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


data_sw9803 
_database_code_CSD                  168126

_journal_coden_Cambridge      207

_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'J. Eames'
'J.E. Davies'
'M. Christlieb'
'R. Hooley'
'S. Warren'

_publ_contact_author_name     	'Dr Stuart Warren'  
_publ_contact_author_address 
;
University Chemical Laboratories
Cambridge University
Lensfield Road
Cambridge
Cambs
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       'SW134@CAM.AC.UK'

_publ_section_title		
;
The stereoselective synthesis of oxetanes; exploration of a new,
Mitsunobu-style procedure for the cyclisation of 1,3-diols.
;

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C23 H26 N2 O9 S' 
_chemical_formula_weight          506.52 

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' 
'S'  'S'   0.1246   0.1234 
'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)/c 

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

_cell_length_a                    17.086(11) 
_cell_length_b                    6.566(7) 
_cell_length_c                    20.949(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  101.53(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      2303(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       9 
_cell_measurement_theta_max       15 

_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.25 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.461 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1064 
_exptl_absorpt_coefficient_mu     0.199 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       180(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Rigaku AFC7r' 
_diffrn_measurement_method        \w/2\q 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  200 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         1.2
_diffrn_reflns_number             4181 
_diffrn_reflns_av_R_equivalents   0.0840 
_diffrn_reflns_av_sigmaI/netI     0.1173 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        20 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          3.55 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              4039 
_reflns_number_gt                 2208 
_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 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 w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.0000P] 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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4039 
_refine_ls_number_parameters      319 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1434 
_refine_ls_R_factor_gt            0.0695 
_refine_ls_wR_factor_ref          0.1781 
_refine_ls_wR_factor_gt           0.1457 
_refine_ls_goodness_of_fit_ref    1.013 
_refine_ls_restrained_S_all       1.013 
_refine_ls_shift/su_max           0.045 
_refine_ls_shift/su_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_adp_type 
