 
data_vm2084 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C21.50 H21 N4 O4.50' 
_chemical_formula_weight          407.42 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    7.477(3) 
_cell_length_b                    11.703(4) 
_cell_length_c                    12.598(4) 
_cell_angle_alpha                 73.99(3) 
_cell_angle_beta                  74.91(3) 
_cell_angle_gamma                 77.42(3) 
_cell_volume                      1010.3(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       25.0 
_cell_measurement_theta_max       35.0
 
_exptl_crystal_description        block 
_exptl_crystal_colour             orange 
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.339 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              428 
_exptl_absorpt_coefficient_mu     0.793 
_exptl_absorpt_correction_type    psi-scan 
_exptl_absorpt_correction_T_min   0.8903 
_exptl_absorpt_correction_T_max   0.9108 
_exptl_absorpt_process_details    '(North et al., 1968)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54180 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius cad-4 diffractometer' 
_diffrn_measurement_method        'Ω-2\Scan' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          2 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   90
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             3748 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0148 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.74 
_diffrn_reflns_theta_max          68.91 
_reflns_number_total              3748 
_reflns_number_gt                 2850 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0641P)²+0.9419P] 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        0.037(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3748 
_refine_ls_number_parameters      292 
_refine_ls_number_restraints      31 
_refine_ls_R_factor_all           0.0901 
_refine_ls_R_factor_gt            0.0747 
_refine_ls_wR_factor_ref          0.1840 
_refine_ls_wR_factor_gt           0.1730 
_refine_ls_goodness_of_fit_ref    1.052 
_refine_ls_restrained_S_all       1.100 
_refine_ls_shift/su_max           0.001 
_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 
N1 N 0.2928(4) 0.3258(2) 0.4366(2) 0.0582(7) Uani 1 1 d . . . 
H1 H 0.2989 0.3489 0.4946 0.070 Uiso 1 1 calc R . . 
N2 N 0.5531(4) 0.1891(3) 0.5830(2) 0.0604(7) Uani 1 1 d . . . 
N3 N 0.8425(4) -0.0548(2) 0.3163(2) 0.0636(7) Uani 1 1 d . . . 
N4 N 0.5754(4) 0.0792(2) 0.1728(2) 0.0595(7) Uani 1 1 d . . . 
H4 H 0.6693 0.0285 0.1494 0.071 Uiso 1 1 calc R . . 
O1 O 0.9324(4) -0.1108(3) 0.3873(2) 0.1001(10) Uani 1 1 d . . . 
O2 O 0.8642(4) -0.0832(2) 0.2261(2) 0.0844(8) Uani 1 1 d . . . 
O3 O 0.4456(4) 0.2760(3) 0.6139(2) 0.0849(8) Uani 1 1 d . . . 
O4 O 0.6543(4) 0.1208(2) 0.6425(2) 0.0848(8) Uani 1 1 d . . . 
C1 C 0.1153(4) 0.5122(3) 0.3528(2) 0.0545(7) Uani 1 1 d . . . 
C2 C -0.0370(5) 0.5697(3) 0.3035(3) 0.0664(9) Uani 1 1 d . . . 
H2 H -0.0614 0.6534 0.2848 0.080 Uiso 1 1 calc R . . 
C3 C -0.1525(5) 0.5060(3) 0.2816(3) 0.0702(9) Uani 1 1 d . . . 
H3 H -0.2521 0.5467 0.2476 0.084 Uiso 1 1 calc R . . 
C4 C -0.1213(5) 0.3828(3) 0.3099(3) 0.0667(9) Uani 1 1 d . . . 
H4A H -0.1983 0.3398 0.2941 0.080 Uiso 1 1 calc R . . 
C5 C 0.0251(4) 0.3226(3) 0.3620(3) 0.0601(8) Uani 1 1 d . . . 
H5 H 0.0442 0.2389 0.3838 0.072 Uiso 1 1 calc R . . 
C6 C 0.1431(4) 0.3866(3) 0.3816(2) 0.0522(7) Uani 1 1 d . . . 
C7 C 0.2422(5) 0.5816(3) 0.3735(3) 0.0721(9) Uani 1 1 d . . . 
H7A H 0.2418 0.5620 0.4527 0.108 Uiso 1 1 calc R . . 
H7B H 0.1994 0.6662 0.3493 0.108 Uiso 1 1 calc R . . 
H7C H 0.3672 0.5616 0.3318 0.108 Uiso 1 1 calc R . . 
C9 C 0.4264(4) 0.2352(2) 0.4065(2) 0.0492(7) Uani 1 1 d . . . 
C10 C 0.5559(4) 0.1675(3) 0.4752(2) 0.0487(7) Uani 1 1 d . . . 
