4) . . ?
N2 C6 N4 109.8(3) . . ?
N2 C6 C5 123.9(3) . . ?
N4 C6 C5 126.3(4) . . ?
N3 C7 N4 109.8(3) . . ?
N3 C7 C8 121.5(4) . . ?
N4 C7 C8 128.7(4) . . ?
C9 C8 C12 117.5(4) . . ?
C9 C8 C7 124.1(3) . . ?
C12 C8 C7 118.4(4) . . ?
C8 C9 C10 118.4(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N6 C10 C9 125.1(4) . . ?
N6 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
N6 C11 C12 123.9(4) . . ?
N6 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
C11 C12 C8 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 . . ?
O2 C13 O1 122.2(3) . . ?
O2 C13 C14 123.4(4) . . ?
O1 C13 C14 114.3(3) . . ?
C15 C14 C20 119.3(3) . . ?
C15 C14 C13 117.7(3) . . ?
C20 C14 C13 123.0(4) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C20 C18 C17 119.9(3) . . ?
C20 C18 C19 123.7(4) . . ?
C17 C18 C19 116.3(3) . . ?
O3 C19 O4 123.0(4) . . ?
O3 C19 C18 123.2(4) . . ?
O4 C19 C18 113.9(3) . . ?
C18 C20 C14 120.3(3) . . ?
C18 C20 H20 119.9 . . ?
C14 C20 H20 119.9 . . ?

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
C6 N2 N3 C7 -0.6(4) . . . . ?
C3 N1 C2 C1 -1.4(6) . . . . ?
C5 C1 C2 N1 2.1(6) . . . . ?
C2 N1 C3 C4 0.8(6) . . . . ?
N1 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C1 1.8(5) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C2 C1 C5 C4 -2.2(5) . . . . ?
C2 C1 C5 C6 178.7(3) . . . . ?
N3 N2 C6 N4 0.3(4) . . . . ?
N3 N2 C6 C5 -176.9(3) . . . . ?
C7 N4 C6 N2 0.1(4) . . . . ?
N5 N4 C6 N2 172.5(3) . . . . ?
C7 N4 C6 C5 177.3(3) . . . . ?
N5 N4 C6 C5 -10.3(6) . . . . ?
C4 C5 C6 N2 146.7(4) . . . . ?
C1 C5 C6 N2 -34.3(5) . . . . ?
C4 C5 C6 N4 -30.1(6) . . . . ?
C1 C5 C6 N4 148.9(3) . . . . ?
N2 N3 C7 N4 0.7(4) . . . . ?
N2 N3 C7 C8 179.4(3) . . . . ?
C6 N4 C7 N3 -0.6(4) . . . . ?
N5 N4 C7 N3 -173.3(3) . . . . ?
C6 N4 C7 C8 -179.1(3) . . . . ?
N5 N4 C7 C8 8.1(5) . . . . ?
N3 C7 C8 C9 176.6(4) . . . . ?
N4 C7 C8 C9 -5.0(6) . . . . ?
N3 C7 C8 C12 -5.1(5) . . . . ?
N4 C7 C8 C12 173.4(3) . . . . ?
C12 C8 C9 C10 0.9(6) . . . . ?
C7 C8 C9 C10 179.3(4) . . . . ?
C11 N6 C10 C9 0.7(6) . . . . ?
C8 C9 C10 N6 -0.4(6) . . . . ?
C10 N6 C11 C12 -1.5(6) . . . . ?
N6 C11 C12 C8 2.0(6) . . . . ?
C9 C8 C12 C11 -1.6(5) . . . . ?
C7 C8 C12 C11 179.9(3) . . . . ?
O2 C13 C14 C15 3.9(6) . . . . ?
O1 C13 C14 C15 -175.9(4) . . . . ?
O2 C13 C14 C20 -176.3(4) . . . . ?
O1 C13 C14 C20 4.0(5) . . . . ?
C20 C14 C15 C16 0.7(6) . . . . ?
C13 C14 C15 C16 -179.4(3) . . . . ?
C14 C15 C16 C17 -0.6(6) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C17 C18 C20 0.2(6) . . . . ?
C16 C17 C18 C19 177.9(3) . . . . ?
C20 C18 C19 O3 178.9(4) . . . . ?
C17 C18 C19 O3 1.3(6) . . . . ?
C20 C18 C19 O4 -1.4(6) . . . . ?
C17 C18 C19 O4 -179.0(4) . . . . ?
C17 C18 C20 C14 -0.1(6) . . . . ?
C19 C18 C20 C14 -177.6(4) . . . . ?
C15 C14 C20 C18 -0.3(6) . . . . ?
C13 C14 C20 C18 179.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.081

#===END

data_3
_database_code_depnum_ccdc_archive 'CCDC 693291'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N7 O4'
_chemical_formula_weight         419.41

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   17.5638(13)
_cell_length_b                   7.3710(6)
_cell_length_c                   14.4866(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.0100(10)
_cell_angle_gamma                90.00
_cell_volume                     1872.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2542
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.46

