# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Karl Jorgensen'

_publ_contact_author_name        'Karl Jorgensen'
_publ_contact_author_email       KAJ@CHEM.AU.DK

_publ_section_title              
;
Organocatalytic Asymmetric Ring-opening of Aziridines
;

data_freds
_database_code_depnum_ccdc_archive 'CCDC 695828'
_audit_creation_date             2008-07-11T10:39:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION
#
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C24 H29 N1 O6 S1'
_chemical_formula_sum            'C24 H29 N O6 S'
_chemical_formula_weight         459.54
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION
#
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a                   5.7683(2)
_cell_length_b                   9.0468(3)
_cell_length_c                   43.5087(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2270.49(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.438
_cell_measurement_theta_max      26.128
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION
#
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_special_details           
;
?
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION
#
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.997
#----------------------------------------------------------------------------#
# DATA COLLECTION
#
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       
;
Narrow slices collected using \f- and \w-scans
;
_diffrn_detector_area_resol_mean 12.00
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_number            4819
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         2.3
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4819
_reflns_number_gt                4261
_reflns_threshold_expression     >2\s(I)
_diffrn_reflns_reduction_process 
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED
#
#----------------------------------------------------------------------------#
_computing_data_collection       'Apex2 (Bruker-Nonius, 2007)'
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2007)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2007)'
_computing_structure_solution    'SHELXS-96 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines(Farrugia, 1999)'
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION
#
#----------------------------------------------------------------------------#
_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^ > 2\s(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 Rfactors
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^)+(0.0496P)^2^+1.2752P] 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_number_reflns         4819
_refine_ls_number_parameters     351
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 1979 Friedel pairs'
#_refine_Friedel_coverage 0.697
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.047
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS
#
#----------------------------------------------------------------------------#
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 0 '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 and6.1.1.4'
O O 0.0106 0.006 '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'
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

S1 S 0.5454(4) 0.0449(2) 0.07087(4) 0.0607(5) Uani 0.701(3) 1 d PD A 1
O1 O 1.2291(4) 0.1411(3) 0.16995(7) 0.0266(6) Uani 0.701(3) 1 d P A 1
O2 O 0.3136(10) 0.0522(5) 0.08246(10) 0.0730(13) Uani 0.701(3) 1 d PD A 1
O3 O 0.6115(7) -0.0720(4) 0.05107(8) 0.0625(10) Uani 0.701(3) 1 d PD A 1
S1A S 0.4522(6) 0.0570(2) 0.08074(6) 0.0206(6) Uani 0.299(3) 1 d PD A 2
O1A O 1.2686(11) 0.1747(7) 0.18344(16) 0.0261(15) Uiso 0.299(3) 1 d P A 2
O2A O 0.2058(12) 0.0493(7) 0.07640(14) 0.0238(14) Uiso 0.299(3) 1 d PD A 2
O3A O 0.5915(11) -0.0723(7) 0.07244(15) 0.0304(14) Uiso 0.299(3) 1 d PD A 2
O4 O 0.5523(4) 0.2577(2) 0.28798(5) 0.0484(5) Uani 1 1 d . . .
O5 O 1.2157(4) 0.4943(3) 0.17227(5) 0.0262(6) Uani 0.701(3) 1 d P A 1
O6 O 1.0462(4) 0.5203(2) 0.12587(5) 0.0240(5) Uani 0.701(3) 1 d PD A 1
O5A O 1.1950(10) 0.3528(6) 0.12405(13) 0.0285(13) Uiso 0.299(3) 1 d P A 2
O6A O 1.0354(9) 0.5423(6) 0.14867(12) 0.0217(12) Uiso 0.299(3) 1 d PD A 2
C0 C 0.7180(4) 0.3707(3) 0.17766(6) 0.0302(5) Uani 1 1 d . . .
H0A H 0.7182 0.48 0.1787 0.036 Uiso 1 1 calc R . .
H0B H 0.5694 0.3375 0.1686 0.036 Uiso 1 1 calc R . .