C11 C 0.6890(4) 0.0767(3) 0.4413(2) 0.0513(7) Uani 1 1 d . . . 
H11 H 0.7743 0.0352 0.4863 0.062 Uiso 1 1 calc R . . 
C12 C 0.6994(4) 0.0453(2) 0.3416(2) 0.0507(7) Uani 1 1 d . . . 
C13 C 0.5727(4) 0.1079(3) 0.2702(2) 0.0491(7) Uani 1 1 d . . . 
C14 C 0.4423(4) 0.2029(3) 0.3055(2) 0.0499(7) Uani 1 1 d . . . 
H14 H 0.3612 0.2472 0.2587 0.060 Uiso 1 1 calc R . . 
C20 C 0.4389(4) 0.1244(3) 0.1053(2) 0.0531(7) Uani 1 1 d . . . 
C21 C 0.2486(5) 0.1292(3) 0.1536(3) 0.0652(9) Uani 1 1 d . . . 
H21 H 0.2096 0.1036 0.2315 0.078 Uiso 1 1 calc R . . 
C22 C 0.1179(5) 0.1714(3) 0.0876(3) 0.0721(9) Uani 1 1 d . . . 
H22 H -0.0093 0.1754 0.1205 0.087 Uiso 1 1 calc R . . 
C23 C 0.1769(5) 0.2080(3) -0.0288(3) 0.0731(10) Uani 1 1 d . . . 
H23 H 0.0892 0.2379 -0.0742 0.088 Uiso 1 1 calc R . . 
C24 C 0.3650(5) 0.1999(3) -0.0766(3) 0.0681(9) Uani 1 1 d . . . 
H24 H 0.4028 0.2217 -0.1549 0.082 Uiso 1 1 calc R . . 
C25 C 0.5000(5) 0.1604(3) -0.0122(2) 0.0579(8) Uani 1 1 d . . . 
C26 C 0.7048(5) 0.1547(4) -0.0662(3) 0.0804(11) Uani 1 1 d . . . 
H26A H 0.7197 0.1836 -0.1466 0.121 Uiso 1 1 calc R . . 
H26B H 0.7667 0.0729 -0.0492 0.121 Uiso 1 1 calc R . . 
H26C H 0.7591 0.2039 -0.0375 0.121 Uiso 1 1 calc R . . 
C80 C 0.491(2) 0.5078(18) 0.9625(10) 0.144(5) Uani 0.50 1 d PDU . . 
O81 O 0.634(3) 0.480(2) 1.0145(18) 0.271(9) Uani 0.50 1 d PDU . . 
C82 C 0.297(3) 0.4894(17) 1.0454(14) 0.197(9) Uani 0.50 1 d PDU . . 
C83 C 0.4807(19) 0.5409(14) 0.8556(8) 0.147(5) Uani 0.50 1 d PDU . . 
 
 
_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 
N1 C9 1.353(4) . ? 
N1 C6 1.423(4) . ? 
N2 O4 1.214(3) . ? 
N2 O3 1.238(3) . ? 
N2 C10 1.442(4) . ? 
N3 O1 1.216(3) . ? 
N3 O2 1.231(4) . ? 
N3 C12 1.449(4) . ? 
N4 C13 1.352(4) . ? 
N4 C20 1.419(4) . ? 
C1 C2 1.393(4) . ? 
C1 C6 1.395(4) . ? 
C1 C7 1.486(5) . ? 
C2 C3 1.377(5) . ? 
C3 C4 1.368(5) . ? 
C4 C5 1.382(4) . ? 
C5 C6 1.381(4) . ? 
C9 C14 1.394(4) . ? 
C9 C10 1.428(4) . ? 
C10 C11 1.368(4) . ? 
C11 C12 1.383(4) . ? 
C12 C13 1.422(4) . ? 
C13 C14 1.400(4) . ? 
C20 C21 1.389(4) . ? 
C20 C25 1.402(4) . ? 
C21 C22 1.370(5) . ? 
C22 C23 1.388(5) . ? 
C23 C24 1.372(5) . ? 
C24 C25 1.381(4) . ? 
C25 C26 1.500(5) . ? 
C80 O81 0.90(3) 2_667 ? 
C80 C80 0.95(3) 2_667 ? 
C80 C83 1.314(13) . ? 
C80 O81 1.331(14) . ? 
C80 C82 1.56(3) 2_667 ? 
C80 C82 1.571(17) . ? 
O81 C82 0.83(3) 2_667 ? 
O81 C80 0.90(3) 2_667 ? 
O81 C83 1.62(2) 2_667 ? 
C82 O81 0.83(3) 2_667 ? 
C82 C80 1.56(3) 2_667 ? 
C83 O81 1.62(2) 2_667 ? 