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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  'APEX II 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            9849
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3302
_reflns_number_gt                2338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_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 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)+(0.0551P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3302
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_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 0.27304(7) -0.32428(18) 0.00052(9) 0.0451(4) Uani 1 1 d . . .
O2 O 0.32301(7) -0.06809(17) -0.05254(10) 0.0458(4) Uani 1 1 d . . .
H2 H 0.3587 -0.1354 -0.0632 0.069 Uiso 1 1 calc R . .
O3 O 0.01481(7) -0.31371(18) 0.09825(11) 0.0539(4) Uani 1 1 d . . .
H3 H -0.0249 -0.3600 0.1142 0.081 Uiso 1 1 calc R . .
O4 O -0.03737(8) -0.06270(18) 0.15351(11) 0.0578(4) Uani 1 1 d . . .
N1 N 0.43487(9) 0.7225(2) 0.90969(11) 0.0410(4) Uani 1 1 d . . .
N2 N 0.58631(8) 0.1668(2) 0.84415(11) 0.0402(4) Uani 1 1 d . . .
N3 N 0.64609(8) 0.0702(2) 0.81131(11) 0.0400(4) Uani 1 1 d . . .
N4 N 0.66564(8) 0.35906(19) 0.78559(10) 0.0317(4) Uani 1 1 d . . .
N5 N 0.69460(8) 0.52526(19) 0.75480(11) 0.0397(4) Uani 1 1 d . . .
H5A H 0.6994 0.5204 0.6933 0.048 Uiso 1 1 d R . .
H5B H 0.7357 0.5731 0.7854 0.048 Uiso 1 1 d R . .
N6 N 0.89049(9) -0.0187(2) 0.65239(11) 0.0421(4) Uani 1 1 d . . .
N7 N 0.16817(9) 0.4172(2) 0.10274(12) 0.0464(4) Uani 1 1 d . . .
H7A H 0.1245 0.4769 0.1120 0.056 Uiso 1 1 d R . .
H7B H 0.1977 0.4747 0.0631 0.056 Uiso 1 1 d R . .
C1 C 0.54470(10) 0.4806(2) 0.85433(12) 0.0336(4) Uani 1 1 d . . .
C2 C 0.47304(10) 0.4211(3) 0.87930(13) 0.0397(5) Uani 1 1 d . . .
H2A H 0.4610 0.2983 0.8773 0.048 Uiso 1 1 calc R . .
C3 C 0.42070(10) 0.5452(3) 0.90669(13) 0.0411(5) Uani 1 1 d . . .
H3A H 0.3734 0.5039 0.9239 0.049 Uiso 1 1 calc R . .
C4 C 0.50336(11) 0.7804(3) 0.88599(14) 0.0462(5) Uani 1 1 d . . .
H4 H 0.5135 0.9042 0.8880 0.055 Uiso 1 1 calc R . .
C5 C 0.55924(10) 0.6649(3) 0.85883(13) 0.0419(5) Uani 1 1 d . . .
H5 H 0.6064 0.7101 0.8436 0.050 Uiso 1 1 calc R . .
C6 C 0.59868(10) 0.3399(2) 0.82768(12) 0.0341(4) Uani 1 1 d . . .
C7 C 0.69311(10) 0.1867(2) 0.77642(12) 0.0329(4) Uani 1 1 d . . .
C8 C 0.76247(10) 0.1262(2) 0.73245(12) 0.0322(4) Uani 1 1 d . . .
C9 C 0.82442(10) 0.2345(2) 0.71331(13) 0.0391(5) Uani 1 1 d . . .
H9 H 0.8242 0.3578 0.7271 0.047 Uiso 1 1 calc R . .
C10 C 0.88634(11) 0.1567(3) 0.67348(13) 0.0433(5) Uani 1 1 d . . .
H10 H 0.9273 0.2309 0.6607 0.052 Uiso 1 1 calc R . .
C11 C 0.83103(11) -0.1218(3) 0.67087(13) 0.0429(5) Uani 1 1 d . . .
H11 H 0.8332 -0.2449 0.6572 0.052 Uiso 1 1 calc R . .
C12 C 0.76670(10) -0.0560(2) 0.70910(13) 0.0396(5) Uani 1 1 d . . .
H12 H 0.7261 -0.1332 0.7193 0.047 Uiso 1 1 calc R . .
C13 C 0.27107(10) -0.1595(3) -0.01102(12) 0.0365(4) Uani 1 1 d . . .
C14 C 0.20733(10) -0.0478(2) 0.02357(12) 0.0340(4) Uani 1 1 d . . .
C15 C 0.14100(10) -0.1352(2) 0.04533(12) 0.0358(4) Uani 1 1 d . . .
H15 H 0.1349 -0.2579 0.0320 0.043 Uiso 1 1 calc R . .
C16 C 0.08377(10) -0.0419(2) 0.08676(13) 0.0353(4) Uani 1 1 d . . .
C17 C 0.01389(10) -0.1381(3) 0.11610(13) 0.0392(5) Uani 1 1 d . . .
C18 C 0.09269(10) 0.1416(2) 0.10479(13) 0.0372(5) Uani 1 1 d . . .
H18 H 0.0545 0.2044 0.1335 0.045 Uiso 1 1 calc R . .
C19 C 0.15780(10) 0.2334(2) 0.08062(13) 0.0349(4) Uani 1 1 d . . .
C20 C 0.21553(10) 0.1365(2) 0.03995(12) 0.0360(4) Uani 1 1 d . . .
H20 H 0.2596 0.1958 0.0238 0.043 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 C13 1.226(2) . ?
O2 C13 1.306(2) . ?
O2 H2 0.8200 . ?
O3 C17 1.320(2) . ?
O3 H3 0.8200 . ?
O4 C17 1.210(2) . ?
N1 C3 1.330(2) . ?
N1 C4 1.338(2) . ?
N2 C6 1.318(2) . ?
N2 N3 1.3741(19) . ?
N3 C7 1.311(2) . ?
N4 C6 1.360(2) . ?
N4 C7 1.368(2) . ?
N4 N5 1.4080(19) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.8998 . ?
N6 C11 1.330(2) . ?
N6 C10 1.331(2) . ?
N7 C19 1.402(2) . ?
N7 H7A 0.9000 . ?
N7 H7B 0.9000 . ?
C1 C5 1.383(3) . ?
C1 C2 1.398(2) . ?
C1 C6 1.470(2) . ?
C2 C3 1.370(2) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.473(2) . ?
C8 C12 1.388(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.373(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.497(2) . ?
C14 C15 1.382(2) . ?
C14 C20 1.385(2) . ?
C15 C16 1.381(2) . ?
C15 H15 0.9300 . ?
C16 C18 1.385(2) . ?
C16 C17 1.498(2) . ?
C18 C19 1.389(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(2) . ?
C20 H20 0.9300 . ?

