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#                                CCDC 
# 
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#  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.
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#  fide research purposes only. It may contain copyright material
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data_cd214258

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O4 S'
_chemical_formula_weight         460.53

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                   8.7752(9)
_cell_length_b                   24.925(3)
_cell_length_c                   10.2418(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.290(2)
_cell_angle_gamma                90
_cell_volume                     2238.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3970
_cell_measurement_theta_min      4.925
_cell_measurement_theta_max      51.790

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13152
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4398
_reflns_number_gt                3547
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0759P)²+0.2989P] 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         4398
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_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 0.15770(5) 0.59113(2) 0.34762(5) 0.04001(17) Uani 1 1 d . . . . .
N1 N 0.06809(16) 0.64116(6) 0.41372(15) 0.0379(4) Uani 1 1 d . . . . .
N2 N 0.1036(2) 0.59377(8) 0.84003(18) 0.0589(5) Uani 1 1 d . . . . .
O1 O -0.28161(15) 0.66247(6) 0.40067(14) 0.0495(4) Uani 1 1 d . . . . .
O2 O -0.06646(15) 0.71709(5) 0.42164(14) 0.0439(3) Uani 1 1 d . . . . .
O3 O 0.05594(17) 0.54854(6) 0.30982(15) 0.0547(4) Uani 1 1 d . . . . .
O4 O 0.24677(16) 0.61514(6) 0.24937(15) 0.0537(4) Uani 1 1 d . . . . .
C1 C -0.2494(2) 0.65630(8) 0.2711(2) 0.0437(5) Uani 1 1 d . . . . .
C2 C -0.3646(3) 0.63982(9) 0.1853(2) 0.0566(6) Uani 1 1 d . . . . .
H2 H -0.4614 0.6326 0.2147 0.068 Uiso 1 1 calc R U . . .
C3 C -0.3339(3) 0.63423(11) 0.0555(3) 0.0696(7) Uani 1 1 d . . . . .
H3 H -0.4106 0.6223 -0.0027 0.084 Uiso 1 1 calc R U . . .
C4 C -0.1930(3) 0.64590(12) 0.0096(2) 0.0707(8) Uani 1 1 d . . . . .
H4 H -0.1749 0.6425 -0.0788 0.085 Uiso 1 1 calc R U . . .
C5 C -0.0783(3) 0.66271(10) 0.0964(2) 0.0547(6) Uani 1 1 d . . . . .
H5 H 0.0175 0.6709 0.0662 0.066 Uiso 1 1 calc R U . . .
C6 C -0.1056(2) 0.66731(8) 0.2274(2) 0.0427(5) Uani 1 1 d . . . . .
C7 C 0.0102(2) 0.68550(7) 0.32914(19) 0.0401(4) Uani 1 1 d . . . . .
H7 H 0.0936 0.7054 0.2906 0.048 Uiso 1 1 calc R U . . .
C8 C -0.0471(2) 0.63109(7) 0.51365(18) 0.0382(4) Uani 1 1 d . . . . .
H8 H -0.1010 0.5975 0.4937 0.046 Uiso 1 1 calc R U . . .
C9 C -0.1566(2) 0.67958(8) 0.48645(19) 0.0411(4) Uani 1 1 d . . . . .
C10 C -0.2262(2) 0.70483(9) 0.6022(2) 0.0537(5) Uani 1 1 d . . . . .
H10A H -0.1471 0.7154 0.6643 0.081 Uiso 1 1 calc R U . . .
H10B H -0.2924 0.6795 0.6420 0.081 Uiso 1 1 calc R U . . .
H10C H -0.2840 0.7358 0.5746 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0281(2) 0.62786(8) 0.64622(19) 0.0425(4) Uani 1 1 d . . . . .
C12 C 0.0112(3) 0.58697(9) 0.7323(2) 0.0513(5) Uani 1 1 d . . . . .
H12 H -0.0549 0.5582 0.7189 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1863(2) 0.64007(10) 0.8252(2) 0.0528(6) Uani 1 1 d . . . . .
C14 C 0.1426(2) 0.66244(8) 0.70313(19) 0.0440(5) Uani 1 1 d . . . . .
C15 C 0.2172(2) 0.70872(9) 0.6611(2) 0.0505(5) Uani 1 1 d . . . . .
H15 H 0.1909 0.7242 0.5808 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3301(3) 0.73063(11) 0.7414(3) 0.0661(7) Uani 1 1 d . . . . .
H16 H 0.3824 0.7608 0.7141 0.079 Uiso 1 1 calc R U . . .
C17 C 0.3673(3) 0.70803(13) 0.8640(3) 0.0752(8) Uani 1 1 d . . . . .
H17 H 0.4425 0.7242 0.9171 0.090 Uiso 1 1 calc R U . . .
