# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_III

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O4 S'
_chemical_formula_weight         290.29

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   C2/c

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

_cell_length_a                   24.4212(6)
_cell_length_b                   8.3161(2)
_cell_length_c                   13.2973(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.341(2)
_cell_angle_gamma                90.00
_cell_volume                     2698.28(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   Multi-SCAN
_exptl_absorpt_correction_T_min  0.6703
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEXII CCD area detector'
_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            11775
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         27.98
_reflns_number_total             3224
_reflns_number_gt                1658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker 2007)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and PLATON (Spek,2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0648P)²+0.4375P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         3224
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_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
S1 S 0.62530(2) 0.21458(8) 0.66261(5) 0.0951(3) Uani 1 1 d . . .
O1 O 0.36015(10) 0.2233(3) 0.53937(18) 0.1520(9) Uani 1 1 d . . .
O2 O 0.37030(8) 0.4744(3) 0.56949(18) 0.1387(8) Uani 1 1 d . . .
O3 O 0.90814(8) 0.2782(3) 0.8086(3) 0.1682(12) Uani 1 1 d . . .
O4 O 0.91621(10) 0.3181(3) 0.6497(3) 0.1778(13) Uani 1 1 d . . .
N1 N 0.38832(9) 0.3391(4) 0.56381(16) 0.1078(8) Uani 1 1 d . . .
N2 N 0.88889(10) 0.3080(3) 0.7249(4) 0.1296(11) Uani 1 1 d . . .
C1 C 0.44696(9) 0.3121(4) 0.58956(16) 0.0855(7) Uani 1 1 d . . .
C2 C 0.46655(11) 0.1598(4) 0.5903(2) 0.1103(8) Uani 1 1 d . . .
H2A H 0.4433 0.0737 0.5753 0.132 Uiso 1 1 calc R . .
C3 C 0.52145(11) 0.1340(3) 0.6137(2) 0.1081(8) Uani 1 1 d . . .
H3A H 0.5351 0.0296 0.6152 0.130 Uiso 1 1 calc R . .
C4 C 0.55639(9) 0.2619(3) 0.63506(16) 0.0782(6) Uani 1 1 d . . .
C5 C 0.53476(9) 0.4159(3) 0.63381(15) 0.0817(6) Uani 1 1 d . . .
H5A H 0.5575 0.5033 0.6482 0.098 Uiso 1 1 calc R . .
C6 C 0.47986(9) 0.4403(3) 0.61148(16) 0.0870(7) Uani 1 1 d . . .
H6A H 0.4654 0.5437 0.6114 0.104 Uiso 1 1 calc R . .
C7 C 0.65790(9) 0.4075(3) 0.67762(19) 0.0880(7) Uani 1 1 d . . .
H7A H 0.6496 0.4740 0.6190 0.106 Uiso 1 1 calc R . .
H7B H 0.6446 0.4618 0.7364 0.106 Uiso 1 1 calc R . .
C8 C 0.71892(9) 0.3816(3) 0.68993(18) 0.0811(6) Uani 1 1 d . . .
C9 C 0.74292(9) 0.3489(3) 0.78267(19) 0.0973(7) Uani 1 1 d . . .
H9A H 0.7213 0.3427 0.8386 0.117 Uiso 1 1 calc R . .
C10 C 0.79887(11) 0.3250(3) 0.7940(2) 0.1035(8) Uani 1 1 d . . .
H10A H 0.8152 0.3033 0.8570 0.124 Uiso 1 1 calc R . .
C11 C 0.82949(9) 0.3340(3) 0.7114(3) 0.0958(8) Uani 1 1 d . . .
C12 C 0.80733(11) 0.3670(3) 0.6179(2) 0.1099(8) Uani 1 1 d . . .
H12A H 0.8292 0.3734 0.5624 0.132 Uiso 1 1 calc R . .
C13 C 0.75123(10) 0.3906(3) 0.6081(2) 0.1016(7) Uani 1 1 d . . .
H13A H 0.7352 0.4130 0.5450 0.122 Uiso 1 1 calc R . .


_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 C4 1.752(2) . ?
S1 C7 1.799(2) . ?
O1 N1 1.220(3) . ?
O2 N1 1.211(3) . ?
O3 N2 1.215(4) . ?
O4 N2 1.227(4) . ?
N1 C1 1.476(3) . ?
N2 C11 1.470(3) . ?
C1 C2 1.354(3) . ?
C1 C6 1.359(3) . ?
C2 C3 1.381(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(3) . ?
C5 C6 1.377(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.508(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.371(3) . ?
C8 C13 1.372(3) . ?
C9 C10 1.383(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.356(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.364(4) . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
C4 S1 C7 103.88(10) . . ?
O2 N1 O1 123.2(3) . . ?
O2 N1 C1 118.6(3) . . ?
O1 N1 C1 118.2(3) . . ?
O3 N2 O4 123.8(3) . . ?
O3 N2 C11 119.0(4) . . ?
O4 N2 C11 117.2(4) . . ?
C2 C1 C6 121.8(2) . . ?
C2 C1 N1 118.9(2) . . ?
C6 C1 N1 119.3(3) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 S1 124.93(17) . . ?
C3 C4 S1 116.66(19) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
C8 C7 S1 108.38(15) . . ?
C8 C7 H7A 110.0 . . ?
S1 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
S1 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C13 119.1(2) . . ?
C9 C8 C7 120.7(2) . . ?
C13 C8 C7 120.3(2) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C10 C11 C12 122.6(2) . . ?
C10 C11 N2 117.8(3) . . ?
C12 C11 N2 119.6(3) . . ?
C11 C12 C13 117.9(3) . . ?
C11 C12 H12A 121.0 . . ?
C13 C12 H12A 121.0 . . ?
C8 C13 C12 121.1(3) . . ?
C8 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?

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
O2 N1 C1 C2 175.3(2) . . . . ?
O1 N1 C1 C2 -3.5(3) . . . . ?
O2 N1 C1 C6 -4.9(3) . . . . ?
O1 N1 C1 C6 176.3(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 S1 -179.5(2) . . . . ?
C7 S1 C4 C5 -4.0(2) . . . . ?
C7 S1 C4 C3 176.38(19) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
S1 C4 C5 C6 -179.80(17) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
N1 C1 C6 C5 -178.87(19) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 S1 C7 C8 -173.58(16) . . . . ?
S1 C7 C8 C9 -85.3(2) . . . . ?
S1 C7 C8 C13 94.8(2) . . . . ?
C13 C8 C9 C10 -0.1(4) . . . . ?
C7 C8 C9 C10 180.0(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C11 N2 -179.9(2) . . . . ?
O3 N2 C11 C10 0.7(4) . . . . ?
O4 N2 C11 C10 -179.2(3) . . . . ?
O3 N2 C11 C12 -179.8(3) . . . . ?
O4 N2 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
N2 C11 C12 C13 180.0(2) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
C7 C8 C13 C12 -179.9(2) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 918677'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O4 S'
_chemical_formula_weight         290.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.1653(7)
_cell_length_b                   17.4934(18)
_cell_length_c                   12.4757(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.928(7)
_cell_angle_gamma                90
_cell_volume                     1300.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.264
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29694
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         27.925
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3098
_reflns_number_gt                2105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1432P)²+0.4622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     200
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0838
_refine_ls_wR_factor_ref         0.2906
_refine_ls_wR_factor_gt          0.2643
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.280
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4897(3) 0.50523(9) 0.65777(15) 0.0981(8) Uani 0.791(5) 1 d . U P A 1
C7' C 0.596(2) 0.5101(6) 0.6417(7) 0.042(3) Uani 0.209(5) 1 d D U P A 2
H7'1 H 0.5298 0.4696 0.5908 0.050 Uiso 0.209(5) 1 calc R U P A 2
H7'2 H 0.7018 0.5383 0.6111 0.050 Uiso 0.209(5) 1 calc R U P A 2
O1 O 1.4305(4) 0.40446(17) 1.0325(3) 0.0954(9) Uani 1 1 d . . . . .
O2 O 1.1954(5) 0.32678(17) 1.0678(3) 0.0985(9) Uani 1 1 d . . . . .
O3 O 0.0224(6) 0.78833(18) 0.2184(3) 0.1051(10) Uani 1 1 d . . . . .
O4 O -0.2459(5) 0.71313(17) 0.2248(2) 0.0981(9) Uani 1 1 d . . . . .
N1 N 1.2418(5) 0.37953(14) 1.0151(2) 0.0632(7) Uani 1 1 d . . . . .
N2 N -0.0547(5) 0.73617(17) 0.2611(2) 0.0724(8) Uani 1 1 d . . . . .
C1 C 1.0653(5) 0.41468(15) 0.9281(2) 0.0539(7) Uani 1 1 d . . . . .
C2 C 1.1119(6) 0.47884(17) 0.8760(3) 0.0650(8) Uani 1 1 d . . . . .
H2A H 1.2540 0.5008 0.8942 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9322(8) 0.51048(19) 0.7924(3) 0.0771(10) Uani 1 1 d . U . . .
H3A H 0.9555 0.5545 0.7552 0.093 Uiso 1 1 calc R U . . .
C4 C 0.7197(6) 0.4756(2) 0.7659(3) 0.0734(9) Uani 1 1 d D U . . .
C5 C 0.6877(6) 0.4121(2) 0.8219(3) 0.0783(10) Uani 1 1 d . . . . .
H5A H 0.5472 0.3890 0.8043 0.094 Uiso 1 1 calc R U . . .
C6 C 0.8532(6) 0.3818(2) 0.9020(3) 0.0687(8) Uani 1 1 d . . . . .
H6A H 0.8259 0.3387 0.9401 0.082 Uiso 1 1 calc R U . . .
S1' S 0.3980(13) 0.5682(7) 0.6669(7) 0.143(4) Uani 0.209(5) 1 d D U P A 2
C7 C 0.5225(12) 0.6055(3) 0.6529(6) 0.103(2) Uani 0.791(5) 1 d . U P A 1
H7A H 0.4938 0.6288 0.7185 0.124 Uiso 0.791(5) 1 calc R U P A 1
H7B H 0.6750 0.6178 0.6512 0.124 Uiso 0.791(5) 1 calc R U P A 1
C8 C 0.3572(8) 0.6366(2) 0.5488(3) 0.0857(11) Uani 1 1 d D U . . .
C9 C 0.4378(7) 0.6917(2) 0.4915(3) 0.0832(11) Uani 1 1 d . . . . .
H9A H 0.5864 0.7073 0.5170 0.100 Uiso 1 1 calc R U . . .
C10 C 0.3077(6) 0.7239(2) 0.3990(3) 0.0723(9) Uani 1 1 d . . . . .
H10A H 0.3657 0.7613 0.3613 0.087 Uiso 1 1 calc R U . . .
C11 C 0.0868(5) 0.70058(16) 0.3607(2) 0.0592(7) Uani 1 1 d . . . . .
C12 C -0.0041(6) 0.6449(2) 0.4129(3) 0.0745(9) Uani 1 1 d . . . . .
H12A H -0.1521 0.6290 0.3861 0.089 Uiso 1 1 calc R U . . .
C13 C 0.1376(8) 0.6129(2) 0.5089(3) 0.0891(11) Uani 1 1 d . U . . .
H13A H 0.0820 0.5748 0.5466 0.107 Uiso 1 1 calc R U . . .


