Electronic Supplementary Material for rystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_section_title              
;Preferential Crystallization (AS3PC Mode) of Modafinic Acid:
an Example of Productivity Enhancement by Addition of a
Non-Chiral Base
;
_publ_contact_author_name        'Prof. Gerard Coquerel'
_publ_contact_author_email       GERARD.COQUEREL@UNIV-ROUEN.FR
loop_
_publ_author_name
G.Coquerel
O.Lambert
N.Wermester

# Attachment 'conv016m.cif'

data_conv016m
_database_code_depnum_ccdc_archive 'CCDC 666297'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 O3 S, C6 H16 N O3, H2 O'
_chemical_formula_sum            'C21 H29 N O7 S'
_chemical_formula_weight         439.51

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   5.4997(4)
_cell_length_b                   13.5883(9)
_cell_length_c                   30.125(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2251.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18106
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0943
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         26.40
_reflns_number_total             4593
_reflns_number_gt                2672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4587(7) 0.9786(3) 0.07259(11) 0.0394(9) Uani 1 1 d . . .
H1 H 0.3177 0.9990 0.0902 0.047 Uiso 1 1 calc R . .
C2 C 0.4570(8) 0.8672(3) 0.06997(13) 0.0478(11) Uani 1 1 d . . .
C3 C 0.2827(10) 0.8156(4) 0.09194(17) 0.0812(16) Uani 1 1 d . . .
H3 H 0.1628 0.8489 0.1077 0.097 Uiso 1 1 calc R . .
C4 C 0.2827(14) 0.7128(5) 0.0909(2) 0.116(2) Uani 1 1 d . . .
H4A H 0.1613 0.6787 0.1059 0.139 Uiso 1 1 calc R . .
C5 C 0.4530(15) 0.6622(4) 0.0689(2) 0.096(2) Uani 1 1 d . . .
H5A H 0.4518 0.5937 0.0689 0.115 Uiso 1 1 calc R . .
C6 C 0.6254(14) 0.7119(4) 0.04685(19) 0.104(2) Uani 1 1 d . . .
H6A H 0.7443 0.6782 0.0310 0.125 Uiso 1 1 calc R . .
C7 C 0.6252(12) 0.8145(4) 0.04774(17) 0.0879(19) Uani 1 1 d . . .
H7 H 0.7462 0.8479 0.0323 0.105 Uiso 1 1 calc R . .
C8 C 0.4524(7) 1.0354(3) 0.02941(12) 0.0397(9) Uani 1 1 d . . .
C9 C 0.6294(9) 1.0273(3) -0.00206(13) 0.0606(13) Uani 1 1 d . . .
H9 H 0.7580 0.9840 0.0024 0.073 Uiso 1 1 calc R . .
C10 C 0.6202(10) 1.0824(3) -0.04034(14) 0.0696(15) Uani 1 1 d . . .
H10 H 0.7438 1.0773 -0.0613 0.084 Uiso 1 1 calc R . .
C11 C 0.4297(11) 1.1444(3) -0.04749(16) 0.0723(15) Uani 1 1 d . . .