 
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 N1 C6 126.2(2) . . ? 
O4 N2 O3 121.2(3) . . ? 
O4 N2 C10 119.4(3) . . ? 
O3 N2 C10 119.3(3) . . ? 
O1 N3 O2 122.2(3) . . ? 
O1 N3 C12 118.5(3) . . ? 
O2 N3 C12 119.3(3) . . ? 
C13 N4 C20 126.6(3) . . ? 
C2 C1 C6 116.9(3) . . ? 
C2 C1 C7 121.4(3) . . ? 
C6 C1 C7 121.7(3) . . ? 
C3 C2 C1 121.7(3) . . ? 
C4 C3 C2 120.2(3) . . ? 
C3 C4 C5 119.7(3) . . ? 
C6 C5 C4 119.9(3) . . ? 
C5 C6 C1 121.4(3) . . ? 
C5 C6 N1 120.5(3) . . ? 
C1 C6 N1 118.0(3) . . ? 
N1 C9 C14 120.7(3) . . ? 
N1 C9 C10 122.7(3) . . ? 
C14 C9 C10 116.7(3) . . ? 
C11 C10 C9 120.7(3) . . ? 
C11 C10 N2 116.6(3) . . ? 
C9 C10 N2 122.7(3) . . ? 
C10 C11 C12 121.3(3) . . ? 
C11 C12 C13 120.8(3) . . ? 
C11 C12 N3 116.4(3) . . ? 
C13 C12 N3 122.9(3) . . ? 
N4 C13 C14 120.7(3) . . ? 
N4 C13 C12 122.9(3) . . ? 
C14 C13 C12 116.4(3) . . ? 
C9 C14 C13 124.1(3) . . ? 
C21 C20 C25 120.3(3) . . ? 
C21 C20 N4 121.1(3) . . ? 
C25 C20 N4 118.6(3) . . ? 
C22 C21 C20 120.6(3) . . ? 
C21 C22 C23 119.5(3) . . ? 
C24 C23 C22 119.8(3) . . ? 
C23 C24 C25 122.1(3) . . ? 
C24 C25 C20 117.6(3) . . ? 
C24 C25 C26 121.2(3) . . ? 
C20 C25 C26 121.2(3) . . ? 
O81 C80 C80 92(2) 2_667 2_667 ? 
O81 C80 C83 91.9(19) 2_667 . ? 
C80 C80 C83 172(3) 2_667 . ? 
O81 C80 O81 134.6(15) 2_667 . ? 
C80 C80 O81 42.6(17) 2_667 . ? 
C83 C80 O81 133.1(16) . . ? 
O81 C80 C82 160(3) 2_667 2_667 ? 
C80 C80 C82 73(2) 2_667 2_667 ? 
C83 C80 C82 101.8(12) . 2_667 ? 
O81 C80 C82 32.1(11) . 2_667 ? 
O81 C80 C82 23.8(17) 2_667 . ? 
C80 C80 C82 72(2) 2_667 . ? 
C83 C80 C82 113.2(13) . . ? 
O81 C80 C82 113.6(11) . . ? 
C82 C80 C82 144.8(10) 2_667 . ? 
C82 O81 C80 130(3) 2_667 2_667 ? 
C82 O81 C80 90(2) 2_667 . ? 
C80 O81 C80 45.4(15) 2_667 . ? 
C82 O81 C83 159(3) 2_667 2_667 ? 
C80 O81 C83 54.3(16) 2_667 2_667 ? 
C80 O81 C83 99.4(14) . 2_667 ? 
O81 C82 C80 58.3(18) 2_667 2_667 ? 
O81 C82 C80 26.0(19) 2_667 . ? 
C80 C82 C80 35.2(10) 2_667 . ? 
C80 C83 O81 33.8(10) . 2_667 ? 
 
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 C1 C2 C3 -1.5(5) . . . . ? 
C7 C1 C2 C3 178.4(3) . . . . ? 
C1 C2 C3 C4 1.0(5) . . . . ? 
C2 C3 C4 C5 0.9(5) . . . . ? 
C3 C4 C5 C6 -2.3(5) . . . . ? 
C4 C5 C6 C1 1.8(5) . . . . ? 
C4 C5 C6 N1 179.1(3) . . . . ? 
C2 C1 C6 C5 0.1(4) . . . . ? 
C7 C1 C6 C5 -179.8(3) . . . . ? 
C2 C1 C6 N1 -177.3(3) . . . . ? 
C7 C1 C6 N1 2.8(4) . . . . ? 
C9 N1 C6 C5 52.9(4) . . . . ? 
C9 N1 C6 C1 -129.7(3) . . . . ? 
C6 N1 C9 C14 8.5(5) . . . . ? 
