data_07074a 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             07074a 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C18 H17 N O6, 0.5(C4 H8 O2)'  
_chemical_formula_sum             'C20 H21 N O7' 
_chemical_formula_weight          387.38 
_chemical_absolute_configuration  rm
 
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   'C2   '
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z' 
 
_cell_length_a                    15.8983(19) 
_cell_length_b                    11.2009(13) 
_cell_length_c                    10.8406(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  103.385(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1878.0(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     2263
_cell_measurement_theta_min       2.63
_cell_measurement_theta_max       27.10
 
_exptl_crystal_description        Block 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.38 
_exptl_crystal_size_min           0.25 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.370 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     0.104 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.9496 
_exptl_absorpt_correction_T_max   0.9744 
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2003)' 
 
_exptl_special_details 'J. Antoline/Prof. R. Hsung -  University of Wisconsin'
 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  'graphite'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10967 
_diffrn_reflns_av_R_equivalents   0.0226 
_diffrn_reflns_av_sigmaI/netI     0.0141 
_diffrn_reflns_limit_h_min        -20 
_diffrn_reflns_limit_h_max        19 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          1.93 
_diffrn_reflns_theta_max          27.13 
_reflns_number_total              2191 
_reflns_number_gt                 2101 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'Bruker SHELXTL'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_molecular_graphics   'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
 
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.4917P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.3(8) 
_refine_ls_number_reflns          2191 
_refine_ls_number_parameters      283 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0292 
_refine_ls_R_factor_gt            0.0277 
_refine_ls_wR_factor_ref          0.0715 
_refine_ls_wR_factor_gt           0.0705 
_refine_ls_goodness_of_fit_ref    1.031 
_refine_ls_restrained_S_all       1.030 
_refine_ls_shift/su_max           0.003 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.31576(10) 0.57141(15) 0.26100(15) 0.0284(3) Uani 1 1 d . . . 
O1 O 0.33848(8) 0.49098(13) 0.17167(11) 0.0353(3) Uani 1 1 d . . . 
C2 C 0.42063(12) 0.44285(19) 0.23887(19) 0.0393(4) Uani 1 1 d . . . 
H2A H 0.4553 0.4112 0.1800 0.047 Uiso 1 1 calc R . . 
C3 C 0.46312(12) 0.54820(19) 0.31382(19) 0.0398(4) Uani 1 1 d . . . 
H3A H 0.5236 0.5591 0.3448 0.048 Uiso 1 1 calc R . . 
C4 C 0.40231(11) 0.62296(16) 0.32934(17) 0.0332(4) Uani 1 1 d . . . 
H4A H 0.4111 0.6960 0.3751 0.040 Uiso 1 1 calc R . . 
C5 C 0.40109(13) 0.34635(18) 0.3290(2) 0.0391(4) Uani 1 1 d . . . 
H5A H 0.3712 0.2784 0.2791 0.047 Uiso 1 1 calc R . . 
H5B H 0.4559 0.3166 0.3834 0.047 Uiso 1 1 calc R . . 
C6 C 0.34444(11) 0.39751(15) 0.41165(16) 0.0302(3) Uani 1 1 d . . . 
O2 O 0.35248(9) 0.36944(12) 0.52120(12) 0.0382(3) Uani 1 1 d . . . 
C7 C 0.27453(10) 0.48733(15) 0.34667(15) 0.0259(3) Uani 1 1 d . . . 
H7A H 0.2303 0.4390 0.2867 0.031 Uiso 1 1 calc R . . 
C8 C 0.24999(11) 0.65983(17) 0.18774(16) 0.0322(4) Uani 1 1 d . . . 
O3 O 0.20090(11) 0.63705(16) 0.09015(15) 0.0598(5) Uani 1 1 d . . . 
O4 O 0.25427(10) 0.76329(13) 0.24689(15) 0.0482(4) Uani 1 1 d . . . 
