 
data_s92 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C32 H32 N8 O8' 
_chemical_formula_weight          656.66 
 
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 
_symmetry_space_group_name_hall   '-P 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    7.9266(4) 
_cell_length_b                    9.6531(5) 
_cell_length_c                    10.3243(6) 
_cell_angle_alpha                 79.14(2) 
_cell_angle_beta                  79.79(2) 
_cell_angle_gamma                 80.26(4) 
_cell_volume                      755.97(12) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     3900 
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       26.02
 
_exptl_crystal_description        platelet
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.07 
_exptl_crystal_size_mid           0.05 
_exptl_crystal_size_min           0.01 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.442 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              344 
_exptl_absorpt_coefficient_mu     0.106 
_exptl_absorpt_correction_type    Empirical 
_exptl_absorpt_correction_T_min   0.9926 
_exptl_absorpt_correction_T_max   0.9989 
_exptl_absorpt_process_details    'SORTAV (R. H. Blessing, 1995, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             5706 
_diffrn_reflns_av_R_equivalents   0.0912 
_diffrn_reflns_av_sigmaI/netI     0.1302 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.03 
_diffrn_reflns_theta_max          25.10 
_reflns_number_total              2675 
_reflns_number_gt                 1828 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0005P)²+0.1700P] 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        0.018(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2675 
_refine_ls_number_parameters      218 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0772 
_refine_ls_R_factor_gt            0.0420 
_refine_ls_wR_factor_ref          0.0884 
_refine_ls_wR_factor_gt           0.0810 
_refine_ls_goodness_of_fit_ref    1.069 
_refine_ls_restrained_S_all       1.069 
_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 
O11 O 0.50229(16) 0.11083(15) 0.67851(14) 0.0318(4) Uani 1 1 d . . . 
O12 O 0.32187(16) 0.11021(16) 0.86120(14) 0.0370(4) Uani 1 1 d . . . 
O21 O 0.75879(17) -0.46781(16) 0.70372(15) 0.0398(4) Uani 1 1 d . . . 
O22 O 0.81249(17) -0.43299(15) 0.89344(15) 0.0366(4) Uani 1 1 d . . . 
N1 N 0.84727(17) 0.04180(16) 0.72476(14) 0.0183(4) Uani 1 1 d . . . 
N2 N 0.92839(18) -0.21034(16) 0.54164(14) 0.0199(4) Uani 1 1 d . . . 
N11 N 0.46679(19) 0.12227(17) 0.79673(17) 0.0234(4) Uani 1 1 d . . . 
N21 N 0.8542(2) -0.43836(17) 0.77340(18) 0.0274(4) Uani 1 1 d . . . 
C1 C 1.0334(2) 0.0422(2) 0.67575(18) 0.0195(5) Uani 1 1 d . . . 
H1A H 1.0725 -0.0283 0.6145 0.023 Uiso 1 1 calc R . . 
H1B H 1.0984 0.0124 0.7522 0.023 Uiso 1 1 calc R . . 
C2 C 0.7950(2) -0.1018(2) 0.74622(18) 0.0196(5) Uani 1 1 d . . . 
H2A H 0.6854 -0.1026 0.8094 0.023 Uiso 1 1 calc R . . 
H2B H 0.8843 -0.1712 0.7886 0.023 Uiso 1 1 calc R . . 
C3 C 0.7696(2) -0.1511(2) 0.62017(18) 0.0210(5) Uani 1 1 d . . . 
H3A H 0.6906 -0.2241 0.6456 0.025 Uiso 1 1 calc R . . 
H3B H 0.7120 -0.0691 0.5630 0.025 Uiso 1 1 calc R . . 
C4 C 0.9249(2) -0.1888(2) 0.39744(18) 0.0206(5) Uani 1 1 d . . . 
H4A H 0.8086 -0.2008 0.3825 0.025 Uiso 1 1 calc R . . 
H4B H 1.0096 -0.2633 0.3584 0.025 Uiso 1 1 calc R . . 