C18 C 0.2968(3) 0.66335(13) 0.9073(3) 0.0709(8) Uani 1 1 d . . . . .
H18 H 0.3218 0.6489 0.9891 0.085 Uiso 1 1 calc R U . . .
C19 C 0.1269(4) 0.55519(13) 0.9448(3) 0.0900(10) Uani 1 1 d . . . . .
H19A H 0.0690 0.5658 1.0181 0.135 Uiso 1 1 calc R U . . .
H19B H 0.2333 0.5539 0.9706 0.135 Uiso 1 1 calc R U . . .
H19C H 0.0940 0.5204 0.9151 0.135 Uiso 1 1 calc R U . . .
C20 C 0.2770(2) 0.56756(8) 0.47739(19) 0.0408(4) Uani 1 1 d . . . . .
C21 C 0.2412(3) 0.52039(8) 0.5390(2) 0.0539(5) Uani 1 1 d . . . . .
H21 H 0.1563 0.5006 0.5105 0.065 Uiso 1 1 calc R U . . .
C22 C 0.3314(3) 0.50265(9) 0.6427(2) 0.0612(6) Uani 1 1 d . . . . .
H22 H 0.3065 0.4709 0.6844 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4581(2) 0.53100(9) 0.6862(2) 0.0533(6) Uani 1 1 d . . . . .
C24 C 0.4917(3) 0.57832(10) 0.6222(3) 0.0596(6) Uani 1 1 d . . . . .
H24 H 0.5766 0.5981 0.6505 0.072 Uiso 1 1 calc R U . . .
C25 C 0.4030(2) 0.59686(9) 0.5182(2) 0.0525(5) Uani 1 1 d . . . . .
H25 H 0.4276 0.6286 0.4762 0.063 Uiso 1 1 calc R U . . .
C26 C 0.5554(3) 0.51190(12) 0.8019(2) 0.0760(8) Uani 1 1 d . . . . .
H26A H 0.6578 0.5247 0.7942 0.114 Uiso 1 1 calc R U . . .
H26B H 0.5557 0.4734 0.8039 0.114 Uiso 1 1 calc R U . . .
H26C H 0.5146 0.5254 0.8810 0.114 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 O4 1.4299(15) . ?
S1 O3 1.4306(15) . ?
S1 N1 1.6353(16) . ?
S1 C20 1.760(2) . ?
N1 C7 1.481(2) . ?
N1 C8 1.488(2) . ?
N2 C12 1.353(3) . ?
N2 C13 1.375(3) . ?
N2 C19 1.449(3) . ?
O1 C1 1.377(2) . ?
O1 C9 1.442(2) . ?
O2 C9 1.408(2) . ?
O2 C7 1.422(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(3) . ?
C7 H7 0.9800 . ?
C8 C11 1.488(3) . ?
C8 C9 1.562(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.494(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.360(3) . ?
C11 C14 1.430(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.385(4) . ?
C13 C14 1.408(3) . ?
C14 C15 1.403(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.402(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.376(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(3) . ?
C23 C26 1.510(3) . ?
C24 C25 1.374(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O3 118.23(10) . . ?
O4 S1 N1 104.93(8) . . ?
O3 S1 N1 111.88(8) . . ?
O4 S1 C20 110.23(9) . . ?
O3 S1 C20 107.62(9) . . ?
N1 S1 C20 102.91(8) . . ?
C7 N1 C8 107.54(14) . . ?
C7 N1 S1 119.08(12) . . ?
C8 N1 S1 120.47(12) . . ?
C12 N2 C13 108.47(18) . . ?
C12 N2 C19 125.6(2) . . ?
C13 N2 C19 125.4(2) . . ?
C1 O1 C9 116.08(15) . . ?
C9 O2 C7 103.65(13) . . ?
C2 C1 O1 118.36(19) . . ?
C2 C1 C6 120.6(2) . . ?
O1 C1 C6 121.01(18) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 124.37(19) . . ?
C1 C6 C7 115.93(18) . . ?
O2 C7 N1 100.60(14) . . ?
O2 C7 C6 107.80(15) . . ?
N1 C7 C6 112.88(15) . . ?
O2 C7 H7 111.7 . . ?
N1 C7 H7 111.7 . . ?
C6 C7 H7 111.7 . . ?
C11 C8 N1 110.34(15) . . ?
C11 C8 C9 116.86(16) . . ?
N1 C8 C9 100.17(14) . . ?
C11 C8 H8 109.7 . . ?
N1 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
O2 C9 O1 109.70(15) . . ?
O2 C9 C10 110.46(16) . . ?
O1 C9 C10 106.40(16) . . ?
O2 C9 C8 104.19(14) . . ?
O1 C9 C8 109.10(15) . . ?
C10 C9 C8 116.91(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C14 106.28(19) . . ?
C12 C11 C8 125.20(19) . . ?
C14 C11 C8 128.19(17) . . ?
