# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#TrackingRef 'ccdc-deposit.cif'

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2011-03-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#==============================================================================
#
# SUBMISSION DETAILS

_publ_contact_author_name        'Sahin, Ertan'
# Name of author for correspondence

_publ_contact_author_address     
;
Department of Chemistry
Ataturk University
25240 Erzurum Turkey

;
# Address of author for correspondence

_publ_contact_author_email       ertan@atauni.edu.tr
_publ_contact_author_fax         00(000)0000000
_publ_contact_author_phone       90(442)2314380

_publ_contact_letter             
;
Submission dated :2011-03-21

Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.

This CIF is submitted as a personal communication

This CIF is submitted as part of a journal submission
<Advanced Synthesis & Catalysis>

Sahin, Ertan
;

#==============================================================================
#
# TITLE AND AUTHOR LIST

_publ_section_title              
;
Synthesis of Chiral Sulfoximines Derived from 3-Aminoquinazolinones and
Their Catalytic Performance in Enantioselective Diethylzinc Addition to
Aldehydes
;
_publ_section_title_footnote     
; ?
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_footnote
_publ_author_address
#<--'Last name, first name'
; ?
;
;
Department of Chemistry
Ataturk University
25240 Erzurum Turkey

;
_publ_author_name                E.Sahin

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_shelxkafkas-sabri
_database_code_depnum_ccdc_archive 'CCDC 818097'
#TrackingRef 'ccdc-deposit.cif'

_audit_creation_date             2011-03-21T00:38:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_analytical     ?
_chemical_formula_moiety         'C20 H23 N3 O3 S'
_chemical_formula_sum            'C20 H23 N3 O3 S'
_chemical_formula_weight         385.47
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   10.3331(3)
_cell_length_b                   10.8017(3)
_cell_length_c                   18.4984(5)
_cell_angle_alpha                90.0000(0)
_cell_angle_beta                 102.951(45)
_cell_angle_gamma                90.0000(0)
_cell_volume                     2012.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6762
_cell_measurement_theta_min      2.0836
_cell_measurement_theta_max      30.4973

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.964

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_ub_11      0.0021
_diffrn_orient_matrix_ub_12      -0.0103
_diffrn_orient_matrix_ub_13      -0.0987
_diffrn_orient_matrix_ub_21      0.0925
_diffrn_orient_matrix_ub_22      -0.0024
_diffrn_orient_matrix_ub_23      0.0022
_diffrn_orient_matrix_ub_31      -0.0012
_diffrn_orient_matrix_ub_32      -0.055
_diffrn_orient_matrix_ub_33      -0.0068
_diffrn_measurement_device       
;
RAXIS conversion
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_number            57587
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         30.6
_diffrn_reflns_theta_full        30.6
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             11677
_reflns_number_gt                7693
_reflns_threshold_expression     >2\s(I)
_diffrn_reflns_reduction_process 'Lp corrections applied'