C6 N1 C9 C10 -170.8(3) . . . . ? 
N1 C9 C10 C11 -179.9(3) . . . . ? 
C14 C9 C10 C11 0.7(4) . . . . ? 
N1 C9 C10 N2 0.9(4) . . . . ? 
C14 C9 C10 N2 -178.5(3) . . . . ? 
O4 N2 C10 C11 -6.6(4) . . . . ? 
O3 N2 C10 C11 174.4(3) . . . . ? 
O4 N2 C10 C9 172.6(3) . . . . ? 
O3 N2 C10 C9 -6.4(4) . . . . ? 
C9 C10 C11 C12 -1.8(4) . . . . ? 
N2 C10 C11 C12 177.4(2) . . . . ? 
C10 C11 C12 C13 0.8(4) . . . . ? 
C10 C11 C12 N3 -178.1(3) . . . . ? 
O1 N3 C12 C11 6.1(4) . . . . ? 
O2 N3 C12 C11 -176.6(3) . . . . ? 
O1 N3 C12 C13 -172.8(3) . . . . ? 
O2 N3 C12 C13 4.6(4) . . . . ? 
C20 N4 C13 C14 -10.1(5) . . . . ? 
C20 N4 C13 C12 170.1(3) . . . . ? 
C11 C12 C13 N4 -178.9(3) . . . . ? 
N3 C12 C13 N4 -0.1(4) . . . . ? 
C11 C12 C13 C14 1.3(4) . . . . ? 
N3 C12 C13 C14 -179.9(3) . . . . ? 
N1 C9 C14 C13 -177.9(3) . . . . ? 
C10 C9 C14 C13 1.5(4) . . . . ? 
N4 C13 C14 C9 177.7(3) . . . . ? 
C12 C13 C14 C9 -2.5(4) . . . . ? 
C13 N4 C20 C21 -46.7(5) . . . . ? 
C13 N4 C20 C25 135.4(3) . . . . ? 
C25 C20 C21 C22 -1.3(5) . . . . ? 
N4 C20 C21 C22 -179.1(3) . . . . ? 
C20 C21 C22 C23 0.9(6) . . . . ? 
C21 C22 C23 C24 1.0(6) . . . . ? 
C22 C23 C24 C25 -2.5(6) . . . . ? 
C23 C24 C25 C20 2.1(5) . . . . ? 
C23 C24 C25 C26 -178.7(4) . . . . ? 
C21 C20 C25 C24 -0.2(5) . . . . ? 
N4 C20 C25 C24 177.7(3) . . . . ? 
C21 C20 C25 C26 -179.4(3) . . . . ? 
N4 C20 C25 C26 -1.5(5) . . . . ? 
O81 C80 O81 C82 -156(6) 2_667 . . 2_667 ? 
C80 C80 O81 C82 -156(6) 2_667 . . 2_667 ? 
C83 C80 O81 C82 15(3) . . . 2_667 ? 
C82 C80 O81 C82 -170(2) . . . 2_667 ? 
O81 C80 O81 C80 0.000(4) 2_667 . . 2_667 ? 
C83 C80 O81 C80 171(5) . . . 2_667 ? 
C82 C80 O81 C80 156(6) 2_667 . . 2_667 ? 
C82 C80 O81 C80 -14(3) . . . 2_667 ? 
O81 C80 O81 C83 5(3) 2_667 . . 2_667 ? 
C80 C80 O81 C83 5(3) 2_667 . . 2_667 ? 
C83 C80 O81 C83 176.4(19) . . . 2_667 ? 
C82 C80 O81 C83 161(4) 2_667 . . 2_667 ? 
C82 C80 O81 C83 -8.2(16) . . . 2_667 ? 
C80 C80 C82 O81 146(8) 2_667 . . 2_667 ? 
C83 C80 C82 O81 -28(5) . . . 2_667 ? 
O81 C80 C82 O81 156(5) . . . 2_667 ? 
C82 C80 C82 O81 146(8) 2_667 . . 2_667 ? 
O81 C80 C82 C80 -146(8) 2_667 . . 2_667 ? 
C83 C80 C82 C80 -174(4) . . . 2_667 ? 
O81 C80 C82 C80 10(2) . . . 2_667 ? 
C82 C80 C82 C80 0.000(3) 2_667 . . 2_667 ? 
C80 C80 C83 O81 -121(24) 2_667 . . 2_667 ? 
O81 C80 C83 O81 -174(3) . . . 2_667 ? 
C82 C80 C83 O81 -166(4) 2_667 . . 2_667 ? 
C82 C80 C83 O81 11(2) . . . 2_667 ? 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              68.91 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.362 
_refine_diff_density_min   -0.350 
_refine_diff_density_rms    0.074 