_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 C4 1.764(4) . ?
S1 C7 1.769(5) . ?
C7' C4 1.654(9) . ?
C7' S1' 1.679(13) . ?
C7' H7'1 0.9700 . ?
C7' H7'2 0.9700 . ?
O1 N1 1.209(4) . ?
O2 N1 1.209(3) . ?
O3 N2 1.214(4) . ?
O4 N2 1.218(4) . ?
N1 C1 1.460(4) . ?
N2 C11 1.460(4) . ?
C1 C2 1.364(4) . ?
C1 C6 1.388(5) . ?
C2 C3 1.424(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.405(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.353(6) . ?
C5 C6 1.340(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
S1' C8 1.864(7) . ?
C7 C8 1.530(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.367(6) . ?
C8 C13 1.380(6) . ?
C9 C10 1.347(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.370(5) . ?
C12 C13 1.404(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
C4 S1 C7 104.0(2) . . ?
C4 C7' S1' 103.2(6) . . ?
C4 C7' H7'1 111.1 . . ?
S1' C7' H7'1 111.1 . . ?
C4 C7' H7'2 111.1 . . ?
S1' C7' H7'2 111.1 . . ?
H7'1 C7' H7'2 109.1 . . ?
O2 N1 O1 122.0(3) . . ?
O2 N1 C1 119.4(3) . . ?
O1 N1 C1 118.7(3) . . ?
O3 N2 O4 122.4(3) . . ?
O3 N2 C11 118.6(3) . . ?
O4 N2 C11 119.0(3) . . ?
C2 C1 C6 122.0(3) . . ?
C2 C1 N1 119.5(3) . . ?
C6 C1 N1 118.5(3) . . ?
C1 C2 C3 116.7(3) . . ?
C1 C2 H2A 121.7 . . ?
C3 C2 H2A 121.7 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 C7' 133.6(5) . . ?
C3 C4 C7' 103.8(5) . . ?
C5 C4 S1 116.1(3) . . ?
C3 C4 S1 124.7(3) . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C7' S1' C8 101.4(5) . . ?
C8 C7 S1 108.9(3) . . ?
C8 C7 H7A 109.9 . . ?
S1 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
S1 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C13 118.6(3) . . ?
C9 C8 C7 116.2(4) . . ?
C13 C8 C7 125.2(4) . . ?
C9 C8 S1' 150.7(4) . . ?
C13 C8 S1' 90.7(4) . . ?
C10 C9 C8 121.7(4) . . ?
C10 C9 H9A 119.1 . . ?
C8 C9 H9A 119.1 . . ?
C9 C10 C11 119.2(4) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C12 C11 C10 122.2(3) . . ?
C12 C11 N2 118.7(3) . . ?
C10 C11 N2 119.2(3) . . ?
C11 C12 C13 116.6(3) . . ?
C11 C12 H12A 121.7 . . ?
C13 C12 H12A 121.7 . . ?
C8 C13 C12 121.6(4) . . ?
C8 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?

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
O2 N1 C1 C2 173.5(3) . . . . ?
O1 N1 C1 C2 -6.2(4) . . . . ?
O2 N1 C1 C6 -5.7(4) . . . . ?
O1 N1 C1 C6 174.5(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C7' -160.8(4) . . . . ?
C2 C3 C4 S1 -175.4(3) . . . . ?
S1' C7' C4 C5 92.7(8) . . . . ?
S1' C7' C4 C3 -109.6(8) . . . . ?
S1' C7' C4 S1 40.8(7) . . . . ?
C7 S1 C4 C5 150.5(4) . . . . ?
C7 S1 C4 C3 -33.2(5) . . . . ?
C7 S1 C4 C7' -68.9(9) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C7' C4 C5 C6 155.1(6) . . . . ?
S1 C4 C5 C6 176.6(3) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
N1 C1 C6 C5 -179.4(3) . . . . ?
C4 C7' S1' C8 155.1(6) . . . . ?
C4 S1 C7 C8 169.9(5) . . . . ?
S1 C7 C8 C9 -138.3(5) . . . . ?
S1 C7 C8 C13 41.1(8) . . . . ?
S1 C7 C8 S1' 41.2(6) . . . . ?
C7' S1' C8 C9 -62.2(14) . . . . ?
C7' S1' C8 C13 116.8(7) . . . . ?
C7' S1' C8 C7 -63.1(7) . . . . ?
C13 C8 C9 C10 1.1(6) . . . . ?
C7 C8 C9 C10 -179.4(4) . . . . ?
S1' C8 C9 C10 180.0(9) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C9 C10 C11 N2 179.3(3) . . . . ?
O3 N2 C11 C12 176.1(3) . . . . ?
O4 N2 C11 C12 -3.1(4) . . . . ?
O3 N2 C11 C10 -4.1(4) . . . . ?
O4 N2 C11 C10 176.7(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
N2 C11 C12 C13 -179.3(3) . . . . ?
C9 C8 C13 C12 -1.1(6) . . . . ?
C7 C8 C13 C12 179.5(5) . . . . ?
S1' C8 C13 C12 179.4(5) . . . . ?
C11 C12 C13 C8 0.1(6) . . . . ?

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
C7 H7B O3 0.97 2.66 3.509(7) 146.8 4_676
C5 H5A O4 0.93 2.53 3.427(5) 160.8 3_566
C2 H2A O1 0.93 2.54 3.431(4) 160.7 3_867
C2 H2A O1 0.93 2.54 3.431(4) 160.7 3_867
C5 H5A O4 0.93 2.53 3.427(5) 160.8 3_566
C7 H7B O3 0.97 2.66 3.509(7) 146.8 4_676

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 918678'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_II

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O4 S'
_chemical_formula_weight         290.29

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           ?
_symmetry_space_group_name_H-M   ?

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                   4.0558(3)
_cell_length_b                   20.4472(16)
_cell_length_c                   16.1833(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.878(5)
_cell_angle_gamma                90.00
_cell_volume                     1308.32(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            9404
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2296
_reflns_number_gt                1649
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0660P)²+0.2588P] where P=(Fo²+2Fc²)/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         2296
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
S1 S 0.57549(19) 0.45117(3) 0.39761(4) 0.0590(3) Uani 1 1 d . . .
O1 O -0.1025(7) 0.63471(15) 0.06848(17) 0.1159(10) Uani 1 1 d . . .
O2 O 0.1784(8) 0.57007(13) 0.00453(15) 0.1088(9) Uani 1 1 d . . .
O3 O 1.2439(9) 0.25380(14) 0.74730(16) 0.1294(11) Uani 1 1 d . . .
O4 O 0.9400(9) 0.17484(13) 0.69054(16) 0.1245(11) Uani 1 1 d . . .
N1 N 0.0890(8) 0.58839(15) 0.06753(18) 0.0828(8) Uani 1 1 d . . .
N2 N 1.0587(8) 0.22827(14) 0.68725(16) 0.0788(8) Uani 1 1 d . . .
C1 C 0.2173(7) 0.55353(14) 0.14789(17) 0.0600(7) Uani 1 1 d . . .
C2 C 0.1613(7) 0.58038(13) 0.22175(18) 0.0643(7) Uani 1 1 d . . .
H2A H 0.0490 0.6201 0.2211 0.077 Uiso 1 1 calc R . .
C3 C 0.2759(7) 0.54692(12) 0.29634(16) 0.0570(7) Uani 1 1 d . . .
H3A H 0.2407 0.5644 0.3467 0.068 Uiso 1 1 calc R . .
C4 C 0.4430(6) 0.48756(11) 0.29785(14) 0.0473(6) Uani 1 1 d . . .
C5 C 0.4970(7) 0.46210(13) 0.22200(15) 0.0567(7) Uani 1 1 d . . .
H5A H 0.6093 0.4225 0.2218 0.068 Uiso 1 1 calc R . .
C6 C 0.3833(7) 0.49586(14) 0.14731(16) 0.0631(7) Uani 1 1 d . . .
H6A H 0.4201 0.4792 0.0967 0.076 Uiso 1 1 calc R . .
C7 C 0.7371(7) 0.37210(12) 0.37617(14) 0.0537(6) Uani 1 1 d . . .
H7A H 0.5686 0.3488 0.3346 0.064 Uiso 1 1 calc R . .
H7B H 0.9379 0.3774 0.3536 0.064 Uiso 1 1 calc R . .
C8 C 0.8215(6) 0.33417(12) 0.45771(14) 0.0470(6) Uani 1 1 d . . .
C9 C 1.0411(6) 0.35987(12) 0.52893(14) 0.0515(6) Uani 1 1 d . . .
H9A H 1.1360 0.4010 0.5259 0.062 Uiso 1 1 calc R . .
C10 C 1.1192(7) 0.32537(12) 0.60347(15) 0.0540(6) Uani 1 1 d . . .
H10A H 1.2666 0.3426 0.6509 0.065 Uiso 1 1 calc R . .
C11 C 0.9746(7) 0.26479(12) 0.60659(15) 0.0543(7) Uani 1 1 d . . .
C12 C 0.7601(7) 0.23786(13) 0.53814(17) 0.0608(7) Uani 1 1 d . . .
H12A H 0.6680 0.1966 0.5417 0.073 Uiso 1 1 calc R . .
C13 C 0.6820(7) 0.27283(12) 0.46348(15) 0.0562(7) Uani 1 1 d . . .
H13A H 0.5343 0.2551 0.4165 0.067 Uiso 1 1 calc R . .


_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 C4 1.750(2) . ?
S1 C7 1.807(2) . ?
O1 N1 1.227(4) . ?
O2 N1 1.215(4) . ?
O3 N2 1.207(3) . ?
O4 N2 1.200(3) . ?
N1 C1 1.473(4) . ?
N2 C11 1.476(3) . ?
C1 C6 1.359(4) . ?
C1 C2 1.379(4) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(3) . ?
C5 C6 1.379(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.503(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.387(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.372(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.363(4) . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
C4 S1 C7 104.67(11) . . ?
O2 N1 O1 123.8(3) . . ?
O2 N1 C1 118.6(3) . . ?
O1 N1 C1 117.6(3) . . ?
O4 N2 O3 122.8(3) . . ?
O4 N2 C11 119.0(3) . . ?
O3 N2 C11 118.2(3) . . ?
C6 C1 C2 121.9(2) . . ?
C6 C1 N1 119.5(3) . . ?
C2 C1 N1 118.6(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 S1 115.88(18) . . ?
C5 C4 S1 125.24(19) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 S1 108.33(15) . . ?
C8 C7 H7A 110.0 . . ?
S1 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
S1 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 C7 120.6(2) . . ?
C9 C8 C7 120.7(2) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 118.6(2) . . ?
C9 C10 H10A 120.7 . . ?
C11 C10 H10A 120.7 . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 N2 119.6(2) . . ?
C10 C11 N2 118.1(2) . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 H13A 119.7 . . ?
C8 C13 H13A 119.7 . . ?