C11 C 0.5968(2) 0.1577(2) 0.86552(18) 0.0188(5) Uani 1 1 d . . . 
C12 C 0.7760(2) 0.1218(2) 0.82754(18) 0.0177(4) Uani 1 1 d . . . 
C13 C 0.8812(2) 0.1720(2) 0.89973(18) 0.0217(5) Uani 1 1 d . . . 
H13 H 1.0034 0.1522 0.8775 0.026 Uiso 1 1 calc R . . 
C14 C 0.8134(2) 0.2487(2) 1.00149(19) 0.0252(5) Uani 1 1 d . . . 
H14 H 0.8895 0.2798 1.0480 0.030 Uiso 1 1 calc R . . 
C15 C 0.6358(2) 0.2813(2) 1.03708(19) 0.0253(5) Uani 1 1 d . . . 
H15 H 0.5896 0.3346 1.1071 0.030 Uiso 1 1 calc R . . 
C16 C 0.5284(2) 0.2348(2) 0.96869(19) 0.0235(5) Uani 1 1 d . . . 
H16 H 0.4064 0.2554 0.9920 0.028 Uiso 1 1 calc R . . 
C21 C 1.0294(2) -0.4122(2) 0.71121(18) 0.0191(5) Uani 1 1 d . . . 
C22 C 1.0561(2) -0.3113(2) 0.59594(18) 0.0187(5) Uani 1 1 d . . . 
C23 C 1.2304(2) -0.3055(2) 0.53822(19) 0.0229(5) Uani 1 1 d . . . 
H23 H 1.2565 -0.2403 0.4587 0.028 Uiso 1 1 calc R . . 
C24 C 1.3636(2) -0.3925(2) 0.5950(2) 0.0249(5) Uani 1 1 d . . . 
H24 H 1.4797 -0.3868 0.5532 0.030 Uiso 1 1 calc R . . 
C25 C 1.3319(2) -0.4884(2) 0.7121(2) 0.0259(5) Uani 1 1 d . . . 
H25 H 1.4251 -0.5469 0.7508 0.031 Uiso 1 1 calc R . . 
C26 C 1.1635(2) -0.4973(2) 0.77128(19) 0.0232(5) Uani 1 1 d . . . 
H26 H 1.1390 -0.5608 0.8523 0.028 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 
O11 N11 1.2245(19) . ? 
O12 N11 1.2334(19) . ? 
O21 N21 1.230(2) . ? 
O22 N21 1.233(2) . ? 
N1 C12 1.410(2) . ? 
N1 C1 1.473(2) . ? 
N1 C2 1.479(2) . ? 
N2 C22 1.397(2) . ? 
N2 C3 1.462(2) . ? 
N2 C4 1.469(2) . ? 
N11 C11 1.467(2) . ? 
N21 C21 1.465(2) . ? 
C1 C4 1.534(3) 2_756 ? 
C1 H1A 0.9900 . ? 
C1 H1B 0.9900 . ? 
C2 C3 1.523(3) . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
C4 C1 1.534(3) 2_756 ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C11 C16 1.393(3) . ? 
C11 C12 1.407(2) . ? 
C12 C13 1.407(3) . ? 
C13 C14 1.378(3) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.388(3) . ? 
C14 H14 0.9500 . ? 
C15 C16 1.374(3) . ? 
C15 H15 0.9500 . ? 
C16 H16 0.9500 . ? 
C21 C26 1.391(2) . ? 
C21 C22 1.398(3) . ? 
C22 C23 1.411(2) . ? 
C23 C24 1.378(3) . ? 
C23 H23 0.9500 . ? 
C24 C25 1.390(3) . ? 
C24 H24 0.9500 . ? 
C25 C26 1.376(3) . ? 
C25 H25 0.9500 . ? 
C26 H26 0.9500 . ? 
 
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 
C12 N1 C1 116.28(14) . . ? 
C12 N1 C2 114.57(14) . . ? 