C1 C 0.7518(4) 0.3049(3) 0.20900(6) 0.0285(5) Uani 1 1 d . . .
C2 C 0.6119(4) 0.3232(3) 0.23473(6) 0.0316(5) Uani 1 1 d . . .
H2 H 0.4791 0.3852 0.2341 0.038 Uiso 1 1 calc R . .
C3 C 0.6716(5) 0.2485(3) 0.26124(6) 0.0367(6) Uani 1 1 d . . .
C4 C 0.8655(5) 0.1540(3) 0.26204(8) 0.0458(7) Uani 1 1 d . . .
H4 H 0.9012 0.1012 0.2803 0.055 Uiso 1 1 calc R . .
C5 C 1.0027(5) 0.1380(3) 0.23657(8) 0.0473(8) Uani 1 1 d . . .
H5 H 1.1355 0.0759 0.2372 0.057 Uiso 1 1 calc R . .
C6 C 0.9452(4) 0.2140(3) 0.20973(7) 0.0383(6) Uani 1 1 d . A .
C7 C 1.0636(4) 0.2153(3) 0.18018(8) 0.0404(7) Uani 1 1 d . . .
C8 C 0.9265(4) 0.3139(3) 0.15832(6) 0.0314(6) Uani 1 1 d . A .
C9 C 0.8680(6) 0.2469(4) 0.12563(8) 0.0274(8) Uani 0.701(3) 1 d P A 1
H9A H 0.7805 0.3204 0.1134 0.033 Uiso 0.701(3) 1 calc PR A 1
H9B H 1.0138 0.2243 0.1146 0.033 Uiso 0.701(3) 1 calc PR A 1
C10 C 0.7244(7) 0.1061(4) 0.12890(8) 0.0311(8) Uani 0.701(3) 1 d P A 1
H10A H 0.7958 0.0386 0.1441 0.037 Uiso 0.701(3) 1 calc PR A 1
H10B H 0.5649 0.1298 0.1357 0.037 Uiso 0.701(3) 1 calc PR A 1
N1 N 0.7218(8) 0.0404(6) 0.09951(9) 0.0678(14) Uani 0.701(3) 1 d P A 1
H1 H 0.8439 -0.0156 0.0961 0.081 Uiso 0.701(3) 1 calc PR A 1
C9A C 0.8432(13) 0.1655(8) 0.14504(17) 0.0220(16) Uiso 0.299(3) 1 d P A 2
H9A1 H 0.9775 0.1051 0.1384 0.026 Uiso 0.299(3) 1 calc PR A 2
H9A2 H 0.7556 0.1095 0.1608 0.026 Uiso 0.299(3) 1 calc PR A 2
C10A C 0.6895(14) 0.1998(9) 0.11791(18) 0.0254(17) Uiso 0.299(3) 1 d P A 2
H10C H 0.6319 0.3025 0.1196 0.031 Uiso 0.299(3) 1 calc PR A 2
H10D H 0.7811 0.1921 0.0987 0.031 Uiso 0.299(3) 1 calc PR A 2
N1A N 0.4891(11) 0.0967(7) 0.11632(14) 0.0211(14) Uiso 0.299(3) 1 d P A 2
H1A H 0.4067 0.0638 0.1319 0.025 Uiso 0.299(3) 1 calc PR A 2
C12 C 0.5811(6) 0.2097(4) 0.05397(8) 0.0539(8) Uani 1 1 d D . .
C13 C 0.7914(7) 0.2213(5) 0.03847(10) 0.0699(12) Uani 1 1 d . A .
H13 H 0.8979 0.1412 0.0385 0.084 Uiso 1 1 calc R . .
C14 C 0.8428(6) 0.3491(6) 0.02321(9) 0.0723(13) Uani 1 1 d . . .
H14 H 0.987 0.3571 0.0128 0.087 Uiso 1 1 calc R A .
C15 C 0.6935(7) 0.4649(5) 0.02254(8) 0.0620(10) Uani 1 1 d . A .