_atom_site_occupancy 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
S1 S 0.71121(7) 0.0446(2) 0.12254(6) 0.0299(3) Uani 1 d . . . 
O1 O 0.8756(2) -0.3481(6) 0.38080(17) 0.0456(10) Uani 1 d . . . 
O2 O 0.80537(18) -0.1695(5) 0.29753(15) 0.0302(8) Uani 1 d . . . 
O3 O 0.86758(19) -0.2055(5) 0.18423(17) 0.0343(9) Uani 1 d . . . 
H100 H 0.8210 -0.2440 0.1853 0.041 Uiso 1 calc R . . 
O4 O 0.68757(19) 0.1913(6) 0.16583(16) 0.0430(10) Uani 1 d . . . 
O5 O 0.7052(2) -0.1696(6) 0.13794(17) 0.0445(10) Uani 1 d . . . 
O6 O 0.5575(2) -0.4620(6) 0.17433(19) 0.0504(11) Uani 1 d . . . 
O7 O 0.5078(2) -0.7321(7) 0.2090(2) 0.0628(13) Uani 1 d . . . 
O8 O 0.6620(2) -1.1131(6) 0.38462(19) 0.0481(10) Uani 1 d . . . 
O9 O 0.7649(2) -0.9784(6) 0.44582(19) 0.0551(12) Uani 1 d . . . 
N1 N 0.5593(2) -0.6013(8) 0.2125(2) 0.0399(12) Uani 1 d . . . 
N2 N 0.7102(3) -0.9736(7) 0.3989(2) 0.0367(11) Uani 1 d . . . 
C1 C 0.8166(3) -0.3258(7) 0.3387(2) 0.0295(12) Uani 1 d . . . 
C2 C 0.8744(3) -0.0337(8) 0.3030(2) 0.0291(11) Uani 1 d . . . 
H2A H 0.9232 -0.1145 0.3023 0.035 Uiso 1 calc R . . 
H2B H 0.8824 0.0417 0.3447 0.035 Uiso 1 calc R . . 
C3 C 0.8600(3) 0.1147(7) 0.2465(2) 0.0259(11) Uani 1 d . . . 
H3 H 0.8049 0.1726 0.2413 0.031 Uiso 1 calc R . . 
C4 C 0.9215(3) 0.2848(8) 0.2658(2) 0.0343(12) Uani 1 d . . . 
H4A H 0.9132 0.3906 0.2321 0.041 Uiso 1 calc R . . 
H4B H 0.9755 0.2286 0.2702 0.041 Uiso 1 calc R . . 
H4C H 0.9153 0.3441 0.3074 0.041 Uiso 1 calc R . . 
C5 C 0.8698(3) 0.0121(7) 0.1817(2) 0.0252(11) Uani 1 d . . . 
H5 H 0.9255 0.0456 0.1774 0.030 Uiso 1 calc R . . 
C6 C 0.8156(2) 0.0929(7) 0.1173(2) 0.0231(11) Uani 1 d . . . 
C7 C 0.8258(3) 0.3218(7) 0.1074(2) 0.0280(12) Uani 1 d . . . 
H7A H 0.7846 0.3690 0.0702 0.034 Uiso 1 calc R . . 
H7B H 0.8180 0.3959 0.1468 0.034 Uiso 1 calc R . . 
C8 C 0.9086(3) 0.3707(8) 0.0942(2) 0.0317(12) Uani 1 d . . . 
H8A H 0.9116 0.5181 0.0850 0.038 Uiso 1 calc R . . 
H8B H 0.9493 0.3403 0.1338 0.038 Uiso 1 calc R . . 
C9 C 0.9280(3) 0.2507(8) 0.0374(2) 0.0358(13) Uani 1 d . . . 
H9A H 0.9841 0.2767 0.0340 0.043 Uiso 1 calc R . . 
H9B H 0.8931 0.2974 -0.0036 0.043 Uiso 1 calc R . . 
C10 C 0.9160(3) 0.0235(8) 0.0456(2) 0.0350(13) Uani 1 d . . . 
H10A H 0.9566 -0.0274 0.0826 0.042 Uiso 1 calc R . . 
H10B H 0.9238 -0.0486 0.0058 0.042 Uiso 1 calc R . . 
C11 C 0.8329(3) -0.0233(8) 0.0578(2) 0.0287(11) Uani 1 d . . . 
H11A H 0.8282 -0.1714 0.0650 0.034 Uiso 1 calc R . . 
H11B H 0.7925 0.0146 0.0188 0.034 Uiso 1 calc R . . 
C12 C 0.6496(2) 0.0864(7) 0.0449(2) 0.0252(11) Uani 1 d . . . 
C13 C 0.6172(3) 0.2798(8) 0.0300(3) 0.0327(12) Uani 1 d . . . 
H13 H 0.6312 0.3902 0.0594 0.039 Uiso 1 calc R . . 
C14 C 0.5643(3) 0.3067(8) -0.0285(3) 0.0356(13) Uani 1 d . . . 
H14 H 0.5426 0.4379 -0.0400 0.043 Uiso 1 calc R . . 
C15 C 0.5427(3) 0.1449(9) -0.0704(2) 0.0356(13) Uani 1 d . . . 
H15 H 0.5051 0.1645 -0.1099 0.043 Uiso 1 calc R . . 