C1 N1 C2 112.89(14) . . ? 
C22 N2 C3 123.92(15) . . ? 
C22 N2 C4 119.16(15) . . ? 
C3 N2 C4 114.81(14) . . ? 
O11 N11 O12 122.53(16) . . ? 
O11 N11 C11 120.00(15) . . ? 
O12 N11 C11 117.42(16) . . ? 
O21 N21 O22 123.84(16) . . ? 
O21 N21 C21 118.14(17) . . ? 
O22 N21 C21 117.98(17) . . ? 
N1 C1 C4 112.55(15) . 2_756 ? 
N1 C1 H1A 109.1 . . ? 
C4 C1 H1A 109.1 2_756 . ? 
N1 C1 H1B 109.1 . . ? 
C4 C1 H1B 109.1 2_756 . ? 
H1A C1 H1B 107.8 . . ? 
N1 C2 C3 114.74(15) . . ? 
N1 C2 H2A 108.6 . . ? 
C3 C2 H2A 108.6 . . ? 
N1 C2 H2B 108.6 . . ? 
C3 C2 H2B 108.6 . . ? 
H2A C2 H2B 107.6 . . ? 
N2 C3 C2 115.09(14) . . ? 
N2 C3 H3A 108.5 . . ? 
C2 C3 H3A 108.5 . . ? 
N2 C3 H3B 108.5 . . ? 
C2 C3 H3B 108.5 . . ? 
H3A C3 H3B 107.5 . . ? 
N2 C4 C1 113.68(16) . 2_756 ? 
N2 C4 H4A 108.8 . . ? 
C1 C4 H4A 108.8 2_756 . ? 
N2 C4 H4B 108.8 . . ? 
C1 C4 H4B 108.8 2_756 . ? 
H4A C4 H4B 107.7 . . ? 
C16 C11 C12 122.54(17) . . ? 
C16 C11 N11 114.43(15) . . ? 
C12 C11 N11 122.99(17) . . ? 
C13 C12 C11 115.01(17) . . ? 
C13 C12 N1 121.77(16) . . ? 
C11 C12 N1 123.22(16) . . ? 
C14 C13 C12 122.42(17) . . ? 
C14 C13 H13 118.8 . . ? 
C12 C13 H13 118.8 . . ? 
C13 C14 C15 121.04(18) . . ? 
C13 C14 H14 119.5 . . ? 
C15 C14 H14 119.5 . . ? 
C16 C15 C14 118.41(19) . . ? 
C16 C15 H15 120.8 . . ? 
C14 C15 H15 120.8 . . ? 
C15 C16 C11 120.57(17) . . ? 
C15 C16 H16 119.7 . . ? 
C11 C16 H16 119.7 . . ? 
C26 C21 C22 123.42(17) . . ? 
C26 C21 N21 115.71(17) . . ? 
C22 C21 N21 120.83(15) . . ? 
N2 C22 C21 125.81(16) . . ? 
N2 C22 C23 118.39(17) . . ? 
C21 C22 C23 115.55(16) . . ? 
C24 C23 C22 121.26(19) . . ? 
C24 C23 H23 119.4 . . ? 
C22 C23 H23 119.4 . . ? 
C23 C24 C25 121.42(18) . . ? 
C23 C24 H24 119.3 . . ? 
C25 C24 H24 119.3 . . ? 
C26 C25 C24 118.99(17) . . ? 
C26 C25 H25 120.5 . . ? 
C24 C25 H25 120.5 . . ? 
C25 C26 C21 119.29(18) . . ? 
C25 C26 H26 120.4 . . ? 
C21 C26 H26 120.4 . . ? 
 
_diffrn_measured_fraction_theta_max    0.991 
_diffrn_reflns_theta_full              25.10 
_diffrn_measured_fraction_theta_full   0.991 
_refine_diff_density_max    0.234 
_refine_diff_density_min   -0.208 
_refine_diff_density_rms    0.050 