C16 C 0.4850(7) 0.4504(4) 0.03785(8) 0.0596(9) Uani 1 1 d . . .
H16 H 0.3785 0.5305 0.0375 0.072 Uiso 1 1 calc R A .
C17 C 0.4273(6) 0.3256(4) 0.05340(8) 0.0539(8) Uani 1 1 d . A .
H17 H 0.2826 0.3185 0.0637 0.065 Uiso 1 1 calc R . .
C18 C 0.7526(11) 0.6038(6) 0.00533(12) 0.107(2) Uani 1 1 d . . .
H18A H 0.6265 0.6755 0.0077 0.16 Uiso 1 1 calc R A .
H18B H 0.7737 0.5807 -0.0165 0.16 Uiso 1 1 calc R . .
H18C H 0.8963 0.6458 0.0136 0.16 Uiso 1 1 calc R . .
C19 C 0.3813(6) 0.3702(3) 0.29046(7) 0.0502(8) Uani 1 1 d . . .
H19A H 0.3087 0.3653 0.3108 0.075 Uiso 1 1 calc R . .
H19B H 0.2631 0.3557 0.2746 0.075 Uiso 1 1 calc R . .
H19C H 0.4543 0.4672 0.2877 0.075 Uiso 1 1 calc R . .
C20 C 1.0835(6) 0.4533(5) 0.15247(8) 0.0217(7) Uani 0.701(3) 1 d P A 1
C21 C 1.1643(6) 0.6601(4) 0.11762(11) 0.0241(8) Uani 0.701(3) 1 d PD A 1
C22 C 1.4241(6) 0.6357(4) 0.11624(11) 0.0317(8) Uani 0.701(3) 1 d PD A 1
H22A H 1.4589 0.5583 0.1012 0.048 Uiso 0.701(3) 1 calc PR A 1
H22B H 1.4804 0.6053 0.1365 0.048 Uiso 0.701(3) 1 calc PR A 1
H22C H 1.5008 0.7278 0.1101 0.048 Uiso 0.701(3) 1 calc PR A 1
C23 C 1.0649(7) 0.6934(5) 0.08591(9) 0.0321(8) Uani 0.701(3) 1 d PD A 1
H23A H 0.8972 0.7089 0.0876 0.048 Uiso 0.701(3) 1 calc PR A 1
H23B H 1.0955 0.6099 0.0721 0.048 Uiso 0.701(3) 1 calc PR A 1
H23C H 1.138 0.7827 0.0776 0.048 Uiso 0.701(3) 1 calc PR A 1
C24 C 1.0970(17) 0.7783(7) 0.1416(2) 0.0347(17) Uani 0.701(3) 1 d PD A 1
H24A H 0.928 0.7894 0.142 0.052 Uiso 0.701(3) 1 calc PR A 1
H24B H 1.1686 0.8729 0.1361 0.052 Uiso 0.701(3) 1 calc PR A 1
H24C H 1.1515 0.7475 0.162 0.052 Uiso 0.701(3) 1 calc PR A 1
C20A C 1.0644(18) 0.3990(12) 0.1434(2) 0.027(2) Uiso 0.299(3) 1 d P A 2
C21A C 1.1529(15) 0.6607(11) 0.1295(2) 0.019(2) Uiso 0.299(3) 1 d PD A 2
C22A C 1.4135(13) 0.6465(9) 0.1317(2) 0.0229(19) Uiso 0.299(3) 1 d PD A 2
H22D H 1.4609 0.5487 0.1244 0.034 Uiso 0.299(3) 1 calc PR A 2
H22E H 1.4618 0.6588 0.1532 0.034 Uiso 0.299(3) 1 calc PR A 2
H22F H 1.4868 0.7229 0.119 0.034 Uiso 0.299(3) 1 calc PR A 2
C23A C 1.0652(17) 0.6489(10) 0.0968(2) 0.025(2) Uiso 0.299(3) 1 d PD A 2
H23D H 1.1126 0.5537 0.0881 0.037 Uiso 0.299(3) 1 calc PR A 2
H23E H 1.1305 0.7294 0.0845 0.037 Uiso 0.299(3) 1 calc PR A 2
H23F H 0.8957 0.6559 0.0967 0.037 Uiso 0.299(3) 1 calc PR A 2