C9 C 0.19452(17) 0.8548(2) 0.1835(2) 0.0567(6) Uani 1 1 d . . . 
H9A H 0.1943 0.9216 0.2417 0.085 Uiso 1 1 calc R . . 
H9B H 0.1362 0.8210 0.1579 0.085 Uiso 1 1 calc R . . 
H9C H 0.2129 0.8832 0.1084 0.085 Uiso 1 1 calc R . . 
N1 N 0.22900(8) 0.54167(13) 0.43345(13) 0.0259(3) Uani 1 1 d . . . 
C10 C 0.26953(10) 0.60434(15) 0.53841(15) 0.0281(3) Uani 1 1 d . . . 
O5 O 0.33946(8) 0.65074(13) 0.56034(12) 0.0378(3) Uani 1 1 d . . . 
O6 O 0.21729(7) 0.61065(12) 0.62143(11) 0.0337(3) Uani 1 1 d . . . 
C11 C 0.13498(11) 0.5561(2) 0.56525(17) 0.0368(4) Uani 1 1 d . . . 
H11A H 0.0903 0.6179 0.5354 0.044 Uiso 1 1 calc R . . 
H11B H 0.1158 0.5042 0.6274 0.044 Uiso 1 1 calc R . . 
C12 C 0.15070(10) 0.48248(16) 0.45359(15) 0.0265(3) Uani 1 1 d . . . 
H12A H 0.1638 0.3977 0.4802 0.032 Uiso 1 1 calc R . . 
C13 C 0.07591(10) 0.48748(15) 0.33862(14) 0.0252(3) Uani 1 1 d . . . 
C14 C 0.03015(11) 0.38392(16) 0.29655(16) 0.0294(3) Uani 1 1 d . . . 
H14A H 0.0465 0.3104 0.3391 0.035 Uiso 1 1 calc R . . 
C15 C -0.04000(12) 0.38797(18) 0.19164(17) 0.0359(4) Uani 1 1 d . . . 
H15A H -0.0715 0.3172 0.1634 0.043 Uiso 1 1 calc R . . 
C16 C -0.06359(12) 0.4940(2) 0.12910(16) 0.0380(4) Uani 1 1 d . . . 
H16A H -0.1113 0.4963 0.0577 0.046 Uiso 1 1 calc R . . 
C17 C -0.01768(12) 0.59763(18) 0.17029(17) 0.0368(4) Uani 1 1 d . . . 
H17A H -0.0336 0.6706 0.1264 0.044 Uiso 1 1 calc R . . 
C18 C 0.05148(11) 0.59492(16) 0.27534(17) 0.0319(4) Uani 1 1 d . . . 
H18A H 0.0822 0.6662 0.3041 0.038 Uiso 1 1 calc R . . 
C19 C 0.5378(3) 0.6020(5) 1.0306(4) 0.0449(10) Uani 0.50 1 d P A -1 
C20 C 0.6222(13) 0.6640(14) 1.0940(16) 0.056(4) Uani 0.50 1 d P A -1 
H20A H 0.6707 0.6232 1.0703 0.084 Uiso 0.50 1 calc PR A -1 
H20B H 0.6298 0.6611 1.1863 0.084 Uiso 0.50 1 calc PR A -1 
H20C H 0.6203 0.7473 1.0661 0.084 Uiso 0.50 1 calc PR A -1 
O7 O 0.5264(2) 0.4951(3) 1.0253(4) 0.0572(11) Uani 0.50 1 d P A -1 
O8 O 0.47616(19) 0.6813(3) 0.9817(3) 0.0441(8) Uani 0.50 1 d P A -1 
C21 C 0.3924(12) 0.6348(13) 0.9206(14) 0.040(2) Uani 0.50 1 d P A -1 
H21A H 0.3737 0.5747 0.9757 0.048 Uiso 0.50 1 calc PR A -1 
H21B H 0.3950 0.5960 0.8395 0.048 Uiso 0.50 1 calc PR A -1 
C22 C 0.3297(3) 0.7370(6) 0.8966(5) 0.0543(12) Uani 0.50 1 d P A -1 
H22A H 0.2731 0.7084 0.8494 0.081 Uiso 0.50 1 calc PR A -1 