N2 C12 C11 110.9(2) . . ?
N2 C12 H12 124.5 . . ?
C11 C12 H12 124.5 . . ?
N2 C13 C18 130.1(2) . . ?
N2 C13 C14 107.7(2) . . ?
C18 C13 C14 122.2(2) . . ?
C15 C14 C13 118.9(2) . . ?
C15 C14 C11 134.40(19) . . ?
C13 C14 C11 106.59(19) . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C13 117.5(3) . . ?
C17 C18 H18 121.2 . . ?
C13 C18 H18 121.2 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 120.64(19) . . ?
C25 C20 S1 119.92(16) . . ?
C21 C20 S1 119.42(16) . . ?
C22 C21 C20 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.2(2) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 117.9(2) . . ?
C22 C23 C26 121.1(2) . . ?
C24 C23 C26 121.0(2) . . ?
C25 C24 C23 121.9(2) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C20 118.7(2) . . ?
C24 C25 H25 120.6 . . ?
C20 C25 H25 120.6 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N1 C7 38.08(15) . . . . ?
O3 S1 N1 C7 -91.30(15) . . . . ?
C20 S1 N1 C7 153.44(14) . . . . ?
O4 S1 N1 C8 174.75(14) . . . . ?
O3 S1 N1 C8 45.37(16) . . . . ?
C20 S1 N1 C8 -69.89(15) . . . . ?
C9 O1 C1 C2 179.73(18) . . . . ?
C9 O1 C1 C6 -1.5(3) . . . . ?
O1 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
O1 C1 C6 C5 -177.55(18) . . . . ?
C2 C1 C6 C7 179.35(19) . . . . ?
O1 C1 C6 C7 0.6(3) . . . . ?
C9 O2 C7 N1 -48.84(17) . . . . ?
C9 O2 C7 C6 69.55(18) . . . . ?
C8 N1 C7 O2 34.46(17) . . . . ?
S1 N1 C7 O2 176.13(11) . . . . ?
C8 N1 C7 C6 -80.15(19) . . . . ?
S1 N1 C7 C6 61.51(19) . . . . ?
C5 C6 C7 O2 143.05(19) . . . . ?
C1 C6 C7 O2 -35.0(2) . . . . ?
C5 C6 C7 N1 -106.8(2) . . . . ?
C1 C6 C7 N1 75.2(2) . . . . ?
C7 N1 C8 C11 -132.01(16) . . . . ?
S1 N1 C8 C11 86.96(17) . . . . ?
C7 N1 C8 C9 -8.23(17) . . . . ?
S1 N1 C8 C9 -149.26(12) . . . . ?
C7 O2 C9 O1 -72.15(17) . . . . ?
C7 O2 C9 C10 170.87(16) . . . . ?
C7 O2 C9 C8 44.52(18) . . . . ?
C1 O1 C9 O2 37.7(2) . . . . ?
C1 O1 C9 C10 157.16(17) . . . . ?
C1 O1 C9 C8 -75.89(19) . . . . ?
C11 C8 C9 O2 97.86(18) . . . . ?
N1 C8 C9 O2 -21.26(17) . . . . ?
C11 C8 C9 O1 -145.04(16) . . . . ?
N1 C8 C9 O1 95.83(16) . . . . ?
C11 C8 C9 C10 -24.3(2) . . . . ?
N1 C8 C9 C10 -143.45(17) . . . . ?
N1 C8 C11 C12 -127.5(2) . . . . ?
C9 C8 C11 C12 119.0(2) . . . . ?
N1 C8 C11 C14 44.9(2) . . . . ?
C9 C8 C11 C14 -68.6(2) . . . . ?
C13 N2 C12 C11 -0.8(2) . . . . ?
C19 N2 C12 C11 -173.0(2) . . . . ?
C14 C11 C12 N2 1.4(2) . . . . ?
C8 C11 C12 N2 175.17(18) . . . . ?
C12 N2 C13 C18 -178.7(2) . . . . ?
C19 N2 C13 C18 -6.5(4) . . . . ?
C12 N2 C13 C14 -0.1(2) . . . . ?
C19 N2 C13 C14 172.2(2) . . . . ?
N2 C13 C14 C15 -176.44(18) . . . . ?
C18 C13 C14 C15 2.4(3) . . . . ?
N2 C13 C14 C11 0.9(2) . . . . ?
C18 C13 C14 C11 179.7(2) . . . . ?
C12 C11 C14 C15 175.4(2) . . . . ?
C8 C11 C14 C15 1.8(3) . . . . ?
C12 C11 C14 C13 -1.3(2) . . . . ?
C8 C11 C14 C13 -174.91(18) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C11 C14 C15 C16 -176.7(2) . . . . ?
C14 C15 C16 C17 -1.6(3) . . . . ?
C15 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 C13 0.6(4) . . . . ?