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
C13 O2 H2 109.5 . . ?
C17 O3 H3 109.5 . . ?
C3 N1 C4 118.31(16) . . ?
C6 N2 N3 107.63(14) . . ?
C7 N3 N2 107.58(15) . . ?
C6 N4 C7 105.36(14) . . ?
C6 N4 N5 124.58(14) . . ?
C7 N4 N5 129.96(14) . . ?
N4 N5 H5A 109.5 . . ?
N4 N5 H5B 118.6 . . ?
H5A N5 H5B 112.9 . . ?
C11 N6 C10 117.11(16) . . ?
C19 N7 H7A 113.9 . . ?
C19 N7 H7B 112.4 . . ?
H7A N7 H7B 112.9 . . ?
C5 C1 C2 117.54(16) . . ?
C5 C1 C6 125.82(16) . . ?
C2 C1 C6 116.63(16) . . ?
C3 C2 C1 119.48(18) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
N1 C3 C2 122.54(17) . . ?
N1 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
N1 C4 C5 122.79(18) . . ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C1 119.33(17) . . ?
C4 C5 H5 120.3 . . ?
C1 C5 H5 120.3 . . ?
N2 C6 N4 109.64(15) . . ?
N2 C6 C1 121.38(15) . . ?
N4 C6 C1 128.98(16) . . ?
N3 C7 N4 109.79(15) . . ?
N3 C7 C8 121.33(16) . . ?
N4 C7 C8 128.84(16) . . ?
C12 C8 C9 117.06(16) . . ?
C12 C8 C7 117.03(16) . . ?
C9 C8 C7 125.90(16) . . ?
C10 C9 C8 119.11(17) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N6 C10 C9 123.55(18) . . ?
N6 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N6 C11 C12 123.42(18) . . ?
N6 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C8 119.74(17) . . ?
C11 C12 H12 120.1 . . ?
C8 C12 H12 120.1 . . ?
O1 C13 O2 123.95(16) . . ?
O1 C13 C14 121.02(16) . . ?
O2 C13 C14 115.03(16) . . ?
C15 C14 C20 119.96(16) . . ?
C15 C14 C13 118.30(16) . . ?
C20 C14 C13 121.59(16) . . ?
C16 C15 C14 120.57(17) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C18 119.38(16) . . ?
C15 C16 C17 120.90(17) . . ?
C18 C16 C17 119.67(16) . . ?
O4 C17 O3 123.72(17) . . ?
O4 C17 C16 123.33(18) . . ?
O3 C17 C16 112.94(15) . . ?
C16 C18 C19 120.97(16) . . ?
C16 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 118.89(17) . . ?
C18 C19 N7 120.77(16) . . ?
C20 C19 N7 120.17(16) . . ?
C14 C20 C19 120.19(16) . . ?
C14 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?

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
C6 N2 N3 C7 0.3(2) . . . . ?
C5 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C2 C3 178.65(17) . . . . ?
C4 N1 C3 C2 -0.8(3) . . . . ?
C1 C2 C3 N1 0.8(3) . . . . ?
C3 N1 C4 C5 0.0(3) . . . . ?
N1 C4 C5 C1 0.8(3) . . . . ?
C2 C1 C5 C4 -0.8(3) . . . . ?
C6 C1 C5 C4 -179.25(18) . . . . ?
N3 N2 C6 N4 -0.6(2) . . . . ?
N3 N2 C6 C1 179.82(16) . . . . ?
C7 N4 C6 N2 0.6(2) . . . . ?
N5 N4 C6 N2 177.20(15) . . . . ?
C7 N4 C6 C1 -179.83(18) . . . . ?
N5 N4 C6 C1 -3.3(3) . . . . ?
C5 C1 C6 N2 165.16(19) . . . . ?
C2 C1 C6 N2 -13.3(3) . . . . ?
C5 C1 C6 N4 -14.3(3) . . . . ?
C2 C1 C6 N4 167.25(18) . . . . ?
N2 N3 C7 N4 0.1(2) . . . . ?
N2 N3 C7 C8 -178.04(16) . . . . ?
C6 N4 C7 N3 -0.4(2) . . . . ?
N5 N4 C7 N3 -176.73(16) . . . . ?
C6 N4 C7 C8 177.50(18) . . . . ?
N5 N4 C7 C8 1.2(3) . . . . ?
N3 C7 C8 C12 15.4(3) . . . . ?
N4 C7 C8 C12 -162.32(18) . . . . ?
N3 C7 C8 C9 -163.76(18) . . . . ?
N4 C7 C8 C9 18.5(3) . . . . ?
C12 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 178.58(17) . . . . ?
C11 N6 C10 C9 0.3(3) . . . . ?
C8 C9 C10 N6 -0.3(3) . . . . ?
C10 N6 C11 C12 0.6(3) . . . . ?
N6 C11 C12 C8 -1.6(3) . . . . ?
C9 C8 C12 C11 1.5(3) . . . . ?
C7 C8 C12 C11 -177.76(17) . . . . ?
O1 C13 C14 C15 -17.7(3) . . . . ?
O2 C13 C14 C15 162.89(16) . . . . ?
O1 C13 C14 C20 157.84(18) . . . . ?
O2 C13 C14 C20 -21.6(3) . . . . ?
C20 C14 C15 C16 -2.6(3) . . . . ?
C13 C14 C15 C16 173.00(16) . . . . ?
C14 C15 C16 C18 1.3(3) . . . . ?
C14 C15 C16 C17 -176.03(17) . . . . ?
C15 C16 C17 O4 179.19(19) . . . . ?
C18 C16 C17 O4 1.9(3) . . . . ?
C15 C16 C17 O3 0.3(3) . . . . ?
C18 C16 C17 O3 -177.05(18) . . . . ?
C15 C16 C18 C19 0.9(3) . . . . ?
C17 C16 C18 C19 178.27(17) . . . . ?
C16 C18 C19 C20 -1.8(3) . . . . ?
C16 C18 C19 N7 -177.08(18) . . . . ?
C15 C14 C20 C19 1.7(3) . . . . ?
C13 C14 C20 C19 -173.75(16) . . . . ?
C18 C19 C20 C14 0.5(3) . . . . ?
N7 C19 C20 C14 175.80(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043

#===END

data_4
_database_code_depnum_ccdc_archive 'CCDC 693292'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N6 O9 S'
_chemical_formula_weight         520.49

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.1997(8)
_cell_length_b                   21.912(2)
_cell_length_c                   14.1960(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1160(10)
_cell_angle_gamma                90.00
_cell_volume                     2217.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3017
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      23.27

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9122
_exptl_absorpt_correction_T_max  0.9564
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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  'APEX II 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            12004
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3903
_reflns_number_gt                2902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_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 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.