H22B H 0.3508 0.7986 0.8470 0.081 Uiso 0.50 1 calc PR A -1 
H22C H 0.3242 0.7709 0.9777 0.081 Uiso 0.50 1 calc PR A -1 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
C1 0.0292(8) 0.0283(8) 0.0297(8) -0.0010(6) 0.0108(6) -0.0019(6) 
O1 0.0389(6) 0.0371(7) 0.0345(6) -0.0013(6) 0.0178(5) 0.0024(6) 
C2 0.0377(9) 0.0386(9) 0.0502(11) 0.0097(9) 0.0274(8) 0.0089(8) 
C3 0.0282(8) 0.0434(10) 0.0504(11) 0.0156(9) 0.0144(7) -0.0011(8) 
C4 0.0292(8) 0.0319(9) 0.0382(9) 0.0076(7) 0.0075(7) -0.0062(7) 
C5 0.0416(10) 0.0321(9) 0.0508(11) 0.0059(8) 0.0253(9) 0.0078(8) 
C6 0.0305(8) 0.0244(8) 0.0387(9) -0.0009(7) 0.0145(7) -0.0026(7) 
O2 0.0417(7) 0.0382(7) 0.0369(7) 0.0053(6) 0.0135(5) 0.0044(6) 
C7 0.0250(7) 0.0245(7) 0.0299(7) -0.0037(7) 0.0100(6) -0.0041(6) 
C8 0.0302(8) 0.0352(9) 0.0320(8) 0.0007(7) 0.0086(7) -0.0023(7) 
O3 0.0599(9) 0.0564(10) 0.0487(9) -0.0089(8) -0.0167(7) 0.0085(8) 
O4 0.0544(9) 0.0351(7) 0.0466(8) -0.0054(6) -0.0059(7) 0.0130(7) 
C9 0.0635(14) 0.0406(12) 0.0588(13) 0.0051(11) -0.0004(11) 0.0182(11) 
N1 0.0234(6) 0.0274(7) 0.0279(6) -0.0046(6) 0.0081(5) -0.0029(5) 
C10 0.0279(8) 0.0267(8) 0.0292(8) -0.0032(7) 0.0056(6) 0.0014(7) 
O5 0.0294(6) 0.0389(7) 0.0428(7) -0.0111(6) 0.0039(5) -0.0073(6) 
O6 0.0299(6) 0.0430(7) 0.0280(6) -0.0091(5) 0.0062(4) -0.0004(5) 
C11 0.0309(8) 0.0500(11) 0.0321(8) -0.0085(8) 0.0130(7) -0.0048(8) 
C12 0.0244(7) 0.0266(8) 0.0297(7) -0.0001(7) 0.0085(6) -0.0022(6) 
C13 0.0226(7) 0.0272(7) 0.0279(7) -0.0008(7) 0.0104(6) 0.0010(6) 
C14 0.0302(8) 0.0273(8) 0.0308(8) 0.0001(7) 0.0074(6) 0.0010(7) 
C15 0.0355(9) 0.0374(9) 0.0324(8) -0.0059(8) 0.0029(7) -0.0026(8) 
C16 0.0344(9) 0.0493(11) 0.0278(8) 0.0011(8) 0.0022(7) 0.0053(8) 
C17 0.0394(9) 0.0365(9) 0.0362(9) 0.0111(8) 0.0120(7) 0.0104(8) 
C18 0.0335(8) 0.0276(8) 0.0370(8) 0.0010(7) 0.0129(7) 0.0001(7) 
C19 0.063(3) 0.047(3) 0.0309(19) 0.0073(19) 0.0228(18) 0.018(2) 
C20 0.056(7) 0.071(10) 0.040(4) 0.001(5) 0.005(4) 0.020(7) 
O7 0.077(3) 0.0430(15) 0.065(3) 0.0186(17) 0.043(2) 0.0178(15) 
O8 0.053(2) 0.0383(15) 0.0364(19) 0.0061(14) 0.0013(16) 0.0030(13) 
C21 0.052(6) 0.038(4) 0.029(4) -0.003(3) 0.007(4) -0.005(3) 
C22 0.047(2) 0.070(4) 0.040(2) 0.008(2) -0.0017(19) -0.001(3) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 O1 1.429(2) . ? 