C24A C 1.078(4) 0.8043(13) 0.1426(5) 0.033(5) Uiso 0.299(3) 1 d PD A 2
H24D H 0.9089 0.8116 0.1418 0.05 Uiso 0.299(3) 1 calc PR A 2
H24E H 1.1472 0.8851 0.1307 0.05 Uiso 0.299(3) 1 calc PR A 2
H24F H 1.1296 0.811 0.1641 0.05 Uiso 0.299(3) 1 calc PR A 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

S1 0.0572(10) 0.0787(11) 0.0461(8) -0.0300(8) 0.0024(7) -0.0278(9)
O1 0.0208(12) 0.0256(12) 0.0334(14) -0.0015(11) 0.0020(11) 0.0059(10)
O2 0.055(3) 0.089(3) 0.075(3) -0.033(2) 0.004(3) -0.038(3)
O3 0.076(2) 0.069(2) 0.0427(18) -0.0259(17) -0.0130(17) -0.006(2)
S1A 0.0210(13) 0.0215(10) 0.0193(12) -0.0007(9) -0.0063(10) -0.0009(10)
O4 0.0650(14) 0.0421(11) 0.0380(10) 0.0004(9) -0.0004(11) 0.0027(11)
O5 0.0251(11) 0.0250(11) 0.0284(12) -0.0016(9) -0.0047(10) -0.0014(10)
O6 0.0253(11) 0.0241(11) 0.0226(12) 0.0052(9) -0.0020(9) -0.0007(10)
C0 0.0187(10) 0.0266(12) 0.0453(14) 0.0056(11) 0.0052(10) 0.0027(9)
C1 0.0184(10) 0.0213(11) 0.0458(14) 0.0028(10) -0.0020(10) -0.0033(9)
C2 0.0288(12) 0.0226(11) 0.0433(14) -0.0028(10) -0.0020(11) -0.0005(10)
C3 0.0405(15) 0.0308(13) 0.0389(14) -0.0005(11) -0.0030(12) -0.0082(12)
C4 0.0400(15) 0.0406(16) 0.0567(18) 0.0184(14) -0.0097(14) -0.0050(13)
C5 0.0257(13) 0.0382(15) 0.078(2) 0.0258(15) 0.0007(14) 0.0016(12)
C6 0.0234(12) 0.0271(12) 0.0643(18) 0.0144(12) 0.0025(13) -0.0004(11)
C7 0.0199(11) 0.0224(12) 0.079(2) 0.0177(13) 0.0107(13) 0.0022(10)
C8 0.0190(10) 0.0292(12) 0.0460(14) -0.0124(11) -0.0030(11) -0.0004(10)
C9 0.0308(18) 0.0271(17) 0.0243(16) 0.0007(14) -0.0053(14) -0.0021(14)
C10 0.0335(19) 0.0268(18) 0.0331(19) 0.0024(15) -0.0120(16) -0.0032(15)
N1 0.061(3) 0.102(4) 0.041(2) -0.029(2) 0.0042(19) -0.037(3)
C12 0.0548(19) 0.0521(19) 0.0548(19) -0.0166(15) -0.0178(16) -0.0024(17)
C13 0.046(2) 0.085(3) 0.079(3) -0.040(2) -0.0201(19) 0.021(2)
C14 0.0395(18) 0.116(4) 0.062(2) -0.039(3) 0.0086(17) -0.003(2)
C15 0.065(2) 0.076(3) 0.0457(18) -0.0187(18) 0.0153(17) -0.017(2)
C16 0.061(2) 0.062(2) 0.0563(19) -0.0183(17) 0.0155(17) 0.0129(19)
C17 0.0451(17) 0.063(2) 0.0539(18) -0.0130(17) 0.0101(15) -0.0047(17)
C18 0.143(5) 0.098(4) 0.080(3) -0.013(3) 0.032(3) -0.041(4)
C19 0.070(2) 0.0405(16) 0.0404(16) -0.0048(13) 0.0120(15) -0.0024(16)
C20 0.0151(15) 0.0240(19) 0.0259(17) 0.0037(17) 0.0037(14) 0.0050(15)
