# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 1999# CCDC Number: 188/196

 
data_a1140 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          'C21 H32 N2 O6' 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C21 H32 N2 O6' 
_chemical_formula_weight          408.49 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
  
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' 
 'O'  'O'   0.0492   0.0322 
 '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' 
  
_symmetry_cell_setting            orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21' 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
  
_cell_length_a                    13.288(4) 
_cell_length_b                    27.298(5) 
_cell_length_c                    6.235(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2261.7(22) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     13 
_cell_measurement_theta_min       31.5 
_cell_measurement_theta_max       45.6 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             transp. 
_exptl_crystal_size_max           1.000 
_exptl_crystal_size_mid           0.500 
_exptl_crystal_size_min           0.250 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.200 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              880 
_exptl_absorpt_coefficient_mu     0.721 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        AFC6S 
_diffrn_measurement_method        'omega/2-theta scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  150 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         -0.47 
_diffrn_reflns_number             2658 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0524 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        34 
_diffrn_reflns_limit_l_min        -7 
_diffrn_reflns_limit_l_max        7 
_diffrn_reflns_theta_min          3.24 
_diffrn_reflns_theta_max          75.11 
_reflns_number_total              2658 
_reflns_number_observed           1466 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'MSC/AFC Diffractometer Control' 
_computing_cell_refinement        'MSC/AFC Diffractometer Control' 
_computing_data_reduction         teXsan 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   teXsan 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+1.2569P] 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     noref 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0027(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.04(69) 
_refine_ls_number_reflns          2656 
_refine_ls_number_parameters      271 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1175 
_refine_ls_R_factor_obs           0.0562 
_refine_ls_wR_factor_all          0.1918 
_refine_ls_wR_factor_obs          0.1502 
_refine_ls_goodness_of_fit_all    1.064 
_refine_ls_goodness_of_fit_obs    1.173 
_refine_ls_restrained_S_all       1.069 
_refine_ls_restrained_S_obs       1.173 
_refine_ls_shift/esd_max          0.044 
_refine_ls_shift/esd_mean         0.004 
  
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1 O 0.2183(3) 0.19646(14) 0.4053(7) 0.0613(11) Uani 1 d . . 
O1A O 0.6798(3) 0.23857(13) 0.2763(6) 0.0570(10) Uani 1 d . . 
H1AO H 0.7006(40) 0.2560(15) 0.3738(15) 0.085 Uiso 1 calc R . 
O2A O 0.4114(3) 0.1689(2) 0.4681(6) 0.0620(11) Uani 1 d . . 
H2AO H 0.3534(27) 0.1774(38) 0.4429(30) 0.193(53) Uiso 1 calc R . 
O2 O 0.1078(3) 0.23615(14) 0.2088(6) 0.0664(12) Uani 1 d . . 
O3A O 0.8801(5) 0.0067(2) 0.4369(19) 0.154(4) Uani 1 d . . 
O4A O 0.8380(6) 0.0156(3) 0.7583(19) 0.153(4) Uani 1 d . . 
N1A N 0.4880(3) 0.2375(2) 0.1122(7) 0.0538(11) Uani 1 d . . 
H1AN H 0.5384(3) 0.2529(2) 0.0399(7) 0.055(7) Uiso 1 calc R . 
N2A N 0.8378(6) 0.0286(2) 0.5772(20) 0.105(3) Uani 1 d . . 
C1 C 0.1635(4) 0.1613(2) 0.0763(8) 0.0443(11) Uani 1 d . . 
H1 H 0.1585(4) 0.1736(2) -0.0709(8) 0.055(7) Uiso 1 calc R . 
C1A C 0.6150(4) 0.2019(2) 0.3619(9) 0.0477(13) Uani 1 d . . 
H1A H 0.5830(4) 0.2145(2) 0.4924(9) 0.055(7) Uiso 1 calc R . 
C2A C 0.5337(4) 0.1904(2) 0.1959(9) 0.0489(13) Uani 1 d . . 
H2A H 0.5681(4) 0.1751(2) 0.0742(9) 0.055(7) Uiso 1 calc R . 
C2 C 0.1046(4) 0.1140(2) 0.1153(9) 0.0459(12) Uani 1 d . . 
C3A C 0.4579(4) 0.1537(2) 0.2762(10) 0.0539(14) Uani 1 d . . 
H3A1 H 0.4068(4) 0.1488(2) 0.1672(10) 0.060(12) Uiso 1 calc R . 
H3A2 H 0.4913(4) 0.1226(2) 0.3000(10) 0.060(12) Uiso 1 calc R . 
C3 C 0.2182(4) 0.1127(2) 0.0946(9) 0.0453(12) Uani 1 d . . 
H3 H 0.2537(4) 0.1080(2) 0.2309(9) 0.055(7) Uiso 1 calc R . 
C4A C 0.6732(4) 0.1561(2) 0.4154(10) 0.0546(14) Uani 1 d . . 
C4 C 0.1646(4) 0.2003(2) 0.2420(9) 0.0453(11) Uani 1 d . . 
C5A C 0.7373(5) 0.1349(2) 0.2616(13) 0.075(2) Uani 1 d . . 
H5A H 0.7450(5) 0.1493(2) 0.1273(13) 0.081(10) Uiso 1 calc R . 
C5 C 0.0607(4) 0.1074(2) 0.3364(9) 0.061(2) Uani 1 d . . 
H5B H 0.1056(4) 0.1210(2) 0.4410(9) 0.137(8) Uiso 1 calc R . 
H5C H 0.0516(4) 0.0731(2) 0.3645(9) 0.137(8) Uiso 1 calc R . 
H5D H -0.0032(4) 0.1237(2) 0.3444(9) 0.137(8) Uiso 1 calc R . 
C6A C 0.7896(5) 0.0917(3) 0.3138(18) 0.096(3) Uani 1 d . . 
H6A H 0.8300(5) 0.0760(3) 0.2133(18) 0.081(10) Uiso 1 calc R . 
C6 C 0.0409(5) 0.0941(2) -0.0613(10) 0.066(2) Uani 1 d . . 
H6B H 0.0736(5) 0.0996(2) -0.1964(10) 0.137(8) Uiso 1 calc R . 
H6C H -0.0233(5) 0.1102(2) -0.0606(10) 0.137(8) Uiso 1 calc R . 
H6D H 0.0315(5) 0.0595(2) -0.0405(10) 0.137(8) Uiso 1 calc R . 
C7A C 0.7789(5) 0.0728(3) 0.5250(16) 0.077(2) Uani 1 d . . 
C7 C 0.2721(4) 0.0935(2) -0.0920(9) 0.0494(13) Uani 1 d . . 
H7 H 0.2598(4) 0.1090(2) -0.2223(9) 0.081(10) Uiso 1 calc R . 
C8A C 0.7161(7) 0.0926(3) 0.6631(14) 0.094(2) Uani 1 d . . 
H8A H 0.7067(7) 0.0781(3) 0.7966(14) 0.081(10) Uiso 1 calc R . 
C8 C 0.3368(4) 0.0564(2) -0.0947(9) 0.0513(13) Uani 1 d . . 
C9A C 0.6645(6) 0.1342(2) 0.6119(11) 0.080(2) Uani 1 d . . 
H9A H 0.6222(6) 0.1482(2) 0.7137(11) 0.081(10) Uiso 1 calc R . 
C9 C 0.3608(6) 0.0256(2) 0.0957(12) 0.079(2) Uani 1 d . . 
H9B H 0.4093(6) 0.0011(2) 0.0564(12) 0.137(8) Uiso 1 calc R . 
H9C H 0.3006(6) 0.0099(2) 0.1462(12) 0.137(8) Uiso 1 calc R . 
H9D H 0.3881(6) 0.0458(2) 0.2074(12) 0.137(8) Uiso 1 calc R . 
C10A C 0.4545(5) 0.2726(2) 0.2773(11) 0.071(2) Uani 1 d . . 
H10A H 0.5074(5) 0.2775(2) 0.3798(11) 0.137(8) Uiso 1 calc R . 
H10B H 0.3961(5) 0.2599(2) 0.3489(11) 0.137(8) Uiso 1 calc R . 
H10C H 0.4380(5) 0.3033(2) 0.2106(11) 0.137(8) Uiso 1 calc R . 
C10 C 0.3911(6) 0.0421(3) -0.2988(12) 0.081(2) Uani 1 d . . 
H10D H 0.4344(6) 0.0147(3) -0.2707(12) 0.137(8) Uiso 1 calc R . 
H10E H 0.4306(6) 0.0692(3) -0.3487(12) 0.137(8) Uiso 1 calc R . 
H10F H 0.3427(6) 0.0332(3) -0.4064(12) 0.137(8) Uiso 1 calc R . 
C11A C 0.4061(5) 0.2292(3) -0.0505(11) 0.080(2) Uani 1 d . . 
H11A H 0.4290(5) 0.2063(3) -0.1566(11) 0.137(8) Uiso 1 calc R . 
H11B H 0.3895(5) 0.2597(3) -0.1184(11) 0.137(8) Uiso 1 calc R . 
H11C H 0.3476(5) 0.2163(3) 0.0199(11) 0.137(8) Uiso 1 calc R . 
  