C1 C4 1.518(2) . ? 
C1 C8 1.523(2) . ? 
C1 C7 1.569(2) . ? 
O1 C2 1.445(2) . ? 
C2 C3 1.502(3) . ? 
C2 C5 1.537(3) . ? 
C2 H2A 1.0000 . ? 
C3 C4 1.319(3) . ? 
C3 H3A 0.9500 . ? 
C4 H4A 0.9500 . ? 
C5 C6 1.522(2) . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 O2 1.206(2) . ? 
C6 C7 1.543(2) . ? 
C7 N1 1.447(2) . ? 
C7 H7A 1.0000 . ? 
C8 O3 1.188(2) . ? 
C8 O4 1.319(2) . ? 
O4 C9 1.457(2) . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
N1 C10 1.365(2) . ? 
N1 C12 1.471(2) . ? 
C10 O5 1.200(2) . ? 
C10 O6 1.361(2) . ? 
O6 C11 1.445(2) . ? 
C11 C12 1.532(2) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C13 1.511(2) . ? 
C12 H12A 1.0000 . ? 
C13 C14 1.389(2) . ? 
C13 C18 1.395(2) . ? 
C14 C15 1.397(2) . ? 
C14 H14A 0.9500 . ? 
C15 C16 1.376(3) . ? 
C15 H15A 0.9500 . ? 
C16 C17 1.389(3) . ? 
C16 H16A 0.9500 . ? 
C17 C18 1.388(3) . ? 
C17 H17A 0.9500 . ? 
C18 H18A 0.9500 . ? 
C19 O7 1.211(6) . ? 
C19 O8 1.337(5) . ? 
C19 C20 1.526(15) . ? 
C20 H20A 0.9800 . ? 
C20 H20B 0.9800 . ? 
C20 H20C 0.9800 . ? 
O8 C21 1.44(2) . ? 
C21 C22 1.501(12) . ? 
C21 H21A 0.9900 . ? 
C21 H21B 0.9900 . ? 
C22 H22A 0.9800 . ? 
C22 H22B 0.9800 . ? 
C22 H22C 0.9800 . ? 
 
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 
O1 C1 C4 103.17(13) . . ? 
O1 C1 C8 107.90(13) . . ? 
C4 C1 C8 116.26(14) . . ? 
O1 C1 C7 103.21(13) . . ? 
C4 C1 C7 113.28(13) . . ? 
C8 C1 C7 111.63(13) . . ? 
C1 O1 C2 103.56(13) . . ? 
O1 C2 C3 102.75(15) . . ? 
O1 C2 C5 106.92(14) . . ? 
C3 C2 C5 109.90(16) . . ? 
O1 C2 H2A 112.2 . . ? 
C3 C2 H2A 112.2 . . ? 
C5 C2 H2A 112.2 . . ? 
C4 C3 C2 108.46(16) . . ? 
C4 C3 H3A 125.8 . . ? 
C2 C3 H3A 125.8 . . ? 
C3 C4 C1 107.74(17) . . ? 
C3 C4 H4A 126.1 . . ? 
C1 C4 H4A 126.1 . . ? 
C6 C5 C2 110.12(15) . . ? 
C6 C5 H5A 109.6 . . ? 
C2 C5 H5A 109.6 . . ? 