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    
;
????
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# 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 R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.0306(17)
_refine_ls_number_reflns         11677
_refine_ls_number_parameters     498
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.123
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
# 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 and 6.1.1.4'
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
S S 1.04798(6) 0.58773(6) 0.62105(4) 0.05396(16) Uani 1 1 d . . .
S' S 0.74406(7) 0.23489(6) 0.99331(3) 0.05569(17) Uani 1 1 d . . .
N1 N 0.9088(2) 0.5290(2) 0.62131(12) 0.0534(5) Uani 1 1 d . . .
N2 N 0.80496(19) 0.61330(19) 0.58726(11) 0.0508(5) Uani 1 1 d . . .
O1' O 0.79544(19) 0.10893(19) 1.00293(11) 0.0672(5) Uani 1 1 d . . .
O2 O 0.7682(2) 0.5061(2) 0.47768(11) 0.0719(6) Uani 1 1 d . . .
O1 O 1.07442(19) 0.71253(18) 0.64916(12) 0.0698(5) Uani 1 1 d . . .
N1' N 0.7139(2) 0.2931(2) 0.91338(11) 0.0559(5) Uani 1 1 d . . .
N3' N 0.6310(2) 0.0401(2) 0.78143(12) 0.0578(5) Uani 1 1 d . . .
N2' N 0.63317(19) 0.20919(19) 0.86219(11) 0.0501(5) Uani 1 1 d . . .
O2' O 0.4437(2) 0.3206(2) 0.86284(13) 0.0781(6) Uani 1 1 d . . .
N3 N 0.6649(2) 0.7753(2) 0.60692(12) 0.0607(6) Uani 1 1 d . . .
O3 O 0.7662(2) 0.7944(2) 0.74813(12) 0.0798(6) Uani 1 1 d . . .
H3O H 0.7002 0.824 0.7205 0.12 Uiso 1 1 calc R . .
C12 C 0.6440(2) 0.6897(3) 0.48338(14) 0.0542(6) Uani 1 1 d . . .
C6 C 1.0892(2) 0.5858(3) 0.53294(15) 0.0573(6) Uani 1 1 d . . .
C17' C 0.4934(3) 0.0356(3) 0.77137(14) 0.0563(6) Uani 1 1 d . . .
C18' C 0.6938(2) 0.1235(2) 0.82537(13) 0.0521(6) Uani 1 1 d . . .
C19 C 0.8051(3) 0.6867(3) 0.71567(15) 0.0640(7) Uani 1 1 d . . .
H19 H 0.9022 0.6802 0.7282 0.077 Uiso 1 1 calc R . .
C18 C 0.7565(2) 0.6952(2) 0.63183(14) 0.0539(6) Uani 1 1 d . . .
C11 C 0.7413(2) 0.5940(3) 0.51253(14) 0.0547(6) Uani 1 1 d . . .
C12' C 0.4238(2) 0.1262(3) 0.80046(13) 0.0537(6) Uani 1 1 d . . .
C17 C 0.6117(3) 0.7789(3) 0.53097(16) 0.0591(6) Uani 1 1 d . . .
C11' C 0.4948(2) 0.2288(3) 0.84299(14) 0.0564(6) Uani 1 1 d . . .
C1' C 0.5836(3) 0.1369(3) 1.07849(15) 0.0665(7) Uani 1 1 d . . .
H1' H 0.6403 0.069 1.0849 0.08 Uiso 1 1 calc R . .
C7' C 0.8670(3) 0.3422(3) 1.04526(16) 0.0688(8) Uani 1 1 d . . .
C6' C 0.6053(3) 0.2373(3) 1.03509(13) 0.0586(6) Uani 1 1 d . . .
C7 C 1.1609(3) 0.4801(3) 0.67977(17) 0.0690(8) Uani 1 1 d . . .
C16 C 0.5235(3) 0.8733(3) 0.5015(2) 0.0781(9) Uani 1 1 d . . .