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 
O1 0.060(2) 0.069(2) 0.055(2) -0.022(2) -0.019(2) 0.022(2) 
O1A 0.060(2) 0.058(2) 0.052(2) -0.006(2) 0.001(2) -0.019(2) 
O2A 0.047(2) 0.081(3) 0.059(3) 0.012(2) 0.006(2) -0.002(2) 
O2 0.083(3) 0.064(2) 0.052(2) -0.011(2) -0.011(2) 0.031(2) 
O3A 0.088(4) 0.095(4) 0.279(12) -0.038(6) -0.007(6) 0.035(3) 
O4A 0.109(5) 0.112(5) 0.237(11) 0.074(7) 0.012(7) 0.027(4) 
N1A 0.051(2) 0.065(3) 0.045(2) 0.005(3) 0.002(2) -0.012(2) 
N2A 0.065(4) 0.062(4) 0.188(9) 0.019(5) -0.003(6) 0.003(3) 
C1 0.053(3) 0.041(2) 0.038(3) 0.003(2) 0.004(3) 0.003(2) 
C1A 0.046(3) 0.047(3) 0.050(3) -0.005(2) 0.004(3) -0.010(2) 
C2A 0.050(3) 0.053(3) 0.043(3) -0.004(3) 0.007(3) -0.005(2) 
C2 0.048(3) 0.046(3) 0.044(3) 0.000(3) -0.001(3) -0.001(2) 
C3A 0.049(3) 0.055(3) 0.057(3) -0.005(3) 0.001(3) -0.010(3) 
C3 0.055(3) 0.041(2) 0.040(3) -0.002(2) -0.001(3) 0.008(2) 
C4A 0.047(3) 0.047(3) 0.069(4) -0.010(3) 0.000(3) -0.009(2) 
C4 0.041(2) 0.048(3) 0.047(3) -0.002(2) 0.004(3) 0.007(2) 
C5A 0.065(4) 0.074(4) 0.087(5) -0.002(4) 0.023(4) 0.002(3) 
C5 0.064(4) 0.067(4) 0.052(3) 0.006(3) 0.015(3) -0.007(3) 
C6A 0.053(4) 0.091(5) 0.145(9) -0.043(6) 0.013(5) 0.007(4) 
C6 0.071(4) 0.066(4) 0.060(4) 0.001(3) -0.005(3) -0.007(3) 
C7A 0.055(4) 0.069(4) 0.106(6) -0.005(4) -0.004(4) 0.001(3) 
C7 0.066(3) 0.045(3) 0.037(3) -0.008(2) 0.004(3) 0.003(3) 
C8A 0.121(6) 0.076(5) 0.084(5) 0.020(4) 0.010(5) 0.022(5) 
C8 0.062(3) 0.048(3) 0.044(3) -0.008(2) 0.008(3) 0.004(3) 
C9A 0.107(5) 0.077(4) 0.057(4) 0.007(4) 0.019(4) 0.026(4) 
C9 0.097(5) 0.067(4) 0.072(4) 0.002(4) 0.012(4) 0.026(4) 
C10A 0.086(4) 0.060(3) 0.066(4) 0.002(3) 0.012(4) 0.012(3) 
C10 0.101(5) 0.076(4) 0.067(4) -0.013(4) 0.021(4) 0.018(4) 
C11A 0.057(3) 0.119(6) 0.064(4) 0.016(4) -0.010(3) -0.025(4) 
  
_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 C4 1.248(6) . ? 
O1A C1A 1.423(6) . ? 
O2A C3A 1.409(7) . ? 
O2 C4 1.254(6) . ? 
O3A N2A 1.199(12) . ? 
O4A N2A 1.183(12) . ? 
N1A C10A 1.476(7) . ? 
N1A C11A 1.505(7) . ? 
N1A C2A 1.513(7) . ? 
N2A C7A 1.476(10) . ? 
C1 C4 1.484(7) . ? 
C1 C3 1.517(6) . ? 
C1 C2 1.528(7) . ? 
C1A C4A 1.508(7) . ? 
C1A C2A 1.528(7) . ? 
C2A C3A 1.506(7) . ? 
C2 C6 1.492(8) . ? 
C2 C5 1.509(8) . ? 
C2 C3 1.516(7) . ? 
C3 C7 1.462(7) . ? 
C4A C9A 1.368(9) . ? 
C4A C5A 1.408(9) . ? 
C5A C6A 1.408(10) . ? 
C6A C7A 1.421(12) . ? 
C7A C8A 1.315(10) . ? 
C7 C8 1.330(7) . ? 
C8A C9A 1.365(9) . ? 
C8 C9 1.490(9) . ? 
C8 C10 1.514(8) . ? 
  