C6 C5 H5B 109.6 . . ? 
C2 C5 H5B 109.6 . . ? 
H5A C5 H5B 108.2 . . ? 
O2 C6 C5 122.62(17) . . ? 
O2 C6 C7 121.35(15) . . ? 
C5 C6 C7 116.02(14) . . ? 
N1 C7 C6 113.15(13) . . ? 
N1 C7 C1 118.21(14) . . ? 
C6 C7 C1 107.83(12) . . ? 
N1 C7 H7A 105.5 . . ? 
C6 C7 H7A 105.5 . . ? 
C1 C7 H7A 105.5 . . ? 
O3 C8 O4 124.83(18) . . ? 
O3 C8 C1 123.70(18) . . ? 
O4 C8 C1 111.47(14) . . ? 
C8 O4 C9 115.73(16) . . ? 
O4 C9 H9A 109.5 . . ? 
O4 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
O4 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C10 N1 C7 123.19(12) . . ? 
C10 N1 C12 111.14(13) . . ? 
C7 N1 C12 118.35(13) . . ? 
O5 C10 O6 121.72(15) . . ? 
O5 C10 N1 128.67(15) . . ? 
O6 C10 N1 109.60(13) . . ? 
C10 O6 C11 109.34(12) . . ? 
O6 C11 C12 105.25(13) . . ? 
O6 C11 H11A 110.7 . . ? 
C12 C11 H11A 110.7 . . ? 
O6 C11 H11B 110.7 . . ? 
C12 C11 H11B 110.7 . . ? 
H11A C11 H11B 108.8 . . ? 
N1 C12 C13 113.10(13) . . ? 
N1 C12 C11 99.96(13) . . ? 
C13 C12 C11 112.98(14) . . ? 
N1 C12 H12A 110.1 . . ? 
C13 C12 H12A 110.1 . . ? 
C11 C12 H12A 110.1 . . ? 
C14 C13 C18 119.60(14) . . ? 
C14 C13 C12 119.48(15) . . ? 
C18 C13 C12 120.91(15) . . ? 
C13 C14 C15 119.93(16) . . ? 
C13 C14 H14A 120.0 . . ? 
C15 C14 H14A 120.0 . . ? 
C16 C15 C14 120.28(17) . . ? 
C16 C15 H15A 119.9 . . ? 
C14 C15 H15A 119.9 . . ? 
C15 C16 C17 120.00(15) . . ? 
C15 C16 H16A 120.0 . . ? 
C17 C16 H16A 120.0 . . ? 
C18 C17 C16 120.20(17) . . ? 
C18 C17 H17A 119.9 . . ? 
C16 C17 H17A 119.9 . . ? 
C17 C18 C13 119.98(17) . . ? 
C17 C18 H18A 120.0 . . ? 
C13 C18 H18A 120.0 . . ? 
O7 C19 O8 123.3(5) . . ? 
O7 C19 C20 125.3(8) . . ? 
O8 C19 C20 111.4(8) . . ? 
C19 O8 C21 117.2(6) . . ? 
O8 C21 C22 108.1(10) . . ? 
O8 C21 H21A 110.1 . . ? 
C22 C21 H21A 110.1 . . ? 
O8 C21 H21B 110.1 . . ? 
C22 C21 H21B 110.1 . . ? 
H21A C21 H21B 108.4 . . ? 
 
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 
C4 C1 O1 C2 35.64(16) . . . . ? 
C8 C1 O1 C2 159.22(13) . . . . ? 
C7 C1 O1 C2 -82.51(15) . . . . ? 
C1 O1 C2 C3 -36.60(16) . . . . ? 
C1 O1 C2 C5 79.10(18) . . . . ? 
O1 C2 C3 C4 23.81(19) . . . . ? 
C5 C2 C3 C4 -89.71(18) . . . . ? 
C2 C3 C4 C1 -1.7(2) . . . . ? 