H11 H 0.4197 1.1800 -0.0738 0.087 Uiso 1 1 calc R . .
C12 C 0.2542(11) 1.1539(4) -0.01598(19) 0.0874(16) Uani 1 1 d . . .
H12 H 0.1263 1.1977 -0.0203 0.105 Uiso 1 1 calc R . .
C13 C 0.2653(10) 1.0995(3) 0.02192(16) 0.0693(13) Uani 1 1 d . . .
H13 H 0.1434 1.1062 0.0431 0.083 Uiso 1 1 calc R . .
C14 C 0.6488(7) 1.1363(3) 0.11650(13) 0.0440(10) Uani 1 1 d . . .
H14A H 0.6271 1.1729 0.0891 0.053 Uiso 1 1 calc R . .
H14B H 0.4946 1.1357 0.1321 0.053 Uiso 1 1 calc R . .
C15 C 0.8415(8) 1.1875(3) 0.14531(14) 0.0438(10) Uani 1 1 d . . .
C16 C 0.3469(8) -0.0101(3) 0.25774(14) 0.0607(12) Uani 1 1 d . . .
H16A H 0.3199 -0.0660 0.2771 0.073 Uiso 1 1 calc R . .
H16B H 0.5205 -0.0036 0.2529 0.073 Uiso 1 1 calc R . .
C17 C 0.2197(9) -0.0267(3) 0.21393(14) 0.0624(12) Uani 1 1 d . . .
H17A H 0.2743 0.0209 0.1921 0.075 Uiso 1 1 calc R . .
H17B H 0.2533 -0.0923 0.2028 0.075 Uiso 1 1 calc R . .
C18 C 0.3411(8) 0.1720(3) 0.25722(16) 0.0647(13) Uani 1 1 d . . .
H18A H 0.3488 0.1610 0.2254 0.078 Uiso 1 1 calc R . .
H18B H 0.5045 0.1859 0.2676 0.078 Uiso 1 1 calc R . .
C19 C 0.1811(8) 0.2593(3) 0.26642(16) 0.0625(13) Uani 1 1 d . . .
H19A H 0.1999 0.2794 0.2971 0.075 Uiso 1 1 calc R . .
H19B H 0.2292 0.3139 0.2476 0.075 Uiso 1 1 calc R . .
C20 C 0.2902(8) 0.0831(3) 0.32836(13) 0.0570(12) Uani 1 1 d . . .
H20A H 0.2508 0.1481 0.3395 0.068 Uiso 1 1 calc R . .
H20B H 0.4608 0.0710 0.3344 0.068 Uiso 1 1 calc R . .
C21 C 0.1399(8) 0.0081(3) 0.35276(14) 0.0602(12) Uani 1 1 d . . .
H21A H 0.1988 -0.0577 0.3464 0.072 Uiso 1 1 calc R . .
H21B H 0.1510 0.0190 0.3845 0.072 Uiso 1 1 calc R . .
N1 N 0.2507(6) 0.0815(2) 0.27920(9) 0.0417(7) Uani 1 1 d . . .
H1A H 0.0868 0.0807 0.2750 0.050 Uiso 1 1 calc R . .
O1 O 0.7237(6) 0.95722(19) 0.14647(9) 0.0622(8) Uani 1 1 d . . .
O2 O 1.0550(5) 1.1618(2) 0.13981(10) 0.0609(8) Uani 1 1 d . . .
O3 O 0.7669(6) 1.2525(2) 0.17122(9) 0.0616(8) Uani 1 1 d . . .
O4 O -0.0315(5) -0.0151(2) 0.22236(8) 0.0593(8) Uani 1 1 d . . .
H4 H -0.1054 -0.0125 0.1987 0.089 Uiso 1 1 calc R . .
O5 O -0.0670(5) 0.2347(2) 0.25804(9) 0.0603(8) Uani 1 1 d . . .
H5 H -0.0927 0.2362 0.2312 0.090 Uiso 1 1 calc R . .
O6 O -0.1036(5) 0.0181(2) 0.33852(10) 0.0596(8) Uani 1 1 d . . .
H6 H -0.1796 -0.0319 0.3448 0.089 Uiso 1 1 calc R . .
O7 O 0.3245(5) 0.3387(2) 0.15312(11) 0.0749(10) Uani 1 1 d . . .
S1 S 0.73650(18) 1.01321(6) 0.10385(3) 0.0406(2) Uani 1 1 d . . .