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
O2 N1 C1 C6 -11.1(4) . . . . ?
O1 N1 C1 C6 169.2(3) . . . . ?
O2 N1 C1 C2 169.7(3) . . . . ?
O1 N1 C1 C2 -10.1(4) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C3 178.7(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 S1 179.6(2) . . . . ?
C7 S1 C4 C3 173.79(19) . . . . ?
C7 S1 C4 C5 -7.2(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
S1 C4 C5 C6 -179.3(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
N1 C1 C6 C5 -178.4(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 S1 C7 C8 -173.76(17) . . . . ?
S1 C7 C8 C13 124.7(2) . . . . ?
S1 C7 C8 C9 -55.3(3) . . . . ?
C13 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C11 N2 -179.6(2) . . . . ?
O4 N2 C11 C12 1.2(4) . . . . ?
O3 N2 C11 C12 -178.6(3) . . . . ?
O4 N2 C11 C10 -178.5(3) . . . . ?
O3 N2 C11 C10 1.7(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
N2 C11 C12 C13 179.5(2) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
C7 C8 C13 C12 179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 918679'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_IV

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O4 S'
_chemical_formula_weight         290.29

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.1030(7)
_cell_length_b                   13.8660(8)
_cell_length_c                   15.6862(10)
_cell_angle_alpha                81.809(4)
_cell_angle_beta                 71.861(3)
_cell_angle_gamma                79.628(3)
_cell_volume                     2652.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   Multi-SCAN
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEXII CCD area detector'
_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            24715
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_sigmaI/netI    0.1610
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.01
_reflns_number_total             9332
_reflns_number_gt                3256
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker 2007)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and PLATON (Spek,2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

TITL IV in P-1
CELL 0.71073  13.1030  13.8660  15.6862  81.809  71.861  79.628
ZERR   8.00   0.0007   0.0008   0.0010   0.004   0.003   0.003
LATT  1
SFAC C   H  N  O  S
UNIT 104 80 16 32 8
TEMP 23.000
OMIT 0 1 0
OMIT 1 0 0
OMIT -3 -2 1
OMIT 1 -2 2
OMIT 0 4 0
OMIT 4 0 1
OMIT 4 1 1
OMIT 4 2 3
OMIT 3 3 3
OMIT -4 3 1
OMIT 2 2 2
OMIT 1 -7 4
OMIT -2 -2 5
OMIT 1 -5 3
OMIT 1 -7 1
OMIT -4 -5 1
OMIT -4 1 1
OMIT 0 -3 4
OMIT 3 0 1
OMIT -5 -3 1
OMIT -5 1 0
OMIT 4 -1 1
OMIT -3 1 0
OMIT 3 -1 3
OMIT -2 4 2
OMIT -1 -3 4
OMIT -2 1 0
OMIT 2 -2 1
OMIT -3 50.02
SIMU .02 C46 C47 C48
ISOR .02 C46 C47 C48
SIMU .02 C46 C47 C52
ISOR .02 C46 C47 C52
SIMU .02 S3 C33 C34
ISOR .02 S3 C33 C34
 