O1 C1 C4 C3 -21.32(18) . . . . ? 
C8 C1 C4 C3 -139.18(16) . . . . ? 
C7 C1 C4 C3 89.54(18) . . . . ? 
O1 C2 C5 C6 -53.6(2) . . . . ? 
C3 C2 C5 C6 57.2(2) . . . . ? 
C2 C5 C6 O2 -143.19(19) . . . . ? 
C2 C5 C6 C7 37.5(2) . . . . ? 
O2 C6 C7 N1 6.6(2) . . . . ? 
C5 C6 C7 N1 -174.01(15) . . . . ? 
O2 C6 C7 C1 139.30(16) . . . . ? 
C5 C6 C7 C1 -41.35(19) . . . . ? 
O1 C1 C7 N1 -168.46(13) . . . . ? 
C4 C1 C7 N1 80.70(18) . . . . ? 
C8 C1 C7 N1 -52.83(18) . . . . ? 
O1 C1 C7 C6 61.65(15) . . . . ? 
C4 C1 C7 C6 -49.19(18) . . . . ? 
C8 C1 C7 C6 177.29(13) . . . . ? 
O1 C1 C8 O3 29.0(2) . . . . ? 
C4 C1 C8 O3 144.24(19) . . . . ? 
C7 C1 C8 O3 -83.7(2) . . . . ? 
O1 C1 C8 O4 -151.54(15) . . . . ? 
C4 C1 C8 O4 -36.3(2) . . . . ? 
C7 C1 C8 O4 95.73(17) . . . . ? 
O3 C8 O4 C9 -1.3(3) . . . . ? 
C1 C8 O4 C9 179.25(18) . . . . ? 
C6 C7 N1 C10 57.7(2) . . . . ? 
C1 C7 N1 C10 -69.7(2) . . . . ? 
C6 C7 N1 C12 -89.76(16) . . . . ? 
C1 C7 N1 C12 142.84(14) . . . . ? 
C7 N1 C10 O5 20.8(3) . . . . ? 
C12 N1 C10 O5 170.23(18) . . . . ? 
C7 N1 C10 O6 -160.25(14) . . . . ? 
C12 N1 C10 O6 -10.79(18) . . . . ? 
O5 C10 O6 C11 175.01(17) . . . . ? 
N1 C10 O6 C11 -4.05(19) . . . . ? 
C10 O6 C11 C12 16.3(2) . . . . ? 
C10 N1 C12 C13 139.91(15) . . . . ? 
C7 N1 C12 C13 -68.98(19) . . . . ? 
C10 N1 C12 C11 19.52(17) . . . . ? 
C7 N1 C12 C11 170.63(14) . . . . ? 
O6 C11 C12 N1 -20.72(18) . . . . ? 
O6 C11 C12 C13 -141.20(15) . . . . ? 
N1 C12 C13 C14 131.61(15) . . . . ? 
C11 C12 C13 C14 -115.74(17) . . . . ? 
N1 C12 C13 C18 -49.3(2) . . . . ? 
C11 C12 C13 C18 63.4(2) . . . . ? 
C18 C13 C14 C15 -0.2(2) . . . . ? 
C12 C13 C14 C15 178.94(15) . . . . ? 
C13 C14 C15 C16 0.5(3) . . . . ? 
C14 C15 C16 C17 -0.1(3) . . . . ? 
C15 C16 C17 C18 -0.7(3) . . . . ? 
C16 C17 C18 C13 1.0(3) . . . . ? 
C14 C13 C18 C17 -0.6(2) . . . . ? 
C12 C13 C18 C17 -179.69(15) . . . . ? 
O7 C19 O8 C21 0.3(9) . . . . ? 
C20 C19 O8 C21 -179.0(14) . . . . ? 
C19 O8 C21 C22 168.8(6) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              27.13 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.152 
_refine_diff_density_min   -0.151 
_refine_diff_density_rms    0.030