Standard geometry constraints were applied for sulfonate in order to improve
the refinement stability. In addition, the soft "SADI" restraint was imposed
on the disordered oxygen atoms of sulfonate, and "EADP" constraint was applied
separately to the O5/O5' and O7/O7' atoms.
;

_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)+(0.0555P)²+1.1982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3903
_refine_ls_number_parameters     343
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_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
S1 S 0.26734(11) 0.59226(3) 0.66802(5) 0.0432(2) Uani 1 1 d D . .
O1 O 0.2273(4) 0.85601(9) 0.47864(14) 0.0654(7) Uani 1 1 d . . .
H1 H 0.2371 0.8918 0.4956 0.098 Uiso 1 1 calc R . .
O2 O 0.3286(4) 0.83817(10) 0.63067(15) 0.0710(7) Uani 1 1 d . . .
O3 O -0.0097(4) 0.70341(10) 0.26100(14) 0.0706(8) Uani 1 1 d . A .
H3' H -0.0674 0.6916 0.2103 0.106 Uiso 1 1 calc R . .
O4 O -0.0355(4) 0.60658(9) 0.30104(15) 0.0630(7) Uani 1 1 d . A .
O5 O 0.1257(5) 0.54427(12) 0.63972(19) 0.0547(8) Uani 0.803(4) 1 d PDU A 1
O6 O 0.4522(4) 0.56872(13) 0.6650(2) 0.0571(8) Uani 0.803(4) 1 d PDU A 1
O7 O 0.2450(4) 0.62162(14) 0.75732(19) 0.0455(7) Uani 0.803(4) 1 d PDU A 1
O5' O 0.2495(18) 0.5369(4) 0.6269(7) 0.0547(8) Uani 0.197(4) 1 d PDU A 2
O6' O 0.4761(12) 0.6075(6) 0.7005(8) 0.065(4) Uani 0.197(4) 1 d PDU A 2
O7' O 0.1810(17) 0.6109(6) 0.7484(8) 0.0455(7) Uani 0.197(4) 1 d PDU A 2
N1 N 0.4482(4) 0.44025(11) 0.62474(18) 0.0543(7) Uani 1 1 d . . .
H1A H 0.4725 0.4766 0.6457 0.065 Uiso 1 1 calc R . .
N2 N 0.2318(3) 0.25811(10) 0.43022(15) 0.0395(6) Uani 1 1 d . . .
N3 N 0.2014(3) 0.19699(10) 0.41420(15) 0.0408(6) Uani 1 1 d . . .
N4 N 0.3480(3) 0.20814(9) 0.55850(14) 0.0328(5) Uani 1 1 d . . .
N5 N 0.4457(3) 0.19784(10) 0.65066(15) 0.0436(6) Uani 1 1 d . . .
H5A H 0.3626 0.1810 0.6848 0.052 Uiso 1 1 d R . .
H5B H 0.5385 0.1721 0.6409 0.052 Uiso 1 1 d R . .
N6 N 0.2493(4) -0.02671(11) 0.49903(17) 0.0507(7) Uani 1 1 d . . .
C1 C 0.3710(4) 0.32467(12) 0.55850(18) 0.0336(6) Uani 1 1 d . . .
C2 C 0.3184(4) 0.37537(12) 0.5020(2) 0.0434(7) Uani 1 1 d . . .
H2 H 0.2578 0.3702 0.4403 0.052 Uiso 1 1 calc R . .
C3 C 0.3558(5) 0.43267(14) 0.5372(2) 0.0527(8) Uani 1 1 d . . .
H3 H 0.3168 0.4665 0.5001 0.063 Uiso 1 1 calc R . .
C4 C 0.5039(5) 0.39298(13) 0.6805(2) 0.0521(8) Uani 1 1 d . . .
H4 H 0.5697 0.3997 0.7408 0.062 Uiso 1 1 calc R . .
C5 C 0.4651(4) 0.33435(13) 0.64981(19) 0.0432(7) Uani 1 1 d . . .
H5 H 0.5013 0.3015 0.6896 0.052 Uiso 1 1 calc R . .
C6 C 0.3209(4) 0.26437(11) 0.51714(17) 0.0326(6) Uani 1 1 d . . .
C7 C 0.2714(4) 0.16721(12) 0.49177(17) 0.0349(6) Uani 1 1 d . . .
C8 C 0.2663(4) 0.09998(12) 0.49852(18) 0.0371(6) Uani 1 1 d . . .
C9 C 0.2472(5) 0.06713(13) 0.4147(2) 0.0513(8) Uani 1 1 d . . .
H9 H 0.2400 0.0872 0.3565 0.062 Uiso 1 1 calc R . .
C10 C 0.2391(5) 0.00458(14) 0.4181(2) 0.0549(9) Uani 1 1 d . . .
H10 H 0.2259 -0.0170 0.3611 0.066 Uiso 1 1 calc R . .
C11 C 0.2641(5) 0.00509(14) 0.5793(2) 0.0562(9) Uani 1 1 d . . .
H11 H 0.2680 -0.0162 0.6363 0.067 Uiso 1 1 calc R . .
C12 C 0.2741(5) 0.06810(13) 0.5829(2) 0.0499(8) Uani 1 1 d . . .
H12 H 0.2857 0.0885 0.6409 0.060 Uiso 1 1 calc R . .
C13 C 0.2659(4) 0.82054(12) 0.55255(19) 0.0409(7) Uani 1 1 d . . .
C14 C 0.2253(4) 0.75484(11) 0.52969(17) 0.0336(6) Uani 1 1 d . A .
C15 C 0.1463(4) 0.73767(12) 0.43841(18) 0.0350(6) Uani 1 1 d . . .
H15 H 0.1208 0.7671 0.3912 0.042 Uiso 1 1 calc R . .
C16 C 0.1056(4) 0.67694(11) 0.41746(17) 0.0340(6) Uani 1 1 d . A .
C17 C 0.1437(4) 0.63297(12) 0.48786(17) 0.0353(6) Uani 1 1 d . . .
H17 H 0.1167 0.5922 0.4739 0.042 Uiso 1 1 calc R A .
C18 C 0.2219(4) 0.64985(11) 0.57905(17) 0.0331(6) Uani 1 1 d . A .
C19 C 0.2631(4) 0.71063(12) 0.60028(18) 0.0354(6) Uani 1 1 d . . .
H19 H 0.3157 0.7218 0.6615 0.042 Uiso 1 1 calc R A .
C20 C 0.0147(4) 0.65775(13) 0.32099(18) 0.0398(7) Uani 1 1 d . . .
O8 O 0.2121(4) 0.49402(14) 0.3114(2) 0.1011(10) Uani 1 1 d . . .
H8A H 0.0998 0.4881 0.3214 0.152 Uiso 1 1 d R . .
H8B H 0.2862 0.4637 0.3186 0.152 Uiso 1 1 d R . .
O9 O 0.1464(4) 0.15787(11) 0.75819(18) 0.0740(7) Uani 1 1 d . . .
H9A H 0.1586 0.1824 0.8051 0.111 Uiso 1 1 d R . .
H9B H 0.0366 0.1447 0.7388 0.111 Uiso 1 1 d 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
S1 O5' 1.344(8) . ?
S1 O7' 1.433(9) . ?
S1 O6 1.434(3) . ?
S1 O7 1.451(3) . ?
S1 O5 1.480(3) . ?
S1 O6' 1.545(8) . ?
S1 C18 1.783(3) . ?
O1 C13 1.304(3) . ?
O1 H1 0.8200 . ?
O2 C13 1.201(3) . ?
O3 C20 1.310(3) . ?
O3 H3' 0.8200 . ?
O4 C20 1.200(3) . ?
N1 C4 1.330(4) . ?
N1 C3 1.334(4) . ?
N1 H1A 0.8600 . ?
N2 C6 1.315(3) . ?
N2 N3 1.371(3) . ?
N3 C7 1.317(3) . ?
N4 C7 1.363(3) . ?
N4 C6 1.367(3) . ?
N4 N5 1.413(3) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.9001 . ?
N6 C11 1.327(4) . ?
N6 C10 1.331(4) . ?
C1 C2 1.391(4) . ?
C1 C5 1.391(4) . ?
C1 C6 1.470(4) . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.477(4) . ?
C8 C9 1.381(4) . ?
C8 C12 1.381(4) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.496(4) . ?
C14 C15 1.391(3) . ?
C14 C19 1.393(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 C20 1.492(4) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(4) . ?
C19 H19 0.9300 . ?
O8 H8A 0.8502 . ?
O8 H8B 0.8491 . ?
O9 H9A 0.8503 . ?
O9 H9B 0.8506 . ?