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 
C10A N1A C11A 110.4(5) . . ? 
C10A N1A C2A 115.6(5) . . ? 
C11A N1A C2A 113.2(5) . . ? 
O4A N2A O3A 123.1(9) . . ? 
O4A N2A C7A 117.1(10) . . ? 
O3A N2A C7A 119.7(11) . . ? 
C4 C1 C3 124.8(4) . . ? 
C4 C1 C2 120.0(4) . . ? 
C3 C1 C2 59.7(3) . . ? 
O1A C1A C4A 110.8(4) . . ? 
O1A C1A C2A 108.5(4) . . ? 
C4A C1A C2A 110.0(4) . . ? 
C3A C2A N1A 114.2(4) . . ? 
C3A C2A C1A 112.6(5) . . ? 
N1A C2A C1A 110.0(4) . . ? 
C6 C2 C5 114.3(5) . . ? 
C6 C2 C3 119.6(5) . . ? 
C5 C2 C3 117.4(5) . . ? 
C6 C2 C1 118.8(5) . . ? 
C5 C2 C1 116.5(5) . . ? 
C3 C2 C1 59.8(3) . . ? 
O2A C3A C2A 112.4(4) . . ? 
C7 C3 C2 124.3(5) . . ? 
C7 C3 C1 119.1(5) . . ? 
C2 C3 C1 60.5(3) . . ? 
C9A C4A C5A 118.8(6) . . ? 
C9A C4A C1A 121.2(6) . . ? 
C5A C4A C1A 120.1(6) . . ? 
O1 C4 O2 123.0(5) . . ? 
O1 C4 C1 120.9(4) . . ? 
O2 C4 C1 116.1(5) . . ? 
C6A C5A C4A 119.1(8) . . ? 
C5A C6A C7A 117.9(8) . . ? 
C8A C7A C6A 121.5(7) . . ? 
C8A C7A N2A 121.9(9) . . ? 
C6A C7A N2A 116.6(9) . . ? 
C8 C7 C3 126.8(5) . . ? 
C7A C8A C9A 120.5(8) . . ? 
C7 C8 C9 124.0(5) . . ? 
C7 C8 C10 121.0(5) . . ? 
C9 C8 C10 114.9(5) . . ? 
C8A C9A C4A 122.1(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 
 C10A N1A C2A C3A 77.4(6) . . . . ? 
 C11A N1A C2A C3A -51.5(6) . . . . ? 
 C10A N1A C2A C1A -50.4(6) . . . . ? 
 C11A N1A C2A C1A -179.2(4) . . . . ? 
 O1A C1A C2A C3A -177.1(4) . . . . ? 
 C4A C1A C2A C3A 61.5(6) . . . . ? 
 O1A C1A C2A N1A -48.4(5) . . . . ? 
 C4A C1A C2A N1A -169.8(4) . . . . ? 
 C4 C1 C2 C6 135.5(5) . . . . ? 
 C3 C1 C2 C6 -109.4(6) . . . . ? 
 C4 C1 C2 C5 -7.4(7) . . . . ? 
 C3 C1 C2 C5 107.8(6) . . . . ? 
 C4 C1 C2 C3 -115.2(5) . . . . ? 
 C3 C1 C2 C3 0.0 . . . . ? 
 N1A C2A C3A O2A -70.0(6) . . . . ? 
 C1A C2A C3A O2A 56.5(6) . . . . ? 
 C6 C2 C3 C7 1.2(8) . . . . ? 
 C5 C2 C3 C7 146.9(5) . . . . ? 
 C1 C2 C3 C7 -106.9(6) . . . . ? 
 C6 C2 C3 C1 108.1(5) . . . . ? 
 C5 C2 C3 C1 -106.2(5) . . . . ? 
 C1 C2 C3 C1 0.0 . . . . ? 
 C4 C1 C3 C7 -137.3(5) . . . . ? 
 C2 C1 C3 C7 115.2(6) . . . . ? 
 C4 C1 C3 C2 107.4(5) . . . . ? 
 C2 C1 C3 C2 0.0 . . . . ? 
 O1A C1A C4A C9A 129.6(6) . . . . ? 
 C2A C1A C4A C9A -110.4(7) . . . . ? 
 O1A C1A C4A C5A -50.9(7) . . . . ? 
 C2A C1A C4A C5A 69.1(6) . . . . ? 
 C3 C1 C4 O1 5.2(8) . . . . ? 
 C2 C1 C4 O1 77.2(6) . . . . ? 
 C3 C1 C4 O2 -173.7(5) . . . . ? 
 C2 C1 C4 O2 -101.6(6) . . . . ? 
 C9A C4A C5A C6A 0.6(10) . . . . ? 
 C1A C4A C5A C6A -178.9(5) . . . . ? 
 C4A C5A C6A C7A -3.1(10) . . . . ? 
 C5A C6A C7A C8A 5.3(12) . . . . ? 
 C5A C6A C7A N2A -177.7(6) . . . . ? 
 O4A N2A C7A C8A -10.9(12) . . . . ? 
 O3A N2A C7A C8A 166.8(8) . . . . ? 
 O4A N2A C7A C6A 172.0(9) . . . . ? 
 O3A N2A C7A C6A -10.3(10) . . . . ? 
 C2 C3 C7 C8 -119.5(6) . . . . ? 
 C1 C3 C7 C8 168.1(5) . . . . ? 
 C6A C7A C8A C9A -4.8(13) . . . . ? 
 N2A C7A C8A C9A 178.3(7) . . . . ? 
 C3 C7 C8 C9 3.8(9) . . . . ? 
 C3 C7 C8 C10 -177.0(6) . . . . ? 
 C7A C8A C9A C4A 2.1(13) . . . . ? 
 C5A C4A C9A C8A 0.0(11) . . . . ? 
 C1A C4A C9A C8A 179.6(7) . . . . ? 
  
_refine_diff_density_max    0.222 
_refine_diff_density_min   -0.198 
_refine_diff_density_rms    0.048 

 
data_t1127a 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          'C22 H36 N2 O2' 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C22 H36 N2 O7' 
_chemical_formula_weight          440.53 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'O'  'O'   0.0492   0.0322 
 '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' 
 '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' 
  
_symmetry_cell_setting            orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21' 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
  
_cell_length_a                    13.209(18) 
_cell_length_b                    26.587(21) 
_cell_length_c                    7.218(21) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2534.9(84) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     10 
_cell_measurement_theta_min       19.3 
_cell_measurement_theta_max       29.1 
  
_exptl_crystal_description        needle 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.500 
_exptl_crystal_size_mid           0.150 
_exptl_crystal_size_min           0.150 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.154 
_exptl_crystal_density_method     none 
_exptl_crystal_F_000              952 
_exptl_absorpt_coefficient_mu     0.706 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        AFC6S 
_diffrn_measurement_method        'omega/2-theta scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  150 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         -4.06 
_diffrn_reflns_number             2843 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.2638 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -27 
_diffrn_reflns_limit_k_max        33 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        8 
_diffrn_reflns_theta_min          3.32 
_diffrn_reflns_theta_max          75.13 
_reflns_number_total              2843 
_reflns_number_observed           648 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'MSC/AFC Diffractometer Control' 
_computing_cell_refinement        'MSC/AFC Diffractometer Control' 
_computing_data_reduction         teXsan 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   teXsan 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 24 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.4171P] 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     refU 
_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    0.98(137) 
_refine_ls_number_reflns          2819 
_refine_ls_number_parameters      287 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.3433 
_refine_ls_R_factor_obs           0.0628 
_refine_ls_wR_factor_all          0.2161 
_refine_ls_wR_factor_obs          0.1021 
_refine_ls_goodness_of_fit_all    1.094 
_refine_ls_goodness_of_fit_obs    1.416 
_refine_ls_restrained_S_all       1.149 
_refine_ls_restrained_S_obs       1.416 
_refine_ls_shift/esd_max          -0.033 
_refine_ls_shift/esd_mean         0.004 
  
