# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001

data_jun1098 
_database_code_CSD                  167665

_journal_coden_Cambridge      207

_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'Charrier, J. D.'
'Duffy, J. E. S.'
'Hitchcock, P. B.'
'Young, D.'

_publ_contact_author_name     	'Prof D Young'  
_publ_contact_author_address 
;
The School of Chemistry, Physics and Environmental Science
University of Sussex
Falmer
Brighton
BN1 9QJ
UNITED KINGDOM
;

_publ_contact_author_email       'D.W.YOUNG@SUSSEX.AC.UK'

_publ_section_title		
;
Unusual Stereoselectivity in the Alkylation of Pyroglutamate Ester
Urethanes
;
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C20 H33 N O7' 
_chemical_formula_weight          399.47 
_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'   0.0033   0.0016 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'H'  'H'   0.0000   0.0000 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'N'  'N'   0.0061   0.0033 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'O'  'O'   0.0106   0.0060 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P2(1) 

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

_cell_length_a                    5.634(7) 
_cell_length_b                    16.312(6) 
_cell_length_c                    11.909(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.20(9) 
_cell_angle_gamma                 90.00 
_cell_volume                      1091.5(15) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       7 
_cell_measurement_theta_max       10 

_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.215 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              432 
_exptl_absorpt_coefficient_mu     0.091 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        ' Enraf-Nonius CAD4' 
_diffrn_measurement_method        \w--2\q 
_diffrn_standards_number          2 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   120 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             2196 
_diffrn_reflns_av_R_equivalents   0.0607 
_diffrn_reflns_av_sigmaI/netI     0.0492 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.12 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              1998 
_reflns_number_observed           1768 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection        'Enraf-Nonius CAD4' 
_computing_cell_refinement        'Enraf-Nonius CAD4' 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'CAMERON (Watkin and Pearce,1993)' 
_computing_publication_material   SHELXL-93 

_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 1 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^)+(0.1138P)^2^+0.2090P] 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     riding 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0018(63) 
_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    -0.84(198) 
_refine_ls_number_reflns          1997 
_refine_ls_number_parameters      282 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0769 
_refine_ls_R_factor_obs           0.0603 
_refine_ls_wR_factor_all          0.1694 
_refine_ls_wR_factor_obs          0.1514 
_refine_ls_goodness_of_fit_all    1.095 
_refine_ls_goodness_of_fit_obs    1.092 
_refine_ls_restrained_S_all       1.139 
_refine_ls_restrained_S_obs       1.092 
_refine_ls_shift/esd_max          0.004 
_refine_ls_shift/esd_mean         0.001 