H16 H 0.5031 0.9347 0.5324 0.094 Uiso 1 1 calc R . .
C16' C 0.4226(3) -0.0612(3) 0.73024(18) 0.0758(8) Uani 1 1 d . . .
H16A H 0.4679 -0.123 0.7111 0.091 Uiso 1 1 calc R . .
C5 C 1.0511(3) 0.4858(3) 0.48572(15) 0.0609(6) Uani 1 1 d . . .
H5 H 1.0007 0.4218 0.4988 0.073 Uiso 1 1 calc R . .
C14 C 0.4973(3) 0.7853(4) 0.38043(18) 0.0769(9) Uani 1 1 d . . .
H14 H 0.4583 0.7879 0.33 0.092 Uiso 1 1 calc R . .
C13 C 0.5840(3) 0.6927(3) 0.40788(16) 0.0658(7) Uani 1 1 d . . .
H13 H 0.603 0.6316 0.3764 0.079 Uiso 1 1 calc R . .
C5' C 0.5194(3) 0.3380(3) 1.02473(16) 0.0677(7) Uani 1 1 d . . .
H5' H 0.5322 0.403 0.9941 0.081 Uiso 1 1 calc R . .
C13' C 0.2851(3) 0.1189(3) 0.78852(16) 0.0684(8) Uani 1 1 d . . .
H13A H 0.2388 0.1793 0.8081 0.082 Uiso 1 1 calc R . .
C8 C 1.1316(4) 0.4901(4) 0.75761(18) 0.0910(11) Uani 1 1 d . . .
H8A H 1.1502 0.5727 0.7761 0.136 Uiso 1 1 calc R . .
H8B H 1.1866 0.4326 0.7904 0.136 Uiso 1 1 calc R . .
H8C H 1.0399 0.4711 0.7548 0.136 Uiso 1 1 calc R . .
C1 C 1.1610(3) 0.6830(3) 0.51319(19) 0.0766(9) Uani 1 1 d . . .
H1 H 1.1849 0.7503 0.5447 0.092 Uiso 1 1 calc R . .
C15' C 0.2870(4) -0.0653(4) 0.7180(2) 0.0847(10) Uani 1 1 d . . .
H15A H 0.2407 -0.1284 0.6891 0.102 Uiso 1 1 calc R . .
C9' C 0.8178(4) 0.4738(3) 1.0401(2) 0.0932(11) Uani 1 1 d . . .
H9E H 0.8844 0.5264 1.0694 0.14 Uiso 1 1 calc R . .
H9F H 0.738 0.4786 1.0583 0.14 Uiso 1 1 calc R . .
H9D H 0.7997 0.5004 0.9893 0.14 Uiso 1 1 calc R . .
C14' C 0.2177(3) 0.0242(4) 0.74859(19) 0.0807(10) Uani 1 1 d . . .
H14A H 0.1259 0.0191 0.7416 0.097 Uiso 1 1 calc R . .
C15 C 0.4667(3) 0.8758(4) 0.4270(2) 0.0858(10) Uani 1 1 d . . .
H15 H 0.4074 0.9385 0.4077 0.103 Uiso 1 1 calc R . .
C4 C 1.0896(3) 0.4834(4) 0.41924(18) 0.0765(9) Uani 1 1 d . . .
H4 H 1.0653 0.4168 0.3872 0.092 Uiso 1 1 calc R . .
C20 C 0.7460(4) 0.5737(4) 0.74419(17) 0.0841(10) Uani 1 1 d . . .
H20A H 0.6509 0.5798 0.7319 0.126 Uiso 1 1 calc R . .
H20B H 0.7768 0.5687 0.7971 0.126 Uiso 1 1 calc R . .
H20C H 0.7729 0.5007 0.7217 0.126 Uiso 1 1 calc R . .
C8' C 0.9904(4) 0.3286(5) 1.0126(3) 0.1032(13) Uani 1 1 d . . .
H8F H 1.0604 0.3799 1.0398 0.155 Uiso 1 1 calc R . .
H8E H 0.9691 0.3535 0.9615 0.155 Uiso 1 1 calc R . .
H8D H 1.0188 0.2437 1.0161 0.155 Uiso 1 1 calc R . .
C3 C 1.1627(4) 0.5774(5) 0.3997(2) 0.0977(12) Uani 1 1 d . . .
H3 H 1.1898 0.5736 0.3551 0.117 Uiso 1 1 calc R . .
C4' C 0.4162(4) 0.3409(4) 1.05972(19) 0.0814(9) Uani 1 1 d . . .
H4' H 0.3604 0.4095 1.0544 0.098 Uiso 1 1 calc R . .
C10' C 0.8975(4) 0.2944(4) 1.12529(17) 0.0926(11) Uani 1 1 d . . .