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1 O 0.7547(7) 0.8057(3) 0.2307(14) 0.070(3) Uani 1 d . . 
O1A O 0.7794(7) 0.7088(3) 0.1836(15) 0.064(3) Uani 1 d . . 
H1AO H 0.7629(77) 0.7382(7) 0.1994(114) 0.064(32) Uiso 1 calc R . 
O1M O 0.9624(10) 0.8064(4) 0.7713(20) 0.151(7) Uani 1 d . . 
H1OM H 0.9285(10) 0.7979(4) 0.6846(20) 0.064(32) Uiso 1 d R . 
O2A O 1.1237(8) 0.6702(5) 0.0412(14) 0.081(3) Uani 1 d . . 
H2AO H 1.1699(22) 0.6701(52) -0.0348(41) 0.064(32) Uiso 1 calc R . 
O2 O 0.8564(7) 0.7878(3) 0.4666(14) 0.066(3) Uani 1 d . . 
O3A O 0.6690(12) 0.5215(5) -0.4297(20) 0.165(7) Uani 1 d . . 
O4A O 0.6939(12) 0.5715(5) -0.6514(18) 0.113(5) Uani 1 d . . 
N1A N 0.9846(8) 0.7279(4) 0.2553(19) 0.062(4) Uani 1 d . . 
H1AN H 0.9254(8) 0.7383(4) 0.3074(19) 0.055(20) Uiso 1 calc R . 
N2A N 0.6933(12) 0.5609(6) -0.4903(23) 0.084(5) Uani 1 d . . 
C1 C 0.7755(9) 0.8658(5) 0.4782(25) 0.068(5) Uani 1 d . . 
H1 H 0.7833(9) 0.8652(5) 0.6132(25) 0.055(20) Uiso 1 calc R . 
C1A C 0.8471(10) 0.7056(5) 0.0324(22) 0.061(4) Uani 1 d . . 
H1A H 0.8515(10) 0.7386(5) -0.0273(22) 0.055(20) Uiso 1 calc R . 
C1M C 1.0194(14) 0.8483(6) 0.7548(35) 0.158(10) Uani 1 d . . 
H1M H 1.0654(14) 0.8430(6) 0.6546(35) 0.235(25) Uiso 1 d R . 
H2M H 1.0564(14) 0.8544(6) 0.8648(35) 0.235(25) Uiso 1 d R . 
H3M H 0.9771(14) 0.8760(6) 0.7276(35) 0.235(25) Uiso 1 d R . 
C2A C 0.9532(10) 0.6909(5) 0.1068(20) 0.056(4) Uani 1 d . . 
H2A H 0.9457(10) 0.6582(5) 0.1677(20) 0.055(20) Uiso 1 calc R . 
C2 C 0.8027(16) 0.9158(6) 0.3864(30) 0.087(6) Uani 1 d . . 
C3A C 1.0315(11) 0.6839(6) -0.0484(22) 0.066(5) Uani 1 d . . 
H3A1 H 1.0101(11) 0.6577(6) -0.1331(22) 0.190(69) Uiso 1 calc R . 
H3A2 H 1.0400(11) 0.7149(6) -0.1175(22) 0.190(69) Uiso 1 calc R . 
C3 C 0.6909(12) 0.8999(5) 0.4073(25) 0.069(5) Uani 1 d . . 
H3 H 0.6598(12) 0.8882(5) 0.2918(25) 0.055(20) Uiso 1 calc R . 
C4A C 0.8073(11) 0.6676(5) -0.1075(23) 0.056(4) Uani 1 d . . 
C4 C 0.7942(11) 0.8164(6) 0.3831(23) 0.055(4) Uani 1 d . . 
C5A C 0.7763(11) 0.6207(5) -0.0476(20) 0.057(4) Uani 1 d . . 
H5A H 0.7817(11) 0.6120(5) 0.0768(20) 0.053(19) Uiso 1 calc R . 
C5 C 0.8466(13) 0.9165(6) 0.1995(28) 0.121(8) Uani 1 d . . 
H5B H 0.8590(13) 0.9506(6) 0.1625(28) 0.235(25) Uiso 1 calc R . 
H5C H 0.8003(13) 0.9010(6) 0.1141(28) 0.235(25) Uiso 1 calc R . 
H5D H 0.9092(13) 0.8981(6) 0.1997(28) 0.235(25) Uiso 1 calc R . 
C6A C 0.7373(11) 0.5871(5) -0.1735(22) 0.062(5) Uani 1 d . . 
H6A H 0.7135(11) 0.5560(5) -0.1337(22) 0.053(19) Uiso 1 calc R . 
C6 C 0.8416(11) 0.9555(5) 0.5242(31) 0.131(9) Uani 1 d . . 
H6B H 0.8076(11) 0.9514(5) 0.6408(31) 0.235(25) Uiso 1 calc R . 
H6C H 0.8282(11) 0.9886(5) 0.4763(31) 0.235(25) Uiso 1 calc R . 
H6D H 0.9131(11) 0.9514(5) 0.5415(31) 0.235(25) Uiso 1 calc R . 
C7A C 0.7335(12) 0.5996(6) -0.3600(22) 0.058(5) Uani 1 d . . 
C7 C 0.6215(13) 0.9242(6) 0.5315(28) 0.089(6) Uani 1 d . . 
H7 H 0.6404(13) 0.9237(6) 0.6556(28) 0.053(19) Uiso 1 calc R . 
C8A C 0.7647(11) 0.6458(5) -0.4203(22) 0.061(5) Uani 1 d . . 
H8A H 0.7613(11) 0.6541(5) -0.5454(22) 0.053(19) Uiso 1 calc R . 
C8 C 0.5361(15) 0.9471(7) 0.4969(37) 0.102(8) Uani 1 d . . 
C9A C 0.8014(10) 0.6801(5) -0.2928(22) 0.052(4) Uani 1 d . . 
H9A H 0.8222(10) 0.7117(5) -0.3322(22) 0.053(19) Uiso 1 calc R . 
C9 C 0.5028(13) 0.9562(7) 0.3014(36) 0.151(12) Uani 1 d . . 
H9B H 0.4388(13) 0.9733(7) 0.3017(36) 0.235(25) Uiso 1 calc R . 
H9C H 0.4961(13) 0.9246(7) 0.2381(36) 0.235(25) Uiso 1 calc R . 
H9D H 0.5523(13) 0.9766(7) 0.2391(36) 0.235(25) Uiso 1 calc R . 
C10A C 1.0338(10) 0.7760(5) 0.1840(22) 0.083(6) Uani 1 d . . 
H10A H 0.9944(10) 0.7893(5) 0.0837(22) 0.235(25) Uiso 1 calc R . 
H10B H 1.1010(10) 0.7686(5) 0.1412(22) 0.235(25) Uiso 1 calc R . 
H10C H 1.0370(10) 0.8002(5) 0.2823(22) 0.235(25) Uiso 1 calc R . 
C10 C 0.4683(12) 0.9688(6) 0.6448(31) 0.148(10) Uani 1 d . . 
H10D H 0.4099(12) 0.9838(6) 0.5880(31) 0.235(25) Uiso 1 calc R . 
H10E H 0.5047(12) 0.9940(6) 0.7130(31) 0.235(25) Uiso 1 calc R . 
H10F H 0.4473(12) 0.9426(6) 0.7276(31) 0.235(25) Uiso 1 calc R . 
C11A C 1.0437(11) 0.7055(6) 0.4129(20) 0.083(6) Uani 1 d . . 
H11A H 1.0605(11) 0.7314(6) 0.5004(20) 0.235(25) Uiso 1 calc R . 
H11B H 1.1048(11) 0.6906(6) 0.3661(20) 0.235(25) Uiso 1 calc R . 
H11C H 1.0036(11) 0.6802(6) 0.4730(20) 0.235(25) Uiso 1 calc R . 
  