N2 C13 C18 C17 176.0(2) . . . . ?
C14 C13 C18 C17 -2.5(3) . . . . ?
O4 S1 C20 C25 38.6(2) . . . . ?
O3 S1 C20 C25 168.80(16) . . . . ?
N1 S1 C20 C25 -72.91(18) . . . . ?
O4 S1 C20 C21 -142.85(17) . . . . ?
O3 S1 C20 C21 -12.6(2) . . . . ?
N1 S1 C20 C21 105.68(18) . . . . ?
C25 C20 C21 C22 0.5(3) . . . . ?
S1 C20 C21 C22 -178.11(18) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C21 C22 C23 C26 178.9(2) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C26 C23 C24 C25 -178.8(2) . . . . ?
C23 C24 C25 C20 0.3(4) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
S1 C20 C25 C24 178.12(18) . . . . ?

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
C2 H2 O4 0.93 2.64 3.552(3) 168.7 1_455
C2 H2 O4 0.93 2.64 3.552(3) 168.7 1_455

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1001749'
#######################################################################
#
#                 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
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# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd214247

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 N2 O6 S2'
_chemical_formula_weight         600.68

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                   17.4958(18)
_cell_length_b                   11.4975(12)
_cell_length_c                   15.7284(17)
_cell_angle_alpha                90
_cell_angle_beta                 115.554(2)
_cell_angle_gamma                90
_cell_volume                     2854.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2487
_cell_measurement_theta_min      4.560
_cell_measurement_theta_max      50.875

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6025
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16892
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5602
_reflns_number_gt                3837
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0622P)²+0.0295P] 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         5602
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_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 0.35191(4) 0.03218(6) 1.05472(5) 0.0480(2) Uani 1 1 d . . . . .
S2 S 0.30145(4) 0.34973(6) 0.89349(5) 0.0492(2) Uani 1 1 d . . . . .
N1 N 0.26758(12) 0.11449(17) 1.03295(14) 0.0405(5) Uani 1 1 d . . . . .
N2 N 0.24300(12) 0.29645(16) 0.94342(14) 0.0414(5) Uani 1 1 d . . . . .
O1 O 0.11711(12) 0.19983(15) 1.11599(13) 0.0536(5) Uani 1 1 d . . . . .
O2 O 0.14468(11) 0.01827(14) 1.02450(12) 0.0470(4) Uani 1 1 d . . . . .
O3 O 0.41951(11) 0.10630(17) 1.06310(15) 0.0638(5) Uani 1 1 d . . . . .
O4 O 0.36099(12) -0.04008(16) 1.13232(14) 0.0628(5) Uani 1 1 d . . . . .
O5 O 0.34569(13) 0.25328(17) 0.87891(15) 0.0666(6) Uani 1 1 d . . . . .
O6 O 0.24966(13) 0.41847(18) 0.81378(12) 0.0655(5) Uani 1 1 d . . . . .
C1 C 0.18221(16) 0.2033(2) 1.10751(16) 0.0411(6) Uani 1 1 d . . . . .
C2 C 0.23580(15) 0.3124(2) 1.12562(17) 0.0436(6) Uani 1 1 d . . . . .
H2A H 0.2432 0.3476 1.1847 0.052 Uiso 1 1 calc R U . . .
H2B H 0.2913 0.2930 1.1298 0.052 Uiso 1 1 calc R U . . .
C3 C 0.19165(14) 0.39696(19) 1.04536(16) 0.0384(5) Uani 1 1 d . . . . .
C4 C 0.19305(15) 0.3814(2) 0.96232(17) 0.0417(6) Uani 1 1 d . . . . .
H4 H 0.1589 0.4294 0.9129 0.050 Uiso 1 1 calc R U . . .
C5 C 0.22675(15) 0.1711(2) 0.94071(16) 0.0390(5) Uani 1 1 d . . . . .
H5 H 0.2516 0.1365 0.9014 0.047 Uiso 1 1 calc R U . . .
C6 C 0.13373(15) 0.14118(19) 0.89463(16) 0.0385(5) Uani 1 1 d . . . . .
C7 C 0.08185(16) 0.1835(2) 0.80536(17) 0.0501(6) Uani 1 1 d . . . . .
H7 H 0.1028 0.2392 0.7780 0.060 Uiso 1 1 calc R U . . .
C8 C 0.00018(19) 0.1442(3) 0.7569(2) 0.0647(8) Uani 1 1 d . . . . .
H8 H -0.0338 0.1735 0.6973 0.078 Uiso 1 1 calc R U . . .
C9 C -0.03167(18) 0.0608(3) 0.7969(2) 0.0629(8) Uani 1 1 d . . . . .
H9 H -0.0864 0.0328 0.7631 0.075 Uiso 1 1 calc R U . . .