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
C1 0.025(2) 0.050(2) 0.044(2) -0.0089(19) -0.0025(16) -0.0077(19)
C2 0.049(3) 0.052(3) 0.042(2) 0.003(2) -0.008(2) -0.010(2)
C3 0.063(4) 0.075(3) 0.105(4) 0.027(3) 0.005(3) -0.006(3)
C4 0.093(5) 0.079(4) 0.176(7) 0.060(4) -0.018(5) -0.035(4)
C5 0.130(6) 0.049(3) 0.108(5) 0.007(3) -0.068(5) -0.009(4)
C6 0.159(7) 0.055(4) 0.098(5) -0.006(3) 0.015(5) -0.010(4)
C7 0.124(5) 0.048(3) 0.091(4) -0.008(3) 0.037(4) -0.010(3)
C8 0.037(2) 0.045(2) 0.038(2) -0.0010(18) -0.0046(18) -0.0041(19)
C9 0.069(3) 0.072(3) 0.041(2) 0.006(2) 0.002(2) 0.029(3)
C10 0.091(4) 0.078(3) 0.040(3) -0.002(2) 0.011(3) 0.023(3)
C11 0.100(5) 0.067(3) 0.050(3) 0.009(3) -0.010(3) 0.011(3)
C12 0.068(4) 0.095(4) 0.099(4) 0.039(3) 0.006(4) 0.022(4)
C13 0.054(3) 0.076(3) 0.079(3) 0.020(3) 0.010(3) 0.017(3)
C14 0.034(2) 0.047(2) 0.051(3) -0.0014(19) 0.0011(19) -0.0033(18)
C15 0.040(3) 0.041(2) 0.050(3) 0.008(2) -0.008(2) -0.009(2)
C16 0.048(3) 0.065(3) 0.068(3) -0.011(3) -0.002(2) 0.016(2)
C17 0.069(3) 0.061(3) 0.057(3) -0.009(2) 0.012(3) -0.001(3)
C18 0.046(3) 0.061(3) 0.088(3) 0.015(3) 0.006(3) -0.008(2)
C19 0.066(4) 0.042(3) 0.079(3) 0.001(2) -0.011(3) -0.005(2)
C20 0.042(3) 0.075(3) 0.054(3) -0.002(2) -0.007(2) -0.006(2)
C21 0.059(3) 0.064(3) 0.057(3) 0.011(2) 0.002(2) 0.000(3)
N1 0.0261(16) 0.0459(18) 0.053(2) 0.0007(14) 0.0018(18) -0.0024(19)
O1 0.074(2) 0.0597(18) 0.0531(16) 0.0120(14) -0.0194(18) -0.0140(17)
O2 0.0311(17) 0.074(2) 0.078(2) -0.0073(17) -0.0046(16) -0.0112(16)
O3 0.0561(19) 0.0569(18) 0.0718(19) -0.0187(15) -0.0180(18) 0.0032(18)
O4 0.0562(19) 0.073(2) 0.0483(16) -0.0062(17) -0.0074(14) -0.0066(18)
O5 0.0524(19) 0.0607(19) 0.068(2) -0.0031(18) 0.0004(17) 0.0036(16)
O6 0.0423(17) 0.0577(18) 0.079(2) 0.0074(17) 0.0065(16) 0.0023(15)
O7 0.054(2) 0.0463(18) 0.124(3) -0.0061(18) -0.0138(19) -0.0011(15)
S1 0.0337(5) 0.0473(5) 0.0408(5) -0.0009(5) -0.0029(5) -0.0032(5)