C21 0.0254(19) 0.0199(18) 0.027(2) 0.0019(16) 0.0036(17) -0.0036(13)
C22 0.0223(17) 0.034(2) 0.039(2) 0.0041(17) 0.0016(16) 0.0006(15)
C23 0.0294(18) 0.036(2) 0.031(2) 0.0074(18) 0.0023(17) -0.0021(17)
C24 0.043(3) 0.016(2) 0.045(3) 0.005(2) -0.005(2) 0.001(3)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY
#
#----------------------------------------------------------------------------#
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell s.u.'s are
taken
into account individually in the estimation of s.u.'s in distances,
angles
and torsion angles; correlations between s.u.'s in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 O3 1.416(4) . ?
S1 O2 1.431(5) . ?
S1 N1 1.609(4) . ?
S1 C12 1.675(4) . ?
O1 C7 1.249(4) . ?
S1A O2A 1.435(6) . ?
S1A O3A 1.464(6) . ?
S1A N1A 1.604(6) . ?
S1A C12 1.954(5) . ?
O1A C7 1.246(7) . ?
O4 C3 1.354(4) . ?
O4 C19 1.421(4) . ?
O5 C20 1.209(5) . ?
O6 C20 1.324(4) . ?
O6 C21 1.481(4) . ?
O5A C20A 1.206(12) . ?
O6A C20A 1.326(11) . ?
O6A C21A 1.517(11) . ?
C0 C1 1.501(4) . ?
C0 C8 1.555(3) . ?
C0 H0A 0.99 . ?
C0 H0B 0.99 . ?
C1 C6 1.386(3) . ?
C1 C2 1.390(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.95 . ?
C3 C4 1.408(4) . ?
C4 C5 1.370(4) . ?
C4 H4 0.95 . ?
C5 C6 1.395(4) . ?
C5 H5 0.95 . ?
C6 C7 1.456(4) . ?
C7 C8 1.525(4) . ?
C8 C20A 1.282(10) . ?
C8 C9A 1.539(8) . ?
C8 C20 1.573(4) . ?
C8 C9 1.583(4) . ?
C9 C10 1.526(5) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N1 1.410(5) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
N1 H1 0.88 . ?
C9A C10A 1.508(10) . ?
C9A H9A1 0.99 . ?
C9A H9A2 0.99 . ?
C10A N1A 1.487(10) . ?
C10A H10C 0.99 . ?
C10A H10D 0.99 . ?
N1A H1A 0.88 . ?
C12 C17 1.374(5) . ?
C12 C13 1.392(6) . ?
C13 C14 1.366(7) . ?
C13 H13 0.95 . ?
C14 C15 1.357(6) . ?
C14 H14 0.95 . ?
C15 C16 1.381(5) . ?
C15 C18 1.502(6) . ?
C16 C17 1.358(5) . ?
C16 H16 0.95 . ?
C17 H17 0.95 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C21 C22 1.516(5) . ?
C21 C23 1.524(6) . ?
C21 C24 1.544(8) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C21A C24A 1.483(13) . ?
C21A C22A 1.512(10) . ?
C21A C23A 1.513(10) . ?
C22A H22D 0.98 . ?
C22A H22E 0.98 . ?
C22A H22F 0.98 . ?
C23A H23D 0.98 . ?
C23A H23E 0.98 . ?
C23A H23F 0.98 . ?
C24A H24D 0.98 . ?
C24A H24E 0.98 . ?
C24A H24F 0.98 . ?