C10 C 0.01662(17) 0.0194(2) 0.8854(2) 0.0540(7) Uani 1 1 d . . . . .
H10 H -0.0051 -0.0358 0.9124 0.065 Uiso 1 1 calc R U . . .
C11 C 0.09934(15) 0.0612(2) 0.93507(17) 0.0418(6) Uani 1 1 d . . . . .
C12 C 0.21380(15) 0.0907(2) 1.07907(17) 0.0422(6) Uani 1 1 d . . . . .
H12 H 0.2481 0.0486 1.1373 0.051 Uiso 1 1 calc R U . . .
C13 C 0.14288(15) 0.4956(2) 1.05788(17) 0.0414(6) Uani 1 1 d . . . . .
C14 C 0.13547(18) 0.5993(2) 1.00935(19) 0.0538(7) Uani 1 1 d . . . . .
H14 H 0.1635 0.6074 0.9711 0.065 Uiso 1 1 calc R U . . .
C15 C 0.0874(2) 0.6905(2) 1.0168(2) 0.0638(8) Uani 1 1 d . . . . .
H15 H 0.0820 0.7584 0.9825 0.077 Uiso 1 1 calc R U . . .
C16 C 0.04780(18) 0.6807(3) 1.0750(2) 0.0640(8) Uani 1 1 d . . . . .
H16 H 0.0150 0.7416 1.0800 0.077 Uiso 1 1 calc R U . . .
C17 C 0.05660(19) 0.5818(3) 1.1253(2) 0.0627(8) Uani 1 1 d . . . . .
H17 H 0.0307 0.5762 1.1658 0.075 Uiso 1 1 calc R U . . .
C18 C 0.10352(17) 0.4889(2) 1.11736(19) 0.0518(7) Uani 1 1 d . . . . .
H18 H 0.1086 0.4217 1.1523 0.062 Uiso 1 1 calc R U . . .
C19 C 0.32495(16) -0.0529(2) 0.95329(19) 0.0493(7) Uani 1 1 d . . . . .
C20 C 0.3734(2) -0.0453(3) 0.9043(2) 0.0709(9) Uani 1 1 d . . . . .
H20 H 0.4180 0.0074 0.9223 0.085 Uiso 1 1 calc R U . . .
C21 C 0.3547(2) -0.1174(3) 0.8279(3) 0.0868(11) Uani 1 1 d . . . . .
H21 H 0.3878 -0.1133 0.7950 0.104 Uiso 1 1 calc R U . . .
C22 C 0.2884(2) -0.1953(3) 0.7987(2) 0.0708(9) Uani 1 1 d . . . . .
C23 C 0.2398(2) -0.1980(3) 0.8474(2) 0.0702(9) Uani 1 1 d . . . . .
H23 H 0.1936 -0.2480 0.8276 0.084 Uiso 1 1 calc R U . . .
C24 C 0.25756(18) -0.1286(2) 0.9249(2) 0.0615(8) Uani 1 1 d . . . . .
H24 H 0.2244 -0.1327 0.9578 0.074 Uiso 1 1 calc R U . . .
C25 C 0.2715(3) -0.2773(3) 0.7175(3) 0.1035(13) Uani 1 1 d . . . . .
H25A H 0.3142 -0.3368 0.7370 0.155 Uiso 1 1 calc R U . . .
H25B H 0.2729 -0.2348 0.6656 0.155 Uiso 1 1 calc R U . . .
H25C H 0.2168 -0.3124 0.6983 0.155 Uiso 1 1 calc R U . . .
C26 C 0.36949(16) 0.4443(2) 0.98088(18) 0.0465(6) Uani 1 1 d . . . . .
C27 C 0.3629(2) 0.5600(3) 0.9645(2) 0.0847(11) Uani 1 1 d . . . . .
H27 H 0.3258 0.5883 0.9057 0.102 Uiso 1 1 calc R U . . .
C28 C 0.4111(2) 0.6363(3) 1.0349(3) 0.0926(12) Uani 1 1 d . . . . .
H28 H 0.4062 0.7156 1.0221 0.111 Uiso 1 1 calc R U . . .
C29 C 0.46541(17) 0.5998(3) 1.1220(2) 0.0562(7) Uani 1 1 d . . . . .
C30 C 0.4731(2) 0.4821(3) 1.1361(2) 0.0782(10) Uani 1 1 d . . . . .
H30 H 0.5110 0.4538 1.1945 0.094 Uiso 1 1 calc R U . . .
C31 C 0.42647(19) 0.4043(3) 1.0666(2) 0.0728(9) Uani 1 1 d . . . . .
H31 H 0.4337 0.3248 1.0779 0.087 Uiso 1 1 calc R U . . .
C32 C 0.5144(2) 0.6861(3) 1.1989(2) 0.0768(9) Uani 1 1 d . . . . .
H32A H 0.5148 0.7604 1.1713 0.115 Uiso 1 1 calc R U . . .