L.S. 20
ACTA
BOND $H
HTAB
CONF
FMAP 2
PLAN 5
MPLA 5 C40 c41 c42 c43 c44
MPLA 5 C47 c48 c49 c50 c51
WGHT    0.115800
FVAR       0.06838
S1    5    0.564385    1.000167    0.599820    11.00000    0.05547    0.08119 =
         0.08161    0.01542   -0.01754   -0.01236
S2    5    0.652135   -0.009851    0.893436    11.00000    0.07609    0.06788 =
         0.10092    0.01475   -0.04469   -0.01958
S3    5    0.067637    0.403623    0.902354    11.00000    0.09161    0.08870 =
         0.18589   -0.00218   -0.06737   -0.01111
S4    5    0.147844    0.600306    0.600686    11.00000    0.11113    0.09256 =
         0.19225   -0.01337   -0.03650   -0.02392
O1    4    0.123431    0.789072    0.783332    11.00000    0.06565    0.13413 =
         0.18214   -0.00345   -0.03414   -0.03310
O2    4    0.224440    0.700524    0.858551    11.00000    0.11129    0.11168 =
         0.26426    0.09148   -0.05009   -0.05162
N1    3    0.210109    0.763900    0.800690    11.00000    0.08146    0.06846 =
         0.14503   -0.00428   -0.02473   -0.02740
N2    3    1.026758    1.121530    0.354476    11.00000    0.06056    0.09188 =
         0.08683    0.02007   -0.01986   -0.01519
N3    3    0.336529    0.255592    0.731422    11.00000    0.07594    0.09656 =
         0.08990    0.00408   -0.03268   -0.00215
N4    3    0.976892   -0.138100    1.142717    11.00000    0.08070    0.06460 =
         0.09382    0.00975   -0.03664   -0.02396
N5    3   -0.307770    0.658685    0.810634    11.00000    0.07619    0.10099 =
         0.09288    0.00114   -0.03308    0.00227
N6    3    0.545759    0.280296    0.987538    11.00000    0.06700    0.08852 =
         0.10817   -0.00974   -0.03552   -0.00296
N7    3   -0.194443    0.342184    0.666057    11.00000    0.13249    0.15604 =
         0.11698   -0.01769   -0.01748   -0.08796
N8    3    0.632772    0.726844    0.526509    11.00000    0.08318    0.09297 =
         0.12573   -0.03220   -0.03330   -0.02395
O4    4    1.044728    1.198934    0.369081    11.00000    0.09723    0.09709 =
         0.12511    0.01842   -0.00305   -0.03739
O3    4    1.077008    1.079405    0.288420    11.00000    0.09125    0.15712 =
         0.08630   -0.01012   -0.00176   -0.03321
O12   4    0.623326    0.322727    0.966392    11.00000    0.08146    0.14125 =
         0.25974    0.03336   -0.08576   -0.02198
O11   4    0.542981    0.199372    1.027131    11.00000    0.11025    0.08295 =
         0.13549    0.00523   -0.06230    0.00669
O9    4   -0.387151    0.619807    0.819545    11.00000    0.07707    0.14407 =
         0.14412    0.00530   -0.05475   -0.01233
O10   4   -0.302678    0.746295    0.786777    11.00000    0.10853    0.11116 =
         0.19667    0.03896   -0.07798   -0.00464
C1    1    0.301012    0.819231    0.751727    11.00000    0.05895    0.06003 =
         0.08184   -0.00153   -0.01390   -0.01896
C2    1    0.283155    0.898449    0.692191    11.00000    0.05981    0.08873 =
         0.07955   -0.00576   -0.02187   -0.00371
AFIX  43
H2A   2    0.215602    0.915630    0.682177    11.00000   -1.20000
AFIX   0
C3    1    0.365627    0.952061    0.647597    11.00000    0.06271    0.09572 =
         0.05345    0.01538   -0.02115   -0.02196
AFIX  43
H3A   2    0.353751    1.005884    0.607348    11.00000   -1.20000
AFIX   0
C4    1    0.466807    0.926568    0.662096    11.00000    0.04201    0.07348 =
         0.06396   -0.00570   -0.01968   -0.00380
C5    1    0.482333    0.847144    0.722788    11.00000    0.05437    0.07015 =
         0.09025    0.00836   -0.03360   -0.00852
AFIX  43
H5A   2    0.549437    0.829508    0.733571    11.00000   -1.20000
AFIX   0
C6    1    0.399105    0.793827    0.767492    11.00000    0.06744    0.06196 =
         0.09712   -0.00155   -0.02002   -0.00588
AFIX  43
H6A   2    0.409976    0.740440    0.808469    11.00000   -1.20000
AFIX   0
C7    1    0.690870    0.939403    0.620706    11.00000    0.05480    0.07199 =
         0.07699    0.00511   -0.02053   -0.01818
AFIX  23
H7A   2    0.690571    0.948114    0.681057    11.00000   -1.20000
H7B   2    0.700686    0.869461    0.614478    11.00000   -1.20000
AFIX   0
C8    1    0.779541    0.986686    0.551984    11.00000    0.04993    0.06463 =
         0.05480   -0.00489   -0.01534   -0.00582
C9    1    0.839930    0.940701    0.477844    11.00000    0.05819    0.07393 =
         0.08672   -0.00766   -0.02711   -0.02097
AFIX  43
H9A   2    0.825458    0.879450    0.471061    11.00000   -1.20000
AFIX   0
C10   1    0.923441    0.982322    0.411056    11.00000    0.06351    0.08216 =
         0.05627   -0.02089   -0.01720   -0.00355
AFIX  43
H10A  2    0.965584    0.949916    0.360985    11.00000   -1.20000
AFIX   0
C11   1    0.939424    1.074896    0.424203    11.00000    0.05046    0.07233 =
         0.05871    0.00201   -0.02008   -0.00070
C12   1    0.878887    1.122459    0.495670    11.00000    0.05886    0.06681 =
         0.09585    0.00248   -0.01548   -0.01364
AFIX  43
H12A  2    0.890840    1.185029    0.501357    11.00000   -1.20000
AFIX   0
C13   1    0.798625    1.078613    0.561009    11.00000    0.06576    0.07351 =
         0.06996   -0.01216   -0.00653   -0.01011
AFIX  43
H13A  2    0.757399    1.111244    0.611193    11.00000   -1.20000
AFIX   0
C14   1    0.416309    0.190081    0.768533    11.00000    0.06466    0.06609 =
         0.06317    0.00583   -0.02479   -0.00846
C15   1    0.392506    0.102513    0.816310    11.00000    0.05442    0.08012 =
         0.07729   -0.00424   -0.02232   -0.01463
AFIX  43
H15A  2    0.325319    0.083587    0.824264    11.00000   -1.20000
AFIX   0
C16   1    0.466254    0.042233    0.852644    11.00000    0.06918    0.05971 =
         0.07326    0.00717   -0.02344   -0.02020
AFIX  43
H16A  2    0.449844   -0.017963    0.883817    11.00000   -1.20000
AFIX   0
C17   1    0.565705    0.071283    0.842796    11.00000    0.05930    0.06010 =
         0.05867   -0.00393   -0.01278   -0.01499
C18   1    0.591313    0.159824    0.791507    11.00000    0.05484    0.06688 =
         0.05424    0.00276   -0.00665   -0.01798
AFIX  43
H18A  2    0.659077    0.178399    0.781799    11.00000   -1.20000
AFIX   0
C19   1    0.516307    0.218804    0.755787    11.00000    0.06894    0.06378 =
         0.05827    0.00712   -0.01217   -0.01632
AFIX  43
H19A  2    0.532501    0.278278    0.722895    11.00000   -1.20000
AFIX   0
C20   1    0.762967    0.054909    0.882617    11.00000    0.05763    0.07167 =
         0.08172    0.01420   -0.02348   -0.01776
AFIX  23
H20A  2    0.812450    0.053728    0.822026    11.00000   -1.20000
H20B  2    0.736247    0.122978    0.894832    11.00000   -1.20000
AFIX   0
C38   1    0.450452    0.422564    0.916807    11.00000    0.06212    0.07735 =
         0.13306   -0.00213   -0.03385   -0.01694
AFIX  43
H38A  2    0.510957    0.454358    0.904064    11.00000   -1.20000
AFIX   0
C39   1    0.359538    0.468153    0.892158    11.00000    0.07677    0.07351 =
         0.12516    0.01352   -0.03166   -0.00506
AFIX  43
H39A  2    0.359233    0.531729    0.863624    11.00000   -1.20000
AFIX   0
C40   1   -0.105841    0.399923    0.646992    11.00000    0.08878    0.09791 =
         0.06703    0.00030   -0.01305   -0.04169
C41   1   -0.122399    0.497396    0.624855    11.00000    0.07027    0.10921 =
         0.09060   -0.01768   -0.02488   -0.02221
AFIX  43
H41A  2   -0.190142    0.527327    0.620161    11.00000   -1.20000
AFIX   0
C42   1   -0.042952    0.552411    0.609380    11.00000    0.08480    0.09038 =
         0.09983   -0.01962   -0.02554   -0.01985
AFIX  43
H42A  2   -0.056768    0.619674    0.593663    11.00000   -1.20000
AFIX   0
C43   1    0.055148    0.513229    0.615935    11.00000    0.07956    0.10312 =
         0.07897   -0.01089   -0.00961   -0.03389
C44   1    0.077128    0.411068    0.637359    11.00000    0.06866    0.11545 =
         0.09985    0.00229   -0.02781   -0.02458
AFIX  43
H44A  2    0.145733    0.382259    0.640750    11.00000   -1.20000
AFIX   0
C45   1   -0.004588    0.353874    0.653349    11.00000    0.13532    0.06997 =
         0.06888    0.00204   -0.01455   -0.02217
AFIX  43
H45A  2    0.007938    0.286279    0.667990    11.00000   -1.20000
AFIX   0
C46   1    0.264756    0.528334    0.573630    11.00000    0.11587    0.09984 =
         0.21885   -0.03669    0.00888   -0.03386
AFIX  23
H46A  2    0.263416    0.471071    0.617207    11.00000   -1.20000
H46B  2    0.278049    0.505903    0.514799    11.00000   -1.20000
AFIX   0
C47   1    0.359078    0.587541    0.572047    11.00000    0.08049    0.09516 =
         0.13688    0.00106   -0.03187   -0.03706
C48   1    0.373376    0.672208    0.511061    11.00000    0.08453    0.10886 =
         0.15311    0.00936   -0.06116   -0.01475
AFIX  43
H48A  2    0.323484    0.696404    0.479272    11.00000   -1.20000
AFIX   0
C49   1    0.463138    0.719818    0.498511    11.00000    0.08543    0.08041 =
         0.12705    0.01301   -0.03199   -0.02279
AFIX  43
H49A  2    0.472856    0.777053    0.459856    11.00000   -1.20000
AFIX   0
C50   1    0.534545    0.680963    0.543476    11.00000    0.06333    0.07450 =
         0.10031   -0.01456   -0.02278   -0.02122
C51   1    0.520970    0.601587    0.604974    11.00000    0.09613    0.08784 =
         0.11419    0.00326   -0.04829   -0.02250
AFIX  43
H51A  2    0.570327    0.577959    0.637378    11.00000   -1.20000
AFIX   0
C52   1    0.431616    0.558007    0.617115    11.00000    0.11145    0.11331 =
         0.12266    0.00462   -0.03354   -0.04488
AFIX  43
H52A  2    0.420637    0.504013    0.659762    11.00000   -1.20000
AFIX   0
C21   1    0.819876    0.003781    0.949738    11.00000    0.04896    0.05683 =
         0.07082   -0.00826   -0.01756   -0.00873
C22   1    0.808114    0.044573    1.028468    11.00000    0.05785    0.05255 =
         0.08188   -0.00857   -0.01300   -0.00397
AFIX  43
H22A  2    0.764874    0.105238    1.038795    11.00000   -1.20000
AFIX   0
C23   1    0.857382   -0.000611    1.091525    11.00000    0.07215    0.07647 =
         0.05971   -0.00123   -0.01763   -0.01464
AFIX  43
H23A  2    0.848061    0.028453    1.143842    11.00000   -1.20000
AFIX   0
C24   1    0.921549   -0.090800    1.075507    11.00000    0.05512    0.04592 =
         0.06706    0.00296   -0.02079   -0.01294
C25   1    0.937029   -0.135404    0.998279    11.00000    0.06998    0.05322 =
         0.08375   -0.00124   -0.02546   -0.00969
AFIX  43
H25A  2    0.980798   -0.195871    0.988244    11.00000   -1.20000
AFIX   0
C26   1    0.885348   -0.087230    0.936428    11.00000    0.07956    0.06748 =
         0.07316   -0.01024   -0.02784   -0.01221
AFIX  43
H26A  2    0.894496   -0.116417    0.884212    11.00000   -1.20000
AFIX   0
C27   1   -0.214016    0.599721    0.833410    11.00000    0.05948    0.07600 =
         0.06927   -0.00315   -0.02668    0.00098
C28   1   -0.217879    0.502859    0.864701    11.00000    0.06473    0.08248 =
         0.09613   -0.01132   -0.03785   -0.01224
AFIX  43
H28A  2   -0.279863    0.474864    0.872247    11.00000   -1.20000
AFIX   0
C29   1   -0.129871    0.448070    0.884621    11.00000    0.07433    0.06566 =
         0.12005   -0.01538   -0.03860    0.00195
AFIX  43
H29A  2   -0.132353    0.381999    0.905273    11.00000   -1.20000
AFIX   0
C30   1   -0.037535    0.487017    0.875267    11.00000    0.05335    0.07515 =
         0.08338   -0.01394   -0.02585    0.00240
C31   1   -0.034880    0.585884    0.842038    11.00000    0.04737    0.09366 =
         0.07839    0.00650   -0.00691   -0.01564
AFIX  43
H31A  2    0.027396    0.613900    0.833302    11.00000   -1.20000
AFIX   0
C32   1   -0.124328    0.642213    0.822101    11.00000    0.06582    0.06880 =
         0.06351    0.00417   -0.01107   -0.00010
AFIX  43
H32A  2   -0.123192    0.708352    0.801212    11.00000   -1.20000
AFIX   0
C33   1    0.172260    0.484489    0.876662    11.00000    0.03130    0.06772 =
         0.11386   -0.01194   -0.03027    0.00469
AFIX  23
H33A  2    0.195900    0.504306    0.812546    11.00000   -1.20000
H33B  2    0.144136    0.543101    0.908624    11.00000   -1.20000
AFIX   0
C34   1    0.269773    0.422489    0.908498    11.00000    0.06067    0.07321 =
         0.08954   -0.00918   -0.01792   -0.00934
C35   1    0.273414    0.326838    0.951163    11.00000    0.05831    0.07616 =
         0.08105   -0.01017   -0.02167   -0.01530
AFIX  43
H35A  2    0.214155    0.293722    0.962412    11.00000   -1.20000
AFIX   0
C36   1    0.363234    0.280285    0.977054    11.00000    0.07206    0.06404 =
         0.08909   -0.00443   -0.03144   -0.01465
AFIX  43
H36A  2    0.364650    0.216563    1.005288    11.00000   -1.20000
AFIX   0
C37   1    0.449540    0.329531    0.960417    11.00000    0.06674    0.05710 =
         0.08322   -0.00682   -0.03103    0.00588
O8    4    1.043502   -0.209552    1.123037    11.00000    0.12546    0.07925 =
         0.13775    0.00808   -0.07489   -0.00661
O7    4    0.955005   -0.103065    1.213431    11.00000    0.13581    0.11597 =
         0.08194   -0.01081   -0.04813   -0.02037
O5    4    0.248054    0.225872    0.745199    11.00000    0.08043    0.14285 =
         0.15007    0.02432   -0.05156   -0.00483
O6    4    0.356225    0.333332    0.693355    11.00000    0.12268    0.08923 =
         0.15746    0.03620   -0.06549   -0.01347
O13   4   -0.284582    0.385234    0.671037    11.00000    0.09916    0.23657 =
         0.22566   -0.03157   -0.03515   -0.08406
O14   4   -0.171268    0.251645    0.675805    11.00000    0.19203    0.16074 =
         0.17415   -0.03574   -0.00611   -0.11881
O15   4    0.644581    0.799441    0.471207    11.00000    0.13240    0.13226 =
         0.18106    0.01401   -0.04317   -0.08273
O16   4    0.696715    0.692683    0.567798    11.00000    0.10614    0.14268 =
         0.23087   -0.03342   -0.08908   -0.02200
 
HKLF 4
 
REM  1 in P-1
REM R1 =  0.0877 for   3256 Fo > 4sig(Fo)  and  0.2340 for all   9332 data
REM    721 parameters refined using     78 restraints
 