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 
O1 0.083(7) 0.068(7) 0.060(7) -0.013(6) -0.021(7) 0.013(6) 
O1A 0.056(7) 0.058(6) 0.077(8) -0.013(7) 0.019(6) 0.002(6) 
O1M 0.224(16) 0.118(11) 0.110(12) 0.035(11) -0.101(13) -0.071(11) 
O2A 0.061(7) 0.118(9) 0.065(8) 0.011(8) 0.022(7) 0.015(8) 
O2 0.068(7) 0.061(7) 0.069(8) -0.009(6) -0.019(7) 0.007(6) 
O3A 0.281(19) 0.119(12) 0.095(12) -0.010(11) 0.022(14) -0.107(13) 
O4A 0.166(14) 0.094(10) 0.079(9) 0.010(9) -0.013(11) -0.024(9) 
N1A 0.042(7) 0.072(9) 0.072(9) -0.016(9) -0.004(8) 0.005(7) 
N2A 0.089(12) 0.092(13) 0.071(12) 0.015(12) 0.007(11) -0.015(10) 
C1 0.049(10) 0.067(11) 0.089(14) -0.015(11) -0.024(11) 0.016(9) 
C1A 0.052(9) 0.056(10) 0.075(12) -0.022(10) -0.008(10) 0.011(8) 
C1M 0.152(20) 0.125(18) 0.197(25) 0.047(22) -0.056(22) -0.048(16) 
C2A 0.063(10) 0.053(10) 0.052(10) 0.011(9) 0.003(9) 0.004(9) 
C2 0.108(16) 0.040(10) 0.114(18) -0.006(12) -0.022(15) 0.000(11) 
C3A 0.049(10) 0.101(14) 0.046(10) -0.005(11) 0.021(10) -0.008(11) 
C3 0.059(10) 0.070(11) 0.079(14) -0.030(11) -0.005(11) -0.014(10) 
C4A 0.054(10) 0.045(9) 0.068(12) 0.003(10) 0.000(10) -0.006(8) 
C4 0.051(10) 0.052(10) 0.062(12) 0.007(10) 0.007(10) -0.004(8) 
C5A 0.089(13) 0.044(9) 0.039(9) 0.003(9) 0.005(10) -0.008(9) 
C5 0.137(19) 0.093(14) 0.133(20) 0.012(16) 0.045(18) -0.007(13) 
C6A 0.073(12) 0.048(10) 0.066(12) -0.002(10) 0.005(11) -0.026(9) 
C6 0.086(14) 0.077(13) 0.231(26) -0.074(17) -0.019(18) -0.017(10) 
C7A 0.057(11) 0.068(11) 0.050(11) -0.014(10) 0.001(10) -0.008(9) 
C7 0.087(14) 0.094(14) 0.085(16) -0.033(13) -0.008(15) -0.012(12) 
C8A 0.068(12) 0.052(9) 0.063(12) 0.010(10) 0.013(11) -0.006(9) 
C8 0.066(13) 0.043(11) 0.197(27) -0.019(16) 0.001(19) -0.005(10) 
C9A 0.052(9) 0.025(8) 0.079(12) 0.008(9) 0.004(10) -0.007(7) 
C9 0.077(15) 0.108(17) 0.268(34) 0.089(23) -0.036(19) 0.004(12) 
C10A 0.081(12) 0.081(11) 0.088(14) -0.008(11) 0.004(12) -0.034(10) 
C10 0.060(12) 0.129(17) 0.255(31) -0.068(19) 0.023(18) 0.008(12) 
C11A 0.065(11) 0.119(15) 0.066(12) 0.009(12) -0.012(10) 0.037(11) 
  
_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 C4 1.25(2) . ? 
O1A C1A 1.41(2) . ? 
O1M C1M 1.35(2) . ? 
O2A C3A 1.426(15) . ? 
O2 C4 1.27(2) . ? 
O3A N2A 1.18(2) . ? 
O4A N2A 1.20(2) . ? 
N1A C11A 1.50(2) . ? 
N1A C2A 1.51(2) . ? 
N1A C10A 1.522(15) . ? 
N2A C7A 1.49(2) . ? 
C1 C4 1.50(2) . ? 
C1 C3 1.53(2) . ? 
C1 C2 1.53(2) . ? 
C1A C4A 1.52(2) . ? 
C1A C2A 1.55(2) . ? 
C2A C3A 1.54(2) . ? 
C2 C5 1.47(2) . ? 
C2 C6 1.54(2) . ? 
C2 C3 1.54(2) . ? 
C3 C7 1.44(2) . ? 
C4A C9A 1.38(2) . ? 
C4A C5A 1.38(2) . ? 
C5A C6A 1.38(2) . ? 
C6A C7A 1.39(2) . ? 
C7A C8A 1.37(2) . ? 
C7 C8 1.31(2) . ? 
C8A C9A 1.38(2) . ? 
C8 C9 1.50(3) . ? 
C8 C10 1.51(3) . ? 
  
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 
C11A N1A C2A 114.9(11) . . ? 
C11A N1A C10A 111.5(11) . . ? 
C2A N1A C10A 115.0(12) . . ? 
O3A N2A O4A 124.9(20) . . ? 
O3A N2A C7A 118.4(16) . . ? 
O4A N2A C7A 116.6(17) . . ? 
C4 C1 C3 119.0(14) . . ? 
C4 C1 C2 121.6(15) . . ? 
C3 C1 C2 60.7(10) . . ? 
O1A C1A C4A 109.5(12) . . ? 
O1A C1A C2A 108.6(12) . . ? 
C4A C1A C2A 112.1(12) . . ? 
N1A C2A C3A 114.2(12) . . ? 
N1A C2A C1A 109.3(11) . . ? 
C3A C2A C1A 112.8(13) . . ? 
C5 C2 C1 120.1(17) . . ? 
C5 C2 C6 117.0(18) . . ? 
C1 C2 C6 113.3(17) . . ? 
C5 C2 C3 118.1(18) . . ? 
C1 C2 C3 59.5(10) . . ? 
C6 C2 C3 116.4(17) . . ? 
O2A C3A C2A 106.0(13) . . ? 
C7 C3 C1 121.7(17) . . ? 
C7 C3 C2 123.2(15) . . ? 
C1 C3 C2 59.7(10) . . ? 
C9A C4A C5A 120.2(15) . . ? 
C9A C4A C1A 120.3(14) . . ? 
C5A C4A C1A 119.6(15) . . ? 
O1 C4 O2 123.4(15) . . ? 
O1 C4 C1 122.2(15) . . ? 
O2 C4 C1 114.3(14) . . ? 
C6A C5A C4A 119.4(14) . . ? 
C5A C6A C7A 119.9(14) . . ? 
C8A C7A C6A 120.9(15) . . ? 
C8A C7A N2A 121.8(15) . . ? 
C6A C7A N2A 117.3(15) . . ? 
C8 C7 C3 130.0(22) . . ? 
C7A C8A C9A 119.0(14) . . ? 
C7 C8 C9 120.6(24) . . ? 
C7 C8 C10 123.8(25) . . ? 
C9 C8 C10 115.5(18) . . ? 
C4A C9A C8A 120.5(13) . . ? 
  