H32B H 0.5716 0.6592 1.2334 0.115 Uiso 1 1 calc R U . . .
H32C H 0.4880 0.6934 1.2410 0.115 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 O3 1.4170(19) . ?
S1 O4 1.428(2) . ?
S1 N1 1.6595(19) . ?
S1 C19 1.753(3) . ?
S2 O6 1.427(2) . ?
S2 O5 1.4264(19) . ?
S2 N2 1.6524(19) . ?
S2 C26 1.754(3) . ?
N1 C12 1.440(3) . ?
N1 C5 1.464(3) . ?
N2 C4 1.425(3) . ?
N2 C5 1.466(3) . ?
O1 C1 1.203(3) . ?
O2 C11 1.374(3) . ?
O2 C12 1.413(3) . ?
C1 C2 1.518(3) . ?
C1 C12 1.548(3) . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.329(3) . ?
C3 C13 1.482(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.508(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.390(3) . ?
C6 C11 1.394(3) . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(3) . ?
C10 H10 0.9300 . ?
C12 H12 0.9800 . ?
C13 C18 1.382(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.373(4) . ?
C19 C24 1.376(4) . ?
C20 C21 1.377(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(5) . ?
C22 C25 1.510(4) . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.350(4) . ?
C26 C31 1.365(4) . ?
C27 C28 1.379(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.353(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.368(4) . ?
C29 C32 1.513(4) . ?
C30 C31 1.375(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.33(12) . . ?
O3 S1 N1 107.96(11) . . ?
O4 S1 N1 105.63(11) . . ?
O3 S1 C19 107.83(13) . . ?
O4 S1 C19 109.90(12) . . ?
N1 S1 C19 105.31(11) . . ?
O6 S2 O5 118.18(13) . . ?
O6 S2 N2 109.52(11) . . ?
O5 S2 N2 106.14(11) . . ?
O6 S2 C26 107.70(12) . . ?
O5 S2 C26 112.10(13) . . ?
N2 S2 C26 101.97(11) . . ?
C12 N1 C5 115.96(18) . . ?
C12 N1 S1 120.24(16) . . ?
C5 N1 S1 117.92(15) . . ?
C4 N2 C5 123.44(18) . . ?
C4 N2 S2 113.96(15) . . ?
C5 N2 S2 120.18(15) . . ?
C11 O2 C12 112.03(17) . . ?
O1 C1 C2 123.0(2) . . ?
O1 C1 C12 118.5(2) . . ?
C2 C1 C12 118.5(2) . . ?
C3 C2 C1 108.80(19) . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C13 119.3(2) . . ?
C4 C3 C2 120.9(2) . . ?
C13 C3 C2 119.7(2) . . ?
C3 C4 N2 124.8(2) . . ?
C3 C4 H4 117.6 . . ?
N2 C4 H4 117.6 . . ?
N1 C5 N2 113.74(19) . . ?
N1 C5 C6 109.80(18) . . ?
N2 C5 C6 113.19(19) . . ?
N1 C5 H5 106.5 . . ?
N2 C5 H5 106.5 . . ?
C6 C5 H5 106.5 . . ?
C7 C6 C11 118.0(2) . . ?
C7 C6 C5 120.3(2) . . ?
C11 C6 C5 121.3(2) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
O2 C11 C6 122.1(2) . . ?
O2 C11 C10 116.7(2) . . ?
C6 C11 C10 121.2(2) . . ?
O2 C12 N1 112.32(19) . . ?
O2 C12 C1 110.48(19) . . ?
N1 C12 C1 112.28(19) . . ?
O2 C12 H12 107.1 . . ?
N1 C12 H12 107.1 . . ?
C1 C12 H12 107.1 . . ?
C18 C13 C14 117.5(2) . . ?
C18 C13 C3 122.1(2) . . ?
C14 C13 C3 120.4(2) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 120.4(3) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C24 120.6(3) . . ?
C20 C19 S1 119.1(2) . . ?
C24 C19 S1 120.3(2) . . ?
C19 C20 C21 118.6(3) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C22 122.1(3) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C21 117.7(3) . . ?
C23 C22 C25 121.2(4) . . ?
C21 C22 C25 121.2(4) . . ?
C22 C23 C24 121.7(3) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 119.3(3) . . ?
C23 C24 H24 120.4 . . ?
C19 C24 H24 120.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 119.1(3) . . ?
C27 C26 S2 119.2(2) . . ?
C31 C26 S2 121.6(2) . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 122.4(3) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C28 C29 C30 116.6(3) . . ?
C28 C29 C32 121.0(3) . . ?
C30 C29 C32 122.5(3) . . ?
C29 C30 C31 122.1(3) . . ?
C29 C30 H30 119.0 . . ?
C31 C30 H30 119.0 . . ?
C26 C31 C30 119.7(3) . . ?