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

O3 S1 O2 120.0(2) . . ?
O3 S1 N1 106.4(3) . . ?
O2 S1 N1 108.6(3) . . ?
O3 S1 C12 111.4(2) . . ?
O2 S1 C12 103.2(3) . . ?
N1 S1 C12 106.5(2) . . ?
O2A S1A O3A 118.2(4) . . ?
O2A S1A N1A 105.6(4) . . ?
O3A S1A N1A 110.1(4) . . ?
O2A S1A C12 109.4(3) . . ?
O3A S1A C12 102.1(3) . . ?
N1A S1A C12 111.5(3) . . ?
C3 O4 C19 117.5(2) . . ?
C20 O6 C21 121.9(3) . . ?
C20A O6A C21A 122.6(7) . . ?
C1 C0 C8 105.1(2) . . ?
C1 C0 H0A 110.7 . . ?
C8 C0 H0A 110.7 . . ?
C1 C0 H0B 110.7 . . ?
C8 C0 H0B 110.7 . . ?
H0A C0 H0B 108.8 . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 C0 111.1(2) . . ?
C2 C1 C0 127.5(2) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121 . . ?
C1 C2 H2 121 . . ?
O4 C3 C2 124.1(3) . . ?
O4 C3 C4 114.8(3) . . ?
C2 C3 C4 121.0(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 C7 110.7(2) . . ?
C5 C6 C7 129.1(2) . . ?
O1A C7 C6 110.0(4) . . ?
O1 C7 C6 132.0(3) . . ?
O1A C7 C8 137.3(4) . . ?
O1 C7 C8 119.2(3) . . ?
C6 C7 C8 108.2(2) . . ?
C20A C8 C7 110.2(5) . . ?
C20A C8 C9A 121.9(6) . . ?
C7 C8 C9A 83.4(3) . . ?
C20A C8 C0 123.7(5) . . ?
C7 C8 C0 104.9(2) . . ?
C9A C8 C0 104.5(3) . . ?
C7 C8 C20 105.8(2) . . ?
C9A C8 C20 144.9(4) . . ?
C0 C8 C20 105.5(2) . . ?
C20A C8 C9 84.8(5) . . ?
C7 C8 C9 116.5(2) . . ?
C0 C8 C9 116.6(2) . . ?
C20 C8 C9 106.5(2) . . ?
C10 C9 C8 110.6(3) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C9 105.9(3) . . ?
N1 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
N1 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C10 N1 S1 134.3(4) . . ?
C10 N1 H1 112.9 . . ?
S1 N1 H1 112.9 . . ?
C10A C9A C8 107.3(6) . . ?
C10A C9A H9A1 110.3 . . ?
C8 C9A H9A1 110.3 . . ?
C10A C9A H9A2 110.3 . . ?
C8 C9A H9A2 110.3 . . ?
H9A1 C9A H9A2 108.5 . . ?
N1A C10A C9A 111.4(6) . . ?
N1A C10A H10C 109.4 . . ?
C9A C10A H10C 109.4 . . ?
N1A C10A H10D 109.4 . . ?
C9A C10A H10D 109.4 . . ?
H10C C10A H10D 108 . . ?
C10A N1A S1A 106.8(5) . . ?
C10A N1A H1A 126.6 . . ?
S1A N1A H1A 126.6 . . ?
C17 C12 C13 119.8(4) . . ?
C17 C12 S1 127.5(3) . . ?
C13 C12 S1 112.7(3) . . ?
C17 C12 S1A 107.7(3) . . ?
C13 C12 S1A 132.4(3) . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 121.8(4) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 118.0(4) . . ?
C14 C15 C18 120.8(4) . . ?
C16 C15 C18 121.2(4) . . ?
C17 C16 C15 122.2(4) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C12 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 O6 125.8(3) . . ?
O5 C20 C8 119.6(3) . . ?
O6 C20 C8 114.5(3) . . ?
O6 C21 C22 109.9(3) . . ?