C16 C 0.5755(3) -0.0440(8) -0.0552(2) 0.0337(12) Uani 1 d . . . 
H16 H 0.5612 -0.1544 -0.0845 0.040 Uiso 1 calc R . . 
C17 C 0.6292(3) -0.0741(8) 0.0025(2) 0.0300(12) Uani 1 d . . . 
H17 H 0.6520 -0.2048 0.0130 0.036 Uiso 1 calc R . . 
C18 C 0.7498(3) -0.4758(7) 0.3270(2) 0.0269(11) Uani 1 d . . . 
C19 C 0.6842(3) -0.4607(8) 0.2754(2) 0.0280(11) Uani 1 d . . . 
H19 H 0.6784 -0.3481 0.2463 0.034 Uiso 1 calc R . . 
C20 C 0.6285(3) -0.6131(8) 0.2679(2) 0.0292(12) Uani 1 d . . . 
C21 C 0.6346(3) -0.7827(8) 0.3069(2) 0.0296(12) Uani 1 d . . . 
H21 H 0.5956 -0.8878 0.2996 0.036 Uiso 1 calc R . . 
C22 C 0.7000(3) -0.7926(7) 0.3569(2) 0.0261(11) Uani 1 d . . . 
C23 C 0.7579(3) -0.6434(7) 0.3680(2) 0.0244(11) Uani 1 d . . . 
H23 H 0.8025 -0.6553 0.4031 0.029 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 
S1 0.0213(6) 0.0376(8) 0.0291(7) 0.0024(6) 0.0010(5) 0.0001(6) 
O1 0.045(2) 0.041(2) 0.040(2) 0.0106(18) -0.0182(18) -0.0101(19) 
O2 0.0237(17) 0.033(2) 0.0307(19) 0.0058(16) -0.0031(14) -0.0019(15) 
O3 0.034(2) 0.0200(19) 0.046(2) -0.0035(17) 0.0000(18) 0.0031(16) 
O4 0.0260(18) 0.067(3) 0.035(2) -0.014(2) 0.0040(16) 0.0092(19) 
O5 0.032(2) 0.047(2) 0.048(2) 0.0192(19) -0.0077(17) -0.0121(18) 
O6 0.040(2) 0.057(3) 0.045(2) 0.012(2) -0.0127(18) 0.010(2) 
O7 0.033(2) 0.080(3) 0.064(3) 0.011(3) -0.017(2) -0.023(2) 
O8 0.048(2) 0.032(2) 0.061(3) 0.004(2) 0.002(2) -0.014(2) 
O9 0.052(2) 0.046(3) 0.053(2) 0.020(2) -0.023(2) -0.012(2) 
N1 0.026(2) 0.052(3) 0.038(3) -0.002(3) -0.001(2) 0.007(2) 
N2 0.036(2) 0.032(3) 0.043(3) 0.002(2) 0.010(2) -0.005(2) 
C1 0.031(3) 0.027(3) 0.027(3) 0.005(2) -0.002(2) 0.000(2) 
C2 0.020(2) 0.031(3) 0.033(3) 0.003(2) -0.003(2) -0.006(2) 
C3 0.022(2) 0.026(3) 0.028(3) 0.003(2) 0.000(2) -0.004(2) 
C4 0.037(3) 0.032(3) 0.031(3) -0.006(2) 0.000(2) -0.007(3) 
C5 0.023(2) 0.020(3) 0.030(3) -0.001(2) 0.001(2) 0.003(2) 
C6 0.017(2) 0.022(3) 0.028(3) 0.000(2) -0.0004(19) 0.002(2) 
C7 0.029(3) 0.022(3) 0.028(3) -0.001(2) -0.005(2) 0.005(2) 
C8 0.022(2) 0.032(3) 0.040(3) 0.007(3) 0.003(2) -0.002(2) 
C9 0.017(2) 0.050(4) 0.038(3) 0.007(3) -0.002(2) 0.004(2) 
C10 0.029(3) 0.046(3) 0.029(3) -0.008(3) 0.004(2) 0.010(3) 
C11 0.024(2) 0.034(3) 0.026(2) -0.003(2) -0.0014(19) 0.004(2) 
C12 0.017(2) 0.031(3) 0.028(3) 0.000(2) 0.0048(19) -0.002(2) 
C13 0.025(3) 0.029(3) 0.045(3) 0.001(3) 0.010(2) 0.007(2) 
C14 0.025(3) 0.034(3) 0.048(3) 0.012(3) 0.007(2) 0.007(2) 
C15 0.019(2) 0.051(4) 0.034(3) 0.007(3) -0.003(2) 0.002(3) 
C16 0.026(3) 0.040(3) 0.032(3) -0.007(3) -0.003(2) 0.000(2) 
C17 0.026(2) 0.026(3) 0.036(3) -0.001(2) 0.002(2) 0.002(2) 
C18 0.026(2) 0.026(3) 0.026(2) -0.005(2) -0.001(2) 0.005(2) 
C19 0.027(2) 0.032(3) 0.023(2) -0.002(2) 0.001(2) 0.009(2) 
C20 0.017(2) 0.039(3) 0.029(3) -0.009(3) -0.002(2) 0.002(2) 
C21 0.023(3) 0.036(3) 0.030(3) -0.003(3) 0.007(2) -0.010(2) 
C22 0.025(2) 0.026(3) 0.026(3) 0.003(2) 0.003(2) -0.001(2) 
C23 0.024(2) 0.021(3) 0.025(2) -0.001(2) -0.003(2) 0.001(2) 