C26 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N1 C12 -138.16(19) . . . . ?
O4 S1 N1 C12 -9.4(2) . . . . ?
C19 S1 N1 C12 106.9(2) . . . . ?
O3 S1 N1 C5 69.92(19) . . . . ?
O4 S1 N1 C5 -161.37(17) . . . . ?
C19 S1 N1 C5 -45.1(2) . . . . ?
O6 S2 N2 C4 -50.7(2) . . . . ?
O5 S2 N2 C4 -179.28(18) . . . . ?
C26 S2 N2 C4 63.22(19) . . . . ?
O6 S2 N2 C5 112.30(19) . . . . ?
O5 S2 N2 C5 -16.3(2) . . . . ?
C26 S2 N2 C5 -133.82(19) . . . . ?
O1 C1 C2 C3 -73.3(3) . . . . ?
C12 C1 C2 C3 108.2(2) . . . . ?
C1 C2 C3 C4 -76.5(3) . . . . ?
C1 C2 C3 C13 100.7(2) . . . . ?
C13 C3 C4 N2 174.4(2) . . . . ?
C2 C3 C4 N2 -8.4(4) . . . . ?
C5 N2 C4 C3 69.6(3) . . . . ?
S2 N2 C4 C3 -128.1(2) . . . . ?
C12 N1 C5 N2 101.0(2) . . . . ?
S1 N1 C5 N2 -105.93(19) . . . . ?
C12 N1 C5 C6 -27.0(3) . . . . ?
S1 N1 C5 C6 126.07(17) . . . . ?
C4 N2 C5 N1 -86.8(3) . . . . ?
S2 N2 C5 N1 111.95(19) . . . . ?
C4 N2 C5 C6 39.5(3) . . . . ?
S2 N2 C5 C6 -121.82(19) . . . . ?
N1 C5 C6 C7 -178.9(2) . . . . ?
N2 C5 C6 C7 52.8(3) . . . . ?
N1 C5 C6 C11 -5.9(3) . . . . ?
N2 C5 C6 C11 -134.2(2) . . . . ?
C11 C6 C7 C8 -2.5(4) . . . . ?
C5 C6 C7 C8 170.7(2) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C12 O2 C11 C6 20.4(3) . . . . ?
C12 O2 C11 C10 -160.4(2) . . . . ?
C7 C6 C11 O2 -177.3(2) . . . . ?
C5 C6 C11 O2 9.6(3) . . . . ?
C7 C6 C11 C10 3.6(3) . . . . ?
C5 C6 C11 C10 -169.6(2) . . . . ?
C9 C10 C11 O2 178.8(2) . . . . ?
C9 C10 C11 C6 -2.0(4) . . . . ?
C11 O2 C12 N1 -53.4(2) . . . . ?
C11 O2 C12 C1 72.9(2) . . . . ?
C5 N1 C12 O2 58.9(3) . . . . ?
S1 N1 C12 O2 -93.6(2) . . . . ?
C5 N1 C12 C1 -66.3(3) . . . . ?
S1 N1 C12 C1 141.20(17) . . . . ?
O1 C1 C12 O2 28.7(3) . . . . ?
C2 C1 C12 O2 -152.71(19) . . . . ?
O1 C1 C12 N1 154.9(2) . . . . ?
C2 C1 C12 N1 -26.5(3) . . . . ?
C4 C3 C13 C18 147.6(3) . . . . ?
C2 C3 C13 C18 -29.7(3) . . . . ?
C4 C3 C13 C14 -32.6(4) . . . . ?
C2 C3 C13 C14 150.1(2) . . . . ?
C18 C13 C14 C15 -2.9(4) . . . . ?
C3 C13 C14 C15 177.2(2) . . . . ?
C13 C14 C15 C16 1.8(4) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -1.5(5) . . . . ?
C14 C13 C18 C17 1.9(4) . . . . ?
C3 C13 C18 C17 -178.3(2) . . . . ?
C16 C17 C18 C13 0.3(4) . . . . ?
O3 S1 C19 C20 5.5(3) . . . . ?
O4 S1 C19 C20 -126.1(2) . . . . ?
N1 S1 C19 C20 120.6(2) . . . . ?
O3 S1 C19 C24 -176.3(2) . . . . ?
O4 S1 C19 C24 52.1(2) . . . . ?
N1 S1 C19 C24 -61.2(2) . . . . ?
C24 C19 C20 C21 -1.9(5) . . . . ?
S1 C19 C20 C21 176.3(2) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C23 1.1(5) . . . . ?
C20 C21 C22 C25 -177.2(3) . . . . ?
C21 C22 C23 C24 -2.2(5) . . . . ?
C25 C22 C23 C24 176.1(3) . . . . ?
C22 C23 C24 C19 1.2(5) . . . . ?
C20 C19 C24 C23 0.9(4) . . . . ?