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 0.0418(7) 0.2043(2) -0.0278(3) 0.0403(9) Uani 1 d . . 
O2 O 0.1802(6) 0.0489(3) -0.1968(3) 0.0453(10) Uani 1 d . . 
O3 O -0.1107(5) 0.0686(2) -0.3330(2) 0.0284(7) Uani 1 d . . 
O4 O 0.5061(6) -0.0155(2) 0.1457(3) 0.0428(9) Uani 1 d . . 
O5 O 0.2422(5) -0.0918(2) 0.2309(2) 0.0281(7) Uani 1 d . . 
O6 O 0.3346(7) 0.1262(2) 0.2834(3) 0.0472(10) Uani 1 d . . 
O7 O 0.3610(8) 0.2232(2) 0.1509(3) 0.0462(10) Uani 1 d . . 
N1 N 0.1644(7) 0.1071(2) 0.1082(3) 0.0267(8) Uani 1 d . . 
C1 C 0.0302(8) 0.1379(3) 0.0121(3) 0.0272(9) Uani 1 d . . 
C2 C -0.1422(7) 0.0700(3) -0.0241(3) 0.0261(9) Uani 1 d . . 
H2 H -0.2892(7) 0.0793(3) 0.0163(3) 0.031 Uiso 1 calc R . 
C3 C -0.0266(8) -0.0074(3) 0.0249(3) 0.0267(9) Uani 1 d . . 
H3A H 0.0895(8) -0.0301(3) -0.0253(3) 0.032 Uiso 1 calc R . 
H3B H -0.1470(8) -0.0497(3) 0.0386(3) 0.032 Uiso 1 calc R . 
C4 C 0.0980(8) 0.0237(3) 0.1361(3) 0.0265(9) Uani 1 d . . 
H4 H -0.0161(8) 0.0242(3) 0.1966(3) 0.032 Uiso 1 calc R . 
C5 C -0.2172(7) 0.0726(3) -0.1495(3) 0.0284(9) Uani 1 d . . 
H5A H -0.3374(7) 0.0292(3) -0.1665(3) 0.034 Uiso 1 calc R . 
H5B H -0.2950(7) 0.1260(3) -0.1669(3) 0.034 Uiso 1 calc R . 
C6 C -0.0218(7) 0.0617(3) -0.2252(3) 0.0274(9) Uani 1 d . . 
C7 C 0.0414(8) 0.0624(3) -0.4280(3) 0.0298(9) Uani 1 d . . 
C8 C 0.1348(15) -0.0235(4) -0.4350(5) 0.068(2) Uani 1 d . . 
H8A H 0.0012(15) -0.0621(4) -0.4407(5) 0.102 Uiso 1 calc R . 
H8B H 0.2381(15) -0.0357(4) -0.3673(5) 0.102 Uiso 1 calc R . 
H8C H 0.2260(15) -0.0287(4) -0.5016(5) 0.102 Uiso 1 calc R . 
C9 C 0.2313(10) 0.1271(4) -0.4190(4) 0.0496(14) Uani 1 d . . 
H9A H 0.1572(10) 0.1813(4) -0.4149(4) 0.074 Uiso 1 calc R . 
H9B H 0.3243(10) 0.1246(4) -0.4853(4) 0.074 Uiso 1 calc R . 
H9C H 0.3365(10) 0.1177(4) -0.3510(4) 0.074 Uiso 1 calc R . 
C10 C -0.1350(10) 0.0812(5) -0.5275(4) 0.053(2) Uani 1 d . . 
H10A H -0.2588(10) 0.0389(5) -0.5332(4) 0.079 Uiso 1 calc R . 
H10B H -0.0516(10) 0.0820(5) -0.5969(4) 0.079 Uiso 1 calc R . 
H10C H -0.2082(10) 0.1348(5) -0.5165(4) 0.079 Uiso 1 calc R . 
C11 C 0.3093(8) -0.0281(3) 0.1709(3) 0.0260(9) Uani 1 d . . 
C12 C 0.4075(8) -0.1586(3) 0.2673(4) 0.0290(10) Uani 1 d . . 
C13 C 0.5031(10) -0.1997(3) 0.1666(4) 0.0392(12) Uani 1 d . . 
H13A H 0.6060(10) -0.1614(3) 0.1294(4) 0.059 Uiso 1 calc R . 
H13B H 0.3703(10) -0.2162(3) 0.1137(4) 0.059 Uiso 1 calc R . 
H13C H 0.5952(10) -0.2483(3) 0.1913(4) 0.059 Uiso 1 calc R . 
C14 C 0.2474(9) -0.2160(3) 0.3270(5) 0.0409(12) Uani 1 d . . 
H14A H 0.1876(9) -0.1880(3) 0.3921(5) 0.061 Uiso 1 calc R . 
H14B H 0.3379(9) -0.2647(3) 0.3527(5) 0.061 Uiso 1 calc R . 
H14C H 0.1131(9) -0.2326(3) 0.2751(5) 0.061 Uiso 1 calc R . 
C15 C 0.6033(9) -0.1246(3) 0.3484(4) 0.0366(11) Uani 1 d . . 
H15A H 0.5325(9) -0.0986(3) 0.4122(4) 0.055 Uiso 1 calc R . 
H15B H 0.6956(9) -0.0839(3) 0.3095(4) 0.055 Uiso 1 calc R . 
H15C H 0.7083(9) -0.1693(3) 0.3759(4) 0.055 Uiso 1 calc R . 
C16 C 0.2960(8) 0.1534(3) 0.1899(4) 0.0296(10) Uani 1 d . . 
C17 C 0.4996(9) 0.2830(3) 0.2224(4) 0.0337(10) Uani 1 d . . 
C18 C 0.7129(29) 0.2495(10) 0.2911(19) 0.037(4) Uani 0.42(3) d P 1 
H18A H 0.8175(29) 0.2213(10) 0.2413(19) 0.055 Uiso 0.42(3) calc PR 1 
H18B H 0.6603(29) 0.2107(10) 0.3470(19) 0.055 Uiso 0.42(3) calc PR 1 
H18C H 0.7999(29) 0.2947(10) 0.3295(19) 0.055 Uiso 0.42(3) calc PR 1 
C19 C 0.3318(26) 0.3260(10) 0.2872(17) 0.039(4) Uani 0.42(3) d P 1 
H19A H 0.1988(26) 0.3457(10) 0.2368(17) 0.058 Uiso 0.42(3) calc PR 1 
H19B H 0.4112(26) 0.3727(10) 0.3257(17) 0.058 Uiso 0.42(3) calc PR 1 
H19C H 0.2717(26) 0.2887(10) 0.3431(17) 0.058 Uiso 0.42(3) calc PR 1 
C20 C 0.6036(35) 0.3440(10) 0.1288(12) 0.036(4) Uani 0.42(3) d P 1 
H20A H 0.7169(35) 0.3140(10) 0.0856(12) 0.053 Uiso 0.42(3) calc PR 1 
H20B H 0.6843(35) 0.3906(10) 0.1670(12) 0.053 Uiso 0.42(3) calc PR 1 
H20C H 0.4720(35) 0.3641(10) 0.0778(12) 0.053 Uiso 0.42(3) calc PR 1 
C18A C 0.7399(22) 0.2485(10) 0.2345(19) 0.057(4) Uani 0.58(3) d P 2 
H18D H 0.7386(22) 0.1979(10) 0.2788(19) 0.086 Uiso 0.58(3) calc PR 2 
H18E H 0.8484(22) 0.2881(10) 0.2729(19) 0.086 Uiso 0.58(3) calc PR 2 
H18F H 0.7936(22) 0.2364(10) 0.1598(19) 0.086 Uiso 0.58(3) calc PR 2 
C19A C 0.3992(29) 0.2929(11) 0.3401(15) 0.061(5) Uani 0.58(3) d P 2 
H19D H 0.4168(29) 0.2411(11) 0.3815(15) 0.091 Uiso 0.58(3) calc PR 2 
H19E H 0.2304(29) 0.3077(11) 0.3304(15) 0.091 Uiso 0.58(3) calc PR 2 
H19F H 0.4873(29) 0.3361(11) 0.3824(15) 0.091 Uiso 0.58(3) calc PR 2 
C20A C 0.4770(51) 0.3580(8) 0.1586(15) 0.078(7) Uani 0.58(3) d P 2 
H20D H 0.3111(51) 0.3766(8) 0.1549(15) 0.117 Uiso 0.58(3) calc PR 2 
H20E H 0.5248(51) 0.3484(8) 0.0823(15) 0.117 Uiso 0.58(3) calc PR 2 
H20F H 0.5796(51) 0.4001(8) 0.1954(15) 0.117 Uiso 0.58(3) calc PR 2 