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 
 C11A N1A C2A C3A -88.7(15) . . . . ? 
 C10A N1A C2A C3A 42.8(16) . . . . ? 
 C11A N1A C2A C1A 143.9(12) . . . . ? 
 C10A N1A C2A C1A -84.5(14) . . . . ? 
 O1A C1A C2A N1A -54.6(15) . . . . ? 
 C4A C1A C2A N1A -175.7(12) . . . . ? 
 O1A C1A C2A C3A 177.2(12) . . . . ? 
 C4A C1A C2A C3A 56.1(17) . . . . ? 
 C4 C1 C2 C5 1.1(26) . . . . ? 
 C3 C1 C2 C5 -106.9(21) . . . . ? 
 C4 C1 C2 C6 -144.0(15) . . . . ? 
 C3 C1 C2 C6 108.0(19) . . . . ? 
 C4 C1 C2 C3 108.0(18) . . . . ? 
 C3 C1 C2 C3 0.0 . . . . ? 
 N1A C2A C3A O2A 55.0(16) . . . . ? 
 C1A C2A C3A O2A -179.4(12) . . . . ? 
 C4 C1 C3 C7 135.3(16) . . . . ? 
 C2 C1 C3 C7 -112.6(17) . . . . ? 
 C4 C1 C3 C2 -112.1(17) . . . . ? 
 C2 C1 C3 C2 0.0 . . . . ? 
 C5 C2 C3 C7 -139.6(19) . . . . ? 
 C1 C2 C3 C7 110.2(20) . . . . ? 
 C6 C2 C3 C7 7.5(27) . . . . ? 
 C5 C2 C3 C1 110.2(20) . . . . ? 
 C1 C2 C3 C1 0.0 . . . . ? 
 C6 C2 C3 C1 -102.7(18) . . . . ? 
 O1A C1A C4A C9A 130.6(15) . . . . ? 
 C2A C1A C4A C9A -108.8(17) . . . . ? 
 O1A C1A C4A C5A -48.8(18) . . . . ? 
 C2A C1A C4A C5A 71.8(18) . . . . ? 
 C3 C1 C4 O1 11.9(22) . . . . ? 
 C2 C1 C4 O1 -59.7(21) . . . . ? 
 C3 C1 C4 O2 -171.0(13) . . . . ? 
 C2 C1 C4 O2 117.4(16) . . . . ? 
 C9A C4A C5A C6A -1.5(23) . . . . ? 
 C1A C4A C5A C6A 177.9(14) . . . . ? 
 C4A C5A C6A C7A 2.7(24) . . . . ? 
 C5A C6A C7A C8A -2.3(27) . . . . ? 
 C5A C6A C7A N2A 178.2(13) . . . . ? 
 O3A N2A C7A C8A 178.9(18) . . . . ? 
 O4A N2A C7A C8A 3.1(25) . . . . ? 
 O3A N2A C7A C6A -1.6(25) . . . . ? 
 O4A N2A C7A C6A -177.4(18) . . . . ? 
 C1 C3 C7 C8 -166.9(17) . . . . ? 
 C2 C3 C7 C8 120.8(21) . . . . ? 
 C6A C7A C8A C9A 0.6(24) . . . . ? 
 N2A C7A C8A C9A -179.9(14) . . . . ? 
 C3 C7 C8 C9 -7.4(31) . . . . ? 
 C3 C7 C8 C10 176.8(16) . . . . ? 
 C5A C4A C9A C8A -0.2(24) . . . . ? 
 C1A C4A C9A C8A -179.6(13) . . . . ? 
 C7A C8A C9A C4A 0.6(22) . . . . ? 
  
_refine_diff_density_max    0.237 
_refine_diff_density_min   -0.214 
_refine_diff_density_rms    0.051 


data_a1146 
    
_publ_contact_author               'Zsolt Bocskei'
_publ_contact_author_email         zbocskei@strasbourg.synthelabo.fr

     
loop_
_publ_author_name
?
_journal_name_full                 '?'
_journal_volume                    '?'
_journal_page_first                '?'
_journal_page_last                 '?'
_journal_year                      '?'
_ccdc_journal_depnumber            '?'

    
_chemical_name_systematic 
; 
(1R,3R)-2,2-dimethyl-3-(methylpropenyl)-cyclopropanecarboxylic 
acid (1R,2R)-1-(4-nitrophenyl)-
-2-dimethylamino-1,3-propanediol salt
; 
_chemical_name_common             ' d-trans chrysanthemic acid DMAD salt'
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C21 H32 N2 O6' 
_chemical_formula_weight          408.49 
_chemical_melting_point           '114.8 C' 
_chemical_compound_source         preparation

_ccdc_compound_id                  '?'
_ccdc_biological_activity          '?'
_ccdc_polymorph                    '?'

_ccdc_chemdiag_type                '?'
_ccdc_chemdiag_records
?

_exptl_crystal_density_diffrn     1.199 
_exptl_crystal_colour             colourless

_diffrn_radiation_type            MoK\a 
_diffrn_measurement_device        'Rigaku Raxis-II' 
_ccdc_temp_data_collection          293(2)
_ccdc_ls_R_squared                  ?
_ccdc_disorder                     '?'
_ccdc_comments                     '?'

  
_audit_creation_method            SHELXL 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'O'  'O'   0.0106   0.0060 
 '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' 
 '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' 
  
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    'P 21' 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    9.923(10) 
_cell_length_b                    7.658(10) 
_cell_length_c                    15.573(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  107.02(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1131.6(20) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     0 
_cell_measurement_theta_min       0.00 
_cell_measurement_theta_max       0.00 
  
_exptl_crystal_description       ' colourless plates'
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              440 
_exptl_absorpt_coefficient_mu     0.088 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_method        'omega scans with profile analysis' 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0.00 
_diffrn_reflns_number             1269 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0905 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.15 
_diffrn_reflns_theta_max          20.89 
_reflns_number_total              1269 
_reflns_number_observed           849 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'MSC/AFC Diffractometer Control' 
_computing_cell_refinement        'MSC/AFC Diffractometer Control' 
_computing_data_reduction         'teXsan: PROCESS (MSC)' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   'teXsan: FINISH (MSC)' 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.2301P)^2^+0.0282P] 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     ? 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.1589(369) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.64(613) 
_refine_ls_number_reflns          1269 
_refine_ls_number_parameters      268 
_refine_ls_number_restraints      179 
_refine_ls_R_factor_all           0.1323 
_refine_ls_R_factor_obs           0.0989 
_refine_ls_wR_factor_all          0.3124 
_refine_ls_wR_factor_obs          0.2649 
_refine_ls_goodness_of_fit_all    1.017 
_refine_ls_goodness_of_fit_obs    1.105 
_refine_ls_restrained_S_all       0.941 
_refine_ls_restrained_S_obs       0.973 
_refine_ls_shift/esd_max          0.026 
_refine_ls_shift/esd_mean         0.004 
  