H10E H 0.8201 0.3034 1.1455 0.139 Uiso 1 1 calc R . .
H10F H 0.9694 0.3413 1.1546 0.139 Uiso 1 1 calc R . .
H10D H 0.922 0.2087 1.1259 0.139 Uiso 1 1 calc R . .
C3' C 0.3945(4) 0.2421(4) 1.10302(19) 0.0875(10) Uani 1 1 d . . .
H3' H 0.3239 0.2442 1.1266 0.105 Uiso 1 1 calc R . .
C2 C 1.1965(4) 0.6778(4) 0.4455(2) 0.1048(13) Uani 1 1 d . . .
H2 H 1.2437 0.7429 0.4309 0.126 Uiso 1 1 calc R . .
C10 C 1.3007(3) 0.5241(5) 0.6810(2) 0.1003(12) Uani 1 1 d . . .
H10A H 1.3191 0.5128 0.6328 0.15 Uiso 1 1 calc R . .
H10B H 1.363 0.477 0.7168 0.15 Uiso 1 1 calc R . .
H10C H 1.3085 0.6102 0.694 0.15 Uiso 1 1 calc R . .
C9 C 1.1383(4) 0.3488(3) 0.6501(2) 0.0881(11) Uani 1 1 d . . .
H9A H 1.1935 0.2928 0.6838 0.132 Uiso 1 1 calc R . .
H9B H 1.1604 0.3441 0.6024 0.132 Uiso 1 1 calc R . .
H9C H 1.0468 0.3268 0.6453 0.132 Uiso 1 1 calc R . .
C2' C 0.4774(4) 0.1403(4) 1.11144(19) 0.0841(10) Uani 1 1 d . . .
H2' H 0.4609 0.0734 1.1397 0.101 Uiso 1 1 calc R . .
O3' O 0.8927(2) 0.0268(2) 0.80418(15) 0.0834(7) Uani 1 1 d . . .
H3O' H 0.8375 -0.0289 0.7992 0.125 Uiso 1 1 calc R . .
C19' C 0.8440(3) 0.1319(3) 0.83418(16) 0.0617(7) Uani 1 1 d . . .
H19A H 0.8859 0.1369 0.8871 0.074 Uiso 1 1 calc R . .
C20' C 0.8805(4) 0.2456(4) 0.7960(2) 0.0840(10) Uani 1 1 d . . .
H20D H 0.8355 0.2442 0.7447 0.126 Uiso 1 1 calc R . .
H20E H 0.9747 0.247 0.8 0.126 Uiso 1 1 calc R . .
H20F H 0.8545 0.3182 0.8192 0.126 Uiso 1 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
S 0.0476(3) 0.0461(3) 0.0664(4) -0.0070(3) 0.0091(2) 0.0022(3)
S' 0.0557(4) 0.0520(4) 0.0552(3) -0.0037(3) 0.0035(2) -0.0031(3)
N1 0.0485(11) 0.0470(12) 0.0636(12) -0.0027(10) 0.0098(9) 0.0043(9)
N2 0.0454(10) 0.0478(12) 0.0585(12) -0.0054(9) 0.0103(8) 0.0019(9)
O1' 0.0670(12) 0.0559(12) 0.0738(12) 0.0026(9) 0.0051(9) 0.0091(10)
O2 0.0684(12) 0.0721(14) 0.0714(12) -0.0230(11) 0.0072(9) 0.0077(11)
O1 0.0636(11) 0.0497(12) 0.0940(14) -0.0220(10) 0.0133(10) -0.0051(9)
N1' 0.0580(13) 0.0530(13) 0.0538(11) -0.0035(9) 0.0065(9) -0.0048(10)
N3' 0.0571(12) 0.0539(13) 0.0591(12) -0.0038(10) 0.0058(9) 0.0026(10)
N2' 0.0493(11) 0.0480(12) 0.0498(10) -0.0042(8) 0.0044(8) -0.0001(9)
O2' 0.0653(13) 0.0747(15) 0.0885(14) -0.0187(12) 0.0051(10) 0.0190(11)
N3 0.0555(13) 0.0578(14) 0.0679(14) -0.0067(10) 0.0120(10) 0.0108(10)
O3 0.0905(17) 0.0727(14) 0.0742(14) -0.0243(11) 0.0141(11) 0.0179(12)
C12 0.0422(12) 0.0562(15) 0.0636(14) -0.0026(12) 0.0107(10) -0.0035(11)
C6 0.0518(13) 0.0499(14) 0.0697(15) 0.0045(13) 0.0126(11) 0.0036(12)
C17' 0.0603(15) 0.0527(15) 0.0513(13) 0.0009(11) 0.0025(11) -0.0048(12)