END  
     
WGHT      0.1160      0.0000 
REM Highest difference peak  0.763,  deepest hole -0.585,  1-sigma level  0.057
Q1    1   0.2255  0.5768  0.5219  11.00000  0.05    0.76
Q2    1   0.2195  0.5652  0.6513  11.00000  0.05    0.47
Q3    1   0.1783  0.4828  0.6216  11.00000  0.05    0.26
Q4    1   0.1808  0.4435  0.8315  11.00000  0.05    0.26
Q5    1  -0.2416  0.2608  0.6510  11.00000  0.05    0.24
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1158P)²+0.0000P] where P=(Fo²+2Fc²)/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         9332
_refine_ls_number_parameters     721
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.2340
_refine_ls_R_factor_gt           0.0877
_refine_ls_wR_factor_ref         0.2894
_refine_ls_wR_factor_gt          0.2065
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.991
_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
S1 S 0.56439(14) 1.00017(14) 0.59982(14) 0.0754(6) Uani 1 1 d . . .
S2 S 0.65214(15) -0.00985(14) 0.89344(15) 0.0784(6) Uani 1 1 d . . .
S3 S 0.06764(19) 0.40362(17) 0.9024(2) 0.1172(10) Uani 1 1 d U . .
S4 S 0.1478(2) 0.60031(19) 0.6007(2) 0.1326(11) Uani 1 1 d . . .
O1 O 0.1234(5) 0.7891(5) 0.7833(5) 0.127(2) Uani 1 1 d . . .
O2 O 0.2244(5) 0.7005(5) 0.8586(7) 0.170(4) Uani 1 1 d . . .
N1 N 0.2101(6) 0.7639(5) 0.8007(6) 0.099(2) Uani 1 1 d . . .
N2 N 1.0268(5) 1.1215(6) 0.3545(6) 0.083(2) Uani 1 1 d . . .
N3 N 0.3365(6) 0.2556(6) 0.7314(5) 0.088(2) Uani 1 1 d . . .
N4 N 0.9769(6) -0.1381(5) 1.1427(6) 0.0771(19) Uani 1 1 d . . .
N5 N -0.3078(6) 0.6587(6) 0.8106(5) 0.091(2) Uani 1 1 d . . .
N6 N 0.5458(5) 0.2803(6) 0.9875(5) 0.087(2) Uani 1 1 d . . .
N7 N -0.1944(9) 0.3422(10) 0.6661(6) 0.130(3) Uani 1 1 d . . .
N8 N 0.6328(6) 0.7268(6) 0.5265(6) 0.096(2) Uani 1 1 d . . .
O4 O 1.0447(5) 1.1989(5) 0.3691(5) 0.113(2) Uani 1 1 d . . .
O3 O 1.0770(5) 1.0794(5) 0.2884(5) 0.115(2) Uani 1 1 d . . .
O12 O 0.6233(5) 0.3227(5) 0.9664(6) 0.157(3) Uani 1 1 d . . .
O11 O 0.5430(5) 0.1994(5) 1.0271(4) 0.108(2) Uani 1 1 d . . .
O9 O -0.3872(5) 0.6198(5) 0.8195(5) 0.119(2) Uani 1 1 d . . .
O10 O -0.3027(5) 0.7463(6) 0.7868(5) 0.138(3) Uani 1 1 d . . .
C1 C 0.3010(6) 0.8192(5) 0.7517(5) 0.068(2) Uani 1 1 d . . .
C2 C 0.2832(6) 0.8984(6) 0.6922(5) 0.077(2) Uani 1 1 d . . .
H2A H 0.2156 0.9156 0.6822 0.092 Uiso 1 1 calc R . .
C3 C 0.3656(5) 0.9521(6) 0.6476(5) 0.071(2) Uani 1 1 d . . .
H3A H 0.3538 1.0059 0.6073 0.085 Uiso 1 1 calc R . .
C4 C 0.4668(5) 0.9266(5) 0.6621(5) 0.0595(18) Uani 1 1 d . . .
C5 C 0.4823(5) 0.8471(5) 0.7228(5) 0.070(2) Uani 1 1 d . . .
H5A H 0.5494 0.8295 0.7336 0.084 Uiso 1 1 calc R . .
C6 C 0.3991(6) 0.7938(5) 0.7675(5) 0.078(2) Uani 1 1 d . . .
H6A H 0.4100 0.7404 0.8085 0.093 Uiso 1 1 calc R . .
C7 C 0.6909(5) 0.9394(5) 0.6207(5) 0.0677(19) Uani 1 1 d . . .
H7A H 0.6906 0.9481 0.6811 0.081 Uiso 1 1 calc R . .
H7B H 0.7007 0.8695 0.6145 0.081 Uiso 1 1 calc R . .
C8 C 0.7795(5) 0.9867(5) 0.5520(5) 0.0568(17) Uani 1 1 d . . .
C9 C 0.8399(6) 0.9407(5) 0.4778(6) 0.070(2) Uani 1 1 d . . .
H9A H 0.8255 0.8794 0.4711 0.084 Uiso 1 1 calc R . .
C10 C 0.9234(6) 0.9823(6) 0.4111(5) 0.0668(19) Uani 1 1 d . . .
H10A H 0.9656 0.9499 0.3610 0.080 Uiso 1 1 calc R . .
C11 C 0.9394(5) 1.0749(6) 0.4242(5) 0.0614(19) Uani 1 1 d . . .
C12 C 0.8789(6) 1.1225(6) 0.4957(6) 0.076(2) Uani 1 1 d . . .
H12A H 0.8908 1.1850 0.5014 0.091 Uiso 1 1 calc R . .
C13 C 0.7986(6) 1.0786(6) 0.5610(5) 0.072(2) Uani 1 1 d . . .
H13A H 0.7574 1.1112 0.6112 0.087 Uiso 1 1 calc R . .
C14 C 0.4163(5) 0.1901(5) 0.7685(5) 0.0646(19) Uani 1 1 d . . .
C15 C 0.3925(5) 0.1025(5) 0.8163(5) 0.070(2) Uani 1 1 d . . .
H15A H 0.3253 0.0836 0.8243 0.083 Uiso 1 1 calc R . .
C16 C 0.4663(5) 0.0422(5) 0.8526(5) 0.0667(19) Uani 1 1 d . . .
H16A H 0.4498 -0.0180 0.8838 0.080 Uiso 1 1 calc R . .
C17 C 0.5657(5) 0.0713(5) 0.8428(4) 0.0597(18) Uani 1 1 d . . .
C18 C 0.5913(5) 0.1598(5) 0.7915(4) 0.0605(18) Uani 1 1 d . . .
H18A H 0.6591 0.1784 0.7818 0.073 Uiso 1 1 calc R . .
C19 C 0.5163(6) 0.2188(5) 0.7558(5) 0.0656(19) Uani 1 1 d . . .
H19A H 0.5325 0.2783 0.7229 0.079 Uiso 1 1 calc R . .
C20 C 0.7630(5) 0.0549(5) 0.8826(5) 0.071(2) Uani 1 1 d . . .
H20A H 0.8124 0.0537 0.8220 0.085 Uiso 1 1 calc R . .
H20B H 0.7362 0.1230 0.8948 0.085 Uiso 1 1 calc R . .
C38 C 0.4505(6) 0.4226(6) 0.9168(6) 0.090(3) Uani 1 1 d . . .
H38A H 0.5110 0.4544 0.9041 0.107 Uiso 1 1 calc R . .
C39 C 0.3595(6) 0.4682(6) 0.8922(6) 0.094(3) Uani 1 1 d . . .
H39A H 0.3592 0.5317 0.8636 0.113 Uiso 1 1 calc R . .
C40 C -0.1058(7) 0.3999(8) 0.6470(5) 0.084(2) Uani 1 1 d . . .
C41 C -0.1224(7) 0.4974(7) 0.6249(6) 0.088(2) Uani 1 1 d . . .
H41A H -0.1901 0.5273 0.6202 0.105 Uiso 1 1 calc R . .
C42 C -0.0430(7) 0.5524(6) 0.6094(6) 0.090(2) Uani 1 1 d . . .
H42A H -0.0568 0.6197 0.5937 0.108 Uiso 1 1 calc R . .
C43 C 0.0551(7) 0.5132(7) 0.6159(6) 0.087(2) Uani 1 1 d . . .
C44 C 0.0771(7) 0.4111(8) 0.6374(6) 0.094(3) Uani 1 1 d . . .
H44A H 0.1457 0.3823 0.6407 0.112 Uiso 1 1 calc R . .
C45 C -0.0046(9) 0.3539(6) 0.6533(5) 0.095(3) Uani 1 1 d . . .
H45A H 0.0079 0.2863 0.6680 0.114 Uiso 1 1 calc R . .
C46 C 0.2648(8) 0.5283(7) 0.5736(9) 0.154(4) Uani 1 1 d U . .
H46A H 0.2634 0.4711 0.6172 0.184 Uiso 1 1 calc R . .
H46B H 0.2780 0.5059 0.5148 0.184 Uiso 1 1 calc R . .
C47 C 0.3591(7) 0.5875(7) 0.5720(7) 0.102(3) Uani 1 1 d U . .
C48 C 0.3734(7) 0.6722(7) 0.5111(7) 0.111(3) Uani 1 1 d U . .
H48A H 0.3235 0.6964 0.4793 0.134 Uiso 1 1 calc R . .
C49 C 0.4631(7) 0.7198(6) 0.4985(6) 0.098(3) Uani 1 1 d . . .
H49A H 0.4729 0.7771 0.4599 0.118 Uiso 1 1 calc R . .
C50 C 0.5345(6) 0.6810(6) 0.5435(6) 0.078(2) Uani 1 1 d . . .
C51 C 0.5210(7) 0.6016(6) 0.6050(6) 0.095(3) Uani 1 1 d . . .
H51A H 0.5703 0.5780 0.6374 0.114 Uiso 1 1 calc R . .
C52 C 0.4316(8) 0.5580(7) 0.6171(7) 0.114(3) Uani 1 1 d U . .
H52A H 0.4206 0.5040 0.6598 0.137 Uiso 1 1 calc R . .
C21 C 0.8199(5) 0.0038(5) 0.9497(5) 0.0585(18) Uani 1 1 d . . .
C22 C 0.8081(5) 0.0446(5) 1.0285(5) 0.0661(19) Uani 1 1 d . . .
H22A H 0.7649 0.1052 1.0388 0.079 Uiso 1 1 calc R . .
C23 C 0.8574(6) -0.0006(5) 1.0915(5) 0.070(2) Uani 1 1 d . . .
H23A H 0.8481 0.0285 1.1438 0.084 Uiso 1 1 calc R . .
C24 C 0.9215(5) -0.0908(5) 1.0755(5) 0.0555(17) Uani 1 1 d . . .
C25 C 0.9370(6) -0.1354(5) 0.9983(5) 0.069(2) Uani 1 1 d . . .
H25A H 0.9808 -0.1959 0.9882 0.082 Uiso 1 1 calc R . .
C26 C 0.8853(6) -0.0872(5) 0.9364(5) 0.072(2) Uani 1 1 d . . .
H26A H 0.8945 -0.1164 0.8842 0.086 Uiso 1 1 calc R . .
C27 C -0.2140(6) 0.5997(6) 0.8334(5) 0.068(2) Uani 1 1 d . . .
C28 C -0.2179(6) 0.5029(6) 0.8647(5) 0.077(2) Uani 1 1 d . . .
H28A H -0.2799 0.4749 0.8722 0.093 Uiso 1 1 calc R . .
C29 C -0.1299(6) 0.4481(6) 0.8846(6) 0.085(2) Uani 1 1 d . . .
H29A H -0.1324 0.3820 0.9053 0.102 Uiso 1 1 calc R . .
C30 C -0.0375(5) 0.4870(5) 0.8753(5) 0.070(2) Uani 1 1 d . . .
C31 C -0.0349(5) 0.5859(6) 0.8420(5) 0.077(2) Uani 1 1 d . . .
H31A H 0.0274 0.6139 0.8333 0.092 Uiso 1 1 calc R . .
C32 C -0.1243(6) 0.6422(5) 0.8221(5) 0.070(2) Uani 1 1 d . . .
H32A H -0.1232 0.7084 0.8012 0.084 Uiso 1 1 calc R . .
C33 C 0.1723(4) 0.4845(5) 0.8767(5) 0.070(2) Uani 1 1 d U . .
H33A H 0.1959 0.5043 0.8125 0.084 Uiso 1 1 calc R . .
H33B H 0.1441 0.5431 0.9086 0.084 Uiso 1 1 calc R . .
C34 C 0.2698(6) 0.4225(6) 0.9085(5) 0.075(2) Uani 1 1 d U . .
C35 C 0.2734(5) 0.3268(5) 0.9512(5) 0.071(2) Uani 1 1 d . . .
H35A H 0.2142 0.2937 0.9624 0.085 Uiso 1 1 calc R . .
C36 C 0.3632(6) 0.2803(5) 0.9771(5) 0.073(2) Uani 1 1 d . . .
H36A H 0.3646 0.2166 1.0053 0.087 Uiso 1 1 calc R . .
C37 C 0.4495(6) 0.3295(5) 0.9604(5) 0.069(2) Uani 1 1 d . . .
O8 O 1.0435(5) -0.2096(5) 1.1230(4) 0.109(2) Uani 1 1 d . . .
O7 O 0.9550(5) -0.1031(5) 1.2134(5) 0.107(2) Uani 1 1 d . . .
O5 O 0.2481(5) 0.2259(5) 0.7452(5) 0.126(2) Uani 1 1 d . . .
O6 O 0.3562(5) 0.3333(5) 0.6934(5) 0.123(2) Uani 1 1 d . . .
O13 O -0.2846(7) 0.3852(8) 0.6710(7) 0.181(4) Uani 1 1 d . . .
O14 O -0.1713(8) 0.2516(8) 0.6758(6) 0.172(4) Uani 1 1 d . . .
O15 O 0.6446(6) 0.7994(6) 0.4712(6) 0.144(3) Uani 1 1 d . . .
O16 O 0.6967(6) 0.6927(6) 0.5678(6) 0.148(3) Uani 1 1 d . . .