_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 
S1 O4 1.435(4) . ? 
S1 O5 1.451(4) . ? 
S1 C12 1.773(5) . ? 
S1 C6 1.837(5) . ? 
O1 C1 1.208(5) . ? 
O2 C1 1.330(5) . ? 
O2 C2 1.465(5) . ? 
O3 C5 1.430(5) . ? 
O3 H100 0.8400 . ? 
O6 N1 1.211(5) . ? 
O7 N1 1.221(6) . ? 
O8 N2 1.228(5) . ? 
O9 N2 1.214(5) . ? 
N1 C20 1.485(6) . ? 
N2 C22 1.468(6) . ? 
C1 C18 1.490(7) . ? 
C2 C3 1.515(6) . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C3 C4 1.532(6) . ? 
C3 C5 1.554(6) . ? 
C3 H3 1.0000 . ? 
C4 H4A 0.9800 . ? 
C4 H4B 0.9800 . ? 
C4 H4C 0.9800 . ? 
C5 C6 1.569(6) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.532(6) . ? 
C6 C11 1.538(6) . ? 
C7 C8 1.529(6) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 C9 1.518(7) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C10 1.520(7) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 C11 1.524(7) . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C17 1.377(6) . ? 
C12 C13 1.396(7) . ? 
C13 C14 1.380(7) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.381(7) . ? 
C14 H14 0.9500 . ? 
C15 C16 1.373(7) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.378(6) . ? 
C16 H16 0.9500 . ? 
C17 H17 0.9500 . ? 
C18 C23 1.385(6) . ? 
C18 C19 1.398(6) . ? 
C19 C20 1.368(7) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.372(7) . ? 
C21 C22 1.372(6) . ? 
C21 H21 0.9500 . ? 
C22 C23 1.379(6) . ? 
C23 H23 0.9500 . ? 