_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
C1 C8 1.513(5) . ?
C1 C2 1.516(5) . ?
C1 S1 1.855(3) . ?
C1 H1 0.9800 . ?
C2 C7 1.349(6) . ?
C2 C3 1.360(6) . ?
C3 C4 1.397(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.338(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.341(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(7) . ?
C6 H6A 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.363(5) . ?
C8 C13 1.367(6) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.536(5) . ?
C14 S1 1.782(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.236(5) . ?
C15 O3 1.248(5) . ?
C16 N1 1.498(5) . ?
C16 C17 1.511(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O4 1.413(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N1 1.482(5) . ?
C18 C19 1.503(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O5 1.428(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N1 1.497(5) . ?
C20 C21 1.504(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O6 1.413(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N1 H1A 0.9100 . ?
O1 S1 1.494(3) . ?
O4 H4 0.8200 . ?
O5 H5 0.8200 . ?
O6 H6 0.8200 . ?
O7 O3 2.755(4) 1_545 ?
O7 O2 2.852(4) 1_445 ?

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
C8 C1 C2 117.6(3) . . ?
C8 C1 S1 109.0(2) . . ?
C2 C1 S1 106.5(3) . . ?
C8 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
S1 C1 H1 107.7 . . ?
C7 C2 C3 116.8(4) . . ?
C7 C2 C1 123.5(4) . . ?
C3 C2 C1 119.6(4) . . ?
C2 C3 C4 120.3(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.7(6) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 118.8(6) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C5 C6 C7 119.6(6) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C2 C7 C6 122.8(6) . . ?
C2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C9 C8 C13 118.3(4) . . ?
C9 C8 C1 122.7(4) . . ?
C13 C8 C1 118.9(4) . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C15 C14 S1 111.1(3) . . ?
C15 C14 H14A 109.4 . . ?
S1 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
S1 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O2 C15 O3 126.6(4) . . ?
O2 C15 C14 116.9(4) . . ?
O3 C15 C14 116.6(4) . . ?
N1 C16 C17 109.7(3) . . ?
N1 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N1 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O4 C17 C16 106.2(3) . . ?
O4 C17 H17A 110.5 . . ?
C16 C17 H17A 110.5 . . ?
O4 C17 H17B 110.5 . . ?
C16 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
N1 C18 C19 112.1(3) . . ?
N1 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O5 C19 C18 110.0(3) . . ?
O5 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
O5 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
N1 C20 C21 113.2(3) . . ?
N1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
O6 C21 C20 107.9(3) . . ?
O6 C21 H21A 110.1 . . ?
C20 C21 H21A 110.1 . . ?
O6 C21 H21B 110.1 . . ?
C20 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C18 N1 C20 112.4(3) . . ?
C18 N1 C16 112.2(3) . . ?
C20 N1 C16 112.8(3) . . ?
C18 N1 H1A 106.3 . . ?
C20 N1 H1A 106.3 . . ?
C16 N1 H1A 106.3 . . ?
C17 O4 H4 109.5 . . ?
C19 O5 H5 109.5 . . ?
C21 O6 H6 109.5 . . ?
O3 O7 O2 97.36(11) 1_545 1_445 ?
O1 S1 C14 106.33(17) . . ?
O1 S1 C1 105.57(17) . . ?
C14 S1 C1 97.08(18) . . ?

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 C1 C2 C7 57.5(6) . . . . ?
S1 C1 C2 C7 -65.2(5) . . . . ?
C8 C1 C2 C3 -124.5(4) . . . . ?
S1 C1 C2 C3 112.9(4) . . . . ?
C7 C2 C3 C4 0.0(8) . . . . ?
C1 C2 C3 C4 -178.1(5) . . . . ?
C2 C3 C4 C5 0.5(9) . . . . ?
C3 C4 C5 C6 -0.9(10) . . . . ?
C4 C5 C6 C7 0.8(10) . . . . ?
C3 C2 C7 C6 -0.2(8) . . . . ?
C1 C2 C7 C6 177.9(5) . . . . ?
C5 C6 C7 C2 -0.2(10) . . . . ?
C2 C1 C8 C9 -60.8(5) . . . . ?
S1 C1 C8 C9 60.5(4) . . . . ?
C2 C1 C8 C13 121.0(4) . . . . ?
S1 C1 C8 C13 -117.7(4) . . . . ?
C13 C8 C9 C10 0.1(7) . . . . ?
C1 C8 C9 C10 -178.1(4) . . . . ?
C8 C9 C10 C11 -1.4(7) . . . . ?
C9 C10 C11 C12 2.3(8) . . . . ?
C10 C11 C12 C13 -2.0(8) . . . . ?
C11 C12 C13 C8 0.7(8) . . . . ?
C9 C8 C13 C12 0.3(7) . . . . ?
C1 C8 C13 C12 178.5(5) . . . . ?
S1 C14 C15 O2 31.1(5) . . . . ?
S1 C14 C15 O3 -150.5(3) . . . . ?
N1 C16 C17 O4 -47.7(4) . . . . ?
N1 C18 C19 O5 -49.6(5) . . . . ?
N1 C20 C21 O6 -50.4(5) . . . . ?
C19 C18 N1 C20 -72.9(5) . . . . ?
C19 C18 N1 C16 158.8(4) . . . . ?
C21 C20 N1 C18 163.4(4) . . . . ?
C21 C20 N1 C16 -68.5(5) . . . . ?
C17 C16 N1 C18 -74.1(4) . . . . ?
C17 C16 N1 C20 157.7(4) . . . . ?
C15 C14 S1 O1 68.8(3) . . . . ?
C15 C14 S1 C1 177.4(3) . . . . ?
C8 C1 S1 O1 177.9(3) . . . . ?
C2 C1 S1 O1 -54.2(3) . . . . ?
C8 C1 S1 C14 68.7(3) . . . . ?
C2 C1 S1 C14 -163.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O4 0.91 2.15 2.658(4) 114.1 .
N1 H1A O5 0.91 2.31 2.791(4) 112.5 .
O4 H4 O1 0.82 1.88 2.680(4) 164.9 1_445
O5 H5 O3 0.82 1.98 2.781(4) 165.9 1_445
O6 H6 O7 0.82 1.93 2.734(4) 166.4 3_545

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.049