_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 C4 1.743(7) . ?
S1 C7 1.822(6) . ?
S2 C17 1.740(7) . ?
S2 C20 1.794(6) . ?
S3 C30 1.751(7) . ?
S3 C33 1.838(7) . ?
S4 C46 1.640(10) . ?
S4 C43 1.804(8) . ?
O1 N1 1.228(8) . ?
O2 N1 1.204(9) . ?
N1 C1 1.479(9) . ?
N2 O4 1.206(8) . ?
N2 O3 1.207(8) . ?
N2 C11 1.486(9) . ?
N3 O6 1.186(8) . ?
N3 O5 1.245(8) . ?
N3 C14 1.464(9) . ?
N4 O8 1.203(7) . ?
N4 O7 1.206(8) . ?
N4 C24 1.475(9) . ?
N5 O9 1.217(8) . ?
N5 O10 1.227(8) . ?
N5 C27 1.461(9) . ?
N6 O12 1.200(8) . ?
N6 O11 1.203(8) . ?
N6 C37 1.476(9) . ?
N7 O13 1.208(12) . ?
N7 O14 1.236(12) . ?
N7 C40 1.459(11) . ?
N8 O16 1.206(9) . ?
N8 O15 1.230(9) . ?
N8 C50 1.472(10) . ?
C1 C6 1.359(9) . ?
C1 C2 1.373(9) . ?
C2 C3 1.371(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(9) . ?
C5 C6 1.376(9) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.495(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.357(9) . ?
C8 C13 1.377(9) . ?
C9 C10 1.403(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.390(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.338(9) . ?
C12 C13 1.381(9) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(9) . ?
C14 C19 1.385(9) . ?
C15 C16 1.369(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.389(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.402(8) . ?
C18 C19 1.368(9) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.501(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C38 C37 1.372(10) . ?
C38 C39 1.384(10) . ?
C38 H38A 0.9300 . ?
C39 C34 1.373(10) . ?
C39 H39A 0.9300 . ?
C40 C41 1.342(11) . ?
C40 C45 1.392(11) . ?
C41 C42 1.342(10) . ?
C41 H41A 0.9300 . ?
C42 C43 1.332(11) . ?
C42 H42A 0.9300 . ?
C43 C44 1.407(11) . ?
C44 C45 1.386(11) . ?
C44 H44A 0.9300 . ?
C45 H45A 0.9300 . ?
C46 C47 1.595(12) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C52 1.329(12) . ?
C47 C48 1.406(12) . ?
C48 C49 1.399(11) . ?
C48 H48A 0.9300 . ?
C49 C50 1.336(11) . ?
C49 H49A 0.9300 . ?
C50 C51 1.355(11) . ?
C51 C52 1.362(11) . ?
C51 H51A 0.9300 . ?
C52 H52A 0.9300 . ?
C21 C22 1.385(9) . ?
C21 C26 1.395(9) . ?
C22 C23 1.365(9) . ?
C22 H22A 0.9300 . ?
C23 C24 1.383(9) . ?
C23 H23A 0.9300 . ?
C24 C25 1.381(9) . ?
C25 C26 1.381(9) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
C27 C32 1.360(9) . ?
C27 C28 1.367(9) . ?
C28 C29 1.359(9) . ?
C28 H28A 0.9300 . ?
C29 C30 1.371(9) . ?
C29 H29A 0.9300 . ?
C30 C31 1.398(9) . ?
C31 C32 1.382(9) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9300 . ?
C33 C34 1.581(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.398(9) . ?
C35 C36 1.384(9) . ?
C35 H35A 0.9300 . ?
C36 C37 1.363(9) . ?
C36 H36A 0.9300 . ?

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
C4 S1 C7 105.4(3) . . ?
C17 S2 C20 105.2(3) . . ?
C30 S3 C33 100.0(3) . . ?
C46 S4 C43 100.9(5) . . ?
O2 N1 O1 124.3(8) . . ?
O2 N1 C1 117.5(8) . . ?
O1 N1 C1 118.1(8) . . ?
O4 N2 O3 124.0(8) . . ?
O4 N2 C11 117.1(8) . . ?
O3 N2 C11 118.9(8) . . ?
O6 N3 O5 123.5(7) . . ?
O6 N3 C14 120.4(7) . . ?
O5 N3 C14 116.1(7) . . ?
O8 N4 O7 123.3(8) . . ?
O8 N4 C24 117.6(8) . . ?
O7 N4 C24 119.1(8) . . ?
O9 N5 O10 123.9(7) . . ?
O9 N5 C27 118.9(8) . . ?
O10 N5 C27 117.1(8) . . ?
O12 N6 O11 124.0(7) . . ?
O12 N6 C37 117.6(8) . . ?
O11 N6 C37 118.4(7) . . ?
O13 N7 O14 124.5(11) . . ?
O13 N7 C40 118.5(12) . . ?
O14 N7 C40 117.0(12) . . ?
O16 N8 O15 123.3(8) . . ?
O16 N8 C50 118.9(9) . . ?
O15 N8 C50 117.8(8) . . ?
C6 C1 C2 120.8(7) . . ?
C6 C1 N1 120.6(7) . . ?
C2 C1 N1 118.6(7) . . ?
C3 C2 C1 119.5(7) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.5(6) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 S1 125.7(5) . . ?
C3 C4 S1 115.5(5) . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C1 C6 C5 120.0(7) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 S1 106.2(4) . . ?
C8 C7 H7A 110.5 . . ?
S1 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
S1 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C9 C8 C13 119.0(7) . . ?
C9 C8 C7 120.1(6) . . ?
C13 C8 C7 120.8(7) . . ?
C8 C9 C10 122.3(7) . . ?
C8 C9 H9A 118.8 . . ?
C10 C9 H9A 118.8 . . ?
C11 C10 C9 116.0(7) . . ?
C11 C10 H10A 122.0 . . ?
C9 C10 H10A 122.0 . . ?
C12 C11 C10 122.5(7) . . ?
C12 C11 N2 120.0(7) . . ?
C10 C11 N2 117.5(8) . . ?
C11 C12 C13 120.0(7) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C8 C13 C12 120.1(7) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C19 120.1(6) . . ?
C15 C14 N3 120.9(7) . . ?
C19 C14 N3 119.0(7) . . ?
C14 C15 C16 120.9(6) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C15 C16 C17 119.8(6) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C18 119.3(6) . . ?
C16 C17 S2 115.9(5) . . ?
C18 C17 S2 124.8(5) . . ?
C19 C18 C17 119.8(6) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C18 C19 C14 120.1(6) . . ?
C18 C19 H19A 120.0 . . ?
C14 C19 H19A 120.0 . . ?
C21 C20 S2 107.1(4) . . ?
C21 C20 H20A 110.3 . . ?
S2 C20 H20A 110.3 . . ?
C21 C20 H20B 110.3 . . ?
S2 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C37 C38 C39 118.7(7) . . ?
C37 C38 H38A 120.7 . . ?
C39 C38 H38A 120.7 . . ?
C34 C39 C38 122.1(8) . . ?
C34 C39 H39A 119.0 . . ?
C38 C39 H39A 119.0 . . ?
C41 C40 C45 120.1(8) . . ?
C41 C40 N7 120.1(10) . . ?
C45 C40 N7 119.8(10) . . ?
C42 C41 C40 121.2(8) . . ?
C42 C41 H41A 119.4 . . ?
C40 C41 H41A 119.4 . . ?
C43 C42 C41 121.7(9) . . ?
C43 C42 H42A 119.1 . . ?
C41 C42 H42A 119.1 . . ?
C42 C43 C44 119.2(8) . . ?
C42 C43 S4 115.1(7) . . ?
C44 C43 S4 125.6(7) . . ?
C45 C44 C43 119.3(8) . . ?
C45 C44 H44A 120.4 . . ?
C43 C44 H44A 120.4 . . ?
C44 C45 C40 118.5(8) . . ?
C44 C45 H45A 120.8 . . ?
C40 C45 H45A 120.8 . . ?
C47 C46 S4 109.4(6) . . ?
C47 C46 H46A 109.8 . . ?
S4 C46 H46A 109.8 . . ?
C47 C46 H46B 109.8 . . ?
S4 C46 H46B 109.8 . . ?
H46A C46 H46B 108.2 . . ?
C52 C47 C48 117.4(8) . . ?
C52 C47 C46 125.1(10) . . ?
C48 C47 C46 117.1(10) . . ?
C49 C48 C47 119.6(8) . . ?
C49 C48 H48A 120.2 . . ?
C47 C48 H48A 120.2 . . ?
C50 C49 C48 118.3(8) . . ?
C50 C49 H49A 120.9 . . ?
C48 C49 H49A 120.9 . . ?
C49 C50 C51 123.4(7) . . ?
C49 C50 N8 118.8(9) . . ?
C51 C50 N8 117.8(8) . . ?
C50 C51 C52 116.9(9) . . ?
C50 C51 H51A 121.6 . . ?
C52 C51 H51A 121.6 . . ?
C47 C52 C51 124.3(10) . . ?
C47 C52 H52A 117.8 . . ?
C51 C52 H52A 117.8 . . ?
C22 C21 C26 117.1(6) . . ?
C22 C21 C20 121.2(6) . . ?
C26 C21 C20 121.7(7) . . ?
C23 C22 C21 122.7(7) . . ?
C23 C22 H22A 118.7 . . ?
C21 C22 H22A 118.7 . . ?
C22 C23 C24 118.2(7) . . ?
C22 C23 H23A 120.9 . . ?
C24 C23 H23A 120.9 . . ?
C25 C24 C23 122.1(7) . . ?
C25 C24 N4 119.9(7) . . ?
C23 C24 N4 118.0(7) . . ?
C24 C25 C26 117.8(7) . . ?
C24 C25 H25A 121.1 . . ?
C26 C25 H25A 121.1 . . ?
C25 C26 C21 122.1(7) . . ?
C25 C26 H26A 118.9 . . ?
C21 C26 H26A 118.9 . . ?
C32 C27 C28 121.4(7) . . ?
C32 C27 N5 119.2(7) . . ?
C28 C27 N5 119.3(7) . . ?
C29 C28 C27 119.1(7) . . ?
C29 C28 H28A 120.5 . . ?
C27 C28 H28A 120.5 . . ?
C28 C29 C30 122.1(7) . . ?
C28 C29 H29A 118.9 . . ?
C30 C29 H29A 118.9 . . ?
C29 C30 C31 117.8(6) . . ?
C29 C30 S3 115.1(6) . . ?
C31 C30 S3 127.1(6) . . ?
C32 C31 C30 120.3(7) . . ?
C32 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
C27 C32 C31 119.2(7) . . ?
C27 C32 H32A 120.4 . . ?
C31 C32 H32A 120.4 . . ?
C34 C33 S3 106.3(5) . . ?
C34 C33 H33A 110.5 . . ?
S3 C33 H33A 110.5 . . ?
C34 C33 H33B 110.5 . . ?
S3 C33 H33B 110.5 . . ?
H33A C33 H33B 108.7 . . ?
C39 C34 C35 117.3(7) . . ?
C39 C34 C33 116.0(7) . . ?
C35 C34 C33 126.7(7) . . ?
C36 C35 C34 121.5(7) . . ?
C36 C35 H35A 119.3 . . ?
C34 C35 H35A 119.3 . . ?
C37 C36 C35 118.8(7) . . ?
C37 C36 H36A 120.6 . . ?
C35 C36 H36A 120.6 . . ?
C36 C37 C38 121.7(7) . . ?
C36 C37 N6 119.1(7) . . ?
C38 C37 N6 119.2(7) . . ?