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 0.054(2) 0.027(2) 0.038(2) 0.0128(15) -0.016(2) -0.0049(15) 
O2 0.024(2) 0.085(3) 0.026(2) 0.011(2) -0.0008(12) 0.007(2) 
O3 0.0281(15) 0.037(2) 0.0191(13) 0.0001(13) -0.0031(11) 0.0007(14) 
O4 0.030(2) 0.040(2) 0.060(2) 0.020(2) 0.012(2) 0.0017(15) 
O5 0.0231(15) 0.029(2) 0.031(2) 0.0117(13) -0.0029(12) 0.0004(12) 
O6 0.061(2) 0.058(2) 0.020(2) 0.011(2) -0.0092(15) -0.022(2) 
O7 0.082(3) 0.021(2) 0.031(2) 0.0036(15) -0.025(2) -0.009(2) 
N1 0.040(2) 0.022(2) 0.017(2) 0.0009(14) -0.0058(14) 0.0008(15) 
C1 0.031(2) 0.032(2) 0.018(2) 0.001(2) -0.007(2) 0.000(2) 
C2 0.029(2) 0.031(2) 0.019(2) 0.001(2) 0.002(2) -0.001(2) 
C3 0.034(2) 0.026(2) 0.020(2) 0.001(2) 0.000(2) -0.004(2) 
C4 0.032(2) 0.028(2) 0.020(2) 0.005(2) -0.001(2) -0.003(2) 
C5 0.025(2) 0.039(2) 0.020(2) 0.001(2) -0.007(2) 0.001(2) 
C6 0.031(2) 0.029(2) 0.021(2) 0.000(2) -0.005(2) 0.002(2) 
C7 0.035(2) 0.032(2) 0.022(2) -0.001(2) 0.000(2) 0.002(2) 
C8 0.109(6) 0.054(4) 0.045(3) 0.002(3) 0.028(3) 0.028(4) 
C9 0.054(3) 0.064(4) 0.033(3) -0.002(3) 0.012(2) -0.011(3) 
C10 0.049(3) 0.089(5) 0.020(2) -0.002(3) -0.005(2) 0.002(3) 
C11 0.030(2) 0.025(2) 0.022(2) 0.002(2) 0.001(2) -0.001(2) 
C12 0.034(2) 0.023(2) 0.029(2) 0.007(2) -0.001(2) 0.002(2) 
C13 0.046(3) 0.034(3) 0.038(3) 0.001(2) 0.004(2) 0.004(2) 
C14 0.041(3) 0.032(2) 0.050(3) 0.016(2) 0.008(2) 0.000(2) 
C15 0.037(3) 0.039(3) 0.033(2) 0.000(2) -0.004(2) 0.006(2) 
C16 0.031(2) 0.030(2) 0.026(2) 0.000(2) -0.005(2) 0.002(2) 
C17 0.038(2) 0.032(2) 0.029(2) -0.005(2) -0.010(2) -0.005(2) 
C18 0.027(7) 0.039(7) 0.042(9) 0.011(8) -0.005(7) -0.005(6) 
C19 0.038(7) 0.033(8) 0.046(9) -0.005(7) 0.005(6) -0.006(6) 
C20 0.065(10) 0.017(6) 0.025(6) -0.001(5) 0.003(6) -0.009(6) 
C18A 0.037(6) 0.068(8) 0.069(10) -0.012(9) 0.012(7) -0.007(5) 
C19A 0.069(8) 0.057(8) 0.058(9) -0.029(8) 0.012(7) -0.017(7) 
C20A 0.150(19) 0.024(6) 0.052(9) -0.001(6) -0.039(11) -0.018(9) 