loop_ 
_geom_angle_atom_site_label_1 
_geom_angle_atom_site_label_2 
_geom_angle_atom_site_label_3 
_geom_angle 
_geom_angle_site_symmetry_1 
_geom_angle_site_symmetry_3 
_geom_angle_publ_flag 
O4 S1 O5 117.9(2) . . ? 
O4 S1 C12 106.6(2) . . ? 
O5 S1 C12 107.3(2) . . ? 
O4 S1 C6 108.8(2) . . ? 
O5 S1 C6 107.0(2) . . ? 
C12 S1 C6 108.9(2) . . ? 
C1 O2 C2 114.2(3) . . ? 
C5 O3 H100 109.5 . . ? 
O6 N1 O7 124.7(4) . . ? 
O6 N1 C20 117.9(5) . . ? 
O7 N1 C20 117.5(5) . . ? 
O9 N2 O8 123.2(4) . . ? 
O9 N2 C22 119.1(4) . . ? 
O8 N2 C22 117.7(4) . . ? 
O1 C1 O2 123.9(5) . . ? 
O1 C1 C18 122.6(4) . . ? 
O2 C1 C18 113.4(4) . . ? 
O2 C2 C3 109.1(3) . . ? 
O2 C2 H2A 109.9 . . ? 
C3 C2 H2A 109.9 . . ? 
O2 C2 H2B 109.9 . . ? 
C3 C2 H2B 109.9 . . ? 
H2A C2 H2B 108.3 . . ? 
C2 C3 C4 105.5(4) . . ? 
C2 C3 C5 111.9(4) . . ? 
C4 C3 C5 111.0(4) . . ? 
C2 C3 H3 109.5 . . ? 
C4 C3 H3 109.5 . . ? 
C5 C3 H3 109.5 . . ? 
C3 C4 H4A 109.5 . . ? 
C3 C4 H4B 109.5 . . ? 
H4A C4 H4B 109.5 . . ? 
C3 C4 H4C 109.5 . . ? 
H4A C4 H4C 109.5 . . ? 
H4B C4 H4C 109.5 . . ? 
O3 C5 C3 113.1(4) . . ? 
O3 C5 C6 110.7(4) . . ? 
C3 C5 C6 117.2(4) . . ? 
O3 C5 H5 104.8 . . ? 
C3 C5 H5 104.8 . . ? 
C6 C5 H5 104.8 . . ? 
C7 C6 C11 109.4(4) . . ? 
C7 C6 C5 112.6(4) . . ? 
C11 C6 C5 110.8(4) . . ? 
C7 C6 S1 108.4(3) . . ? 
C11 C6 S1 108.0(3) . . ? 
C5 C6 S1 107.6(3) . . ? 
C8 C7 C6 111.4(4) . . ? 
C8 C7 H7A 109.4 . . ? 
C6 C7 H7A 109.4 . . ? 
C8 C7 H7B 109.4 . . ? 
C6 C7 H7B 109.4 . . ? 
H7A C7 H7B 108.0 . . ? 
C9 C8 C7 112.7(4) . . ? 
C9 C8 H8A 109.0 . . ? 
C7 C8 H8A 109.0 . . ? 
C9 C8 H8B 109.0 . . ? 
C7 C8 H8B 109.0 . . ? 
H8A C8 H8B 107.8 . . ? 
C8 C9 C10 111.5(4) . . ? 
C8 C9 H9A 109.3 . . ? 
C10 C9 H9A 109.3 . . ? 
C8 C9 H9B 109.3 . . ? 
C10 C9 H9B 109.3 . . ? 
H9A C9 H9B 108.0 . . ? 
C9 C10 C11 111.5(4) . . ? 
C9 C10 H10A 109.3 . . ? 
C11 C10 H10A 109.3 . . ? 
C9 C10 H10B 109.3 . . ? 
C11 C10 H10B 109.3 . . ? 
H10A C10 H10B 108.0 . . ? 
C10 C11 C6 111.8(4) . . ? 
C10 C11 H11A 109.2 . . ? 
C6 C11 H11A 109.2 . . ? 
C10 C11 H11B 109.2 . . ? 
C6 C11 H11B 109.2 . . ? 
H11A C11 H11B 107.9 . . ? 
C17 C12 C13 121.0(4) . . ? 
C17 C12 S1 120.0(4) . . ? 
C13 C12 S1 118.8(4) . . ? 
C14 C13 C12 118.4(5) . . ? 
C14 C13 H13 120.8 . . ? 
C12 C13 H13 120.8 . . ? 
C13 C14 C15 120.7(5) . . ? 
C13 C14 H14 119.6 . . ? 
C15 C14 H14 119.6 . . ? 
C16 C15 C14 120.1(5) . . ? 
C16 C15 H15 119.9 . . ? 
C14 C15 H15 119.9 . . ? 
C15 C16 C17 120.2(5) . . ? 
C15 C16 H16 119.9 . . ? 
C17 C16 H16 119.9 . . ? 
C12 C17 C16 119.6(5) . . ? 
C12 C17 H17 120.2 . . ? 
C16 C17 H17 120.2 . . ? 
C23 C18 C19 120.1(4) . . ? 
C23 C18 C1 116.4(4) . . ? 
C19 C18 C1 123.3(4) . . ? 
C20 C19 C18 117.9(5) . . ? 
C20 C19 H19 121.1 . . ? 
C18 C19 H19 121.1 . . ? 
C19 C20 C21 123.9(4) . . ? 
C19 C20 N1 118.5(5) . . ? 
C21 C20 N1 117.5(4) . . ? 
C22 C21 C20 116.5(4) . . ? 
C22 C21 H21 121.8 . . ? 
C20 C21 H21 121.8 . . ? 
C21 C22 C23 122.9(4) . . ? 
C21 C22 N2 118.5(4) . . ? 
C23 C22 N2 118.6(4) . . ? 
C22 C23 C18 118.7(4) . . ? 
C22 C23 H23 120.6 . . ? 
C18 C23 H23 120.6 . . ? 