C18' 0.0519(13) 0.0488(14) 0.0532(13) 0.0028(10) 0.0072(10) 0.0035(11)
C19 0.0641(16) 0.0633(18) 0.0631(15) -0.0140(13) 0.0114(12) 0.0095(13)
C18 0.0490(13) 0.0511(15) 0.0623(14) -0.0068(11) 0.0141(11) -0.0005(11)
C11 0.0455(12) 0.0569(15) 0.0613(14) -0.0054(13) 0.0112(10) -0.0018(12)
C12' 0.0500(13) 0.0563(15) 0.0506(13) 0.0070(11) 0.0025(10) -0.0011(11)
C17 0.0486(14) 0.0592(16) 0.0698(16) 0.0008(13) 0.0140(11) 0.0060(12)
C11' 0.0515(13) 0.0609(16) 0.0533(13) 0.0022(12) 0.0041(10) 0.0053(13)
C1' 0.0721(18) 0.0602(17) 0.0657(16) 0.0055(13) 0.0119(13) -0.0030(14)
C7' 0.0700(19) 0.0660(19) 0.0623(16) -0.0055(14) -0.0022(13) -0.0145(15)
C6' 0.0630(15) 0.0579(15) 0.0516(13) -0.0041(12) 0.0060(10) -0.0038(13)
C7 0.0621(17) 0.072(2) 0.0693(18) 0.0019(15) 0.0070(13) 0.0175(15)
C16 0.076(2) 0.075(2) 0.082(2) 0.0003(17) 0.0147(16) 0.0243(17)
C16' 0.078(2) 0.0610(18) 0.080(2) -0.0095(15) -0.0002(15) -0.0107(16)
C5 0.0604(16) 0.0531(16) 0.0696(17) -0.0020(13) 0.0156(12) 0.0043(13)
C14 0.0665(19) 0.092(3) 0.0688(18) 0.0145(17) 0.0079(14) 0.0047(18)
C13 0.0585(16) 0.074(2) 0.0648(15) -0.0017(14) 0.0130(12) -0.0014(14)
C5' 0.079(2) 0.0574(17) 0.0680(17) -0.0002(14) 0.0200(15) 0.0063(15)
C13' 0.0513(15) 0.081(2) 0.0685(17) 0.0106(15) 0.0035(12) 0.0006(14)
C8 0.092(2) 0.110(3) 0.0666(19) 0.0001(19) 0.0099(16) 0.024(2)
C1 0.076(2) 0.063(2) 0.093(2) 0.0019(17) 0.0241(17) -0.0153(16)
C15' 0.077(2) 0.073(2) 0.090(2) 0.0024(18) -0.0105(17) -0.0261(18)
C9' 0.102(3) 0.069(2) 0.097(3) -0.0146(19) -0.001(2) -0.018(2)
C14' 0.0590(18) 0.087(3) 0.087(2) 0.0122(19) -0.0039(15) -0.0179(18)
C15 0.074(2) 0.092(3) 0.087(2) 0.016(2) 0.0102(17) 0.0263(19)
C4 0.076(2) 0.083(2) 0.0711(19) -0.0028(17) 0.0192(15) 0.0076(18)
C20 0.109(3) 0.083(2) 0.0660(18) 0.0030(17) 0.0326(17) 0.008(2)
C8' 0.071(2) 0.120(3) 0.114(3) -0.025(3) 0.012(2) -0.032(2)
C3 0.116(3) 0.106(3) 0.081(2) 0.009(2) 0.044(2) -0.001(3)
C4' 0.086(2) 0.083(2) 0.079(2) -0.0042(18) 0.0260(17) 0.0151(19)
C10' 0.099(3) 0.102(3) 0.0635(18) -0.0084(19) -0.0096(17) -0.019(2)
C3' 0.086(2) 0.103(3) 0.081(2) 0.004(2) 0.0347(17) 0.005(2)
C2 0.117(3) 0.101(3) 0.107(3) 0.027(3) 0.046(2) -0.026(3)
C10 0.0574(18) 0.121(3) 0.116(3) 0.007(3) 0.0049(17) 0.024(2)
C9 0.108(3) 0.063(2) 0.088(2) 0.0045(17) 0.0117(19) 0.0290(19)
C2' 0.090(2) 0.082(2) 0.083(2) 0.0155(18) 0.0261(18) -0.007(2)
O3' 0.0617(13) 0.0718(15) 0.1178(19) -0.0182(14) 0.0226(12) 0.0106(11)
C19' 0.0508(14) 0.0618(17) 0.0714(17) -0.0044(13) 0.0111(12) 0.0013(12)
C20' 0.078(2) 0.079(2) 0.105(2) 0.009(2) 0.0430(18) -0.0056(19)