_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 C1 1.186(6) . ? 
O2 C6 1.181(5) . ? 
O3 C6 1.349(5) . ? 
O3 C7 1.472(5) . ? 
O4 C11 1.187(6) . ? 
O5 C11 1.331(5) . ? 
O5 C12 1.479(5) . ? 
O6 C16 1.203(6) . ? 
O7 C16 1.292(6) . ? 
O7 C17 1.480(6) . ? 
N1 C16 1.400(6) . ? 
N1 C1 1.416(5) . ? 
N1 C4 1.456(5) . ? 
C1 C2 1.515(6) . ? 
C2 C3 1.517(6) . ? 
C2 C5 1.523(5) . ? 
C3 C4 1.538(6) . ? 
C4 C11 1.494(6) . ? 
C5 C6 1.483(6) . ? 
C7 C9 1.501(8) . ? 
C7 C8 1.501(8) . ? 
C7 C10 1.521(6) . ? 
C12 C13 1.508(7) . ? 
C12 C14 1.513(7) . ? 
C12 C15 1.517(7) . ? 
C17 C20A 1.442(14) . ? 
C17 C19 1.445(15) . ? 
C17 C18A 1.463(15) . ? 
C17 C18 1.506(15) . ? 
C17 C19A 1.557(14) . ? 
C17 C20 1.64(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 
C6 O3 C7 122.0(3) . . ? 
C11 O5 C12 122.4(3) . . ? 
C16 O7 C17 121.6(3) . . ? 
C16 N1 C1 126.5(4) . . ? 
C16 N1 C4 118.5(3) . . ? 
C1 N1 C4 112.6(4) . . ? 
O1 C1 N1 127.3(4) . . ? 
O1 C1 C2 127.3(4) . . ? 
N1 C1 C2 105.3(4) . . ? 
C1 C2 C3 104.5(3) . . ? 
C1 C2 C5 112.6(4) . . ? 
C3 C2 C5 118.8(4) . . ? 
C2 C3 C4 102.3(3) . . ? 
N1 C4 C11 112.3(4) . . ? 
N1 C4 C3 102.7(3) . . ? 
C11 C4 C3 110.9(4) . . ? 
C6 C5 C2 115.3(3) . . ? 
O2 C6 O3 124.7(4) . . ? 
O2 C6 C5 126.2(4) . . ? 
O3 C6 C5 109.1(3) . . ? 
O3 C7 C9 110.4(4) . . ? 
O3 C7 C8 109.5(4) . . ? 
C9 C7 C8 114.2(5) . . ? 
O3 C7 C10 101.6(4) . . ? 
C9 C7 C10 109.6(5) . . ? 
C8 C7 C10 110.9(5) . . ? 
O4 C11 O5 125.3(4) . . ? 
O4 C11 C4 124.9(4) . . ? 
O5 C11 C4 109.8(4) . . ? 
O5 C12 C13 110.4(4) . . ? 
O5 C12 C14 102.1(4) . . ? 
C13 C12 C14 111.0(4) . . ? 
O5 C12 C15 109.3(4) . . ? 
C13 C12 C15 112.5(4) . . ? 
C14 C12 C15 111.0(4) . . ? 
O6 C16 O7 128.3(4) . . ? 
O6 C16 N1 119.6(4) . . ? 
O7 C16 N1 112.0(4) . . ? 
C20A C17 C18A 115.0(12) . . ? 
C20A C17 O7 103.5(6) . . ? 
C19 C17 O7 106.8(7) . . ? 
C18A C17 O7 104.4(7) . . ? 
C19 C17 C18 114.4(10) . . ? 
O7 C17 C18 116.1(8) . . ? 
C20A C17 C19A 111.2(11) . . ? 
C18A C17 C19A 110.2(10) . . ? 
O7 C17 C19A 112.1(6) . . ? 
C19 C17 C20 110.4(9) . . ? 
O7 C17 C20 102.1(6) . . ? 
C18 C17 C20 106.2(9) . . ? 