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1A O 0.8390(7) 0.8719(26) 0.3988(4) 0.100(3) Uani 1 d U . 
H1AO H 0.8688(23) 0.7986(149) 0.4382(75) 0.149 Uiso 1 calc R . 
O2A O 0.4631(11) 1.0634 0.4237(8) 0.182(6) Uani 1 d U . 
H2AO H 0.3773(33) 1.0687(413) 0.4136(97) 0.273 Uiso 1 calc R . 
O3A O 0.4656(21) 0.5231(41) -0.0042(14) 0.240(10) Uani 1 d U . 
O4A O 0.3101(22) 0.4248(34) 0.0552(12) 0.230(8) Uani 1 d U . 
N1A N 0.7604(10) 1.1927(27) 0.4352(6) 0.098(3) Uani 1 d U . 
H1AN H 0.8473(10) 1.1584(27) 0.4333(6) 0.084(12) Uiso 1 calc R . 
N2A N 0.4142(18) 0.5110(31) 0.0571(10) 0.147(5) Uani 1 d DU . 
C1A C 0.6895(11) 0.8874(28) 0.3802(8) 0.094(4) Uani 1 d DU . 
H1A H 0.6606(11) 0.8447(28) 0.4315(8) 0.084(12) Uiso 1 calc R . 
C2A C 0.6570(11) 1.0810(29) 0.3664(8) 0.096(3) Uani 1 d U . 
H2A H 0.6719(11) 1.1100(29) 0.3086(8) 0.084(12) Uiso 1 calc R . 
C3A C 0.4981(13) 1.1284(34) 0.3560(9) 0.130(5) Uani 1 d U . 
H3A H 0.4864(13) 1.2543(34) 0.3546(9) 0.071(17) Uiso 1 calc R . 
H3B H 0.4378(13) 1.0808(34) 0.3003(9) 0.071(17) Uiso 1 calc R . 
C4A C 0.6166(12) 0.7851(28) 0.2979(8) 0.097(3) Uani 1 d DU . 
C7A C 0.4823(19) 0.5963(34) 0.1401(9) 0.128(6) Uani 1 d DU . 
C10A C 0.7623(13) 1.1732(33) 0.5279(7) 0.119(4) Uani 1 d U . 
H10A H 0.7692(13) 1.0516(33) 0.5436(7) 0.244(26) Uiso 1 calc R . 
H10B H 0.6770(13) 1.2204(33) 0.5357(7) 0.244(26) Uiso 1 calc R . 
H10C H 0.8418(13) 1.2346(33) 0.5660(7) 0.244(26) Uiso 1 calc R . 
C11A C 0.7500(15) 1.3830(29) 0.4104(10) 0.123(4) Uani 1 d U . 
H11A H 0.7495(15) 1.3957(29) 0.3490(10) 0.244(26) Uiso 1 calc R . 
H11B H 0.8294(15) 1.4444(29) 0.4487(10) 0.244(26) Uiso 1 calc R . 
H11C H 0.6646(15) 1.4305(29) 0.4178(10) 0.244(26) Uiso 1 calc R . 
O1 O 1.2229(9) 1.2408(25) 0.4085(6) 0.116(3) Uani 1 d U . 
O2 O 1.0363(8) 1.1955(27) 0.4534(5) 0.112(3) Uani 1 d U . 
C1 C 1.0116(13) 1.1520(30) 0.3012(7) 0.103(4) Uani 1 d U . 
H1 H 0.9390(13) 1.0644(30) 0.2999(7) 0.084(12) Uiso 1 calc R . 
C2 C 0.9664(14) 1.2842(31) 0.2296(8) 0.109(4) Uani 1 d U . 
C3 C 1.0704(12) 1.1388(30) 0.2226(8) 0.106(4) Uani 1 d U . 
H3 H 1.1687(12) 1.1758(30) 0.2346(8) 0.084(12) Uiso 1 calc R . 
C4 C 1.0986(12) 1.2007(29) 0.3955(8) 0.096(3) Uani 1 d U . 
C5 C 1.0250(18) 1.4718(34) 0.2485(10) 0.143(6) Uani 1 d U . 
H5B H 0.9872(18) 1.5428(34) 0.1962(10) 0.244(26) Uiso 1 calc R . 
H5C H 1.1259(18) 1.4691(34) 0.2631(10) 0.244(26) Uiso 1 calc R . 
H5D H 0.9983(18) 1.5200(34) 0.2981(10) 0.244(26) Uiso 1 calc R . 
C6 C 0.8156(16) 1.2726(34) 0.1684(9) 0.144(6) Uani 1 d U . 
H6B H 0.7991(16) 1.3644(34) 0.1246(9) 0.244(26) Uiso 1 calc R . 
H6C H 0.7512(16) 1.2844(34) 0.2036(9) 0.244(26) Uiso 1 calc R . 
H6D H 0.8013(16) 1.1616(34) 0.1384(9) 0.244(26) Uiso 1 calc R . 
C7 C 1.0281(14) 0.9912(29) 0.1605(8) 0.110(4) Uani 1 d U . 
H26 H 0.9452(14) 0.9322(29) 0.1582(8) 0.122(19) Uiso 1 calc R . 
C8 C 1.1054(18) 0.9368(29) 0.1061(9) 0.121(5) Uani 1 d U . 
C5A C 0.6687(14) 0.7831(30) 0.2244(8) 0.112(4) Uani 1 d DU . 
H5A H 0.7501(14) 0.8455(30) 0.2268(8) 0.122(19) Uiso 1 calc R . 
C6A C 0.6023(18) 0.6904(31) 0.1479(8) 0.121(4) Uani 1 d DU . 
H6A H 0.6405(18) 0.6919(31) 0.1000(8) 0.122(19) Uiso 1 calc R . 
C9 C 1.0499(22) 0.7932(34) 0.0429(10) 0.154(6) Uani 1 d U . 
H9B H 1.1147(22) 0.7683(34) 0.0093(10) 0.244(26) Uiso 1 calc R . 
H9C H 0.9605(22) 0.8265(34) 0.0025(10) 0.244(26) Uiso 1 calc R . 
H9D H 1.0381(22) 0.6910(34) 0.0757(10) 0.244(26) Uiso 1 calc R . 
C8A C 0.4334(17) 0.5980(30) 0.2083(12) 0.143(6) Uani 1 d DU . 
H8A H 0.3530(17) 0.5325(30) 0.2045(12) 0.122(19) Uiso 1 calc R . 
C9A C 0.4932(15) 0.6921(32) 0.2882(9) 0.123(5) Uani 1 d DU . 
H9A H 0.4504(15) 0.6917(32) 0.3339(9) 0.122(19) Uiso 1 calc R . 
C10 C 1.2419(14) 1.0082(34) 0.1056(10) 0.135(5) Uani 1 d U . 
H10D H 1.2748(14) 0.9477(34) 0.0616(10) 0.244(26) Uiso 1 calc R . 
H10E H 1.3085(14) 0.9935(34) 0.1638(10) 0.244(26) Uiso 1 calc R . 
H10F H 1.2318(14) 1.1302(34) 0.0909(10) 0.244(26) Uiso 1 calc R . 
  
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 
O1A 0.091(5) 0.116(6) 0.102(5) 0.029(5) 0.043(4) 0.023(5) 
O2A 0.136(8) 0.240(16) 0.198(10) 0.067(11) 0.093(8) 0.054(10) 
O3A 0.261(19) 0.306(26) 0.176(10) -0.102(15) 0.098(12) -0.068(17) 
O4A 0.270(20) 0.167(15) 0.219(15) -0.052(12) 0.017(14) -0.053(14) 
N1A 0.098(6) 0.084(6) 0.123(7) 0.013(6) 0.052(5) 0.013(6) 
N2A 0.158(13) 0.141(12) 0.125(10) -0.024(9) 0.015(9) -0.023(10) 
C1A 0.083(8) 0.091(8) 0.123(9) -0.008(7) 0.053(7) -0.014(6) 
C2A 0.089(8) 0.104(9) 0.107(8) -0.013(8) 0.048(6) -0.009(7) 
C3A 0.111(10) 0.150(15) 0.132(9) -0.020(10) 0.041(8) -0.003(9) 
C4A 0.093(8) 0.099(8) 0.109(8) 0.000(8) 0.048(7) 0.009(7) 
C7A 0.152(13) 0.151(14) 0.091(9) 0.021(10) 0.052(9) 0.036(12) 
C10A 0.149(11) 0.138(11) 0.086(6) -0.009(9) 0.059(6) -0.002(10) 
C11A 0.134(11) 0.095(10) 0.148(11) -0.002(9) 0.052(9) 0.003(8) 
O1 0.097(6) 0.125(8) 0.139(6) -0.020(6) 0.055(5) -0.007(5) 
O2 0.103(5) 0.150(7) 0.098(4) -0.013(5) 0.054(4) -0.008(5) 
C1 0.113(8) 0.126(10) 0.085(7) 0.018(8) 0.049(6) 0.029(8) 
C2 0.116(10) 0.124(11) 0.101(7) 0.011(9) 0.052(7) 0.005(9) 
C3 0.089(8) 0.129(12) 0.115(8) 0.010(8) 0.051(6) 0.010(7) 
C4 0.085(8) 0.085(7) 0.129(9) 0.004(8) 0.048(7) 0.002(7) 
C5 0.165(13) 0.159(15) 0.121(10) 0.006(11) 0.066(9) -0.005(13) 
C6 0.168(15) 0.151(14) 0.112(8) 0.024(10) 0.042(9) 0.020(12) 
C7 0.133(10) 0.117(9) 0.092(7) -0.015(8) 0.049(7) -0.011(9) 
C8 0.159(13) 0.089(10) 0.116(9) 0.007(8) 0.041(9) 0.025(9) 
C5A 0.129(9) 0.104(8) 0.099(7) -0.006(8) 0.029(7) -0.020(8) 
C6A 0.150(12) 0.120(10) 0.095(8) -0.013(9) 0.038(8) -0.011(11) 
C9 0.233(18) 0.110(11) 0.128(10) -0.007(11) 0.067(10) 0.015(13) 
C8A 0.144(13) 0.096(10) 0.153(13) 0.000(11) -0.016(12) -0.023(10) 
C9A 0.121(10) 0.136(11) 0.126(10) 0.041(11) 0.060(8) 0.014(10) 
C10 0.118(10) 0.147(12) 0.167(12) 0.011(11) 0.086(9) 0.025(10) 
  