#----------------------------------------------------------------------------#
# 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
S O1 1.449(2) . ?
S N1 1.573(2) . ?
S C6 1.775(3) . ?
S C7 1.823(3) . ?
S' O1' 1.457(2) . ?
S' N1' 1.572(2) . ?
S' C6' 1.775(3) . ?
S' C7' 1.826(3) . ?
N1 N2 1.440(3) . ?
N2 C18 1.378(3) . ?
N2 C11 1.407(3) . ?
O2 C11 1.214(3) . ?
N1' N2' 1.435(3) . ?
N3' C18' 1.287(3) . ?
N3' C17' 1.393(3) . ?
N2' C18' 1.380(3) . ?
N2' C11' 1.410(3) . ?
O2' C11' 1.218(3) . ?
N3 C18 1.289(3) . ?
N3 C17 1.390(4) . ?
O3 C19 1.409(3) . ?
O3 H3O 0.82 . ?
C12 C17 1.395(4) . ?
C12 C13 1.396(4) . ?
C12 C11 1.458(4) . ?
C6 C1 1.381(4) . ?
C6 C5 1.389(4) . ?
C17' C12' 1.392(4) . ?
C17' C16' 1.399(4) . ?
C18' C19' 1.526(4) . ?
C19 C20 1.512(5) . ?
C19 C18 1.522(4) . ?
C19 H19 0.98 . ?
C12' C13' 1.403(4) . ?
C12' C11' 1.458(4) . ?
C17 C16 1.395(4) . ?
C1' C2' 1.370(4) . ?
C1' C6' 1.397(4) . ?
C1' H1' 0.93 . ?
C7' C9' 1.506(5) . ?
C7' C10' 1.532(5) . ?
C7' C8' 1.534(5) . ?
C6' C5' 1.389(4) . ?
C7 C10 1.516(5) . ?
C7 C9 1.520(5) . ?
C7 C8 1.540(4) . ?
C16 C15 1.370(5) . ?
C16 H16 0.93 . ?
C16' C15' 1.368(5) . ?
C16' H16A 0.93 . ?
C5 C4 1.375(4) . ?
C5 H5 0.93 . ?
C14 C13 1.363(5) . ?
C14 C15 1.386(5) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?
C5' C4' 1.367(4) . ?
C5' H5' 0.93 . ?
C13' C14' 1.358(5) . ?
C13' H13A 0.93 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C1 C2 1.383(5) . ?
C1 H1 0.93 . ?
C15' C14' 1.397(5) . ?
C15' H15A 0.93 . ?
C9' H9E 0.96 . ?
C9' H9F 0.96 . ?
C9' H9D 0.96 . ?
C14' H14A 0.93 . ?
C15 H15 0.93 . ?
C4 C3 1.362(6) . ?
C4 H4 0.93 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
C8' H8F 0.96 . ?
C8' H8E 0.96 . ?
C8' H8D 0.96 . ?
C3 C2 1.372(6) . ?
C3 H3 0.93 . ?
C4' C3' 1.382(5) . ?
C4' H4' 0.93 . ?
C10' H10E 0.96 . ?
C10' H10F 0.96 . ?
C10' H10D 0.96 . ?
C3' C2' 1.381(5) . ?
C3' H3' 0.93 . ?
C2 H2 0.93 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C2' H2' 0.93 . ?
O3' C19' 1.406(3) . ?
O3' H3O' 0.82 . ?
C19' C20' 1.506(5) . ?
C19' H19A 0.98 . ?
C20' H20D 0.96 . ?
C20' H20E 0.96 . ?
C20' H20F 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S N1 118.24(12) . . ?
O1 S C6 106.00(14) . . ?
N1 S C6 113.94(12) . . ?
O1 S C7 109.60(14) . . ?
N1 S C7 101.80(14) . . ?
C6 S C7 106.66(13) . . ?
O1' S' N1' 118.59(12) . . ?
O1' S' C6' 105.57(14) . . ?
N1' S' C6' 113.21(13) . . ?
O1' S' C7' 109.69(14) . . ?
N1' S' C7' 102.06(13) . . ?
C6' S' C7' 107.24(15) . . ?
N2 N1 S 109.63(17) . . ?
C18 N2 C11 122.0(2) . . ?
C18 N2 N1 118.6(2) . . ?
C11 N2 N1 118.3(2) . . ?
N2' N1' S' 109.34(16) . . ?
C18' N3' C17' 117.6(2) . . ?
C18' N2' C11' 121.5(2) . . ?
C18' N2' N1' 119.2(2) . . ?
C11' N2' N1' 118.5(2) . . ?
C18 N3 C17 118.2(2) . . ?
C19 O3 H3O 109.5 . . ?
C17 C12 C13 120.0(3) . . ?
C17 C12 C11 119.9(2) . . ?
C13 C12 C11 120.1(2) . . ?
C1 C6 C5 121.2(3) . . ?
C1 C6 S 119.2(2) . . ?
C5 C6 S 119.6(2) . . ?
C12' C17' N3' 121.6(2) . . ?
C12' C17' C16' 118.9(3) . . ?
N3' C17' C16' 119.4(3) . . ?
N3' C18' N2' 124.1(2) . . ?
N3' C18' C19' 117.7(2) . . ?
N2' C18' C19' 118.1(2) . . ?
O3 C19 C20 110.0(2) . . ?
O3 C19 C18 108.9(2) . . ?
C20 C19 C18 109.7(2) . . ?
O3 C19 H19 109.4 . . ?
C20 C19 H19 109.4 . . ?
C18 C19 H19 109.4 . . ?
N3 C18 N2 123.6(2) . . ?
N3 C18 C19 116.9(2) . . ?
N2 C18 C19 119.3(2) . . ?