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
O2 N1 C1 C6 4.8(12) . . . . ?
O1 N1 C1 C6 -179.2(8) . . . . ?
O2 N1 C1 C2 -173.3(9) . . . . ?
O1 N1 C1 C2 2.7(11) . . . . ?
C6 C1 C2 C3 0.5(11) . . . . ?
N1 C1 C2 C3 178.6(7) . . . . ?
C1 C2 C3 C4 0.2(11) . . . . ?
C2 C3 C4 C5 -0.7(11) . . . . ?
C2 C3 C4 S1 179.2(6) . . . . ?
C7 S1 C4 C5 7.7(7) . . . . ?
C7 S1 C4 C3 -172.2(5) . . . . ?
C3 C4 C5 C6 0.5(11) . . . . ?
S1 C4 C5 C6 -179.4(6) . . . . ?
C2 C1 C6 C5 -0.7(11) . . . . ?
N1 C1 C6 C5 -178.7(7) . . . . ?
C4 C5 C6 C1 0.2(11) . . . . ?
C4 S1 C7 C8 166.8(5) . . . . ?
S1 C7 C8 C9 -101.3(6) . . . . ?
S1 C7 C8 C13 76.3(7) . . . . ?
C13 C8 C9 C10 1.8(10) . . . . ?
C7 C8 C9 C10 179.5(6) . . . . ?
C8 C9 C10 C11 -1.4(10) . . . . ?
C9 C10 C11 C12 -0.4(10) . . . . ?
C9 C10 C11 N2 -179.6(5) . . . . ?
O4 N2 C11 C12 5.3(10) . . . . ?
O3 N2 C11 C12 -176.5(7) . . . . ?
O4 N2 C11 C10 -175.4(7) . . . . ?
O3 N2 C11 C10 2.7(10) . . . . ?
C10 C11 C12 C13 1.6(11) . . . . ?
N2 C11 C12 C13 -179.2(6) . . . . ?
C9 C8 C13 C12 -0.6(10) . . . . ?
C7 C8 C13 C12 -178.2(6) . . . . ?
C11 C12 C13 C8 -1.1(10) . . . . ?
O6 N3 C14 C15 176.8(8) . . . . ?
O5 N3 C14 C15 -0.9(11) . . . . ?
O6 N3 C14 C19 -2.2(11) . . . . ?
O5 N3 C14 C19 -179.9(7) . . . . ?
C19 C14 C15 C16 0.4(11) . . . . ?
N3 C14 C15 C16 -178.6(7) . . . . ?
C14 C15 C16 C17 1.6(11) . . . . ?
C15 C16 C17 C18 -3.4(10) . . . . ?
C15 C16 C17 S2 178.8(5) . . . . ?
C20 S2 C17 C16 -172.2(5) . . . . ?
C20 S2 C17 C18 10.1(7) . . . . ?
C16 C17 C18 C19 3.3(10) . . . . ?
S2 C17 C18 C19 -179.1(5) . . . . ?
C17 C18 C19 C14 -1.5(10) . . . . ?
C15 C14 C19 C18 -0.4(11) . . . . ?
N3 C14 C19 C18 178.6(6) . . . . ?
C17 S2 C20 C21 161.8(5) . . . . ?
C37 C38 C39 C34 -1.2(13) . . . . ?
O13 N7 C40 C41 -7.9(15) . . . . ?
O14 N7 C40 C41 171.9(9) . . . . ?
O13 N7 C40 C45 171.0(10) . . . . ?
O14 N7 C40 C45 -9.2(14) . . . . ?
C45 C40 C41 C42 -0.7(13) . . . . ?
N7 C40 C41 C42 178.2(8) . . . . ?
C40 C41 C42 C43 -0.5(14) . . . . ?
C41 C42 C43 C44 1.7(13) . . . . ?
C41 C42 C43 S4 -175.7(7) . . . . ?
C46 S4 C43 C42 -158.8(8) . . . . ?
C46 S4 C43 C44 24.1(9) . . . . ?
C42 C43 C44 C45 -1.6(13) . . . . ?
S4 C43 C44 C45 175.5(6) . . . . ?
C43 C44 C45 C40 0.4(13) . . . . ?
C41 C40 C45 C44 0.7(13) . . . . ?
N7 C40 C45 C44 -178.2(8) . . . . ?
C43 S4 C46 C47 -171.1(8) . . . . ?
S4 C46 C47 C52 126.5(10) . . . . ?
S4 C46 C47 C48 -60.5(12) . . . . ?
C52 C47 C48 C49 1.7(14) . . . . ?
C46 C47 C48 C49 -171.9(8) . . . . ?
C47 C48 C49 C50 2.0(14) . . . . ?
C48 C49 C50 C51 -4.5(14) . . . . ?
C48 C49 C50 N8 176.2(7) . . . . ?
O16 N8 C50 C49 179.1(9) . . . . ?
O15 N8 C50 C49 0.0(12) . . . . ?
O16 N8 C50 C51 -0.3(12) . . . . ?
O15 N8 C50 C51 -179.4(8) . . . . ?
C49 C50 C51 C52 3.1(13) . . . . ?
N8 C50 C51 C52 -177.6(8) . . . . ?
C48 C47 C52 C51 -3.2(16) . . . . ?
C46 C47 C52 C51 169.8(9) . . . . ?
C50 C51 C52 C47 0.9(15) . . . . ?
S2 C20 C21 C22 -105.1(6) . . . . ?
S2 C20 C21 C26 73.9(7) . . . . ?
C26 C21 C22 C23 0.0(10) . . . . ?
C20 C21 C22 C23 179.0(6) . . . . ?
C21 C22 C23 C24 0.0(10) . . . . ?
C22 C23 C24 C25 0.2(10) . . . . ?
C22 C23 C24 N4 178.4(6) . . . . ?
O8 N4 C24 C25 7.9(9) . . . . ?
O7 N4 C24 C25 -173.3(7) . . . . ?
O8 N4 C24 C23 -170.4(6) . . . . ?
O7 N4 C24 C23 8.5(9) . . . . ?
C23 C24 C25 C26 -0.4(10) . . . . ?
N4 C24 C25 C26 -178.6(6) . . . . ?
C24 C25 C26 C21 0.4(10) . . . . ?
C22 C21 C26 C25 -0.2(10) . . . . ?
C20 C21 C26 C25 -179.2(6) . . . . ?
O9 N5 C27 C32 178.8(7) . . . . ?
O10 N5 C27 C32 -3.9(11) . . . . ?
O9 N5 C27 C28 -0.5(11) . . . . ?
O10 N5 C27 C28 176.7(8) . . . . ?
C32 C27 C28 C29 -0.2(12) . . . . ?
N5 C27 C28 C29 179.1(7) . . . . ?
C27 C28 C29 C30 0.7(12) . . . . ?
C28 C29 C30 C31 -1.5(12) . . . . ?
C28 C29 C30 S3 -178.8(6) . . . . ?
C33 S3 C30 C29 178.1(6) . . . . ?
C33 S3 C30 C31 1.1(8) . . . . ?
C29 C30 C31 C32 1.8(11) . . . . ?
S3 C30 C31 C32 178.8(6) . . . . ?
C28 C27 C32 C31 0.5(11) . . . . ?
N5 C27 C32 C31 -178.8(7) . . . . ?
C30 C31 C32 C27 -1.4(11) . . . . ?
C30 S3 C33 C34 173.7(5) . . . . ?
C38 C39 C34 C35 -0.3(13) . . . . ?
C38 C39 C34 C33 179.7(7) . . . . ?
S3 C33 C34 C39 177.5(6) . . . . ?
S3 C33 C34 C35 -2.5(9) . . . . ?
C39 C34 C35 C36 0.8(11) . . . . ?
C33 C34 C35 C36 -179.2(7) . . . . ?
C34 C35 C36 C37 0.1(11) . . . . ?
C35 C36 C37 C38 -1.7(12) . . . . ?
C35 C36 C37 N6 -179.8(7) . . . . ?
C39 C38 C37 C36 2.3(12) . . . . ?
C39 C38 C37 N6 -179.7(7) . . . . ?
O12 N6 C37 C36 174.9(8) . . . . ?
O11 N6 C37 C36 -3.1(11) . . . . ?
O12 N6 C37 C38 -3.3(12) . . . . ?
O11 N6 C37 C38 178.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.585
_database_code_depnum_ccdc_archive 'CCDC 918680'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_hydrate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O5 S'
_chemical_formula_weight         308.29

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                   3.9606(3)
_cell_length_b                   12.1751(8)
_cell_length_c                   31.027(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.629(3)
_cell_angle_gamma                90.00
_cell_volume                     1493.14(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   Multi-SCAN
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEXII CCD area detector'
_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            8925
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2591
_reflns_number_gt                2042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker 2007)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and PLATON (Spek,2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

TITL Monohydrate in P2(1)/c
CELL 0.71073   3.9606  12.1751  31.0269  90.000  93.629  90.000
ZERR    4.00   0.0003   0.0008   0.0020   0.000   0.003   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O S
UNIT 52 40 8 20 4
TEMP 23.000
OMIT 0 2 0
OMIT 0 0 2
OMIT 0 1 1
OMIT 0 2 2
OMIT 0 1 3
OMIT 0 0 8
OMIT 0 0 6
OMIT 0 0 4
OMIT 0 2 4
OMIT 0 2 3
OMIT 0 1 7
OMIT 0 1 2
OMIT 0 3 1
OMIT 0 1 5
REM OMIT 0 3 3
REM OMIT 0 2 6
OMIT -3 50.02
SIMU .02 O1W O1W'
ISOR .02 O1W O1W'
SUMP 1.0 0.01 1.0 2 1.0 3
 