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
O5' S1 O7' 125.2(7) . . ?
O5' S1 O6 72.2(5) . . ?
O7' S1 O6 129.4(6) . . ?
O5' S1 O7 139.8(5) . . ?
O6 S1 O7 113.84(17) . . ?
O7' S1 O5 93.4(5) . . ?
O6 S1 O5 110.05(17) . . ?
O7 S1 O5 113.26(16) . . ?
O5' S1 O6' 110.7(6) . . ?
O7' S1 O6' 102.3(6) . . ?
O7 S1 O6' 82.3(5) . . ?
O5 S1 O6' 146.9(5) . . ?
O5' S1 C18 109.5(5) . . ?
O7' S1 C18 107.8(6) . . ?
O6 S1 C18 108.15(14) . . ?
O7 S1 C18 105.86(15) . . ?
O5 S1 C18 105.08(14) . . ?
O6' S1 C18 97.6(5) . . ?
C13 O1 H1 109.5 . . ?
C20 O3 H3' 109.5 . . ?
C4 N1 C3 121.7(3) . . ?
C4 N1 H1A 119.1 . . ?
C3 N1 H1A 119.1 . . ?
C6 N2 N3 107.6(2) . . ?
C7 N3 N2 108.2(2) . . ?
C7 N4 C6 106.0(2) . . ?
C7 N4 N5 129.6(2) . . ?
C6 N4 N5 124.3(2) . . ?
N4 N5 H5A 106.4 . . ?
N4 N5 H5B 104.0 . . ?
H5A N5 H5B 112.9 . . ?
C11 N6 C10 117.3(3) . . ?
C2 C1 C5 118.2(2) . . ?
C2 C1 C6 117.2(2) . . ?
C5 C1 C6 124.7(2) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N1 C3 C2 120.1(3) . . ?
N1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N1 C4 C5 120.6(3) . . ?
N1 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C1 119.3(3) . . ?
C4 C5 H5 120.4 . . ?
C1 C5 H5 120.4 . . ?
N2 C6 N4 109.3(2) . . ?
N2 C6 C1 121.9(2) . . ?
N4 C6 C1 128.8(2) . . ?
N3 C7 N4 108.9(2) . . ?
N3 C7 C8 122.5(2) . . ?
N4 C7 C8 128.5(2) . . ?
C9 C8 C12 118.1(3) . . ?
C9 C8 C7 117.7(2) . . ?
C12 C8 C7 124.2(2) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N6 C10 C9 123.1(3) . . ?
N6 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N6 C11 C12 123.6(3) . . ?
N6 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C8 C12 C11 118.5(3) . . ?
C8 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
O2 C13 O1 124.1(3) . . ?
O2 C13 C14 123.1(2) . . ?
O1 C13 C14 112.7(2) . . ?
C15 C14 C19 119.7(2) . . ?
C15 C14 C13 120.3(2) . . ?
C19 C14 C13 120.1(2) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 C20 121.3(2) . . ?
C17 C16 C20 118.8(2) . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 S1 118.8(2) . . ?
C19 C18 S1 120.87(19) . . ?
C18 C19 C14 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
O4 C20 O3 123.5(2) . . ?
O4 C20 C16 123.9(2) . . ?
O3 C20 C16 112.5(2) . . ?
H8A O8 H8B 117.2 . . ?
H9A O9 H9B 117.2 . . ?