_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 
O1A C1A 1.431(12) . ? 
O2A C3A 1.30(2) . ? 
O3A N2A 1.21(2) . ? 
O4A N2A 1.22(2) . ? 
N1A C10A 1.447(14) . ? 
N1A C11A 1.50(2) . ? 
N1A C2A 1.51(2) . ? 
N2A C7A 1.43(2) . ? 
C1A C4A 1.50(2) . ? 
C1A C2A 1.52(2) . ? 
C2A C3A 1.58(2) . ? 
C4A C9A 1.39(2) . ? 
C4A C5A 1.39(2) . ? 
C7A C8A 1.29(2) . ? 
C7A C6A 1.37(2) . ? 
O1 C4 1.230(12) . ? 
O2 C4 1.234(12) . ? 
C1 C2 1.48(2) . ? 
C1 C3 1.505(14) . ? 
C1 C4 1.52(2) . ? 
C2 C6 1.52(2) . ? 
C2 C5 1.55(2) . ? 
C2 C3 1.54(2) . ? 
C3 C7 1.47(2) . ? 
C7 C8 1.36(2) . ? 
C8 C10 1.46(2) . ? 
C8 C9 1.47(2) . ? 
C5A C6A 1.38(2) . ? 
C8A C9A 1.41(2) . ? 
  
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 
C10A N1A C11A 109.6(11) . . ? 
C10A N1A C2A 117.1(10) . . ? 
C11A N1A C2A 112.7(10) . . ? 
O3A N2A O4A 124.9(18) . . ? 
O3A N2A C7A 118.7(18) . . ? 
O4A N2A C7A 116.3(18) . . ? 
O1A C1A C4A 110.0(9) . . ? 
O1A C1A C2A 105.9(9) . . ? 
C4A C1A C2A 111.1(10) . . ? 
C1A C2A N1A 112.3(10) . . ? 
C1A C2A C3A 113.8(11) . . ? 
N1A C2A C3A 113.1(10) . . ? 
O2A C3A C2A 108.9(12) . . ? 
C9A C4A C5A 115.8(12) . . ? 
C9A C4A C1A 123.5(10) . . ? 
C5A C4A C1A 120.7(11) . . ? 
C8A C7A C6A 116.6(16) . . ? 
C8A C7A N2A 123.8(19) . . ? 
C6A C7A N2A 119.4(14) . . ? 
C2 C1 C3 62.4(8) . . ? 
C2 C1 C4 121.6(13) . . ? 
C3 C1 C4 124.0(11) . . ? 
C1 C2 C6 117.3(13) . . ? 
C1 C2 C5 118.7(13) . . ? 
C6 C2 C5 114.8(14) . . ? 
C1 C2 C3 59.8(9) . . ? 
C6 C2 C3 117.9(13) . . ? 
C5 C2 C3 117.5(12) . . ? 
C7 C3 C1 118.9(12) . . ? 
C7 C3 C2 122.3(11) . . ? 
C1 C3 C2 57.9(8) . . ? 
O1 C4 O2 125.5(11) . . ? 
O1 C4 C1 118.6(10) . . ? 
O2 C4 C1 115.8(10) . . ? 
C8 C7 C3 122.7(13) . . ? 
C7 C8 C10 125.4(14) . . ? 
C7 C8 C9 118.3(16) . . ? 
C10 C8 C9 116.2(14) . . ? 
C6A C5A C4A 121.3(13) . . ? 
C5A C6A C7A 122.2(13) . . ? 
C7A C8A C9A 124.7(17) . . ? 
C4A C9A C8A 119.3(13) . . ? 
  
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 
 O1A C1A C2A N1A -43.2(12) . . . . ? 
 C4A C1A C2A N1A -162.6(8) . . . . ? 
 O1A C1A C2A C3A -173.3(8) . . . . ? 
 C4A C1A C2A C3A 67.3(12) . . . . ? 
 C10A N1A C2A C1A -64.4(12) . . . . ? 
 C11A N1A C2A C1A 167.1(10) . . . . ? 
 C10A N1A C2A C3A 66.1(15) . . . . ? 
 C11A N1A C2A C3A -62.5(14) . . . . ? 
 C1A C2A C3A O2A 52.8(17) . . . . ? 
 N1A C2A C3A O2A -76.9(17) . . . . ? 
 O1A C1A C4A C9A 142.4(12) . . . . ? 
 C2A C1A C4A C9A -100.6(13) . . . . ? 
 O1A C1A C4A C5A -39.5(14) . . . . ? 
 C2A C1A C4A C5A 77.4(12) . . . . ? 
 O3A N2A C7A C8A 177.0(20) . . . . ? 
 O4A N2A C7A C8A -5.9(25) . . . . ? 
 O3A N2A C7A C6A 0.7(27) . . . . ? 
 O4A N2A C7A C6A 177.8(17) . . . . ? 
 C3 C1 C2 C6 108.0(14) . . . . ? 
 C4 C1 C2 C6 -137.3(13) . . . . ? 
 C3 C1 C2 C5 -106.9(13) . . . . ? 
 C4 C1 C2 C5 7.8(17) . . . . ? 
 C3 C1 C2 C3 0.000(15) . . . . ? 
 C4 C1 C2 C3 114.7(13) . . . . ? 
 C2 C1 C3 C7 -112.0(13) . . . . ? 
 C4 C1 C3 C7 136.9(14) . . . . ? 
 C2 C1 C3 C2 0.00(2) . . . . ? 
 C4 C1 C3 C2 -111.1(16) . . . . ? 
 C1 C2 C3 C7 106.1(14) . . . . ? 
 C6 C2 C3 C7 -0.8(17) . . . . ? 
 C5 C2 C3 C7 -145.1(12) . . . . ? 
 C1 C2 C3 C1 0.00(2) . . . . ? 
 C6 C2 C3 C1 -107.0(14) . . . . ? 
 C5 C2 C3 C1 108.8(14) . . . . ? 
 C2 C1 C4 O1 -72.1(15) . . . . ? 
 C3 C1 C4 O1 3.9(20) . . . . ? 
 C2 C1 C4 O2 108.2(14) . . . . ? 
 C3 C1 C4 O2 -175.8(12) . . . . ? 
 C1 C3 C7 C8 -158.7(13) . . . . ? 
 C2 C3 C7 C8 133.0(14) . . . . ? 
 C3 C7 C8 C10 3.9(21) . . . . ? 
 C3 C7 C8 C9 -176.8(14) . . . . ? 
 C9A C4A C5A C6A -1.4(18) . . . . ? 
 C1A C4A C5A C6A -179.6(12) . . . . ? 
 C4A C5A C6A C7A 0.1(21) . . . . ? 
 C8A C7A C6A C5A -0.1(22) . . . . ? 
 N2A C7A C6A C5A 176.5(13) . . . . ? 
 C6A C7A C8A C9A 1.4(22) . . . . ? 
 N2A C7A C8A C9A -175.0(14) . . . . ? 
 C5A C4A C9A C8A 2.6(18) . . . . ? 
 C1A C4A C9A C8A -179.3(11) . . . . ? 
 C7A C8A C9A C4A -2.8(22) . . . . ? 
  
_refine_diff_density_max    0.556 
_refine_diff_density_min   -0.408 
_refine_diff_density_rms    0.131