L.S. 20
ACTA
BOND $H
HTAB
CONF
FMAP 2
PLAN 5
 
WGHT      0.1099      0.4826 
FVAR       0.14806   0.45117   0.54883
S1    5    0.341886    0.579173    0.118970    11.00000    0.07190    0.06702 =
         0.07058    0.00556   -0.01351   -0.00486
O1    4    0.768785    0.105474    0.211267    11.00000    0.17896    0.06999 =
         0.09513    0.00763    0.00836    0.01817
O2    4    0.987308    0.213656    0.259662    11.00000    0.14999    0.09818 =
         0.07630    0.01819   -0.01306    0.02619
O3    4    0.185006    1.112075    0.024756    11.00000    0.16975    0.09687 =
         0.07547    0.02380    0.01570    0.02105
O4    4   -0.052501    1.164519    0.081605    11.00000    0.14459    0.07214 =
         0.11095    0.00335    0.01498    0.02761
N1    3    0.827866    0.196997    0.225085    11.00000    0.10301    0.07440 =
         0.06628    0.00974    0.01963    0.01713
N2    3    0.106737    1.098006    0.061628    11.00000    0.08769    0.06551 =
         0.07653    0.00094   -0.00386   -0.00380
C1    1    0.709802    0.291271    0.199869    11.00000    0.06706    0.06293 =
         0.05380    0.00731    0.01356    0.00672
C2    1    0.530935    0.275539    0.160650    11.00000    0.08076    0.05879 =
         0.06416   -0.00463    0.00997   -0.00378
AFIX  43
H2A   2    0.482471    0.204980    0.150578    11.00000   -1.20000
AFIX   0
C3    1    0.426220    0.365257    0.136862    11.00000    0.06964    0.06910 =
         0.05592   -0.00195   -0.00514   -0.00542
AFIX  43
H3A   2    0.308950    0.355278    0.110226    11.00000   -1.20000
AFIX   0
C4    1    0.492216    0.470744    0.151849    11.00000    0.04893    0.06185 =
         0.05530    0.00091    0.00408   -0.00271
C5    1    0.673818    0.485026    0.191754    11.00000    0.07043    0.05895 =
         0.05777   -0.00225   -0.00048   -0.00512
AFIX  43
H5A   2    0.722301    0.555340    0.202097    11.00000   -1.20000
AFIX   0
C6    1    0.779789    0.394779    0.215502    11.00000    0.07290    0.07476 =
         0.04898    0.00106    0.00065    0.00071
AFIX  43
H6A   2    0.898591    0.403802    0.242090    11.00000   -1.20000
AFIX   0
C7    1    0.500323    0.699113    0.148849    11.00000    0.05885    0.06019 =
         0.07454    0.00233   -0.00905    0.00131
AFIX  23
H7A   2    0.410888    0.700036    0.177238    11.00000   -1.20000
H7B   2    0.745154    0.695903    0.152554    11.00000   -1.20000
AFIX   0
C8    1    0.394129    0.801954    0.124564    11.00000    0.05176    0.06384 =
         0.05969    0.00064    0.00099   -0.00490
C9    1    0.449698    0.817211    0.081389    11.00000    0.07203    0.06684 =
         0.06317   -0.00499    0.00933    0.00635
AFIX  43
H9A   2    0.550781    0.761696    0.066142    11.00000   -1.20000
AFIX   0
C10   1    0.356764    0.913851    0.060745    11.00000    0.08033    0.07354 =
         0.05439    0.00089    0.00912    0.00045
AFIX  43
H10A  2    0.395339    0.924068    0.031762    11.00000   -1.20000
AFIX   0
C11   1    0.206002    0.994956    0.083715    11.00000    0.06109    0.05664 =
         0.06201    0.00035   -0.00185   -0.00408
C12   1    0.145971    0.981862    0.126067    11.00000    0.07493    0.05757 =
         0.06586   -0.00922    0.01440   -0.00204
AFIX  43
H12A  2    0.042049    1.037333    0.141018    11.00000   -1.20000
AFIX   0
C13   1    0.240916    0.885595    0.146459    11.00000    0.07355    0.06654 =
         0.05511   -0.00383    0.00965   -0.00707
AFIX  43
H13A  2    0.201680    0.876384    0.175474    11.00000   -1.20000
AFIX   0
O1W   4    0.062699    0.411880    0.010042    21.00000    0.36215    0.10812 =
         0.07857    0.00082   -0.01303   -0.00340
O1W'  4    0.457795    0.561680   -0.006668   -21.00000    0.43796    0.35498 =
         0.15077   -0.10871    0.00477    0.02531
 
HKLF 4
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1099P)²+0.4826P] where P=(Fo²+2Fc²)/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         2591
_refine_ls_number_parameters     201
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1888
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.114
_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
S1 S 0.3419(2) 0.57917(7) 0.11897(3) 0.0706(4) Uani 1 1 d . . .
O1 O 0.7688(10) 0.1055(2) 0.21127(10) 0.1147(11) Uani 1 1 d . . .
O2 O 0.9873(9) 0.2137(2) 0.25966(9) 0.1090(10) Uani 1 1 d . . .
O3 O 0.1850(10) 1.1121(3) 0.02476(10) 0.1137(11) Uani 1 1 d . . .
O4 O -0.0525(9) 1.1645(2) 0.08160(10) 0.1089(10) Uani 1 1 d . . .
N1 N 0.8279(9) 0.1970(3) 0.22509(10) 0.0806(9) Uani 1 1 d . . .
N2 N 0.1067(8) 1.0980(2) 0.06163(11) 0.0770(8) Uani 1 1 d . . .
C1 C 0.7098(8) 0.2913(2) 0.19987(9) 0.0609(7) Uani 1 1 d . . .
C2 C 0.5309(9) 0.2755(3) 0.16065(10) 0.0677(8) Uani 1 1 d . . .
H2A H 0.4825 0.2050 0.1506 0.081 Uiso 1 1 calc R . .
C3 C 0.4262(8) 0.3653(3) 0.13686(10) 0.0653(8) Uani 1 1 d . . .
H3A H 0.3090 0.3553 0.1102 0.078 Uiso 1 1 calc R . .
C4 C 0.4922(7) 0.4707(2) 0.15185(9) 0.0553(7) Uani 1 1 d . . .
C5 C 0.6738(8) 0.4850(3) 0.19175(9) 0.0626(8) Uani 1 1 d . . .
H5A H 0.7223 0.5553 0.2021 0.075 Uiso 1 1 calc R . .
C6 C 0.7798(9) 0.3948(3) 0.21550(10) 0.0657(8) Uani 1 1 d . . .
H6A H 0.8986 0.4038 0.2421 0.079 Uiso 1 1 calc R . .
C7 C 0.5003(8) 0.6991(2) 0.14885(11) 0.0651(8) Uani 1 1 d . . .
H7A H 0.4109 0.7000 0.1772 0.078 Uiso 1 1 calc R . .
H7B H 0.7451 0.6959 0.1526 0.078 Uiso 1 1 calc R . .
C8 C 0.3941(7) 0.8020(3) 0.12456(9) 0.0585(7) Uani 1 1 d . . .
C9 C 0.4497(8) 0.8172(3) 0.08139(10) 0.0671(8) Uani 1 1 d . . .
H9A H 0.5508 0.7617 0.0661 0.081 Uiso 1 1 calc R . .
C10 C 0.3567(9) 0.9139(3) 0.06075(10) 0.0692(9) Uani 1 1 d . . .
H10A H 0.3953 0.9241 0.0318 0.083 Uiso 1 1 calc R . .
C11 C 0.2060(7) 0.9950(2) 0.08371(10) 0.0602(7) Uani 1 1 d . . .
C12 C 0.1460(8) 0.9819(3) 0.12607(10) 0.0657(8) Uani 1 1 d . . .
H12A H 0.0421 1.0373 0.1410 0.079 Uiso 1 1 calc R . .
C13 C 0.2409(8) 0.8856(3) 0.14646(10) 0.0648(8) Uani 1 1 d . . .
H13A H 0.2017 0.8764 0.1755 0.078 Uiso 1 1 calc R . .
O1W O 0.063(5) 0.4119(7) 0.0100(3) 0.184(8) Uani 0.451(15) 1 d PU . .
O1W' O 0.457(7) 0.5616(14) -0.0067(5) 0.315(12) Uani 0.549(15) 1 d PU . .


_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 C4 1.750(3) . ?
S1 C7 1.820(3) . ?
O1 N1 1.211(4) . ?
O2 N1 1.227(4) . ?
O3 N2 1.216(4) . ?
O4 N2 1.219(4) . ?
N1 C1 1.450(4) . ?
N2 C11 1.471(4) . ?
C1 C6 1.372(4) . ?
C1 C2 1.382(4) . ?
C2 C3 1.368(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.403(4) . ?
C5 C6 1.374(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.507(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.384(4) . ?
C8 C13 1.385(4) . ?
C9 C10 1.379(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.360(4) . ?
C12 C13 1.373(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
O1W' O1W' 1.59(3) 3_665 ?

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
C4 S1 C7 102.40(14) . . ?
O1 N1 O2 122.6(3) . . ?
O1 N1 C1 119.3(3) . . ?
O2 N1 C1 118.1(3) . . ?
O3 N2 O4 123.7(3) . . ?
O3 N2 C11 118.8(3) . . ?
O4 N2 C11 117.5(3) . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 N1 119.0(3) . . ?
C2 C1 N1 119.7(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 S1 117.0(2) . . ?
C5 C4 S1 123.9(2) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 S1 109.6(2) . . ?
C8 C7 H7A 109.7 . . ?
S1 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
S1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 C7 122.6(3) . . ?
C13 C8 C7 118.9(3) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 N2 119.5(3) . . ?
C10 C11 N2 118.9(3) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C12 C13 C8 121.2(3) . . ?
C12 C13 H13A 119.4 . . ?
C8 C13 H13A 119.4 . . ?

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 N1 C1 C6 -179.5(3) . . . . ?
O2 N1 C1 C6 -0.1(5) . . . . ?
O1 N1 C1 C2 0.3(5) . . . . ?
O2 N1 C1 C2 179.7(3) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
N1 C1 C2 C3 -178.9(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C2 C3 C4 S1 -179.3(3) . . . . ?
C7 S1 C4 C3 -177.1(2) . . . . ?
C7 S1 C4 C5 2.6(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
S1 C4 C5 C6 179.6(2) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
N1 C1 C6 C5 179.1(3) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 S1 C7 C8 179.6(2) . . . . ?
S1 C7 C8 C9 -51.4(4) . . . . ?
S1 C7 C8 C13 130.0(3) . . . . ?
C13 C8 C9 C10 0.5(5) . . . . ?
C7 C8 C9 C10 -178.2(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C9 C10 C11 N2 -180.0(3) . . . . ?
O3 N2 C11 C12 174.4(3) . . . . ?
O4 N2 C11 C12 -6.0(5) . . . . ?
O3 N2 C11 C10 -5.8(5) . . . . ?
O4 N2 C11 C10 173.8(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
N2 C11 C12 C13 -179.7(3) . . . . ?
C11 C12 C13 C8 -0.4(5) . . . . ?
C9 C8 C13 C12 -0.1(5) . . . . ?
C7 C8 C13 C12 178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.216
_database_code_depnum_ccdc_archive 'CCDC 918681'