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
C6 N2 N3 C7 0.3(3) . . . . ?
C5 C1 C2 C3 -1.4(4) . . . . ?
C6 C1 C2 C3 178.1(3) . . . . ?
C4 N1 C3 C2 -1.0(5) . . . . ?
C1 C2 C3 N1 2.2(5) . . . . ?
C3 N1 C4 C5 -1.0(5) . . . . ?
N1 C4 C5 C1 1.7(5) . . . . ?
C2 C1 C5 C4 -0.6(4) . . . . ?
C6 C1 C5 C4 -179.9(3) . . . . ?
N3 N2 C6 N4 -0.4(3) . . . . ?
N3 N2 C6 C1 -178.3(2) . . . . ?
C7 N4 C6 N2 0.3(3) . . . . ?
N5 N4 C6 N2 177.5(2) . . . . ?
C7 N4 C6 C1 178.0(3) . . . . ?
N5 N4 C6 C1 -4.9(4) . . . . ?
C2 C1 C6 N2 0.7(4) . . . . ?
C5 C1 C6 N2 -179.9(3) . . . . ?
C2 C1 C6 N4 -176.7(3) . . . . ?
C5 C1 C6 N4 2.7(5) . . . . ?
N2 N3 C7 N4 -0.1(3) . . . . ?
N2 N3 C7 C8 -178.7(2) . . . . ?
C6 N4 C7 N3 -0.1(3) . . . . ?
N5 N4 C7 N3 -177.0(2) . . . . ?
C6 N4 C7 C8 178.4(3) . . . . ?
N5 N4 C7 C8 1.4(5) . . . . ?
N3 C7 C8 C9 22.1(4) . . . . ?
N4 C7 C8 C9 -156.1(3) . . . . ?
N3 C7 C8 C12 -156.0(3) . . . . ?
N4 C7 C8 C12 25.7(5) . . . . ?
C12 C8 C9 C10 -0.8(5) . . . . ?
C7 C8 C9 C10 -179.0(3) . . . . ?
C11 N6 C10 C9 1.4(5) . . . . ?
C8 C9 C10 N6 -0.2(5) . . . . ?
C10 N6 C11 C12 -1.7(5) . . . . ?
C9 C8 C12 C11 0.6(5) . . . . ?
C7 C8 C12 C11 178.7(3) . . . . ?
N6 C11 C12 C8 0.7(5) . . . . ?
O2 C13 C14 C15 177.7(3) . . . . ?
O1 C13 C14 C15 -2.8(4) . . . . ?
O2 C13 C14 C19 -1.1(5) . . . . ?
O1 C13 C14 C19 178.4(3) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
C13 C14 C15 C16 -178.9(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 C20 177.8(2) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C20 C16 C17 C18 -177.7(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C16 C17 C18 S1 179.5(2) . . . . ?
O5' S1 C18 C17 11.8(6) . . . . ?
O7' S1 C18 C17 -127.4(6) . . . . ?
O6 S1 C18 C17 88.8(3) . . . . ?
O7 S1 C18 C17 -148.9(2) . . . . ?
O5 S1 C18 C17 -28.8(3) . . . . ?
O6' S1 C18 C17 127.0(5) . . . . ?
O5' S1 C18 C19 -168.5(6) . . . . ?
O7' S1 C18 C19 52.3(6) . . . . ?
O6 S1 C18 C19 -91.5(3) . . . . ?
O7 S1 C18 C19 30.9(3) . . . . ?
O5 S1 C18 C19 151.0(2) . . . . ?
O6' S1 C18 C19 -53.3(5) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
S1 C18 C19 C14 -179.6(2) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
C13 C14 C19 C18 178.8(3) . . . . ?
C15 C16 C20 O4 -174.5(3) . . . . ?
C17 C16 C20 O4 3.3(4) . . . . ?
C15 C16 C20 O3 3.5(4) . . . . ?
C17 C16 C20 O3 -178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.049

#===END

data_5
_database_code_depnum_ccdc_archive 'CCDC 693293'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N6 O8'
_chemical_formula_weight         484.43

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.3454(7)
_cell_length_b                   37.522(3)
_cell_length_c                   8.5441(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.3500(10)
_cell_angle_gamma                90.00
_cell_volume                     2162.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6645
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.84