O6 C21 C23 102.4(3) . . ?
C22 C21 C23 111.4(4) . . ?
O6 C21 C24 108.1(4) . . ?
C22 C21 C24 112.1(5) . . ?
C23 C21 C24 112.4(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5A C20A C8 122.2(9) . . ?
O5A C20A O6A 122.5(8) . . ?
C8 C20A O6A 115.0(8) . . ?
C24A C21A C22A 109.8(12) . . ?
C24A C21A C23A 109.1(12) . . ?
C22A C21A C23A 112.7(8) . . ?
C24A C21A O6A 106.1(9) . . ?
C22A C21A O6A 110.5(7) . . ?
C23A C21A O6A 108.5(7) . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C21A C23A H23D 109.5 . . ?
C21A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C21A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C21A C24A H24D 109.5 . . ?
C21A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C21A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
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

C8 C0 C1 C6 -2.4(3) . . . . ?
C8 C0 C1 C2 179.6(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C0 C1 C2 C3 178.1(2) . . . . ?
C19 O4 C3 C2 -11.6(4) . . . . ?
C19 O4 C3 C4 169.0(3) . . . . ?
C1 C2 C3 O4 179.2(2) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
O4 C3 C4 C5 -178.6(3) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C0 C1 C6 C5 -177.9(3) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
C0 C1 C6 C7 2.7(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C1 C6 C7 O1A 158.9(4) . . . . ?
C5 C6 C7 O1A -20.5(5) . . . . ?
C1 C6 C7 O1 -172.7(3) . . . . ?
C5 C6 C7 O1 7.9(6) . . . . ?
C1 C6 C7 C8 -1.7(3) . . . . ?
C5 C6 C7 C8 178.9(3) . . . . ?
O1A C7 C8 C20A -17.3(9) . . . . ?
O1 C7 C8 C20A -52.4(6) . . . . ?
C6 C7 C8 C20A 135.3(6) . . . . ?
O1A C7 C8 C9A 104.3(7) . . . . ?
O1 C7 C8 C9A 69.2(4) . . . . ?
C6 C7 C8 C9A -103.1(4) . . . . ?
O1A C7 C8 C0 -152.5(6) . . . . ?
O1 C7 C8 C0 172.5(3) . . . . ?
C6 C7 C8 C0 0.2(3) . . . . ?
O1A C7 C8 C20 -41.2(7) . . . . ?
O1 C7 C8 C20 -76.2(3) . . . . ?
C6 C7 C8 C20 111.5(3) . . . . ?
O1A C7 C8 C9 76.9(7) . . . . ?
O1 C7 C8 C9 41.9(4) . . . . ?
C6 C7 C8 C9 -130.4(3) . . . . ?
C1 C0 C8 C20A -126.0(6) . . . . ?
C1 C0 C8 C7 1.3(3) . . . . ?
C1 C0 C8 C9A 88.2(4) . . . . ?
C1 C0 C8 C20 -110.2(2) . . . . ?
C1 C0 C8 C9 131.8(2) . . . . ?
C20A C8 C9 C10 169.7(5) . . . . ?
C7 C8 C9 C10 59.7(3) . . . . ?
C9A C8 C9 C10 17.2(5) . . . . ?
C0 C8 C9 C10 -65.1(3) . . . . ?
C20 C8 C9 C10 177.4(3) . . . . ?
C8 C9 C10 N1 -168.6(3) . . . . ?
C9 C10 N1 S1 -94.9(5) . . . . ?
O3 S1 N1 C10 -166.0(5) . . . . ?
O2 S1 N1 C10 -35.5(6) . . . . ?
C12 S1 N1 C10 75.0(5) . . . . ?
C20A C8 C9A C10A -67.4(8) . . . . ?
C7 C8 C9A C10A -177.1(5) . . . . ?
C0 C8 C9A C10A 79.2(5) . . . . ?
C20 C8 C9A C10A -69.0(8) . . . . ?
C9 C8 C9A C10A -34.6(4) . . . . ?