loop_ 
_geom_torsion_atom_site_label_1 
_geom_torsion_atom_site_label_2 
_geom_torsion_atom_site_label_3 
_geom_torsion_atom_site_label_4 
_geom_torsion 
_geom_torsion_site_symmetry_1 
_geom_torsion_site_symmetry_2 
_geom_torsion_site_symmetry_3 
_geom_torsion_site_symmetry_4 
_geom_torsion_publ_flag 
C16 N1 C1 O1 15.9(8) . . . . ? 
C4 N1 C1 O1 177.9(5) . . . . ? 
C16 N1 C1 C2 -160.5(4) . . . . ? 
C4 N1 C1 C2 1.5(5) . . . . ? 
O1 C1 C2 C3 160.8(5) . . . . ? 
N1 C1 C2 C3 -22.9(4) . . . . ? 
O1 C1 C2 C5 30.4(7) . . . . ? 
N1 C1 C2 C5 -153.2(4) . . . . ? 
C1 C2 C3 C4 34.2(4) . . . . ? 
C5 C2 C3 C4 160.8(4) . . . . ? 
C16 N1 C4 C11 -57.3(5) . . . . ? 
C1 N1 C4 C11 139.2(4) . . . . ? 
C16 N1 C4 C3 -176.4(4) . . . . ? 
C1 N1 C4 C3 20.0(4) . . . . ? 
C2 C3 C4 N1 -32.7(4) . . . . ? 
C2 C3 C4 C11 -152.9(3) . . . . ? 
C1 C2 C5 C6 62.0(5) . . . . ? 
C3 C2 C5 C6 -60.6(5) . . . . ? 
C7 O3 C6 O2 -1.3(7) . . . . ? 
C7 O3 C6 C5 178.6(4) . . . . ? 
C2 C5 C6 O2 2.4(7) . . . . ? 
C2 C5 C6 O3 -177.5(4) . . . . ? 
C6 O3 C7 C9 -59.3(6) . . . . ? 
C6 O3 C7 C8 67.3(6) . . . . ? 
C6 O3 C7 C10 -175.5(4) . . . . ? 
C12 O5 C11 O4 -4.2(7) . . . . ? 
C12 O5 C11 C4 173.6(3) . . . . ? 
N1 C4 C11 O4 -23.5(6) . . . . ? 
C3 C4 C11 O4 90.8(5) . . . . ? 
N1 C4 C11 O5 158.7(3) . . . . ? 
C3 C4 C11 O5 -87.0(4) . . . . ? 
C11 O5 C12 C13 -59.8(5) . . . . ? 
C11 O5 C12 C14 -177.9(4) . . . . ? 
C11 O5 C12 C15 64.5(5) . . . . ? 
C17 O7 C16 O6 -0.6(8) . . . . ? 
C17 O7 C16 N1 179.2(4) . . . . ? 
C1 N1 C16 O6 155.1(5) . . . . ? 
C4 N1 C16 O6 -6.0(6) . . . . ? 
C1 N1 C16 O7 -24.8(6) . . . . ? 
C4 N1 C16 O7 174.1(4) . . . . ? 
C16 O7 C17 C20A -164.7(14) . . . . ? 
C16 O7 C17 C19 -80.8(10) . . . . ? 
C16 O7 C17 C18A 74.5(11) . . . . ? 
C16 O7 C17 C18 48.2(11) . . . . ? 
C16 O7 C17 C19A -44.8(11) . . . . ? 
C16 O7 C17 C20 163.2(8) . . . . ? 

_refine_diff_density_max    0.304 
_refine_diff_density_min   -0.444 
_refine_diff_density_rms    0.071