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  'APEX II 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            11617
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3803
_reflns_number_gt                3427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_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 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)+(0.0490P)²+0.9451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3803
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_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 0.8761(2) 0.30544(4) 0.54899(18) 0.0578(4) Uani 1 1 d . . .
O2 O 0.8541(2) 0.24702(3) 0.50116(16) 0.0465(3) Uani 1 1 d . . .
H2 H 0.9434 0.2464 0.5967 0.070 Uiso 1 1 calc R . .
O3 O 0.3271(2) 0.19605(3) 0.02139(16) 0.0481(4) Uani 1 1 d . . .
H3 H 0.2583 0.1798 -0.0365 0.072 Uiso 1 1 calc R . .
O4 O 0.13253(18) 0.22838(3) -0.19684(15) 0.0439(3) Uani 1 1 d . . .
O5 O 0.1893(2) 0.36005(3) -0.13815(18) 0.0568(4) Uani 1 1 d . . .
H5' H 0.1538 0.3809 -0.1556 0.085 Uiso 1 1 calc R . .
O6 O 0.4586(2) 0.38405(3) 0.05737(19) 0.0581(4) Uani 1 1 d . . .
O7 O 0.0617(2) 0.42522(3) 0.78777(19) 0.0635(5) Uani 1 1 d . . .
H7A H -0.0437 0.4290 0.6999 0.095 Uiso 1 1 d R . .
H7B H 0.1174 0.4432 0.8484 0.095 Uiso 1 1 d R . .
O8 O 0.6630(3) 0.35680(5) 0.6743(3) 0.0930(6) Uani 1 1 d . . .
H8B H 0.7622 0.3487 0.6579 0.139 Uiso 1 1 d R . .
H8A H 0.5696 0.3423 0.6622 0.139 Uiso 1 1 d R . .
N1 N 1.1236(2) 0.14407(4) 0.8500(2) 0.0457(4) Uani 1 1 d . . .
N2 N 0.9069(2) 0.01959(4) 0.65458(18) 0.0406(4) Uani 1 1 d . . .
N3 N 0.7961(2) -0.00610(4) 0.54362(18) 0.0385(3) Uani 1 1 d . . .
N4 N 0.6933(2) 0.04587(3) 0.42849(16) 0.0314(3) Uani 1 1 d . . .
N5 N 0.5731(2) 0.07168(4) 0.31397(19) 0.0441(4) Uani 1 1 d . . .
H5A H 0.5277 0.0860 0.3750 0.066 Uiso 1 1 d R . .
H5B H 0.6536 0.0831 0.2737 0.066 Uiso 1 1 d R . .
N6 N 0.2670(2) -0.05002(4) -0.01042(19) 0.0436(4) Uani 1 1 d . . .
C1 C 1.0159(3) 0.14579(5) 0.6835(3) 0.0477(5) Uani 1 1 d . . .
H1 H 1.0053 0.1676 0.6286 0.057 Uiso 1 1 calc R . .
C2 C 0.9191(3) 0.11663(5) 0.5884(2) 0.0439(4) Uani 1 1 d . . .
H2A H 0.8458 0.1187 0.4717 0.053 Uiso 1 1 calc R . .
C3 C 0.9329(2) 0.08421(4) 0.6694(2) 0.0341(4) Uani 1 1 d . . .
C4 C 1.0434(3) 0.08289(5) 0.8442(2) 0.0468(5) Uani 1 1 d . . .
H4 H 1.0546 0.0617 0.9034 0.056 Uiso 1 1 calc R . .
C5 C 1.1356(3) 0.11307(5) 0.9285(2) 0.0532(5) Uani 1 1 d . . .
H5 H 1.2096 0.1118 1.0454 0.064 Uiso 1 1 calc R . .
C6 C 0.8447(2) 0.05070(4) 0.5845(2) 0.0328(4) Uani 1 1 d . . .
C7 C 0.6675(2) 0.00996(4) 0.4081(2) 0.0304(3) Uani 1 1 d . . .
C8 C 0.5256(2) -0.00957(4) 0.2612(2) 0.0314(3) Uani 1 1 d . . .
C9 C 0.3654(3) 0.00601(5) 0.1326(2) 0.0406(4) Uani 1 1 d . . .
H9 H 0.3408 0.0303 0.1348 0.049 Uiso 1 1 calc R . .
C10 C 0.2426(3) -0.01508(5) 0.0011(2) 0.0440(4) Uani 1 1 d . . .
H10 H 0.1359 -0.0042 -0.0851 0.053 Uiso 1 1 calc R . .
C11 C 0.4207(3) -0.06475(5) 0.1149(2) 0.0478(5) Uani 1 1 d . . .
H11 H 0.4406 -0.0891 0.1103 0.057 Uiso 1 1 calc R . .
C12 C 0.5523(3) -0.04585(5) 0.2511(2) 0.0420(4) Uani 1 1 d . . .
H12 H 0.6579 -0.0574 0.3354 0.050 Uiso 1 1 calc R . .
C13 C 0.8006(2) 0.28038(5) 0.4588(2) 0.0361(4) Uani 1 1 d . . .
C14 C 0.6346(2) 0.28376(4) 0.2867(2) 0.0318(4) Uani 1 1 d . . .
C15 C 0.5760(2) 0.31747(4) 0.2184(2) 0.0357(4) Uani 1 1 d . . .
H15 H 0.6429 0.3375 0.2779 0.043 Uiso 1 1 calc R . .
C16 C 0.4179(3) 0.32154(4) 0.0617(2) 0.0343(4) Uani 1 1 d . . .
C17 C 0.3586(3) 0.35816(4) -0.0055(2) 0.0391(4) Uani 1 1 d . . .
C18 C 0.3175(2) 0.29162(4) -0.0277(2) 0.0335(4) Uani 1 1 d . . .
H18 H 0.2109 0.2942 -0.1321 0.040 Uiso 1 1 calc R . .
C19 C 0.3772(2) 0.25790(4) 0.0397(2) 0.0304(3) Uani 1 1 d . . .
C20 C 0.2676(2) 0.22598(4) -0.0564(2) 0.0325(4) Uani 1 1 d . . .
C21 C 0.5353(2) 0.25408(4) 0.1964(2) 0.0309(3) Uani 1 1 d . . .
H21 H 0.5748 0.2314 0.2411 0.037 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 C13 1.203(2) . ?
O2 C13 1.319(2) . ?
O2 H2 0.8200 . ?
O3 C20 1.2898(19) . ?
O3 H3 0.8200 . ?
O4 C20 1.220(2) . ?
O5 C17 1.311(2) . ?
O5 H5' 0.8200 . ?
O6 C17 1.208(2) . ?
O7 H7A 0.8501 . ?
O7 H7B 0.8501 . ?
O8 H8B 0.8501 . ?
O8 H8A 0.8501 . ?
N1 C1 1.327(2) . ?
N1 C5 1.328(3) . ?
N2 C6 1.309(2) . ?
N2 N3 1.3706(19) . ?
N3 C7 1.315(2) . ?
N4 C7 1.362(2) . ?
N4 C6 1.368(2) . ?
N4 N5 1.4106(19) . ?
N5 H5A 0.9001 . ?
N5 H5B 0.9001 . ?
N6 C11 1.330(2) . ?
N6 C10 1.332(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(2) . ?
C3 C6 1.468(2) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.471(2) . ?
C8 C9 1.381(2) . ?
C8 C12 1.383(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.498(2) . ?
C14 C21 1.386(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.390(2) . ?
C15 H15 0.9300 . ?
C16 C18 1.393(2) . ?
C16 C17 1.486(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9300 . ?
C19 C21 1.389(2) . ?
C19 C20 1.494(2) . ?
C21 H21 0.9300 . ?