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 
C2 O2 C1 O1 5.7(7) . . . . ? 
C2 O2 C1 C18 -172.8(4) . . . . ? 
C1 O2 C2 C3 170.1(4) . . . . ? 
O2 C2 C3 C4 164.3(4) . . . . ? 
O2 C2 C3 C5 -74.9(5) . . . . ? 
C2 C3 C5 O3 16.7(5) . . . . ? 
C4 C3 C5 O3 134.3(4) . . . . ? 
C2 C3 C5 C6 147.4(4) . . . . ? 
C4 C3 C5 C6 -95.0(5) . . . . ? 
O3 C5 C6 C7 -171.3(4) . . . . ? 
C3 C5 C6 C7 56.9(5) . . . . ? 
O3 C5 C6 C11 -48.4(5) . . . . ? 
C3 C5 C6 C11 179.7(4) . . . . ? 
O3 C5 C6 S1 69.4(4) . . . . ? 
C3 C5 C6 S1 -62.5(4) . . . . ? 
O4 S1 C6 C7 -46.3(4) . . . . ? 
O5 S1 C6 C7 -174.8(3) . . . . ? 
C12 S1 C6 C7 69.5(4) . . . . ? 
O4 S1 C6 C11 -164.7(3) . . . . ? 
O5 S1 C6 C11 66.9(3) . . . . ? 
C12 S1 C6 C11 -48.9(4) . . . . ? 
O4 S1 C6 C5 75.7(3) . . . . ? 
O5 S1 C6 C5 -52.7(3) . . . . ? 
C12 S1 C6 C5 -168.5(3) . . . . ? 
C11 C6 C7 C8 -55.6(5) . . . . ? 
C5 C6 C7 C8 68.0(5) . . . . ? 
S1 C6 C7 C8 -173.1(3) . . . . ? 
C6 C7 C8 C9 54.7(5) . . . . ? 
C7 C8 C9 C10 -52.9(5) . . . . ? 
C8 C9 C10 C11 53.3(5) . . . . ? 
C9 C10 C11 C6 -56.2(5) . . . . ? 
C7 C6 C11 C10 56.9(5) . . . . ? 
C5 C6 C11 C10 -67.8(5) . . . . ? 
S1 C6 C11 C10 174.6(3) . . . . ? 
O4 S1 C12 C17 -149.0(4) . . . . ? 
O5 S1 C12 C17 -21.8(4) . . . . ? 
C6 S1 C12 C17 93.8(4) . . . . ? 
O4 S1 C12 C13 25.8(4) . . . . ? 
O5 S1 C12 C13 153.1(4) . . . . ? 
C6 S1 C12 C13 -91.4(4) . . . . ? 
C17 C12 C13 C14 -0.2(7) . . . . ? 
S1 C12 C13 C14 -175.0(4) . . . . ? 
C12 C13 C14 C15 1.4(7) . . . . ? 
C13 C14 C15 C16 -1.9(8) . . . . ? 
C14 C15 C16 C17 1.0(8) . . . . ? 
C13 C12 C17 C16 -0.6(7) . . . . ? 
S1 C12 C17 C16 174.1(4) . . . . ? 
C15 C16 C17 C12 0.2(7) . . . . ? 
O1 C1 C18 C23 1.1(7) . . . . ? 
O2 C1 C18 C23 179.6(4) . . . . ? 
O1 C1 C18 C19 -174.7(5) . . . . ? 
O2 C1 C18 C19 3.8(7) . . . . ? 
C23 C18 C19 C20 1.3(7) . . . . ? 
C1 C18 C19 C20 177.0(4) . . . . ? 
C18 C19 C20 C21 -2.1(7) . . . . ? 
C18 C19 C20 N1 -178.7(4) . . . . ? 
O6 N1 C20 C19 3.7(7) . . . . ? 
O7 N1 C20 C19 -175.6(5) . . . . ? 
O6 N1 C20 C21 -173.2(4) . . . . ? 
O7 N1 C20 C21 7.5(7) . . . . ? 
C19 C20 C21 C22 1.8(7) . . . . ? 
N1 C20 C21 C22 178.5(4) . . . . ? 
C20 C21 C22 C23 -0.8(7) . . . . ? 
C20 C21 C22 N2 -178.5(4) . . . . ? 
O9 N2 C22 C21 -175.2(5) . . . . ? 
O8 N2 C22 C21 4.4(7) . . . . ? 
O9 N2 C22 C23 7.0(7) . . . . ? 
O8 N2 C22 C23 -173.4(4) . . . . ? 
C21 C22 C23 C18 0.1(7) . . . . ? 
N2 C22 C23 C18 177.8(4) . . . . ? 
C19 C18 C23 C22 -0.3(7) . . . . ? 
C1 C18 C23 C22 -176.3(4) . . . . ? 

_diffrn_measured_fraction_theta_max    0.908 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.908 
_refine_diff_density_max    0.300 
_refine_diff_density_min   -0.467 
_refine_diff_density_rms    0.074