O2 C11 N2 121.7(2) . . ?
O2 C11 C12 125.4(2) . . ?
N2 C11 C12 113.0(2) . . ?
C17' C12' C13' 119.8(3) . . ?
C17' C12' C11' 120.1(2) . . ?
C13' C12' C11' 120.0(3) . . ?
N3 C17 C16 119.5(3) . . ?
N3 C17 C12 121.5(2) . . ?
C16 C17 C12 119.1(3) . . ?
O2' C11' N2' 122.0(3) . . ?
O2' C11' C12' 125.6(2) . . ?
N2' C11' C12' 112.4(2) . . ?
C2' C1' C6' 118.8(3) . . ?
C2' C1' H1' 120.6 . . ?
C6' C1' H1' 120.6 . . ?
C9' C7' C10' 111.9(3) . . ?
C9' C7' C8' 111.3(3) . . ?
C10' C7' C8' 109.8(3) . . ?
C9' C7' S' 112.4(2) . . ?
C10' C7' S' 105.2(2) . . ?
C8' C7' S' 105.9(2) . . ?
C5' C6' C1' 120.5(3) . . ?
C5' C6' S' 120.3(2) . . ?
C1' C6' S' 119.2(2) . . ?
C10 C7 C9 111.5(3) . . ?
C10 C7 C8 110.5(3) . . ?
C9 C7 C8 110.9(3) . . ?
C10 C7 S 106.8(3) . . ?
C9 C7 S 110.7(2) . . ?
C8 C7 S 106.2(2) . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C15' C16' C17' 120.3(3) . . ?
C15' C16' H16A 119.8 . . ?
C17' C16' H16A 119.8 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C4' C5' C6' 119.7(3) . . ?
C4' C5' H5' 120.2 . . ?
C6' C5' H5' 120.2 . . ?
C14' C13' C12' 120.6(3) . . ?
C14' C13' H13A 119.7 . . ?
C12' C13' H13A 119.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C1 C2 118.5(3) . . ?
C6 C1 H1 120.8 . . ?
C2 C1 H1 120.8 . . ?
C16' C15' C14' 120.6(3) . . ?
C16' C15' H15A 119.7 . . ?
C14' C15' H15A 119.7 . . ?
C7' C9' H9E 109.5 . . ?
C7' C9' H9F 109.5 . . ?
H9E C9' H9F 109.5 . . ?
C7' C9' H9D 109.5 . . ?
H9E C9' H9D 109.5 . . ?
H9F C9' H9D 109.5 . . ?
C13' C14' C15' 119.6(3) . . ?
C13' C14' H14A 120.2 . . ?
C15' C14' H14A 120.2 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7' C8' H8F 109.5 . . ?
C7' C8' H8E 109.5 . . ?
H8F C8' H8E 109.5 . . ?
C7' C8' H8D 109.5 . . ?
H8F C8' H8D 109.5 . . ?
H8E C8' H8D 109.5 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5' C4' C3' 120.0(3) . . ?
C5' C4' H4' 120 . . ?
C3' C4' H4' 120 . . ?
C7' C10' H10E 109.5 . . ?
C7' C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C7' C10' H10D 109.5 . . ?
H10E C10' H10D 109.5 . . ?
H10F C10' H10D 109.5 . . ?
C2' C3' C4' 120.2(3) . . ?
C2' C3' H3' 119.9 . . ?
C4' C3' H3' 119.9 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1' C2' C3' 120.6(3) . . ?
C1' C2' H2' 119.7 . . ?
C3' C2' H2' 119.7 . . ?
C19' O3' H3O' 109.5 . . ?
O3' C19' C20' 108.9(2) . . ?
O3' C19' C18' 110.8(2) . . ?
C20' C19' C18' 110.7(3) . . ?
O3' C19' H19A 108.8 . . ?
C20' C19' H19A 108.8 . . ?
C18' C19' H19A 108.8 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 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
O1 S N1 N2 50.5(2) . . . . ?
C6 S N1 N2 -75.04(19) . . . . ?
C7 S N1 N2 170.56(17) . . . . ?
S N1 N2 C18 -92.6(2) . . . . ?
S N1 N2 C11 98.6(2) . . . . ?
O1' S' N1' N2' 50.6(2) . . . . ?
C6' S' N1' N2' -73.9(2) . . . . ?
C7' S' N1' N2' 171.19(18) . . . . ?
S' N1' N2' C18' -91.2(2) . . . . ?
S' N1' N2' C11' 98.0(2) . . . . ?
O1 S C6 C1 13.5(3) . . . . ?
N1 S C6 C1 145.2(2) . . . . ?
C7 S C6 C1 -103.3(3) . . . . ?
O1 S C6 C5 -167.8(2) . . . . ?
N1 S C6 C5 -36.1(3) . . . . ?
C7 S C6 C5 75.4(2) . . . . ?
C18' N3' C17' C12' 7.4(4) . . . . ?
C18' N3' C17' C16' -173.5(3) . . . . ?
C17' N3' C18' N2' -0.8(4) . . . . ?
C17' N3' C18' C19' -177.6(2) . . . . ?
C11' N2' C18' N3' -13.3(4) . . . . ?
N1' N2' C18' N3' 176.2(2) . . . . ?
C11' N2' C18' C19' 163.5(2) . . . . ?
N1' N2' C18' C19' -7.0(3) . . . . ?