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
C13 O2 H2 109.5 . . ?
C20 O3 H3 109.5 . . ?
C17 O5 H5' 109.5 . . ?
H7A O7 H7B 117.0 . . ?
H8B O8 H8A 117.0 . . ?
C1 N1 C5 118.42(16) . . ?
C6 N2 N3 107.87(13) . . ?
C7 N3 N2 108.01(13) . . ?
C7 N4 C6 105.90(13) . . ?
C7 N4 N5 124.97(13) . . ?
C6 N4 N5 128.93(13) . . ?
N4 N5 H5A 106.4 . . ?
N4 N5 H5B 105.4 . . ?
H5A N5 H5B 112.9 . . ?
C11 N6 C10 116.47(15) . . ?
N1 C1 C2 122.82(17) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.91(17) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 C4 117.73(15) . . ?
C2 C3 C6 125.12(15) . . ?
C4 C3 C6 117.13(15) . . ?
C5 C4 C3 119.51(17) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 122.60(18) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N2 C6 N4 109.20(14) . . ?
N2 C6 C3 122.16(14) . . ?
N4 C6 C3 128.64(15) . . ?
N3 C7 N4 109.01(14) . . ?
N3 C7 C8 122.82(14) . . ?
N4 C7 C8 128.16(14) . . ?
C9 C8 C12 117.66(15) . . ?
C9 C8 C7 124.06(15) . . ?
C12 C8 C7 118.28(15) . . ?
C10 C9 C8 118.77(16) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N6 C10 C9 124.16(17) . . ?
N6 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
N6 C11 C12 123.61(17) . . ?
N6 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C8 119.33(16) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
O1 C13 O2 123.70(15) . . ?
O1 C13 C14 123.50(16) . . ?
O2 C13 C14 112.80(14) . . ?
C21 C14 C15 119.42(15) . . ?
C21 C14 C13 121.50(15) . . ?
C15 C14 C13 119.06(14) . . ?
C14 C15 C16 120.42(15) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C18 119.89(15) . . ?
C15 C16 C17 118.60(15) . . ?
C18 C16 C17 121.51(15) . . ?
O6 C17 O5 122.83(16) . . ?
O6 C17 C16 122.55(16) . . ?
O5 C17 C16 114.61(15) . . ?
C19 C18 C16 119.72(15) . . ?
C19 C18 H18 120.1 . . ?
C16 C18 H18 120.1 . . ?
C18 C19 C21 120.02(14) . . ?
C18 C19 C20 119.35(14) . . ?
C21 C19 C20 120.63(14) . . ?
O4 C20 O3 123.28(15) . . ?
O4 C20 C19 122.15(14) . . ?
O3 C20 C19 114.57(13) . . ?
C14 C21 C19 120.53(15) . . ?
C14 C21 H21 119.7 . . ?
C19 C21 H21 119.7 . . ?

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
C6 N2 N3 C7 -0.3(2) . . . . ?
C5 N1 C1 C2 -1.2(3) . . . . ?
N1 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C6 -177.58(18) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C6 C3 C4 C5 177.34(19) . . . . ?
C1 N1 C5 C4 0.8(3) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
N3 N2 C6 N4 0.2(2) . . . . ?
N3 N2 C6 C3 -179.65(15) . . . . ?
C7 N4 C6 N2 -0.02(19) . . . . ?
N5 N4 C6 N2 175.09(16) . . . . ?
C7 N4 C6 C3 179.81(17) . . . . ?
N5 N4 C6 C3 -5.1(3) . . . . ?
C2 C3 C6 N2 159.82(18) . . . . ?
C4 C3 C6 N2 -18.3(3) . . . . ?
C2 C3 C6 N4 -20.0(3) . . . . ?
C4 C3 C6 N4 161.92(18) . . . . ?
N2 N3 C7 N4 0.29(19) . . . . ?
N2 N3 C7 C8 179.17(15) . . . . ?
C6 N4 C7 N3 -0.17(19) . . . . ?
N5 N4 C7 N3 -175.52(16) . . . . ?
C6 N4 C7 C8 -178.97(16) . . . . ?
N5 N4 C7 C8 5.7(3) . . . . ?
N3 C7 C8 C9 167.12(17) . . . . ?
N4 C7 C8 C9 -14.2(3) . . . . ?
N3 C7 C8 C12 -12.3(3) . . . . ?
N4 C7 C8 C12 166.38(17) . . . . ?
C12 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C10 179.90(17) . . . . ?
C11 N6 C10 C9 0.1(3) . . . . ?
C8 C9 C10 N6 0.5(3) . . . . ?
C10 N6 C11 C12 -0.4(3) . . . . ?
N6 C11 C12 C8 0.2(3) . . . . ?
C9 C8 C12 C11 0.3(3) . . . . ?
C7 C8 C12 C11 179.78(17) . . . . ?
O1 C13 C14 C21 -171.72(18) . . . . ?
O2 C13 C14 C21 7.9(2) . . . . ?
O1 C13 C14 C15 6.6(3) . . . . ?
O2 C13 C14 C15 -173.76(16) . . . . ?
C21 C14 C15 C16 0.7(3) . . . . ?
C13 C14 C15 C16 -177.72(15) . . . . ?
C14 C15 C16 C18 -0.1(3) . . . . ?
C14 C15 C16 C17 179.24(16) . . . . ?
C15 C16 C17 O6 11.0(3) . . . . ?
C18 C16 C17 O6 -169.73(18) . . . . ?
C15 C16 C17 O5 -168.92(17) . . . . ?
C18 C16 C17 O5 10.4(3) . . . . ?
C15 C16 C18 C19 -0.6(3) . . . . ?
C17 C16 C18 C19 -179.84(16) . . . . ?
C16 C18 C19 C21 0.6(2) . . . . ?
C16 C18 C19 C20 179.50(15) . . . . ?
C18 C19 C20 O4 3.6(3) . . . . ?
C21 C19 C20 O4 -177.49(16) . . . . ?
C18 C19 C20 O3 -176.14(16) . . . . ?
C21 C19 C20 O3 2.8(2) . . . . ?
C15 C14 C21 C19 -0.6(2) . . . . ?
C13 C14 C21 C19 177.71(15) . . . . ?
C18 C19 C21 C14 0.0(2) . . . . ?
C20 C19 C21 C14 -178.88(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053

#===END