C8 C9A C10A N1A -141.8(6) . . . . ?
C9A C10A N1A S1A -139.9(6) . . . . ?
O2A S1A N1A C10A -142.2(5) . . . . ?
O3A S1A N1A C10A 89.1(6) . . . . ?
C12 S1A N1A C10A -23.4(5) . . . . ?
O3 S1 C12 C17 133.7(3) . . . . ?
O2 S1 C12 C17 3.6(4) . . . . ?
N1 S1 C12 C17 -110.7(3) . . . . ?
O3 S1 C12 C13 -44.4(3) . . . . ?
O2 S1 C12 C13 -174.4(3) . . . . ?
N1 S1 C12 C13 71.3(3) . . . . ?
O3 S1 C12 S1A 149.5(4) . . . . ?
O2 S1 C12 S1A 19.4(3) . . . . ?
N1 S1 C12 S1A -94.9(3) . . . . ?
O2A S1A C12 C17 38.2(4) . . . . ?
O3A S1A C12 C17 164.1(3) . . . . ?
N1A S1A C12 C17 -78.3(4) . . . . ?
O2A S1A C12 C13 -146.1(4) . . . . ?
O3A S1A C12 C13 -20.2(4) . . . . ?
N1A S1A C12 C13 97.4(4) . . . . ?
O2A S1A C12 S1 -128.7(4) . . . . ?
O3A S1A C12 S1 -2.7(3) . . . . ?
N1A S1A C12 S1 114.8(4) . . . . ?
C17 C12 C13 C14 0.9(5) . . . . ?
S1 C12 C13 C14 179.1(3) . . . . ?
S1A C12 C13 C14 -174.4(3) . . . . ?
C12 C13 C14 C15 -0.5(6) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C13 C14 C15 C18 -179.3(4) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C18 C15 C16 C17 179.6(4) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C13 C12 C17 C16 -0.6(5) . . . . ?
S1 C12 C17 C16 -178.6(3) . . . . ?
S1A C12 C17 C16 175.7(3) . . . . ?
C21 O6 C20 O5 -1.3(5) . . . . ?
C21 O6 C20 C8 174.9(3) . . . . ?
C20A C8 C20 O5 -134.4(14) . . . . ?
C7 C8 C20 O5 -29.8(4) . . . . ?
C9A C8 C20 O5 -131.1(6) . . . . ?
C0 C8 C20 O5 81.0(3) . . . . ?
C9 C8 C20 O5 -154.4(3) . . . . ?
C20A C8 C20 O6 49.1(12) . . . . ?
C7 C8 C20 O6 153.6(3) . . . . ?
C9A C8 C20 O6 52.4(7) . . . . ?
C0 C8 C20 O6 -95.5(3) . . . . ?
C9 C8 C20 O6 29.0(4) . . . . ?
C20 O6 C21 C22 62.2(5) . . . . ?
C20 O6 C21 C23 -179.3(3) . . . . ?
C20 O6 C21 C24 -60.5(5) . . . . ?
C7 C8 C20A O5A 69.8(10) . . . . ?
C9A C8 C20A O5A -25.0(12) . . . . ?
C0 C8 C20A O5A -165.2(7) . . . . ?
C20 C8 C20A O5A 153(2) . . . . ?
C9 C8 C20A O5A -46.6(9) . . . . ?
C7 C8 C20A O6A -116.9(7) . . . . ?
C9A C8 C20A O6A 148.3(7) . . . . ?
C0 C8 C20A O6A 8.1(11) . . . . ?
C20 C8 C20A O6A -34.0(8) . . . . ?
C9 C8 C20A O6A 126.8(8) . . . . ?
C21A O6A C20A O5A 3.7(13) . . . . ?
C21A O6A C20A C8 -169.6(7) . . . . ?
C20A O6A C21A C24A -179.6(13) . . . . ?
C20A O6A C21A C22A -60.7(10) . . . . ?
C20A O6A C21A C23A 63.3(10) . . . . ?