C17 N3 C18 N2 0.3(4) . . . . ?
C17 N3 C18 C19 -175.3(2) . . . . ?
C11 N2 C18 N3 -12.4(4) . . . . ?
N1 N2 C18 N3 179.2(2) . . . . ?
C11 N2 C18 C19 163.1(3) . . . . ?
N1 N2 C18 C19 -5.3(3) . . . . ?
O3 C19 C18 N3 -17.2(4) . . . . ?
C20 C19 C18 N3 103.3(3) . . . . ?
O3 C19 C18 N2 167.0(2) . . . . ?
C20 C19 C18 N2 -72.6(3) . . . . ?
C18 N2 C11 O2 -165.5(2) . . . . ?
N1 N2 C11 O2 2.9(4) . . . . ?
C18 N2 C11 C12 15.1(3) . . . . ?
N1 N2 C11 C12 -176.4(2) . . . . ?
C17 C12 C11 O2 173.2(3) . . . . ?
C13 C12 C11 O2 -7.2(4) . . . . ?
C17 C12 C11 N2 -7.4(3) . . . . ?
C13 C12 C11 N2 172.2(2) . . . . ?
N3' C17' C12' C13' 179.5(2) . . . . ?
C16' C17' C12' C13' 0.3(4) . . . . ?
N3' C17' C12' C11' -0.3(4) . . . . ?
C16' C17' C12' C11' -179.5(3) . . . . ?
C18 N3 C17 C16 -172.9(3) . . . . ?
C18 N3 C17 C12 7.5(4) . . . . ?
C13 C12 C17 N3 176.9(3) . . . . ?
C11 C12 C17 N3 -3.5(4) . . . . ?
C13 C12 C17 C16 -2.7(4) . . . . ?
C11 C12 C17 C16 176.9(3) . . . . ?
C18' N2' C11' O2' -163.5(3) . . . . ?
N1' N2' C11' O2' 7.1(4) . . . . ?
C18' N2' C11' C12' 18.7(3) . . . . ?
N1' N2' C11' C12' -170.7(2) . . . . ?
C17' C12' C11' O2' 170.2(3) . . . . ?
C13' C12' C11' O2' -9.6(4) . . . . ?
C17' C12' C11' N2' -12.1(3) . . . . ?
C13' C12' C11' N2' 168.1(2) . . . . ?
O1' S' C7' C9' -177.7(3) . . . . ?
N1' S' C7' C9' 55.7(3) . . . . ?
C6' S' C7' C9' -63.6(3) . . . . ?
O1' S' C7' C10' -55.8(3) . . . . ?
N1' S' C7' C10' 177.6(2) . . . . ?
C6' S' C7' C10' 58.4(3) . . . . ?
O1' S' C7' C8' 60.5(3) . . . . ?
N1' S' C7' C8' -66.1(3) . . . . ?
C6' S' C7' C8' 174.7(3) . . . . ?
C2' C1' C6' C5' -0.9(4) . . . . ?
C2' C1' C6' S' 179.0(2) . . . . ?
O1' S' C6' C5' -169.0(2) . . . . ?
N1' S' C6' C5' -37.7(3) . . . . ?
C7' S' C6' C5' 74.1(2) . . . . ?
O1' S' C6' C1' 11.0(2) . . . . ?
N1' S' C6' C1' 142.4(2) . . . . ?
C7' S' C6' C1' -105.9(2) . . . . ?
O1 S C7 C10 -56.6(3) . . . . ?
N1 S C7 C10 177.4(2) . . . . ?
C6 S C7 C10 57.7(3) . . . . ?
O1 S C7 C9 -178.2(2) . . . . ?
N1 S C7 C9 55.9(3) . . . . ?
C6 S C7 C9 -63.8(3) . . . . ?
O1 S C7 C8 61.4(3) . . . . ?
N1 S C7 C8 -64.6(3) . . . . ?
C6 S C7 C8 175.7(2) . . . . ?
N3 C17 C16 C15 -177.8(3) . . . . ?
C12 C17 C16 C15 1.9(5) . . . . ?
C12' C17' C16' C15' 1.0(4) . . . . ?
N3' C17' C16' C15' -178.2(3) . . . . ?
C1 C6 C5 C4 1.8(4) . . . . ?
S C6 C5 C4 -176.9(2) . . . . ?
C15 C14 C13 C12 -0.9(5) . . . . ?
C17 C12 C13 C14 2.3(4) . . . . ?
C11 C12 C13 C14 -177.3(3) . . . . ?
C1' C6' C5' C4' 2.7(4) . . . . ?
S' C6' C5' C4' -177.3(3) . . . . ?
C17' C12' C13' C14' -0.2(4) . . . . ?
C11' C12' C13' C14' 179.5(3) . . . . ?
C5 C6 C1 C2 -1.1(5) . . . . ?
S C6 C1 C2 177.6(3) . . . . ?
C17' C16' C15' C14' -2.4(5) . . . . ?
C12' C13' C14' C15' -1.1(5) . . . . ?
C16' C15' C14' C13' 2.4(5) . . . . ?
C17 C16 C15 C14 -0.5(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C6 C5 C4 C3 -0.4(5) . . . . ?
C5 C4 C3 C2 -1.6(6) . . . . ?
C6' C5' C4' C3' -2.3(5) . . . . ?
C5' C4' C3' C2' 0.3(6) . . . . ?
C4 C3 C2 C1 2.3(7) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C6' C1' C2' C3' -1.2(5) . . . . ?
C4' C3' C2' C1' 1.5(6) . . . . ?
N3' C18' C19' O3' -13.1(3) . . . . ?
N2' C18' C19' O3' 169.8(2) . . . . ?
N3' C18' C19' C20' 107.9(3) . . . . ?
N2' C18' C19' C20' -69.2(3) . . . . ?

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# END of CIF