S1 C19 C24 C23 -177.3(2) . . . . ?
O6 S2 C26 C27 2.1(3) . . . . ?
O5 S2 C26 C27 133.8(3) . . . . ?
N2 S2 C26 C27 -113.1(3) . . . . ?
O6 S2 C26 C31 179.2(2) . . . . ?
O5 S2 C26 C31 -49.1(3) . . . . ?
N2 S2 C26 C31 64.0(3) . . . . ?
C31 C26 C27 C28 -2.3(5) . . . . ?
S2 C26 C27 C28 174.9(3) . . . . ?
C26 C27 C28 C29 -0.7(6) . . . . ?
C27 C28 C29 C30 2.7(6) . . . . ?
C27 C28 C29 C32 -177.2(4) . . . . ?
C28 C29 C30 C31 -1.8(5) . . . . ?
C32 C29 C30 C31 178.1(3) . . . . ?
C27 C26 C31 C30 3.1(5) . . . . ?
S2 C26 C31 C30 -174.0(3) . . . . ?
C29 C30 C31 C26 -1.1(5) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1001752'
#######################################################################
#
#                 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_cd213538

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O4 S'
_chemical_formula_weight         329.36

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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'

_cell_length_a                   17.324(8)
_cell_length_b                   15.968(8)
_cell_length_c                   5.799(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1604.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1147
_cell_measurement_theta_min      4.703
_cell_measurement_theta_max      45.070

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.069
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0716
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7871
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3058
_reflns_number_gt                1643
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0851P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.63(16)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     209
_refine_ls_number_restraints     151
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.954
_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 0.49219(7) 0.27863(8) 0.3195(3) 0.0613(4) Uani 1 1 d U . .
N1 N 0.4368(2) 0.1999(2) 0.2365(8) 0.0553(12) Uani 1 1 d U . .
O1 O 0.3590(2) 0.2267(2) -0.0748(7) 0.0678(10) Uani 1 1 d U . .
O2 O 0.33930(18) 0.1086(2) 0.3616(7) 0.0679(11) Uani 1 1 d U . .
O3 O 0.55711(19) 0.2742(2) 0.1672(8) 0.0745(13) Uani 1 1 d U . .
O4 O 0.5014(2) 0.2699(3) 0.5631(7) 0.0801(13) Uani 1 1 d U . .
C1 C 0.3565(3) 0.1949(3) 0.3217(12) 0.0612(14) Uani 1 1 d U . .
H1 H 0.3496 0.2283 0.4621 0.073 Uiso 1 1 calc R . .
C2 C 0.3122(3) 0.2308(3) 0.1250(12) 0.0586(14) Uani 1 1 d U . .
C3 C 0.2426(3) 0.2627(3) 0.1184(15) 0.0829(19) Uani 1 1 d U . .
H3A H 0.2230 0.2833 -0.0197 0.100 Uiso 1 1 calc R . .
H3B H 0.2128 0.2647 0.2517 0.100 Uiso 1 1 calc R . .
C4 C 0.4248(3) 0.1783(3) -0.0031(10) 0.0567(14) Uani 1 1 d U . .
H4 H 0.4704 0.1904 -0.0971 0.068 Uiso 1 1 calc R . .
C5 C 0.4049(3) 0.0862(3) -0.0053(10) 0.0577(14) Uani 1 1 d U . .
C6 C 0.3635(3) 0.0576(3) 0.1808(11) 0.0582(14) Uani 1 1 d U . .
C7 C 0.3441(3) -0.0272(4) 0.2046(13) 0.0793(18) Uani 1 1 d U . .
H7 H 0.3164 -0.0464 0.3314 0.095 Uiso 1 1 calc R . .
C8 C 0.3681(4) -0.0815(4) 0.0301(17) 0.092(2) Uani 1 1 d U . .
H8 H 0.3565 -0.1382 0.0415 0.111 Uiso 1 1 calc R . .
C9 C 0.4081(4) -0.0533(4) -0.1567(16) 0.093(2) Uani 1 1 d U . .
H9 H 0.4228 -0.0907 -0.2716 0.112 Uiso 1 1 calc R . .
C10 C 0.4269(3) 0.0304(4) -0.1765(13) 0.0737(16) Uani 1 1 d U . .
H10 H 0.4543 0.0493 -0.3043 0.088 Uiso 1 1 calc R . .
C11 C 0.4429(3) 0.3726(3) 0.2694(9) 0.0560(15) Uani 1 1 d U . .
C12 C 0.3942(3) 0.4032(4) 0.4399(11) 0.0686(16) Uani 1 1 d U . .
H12 H 0.3875 0.3736 0.5766 0.082 Uiso 1 1 calc R . .
C13 C 0.3557(3) 0.4782(4) 0.4047(12) 0.0745(18) Uani 1 1 d U . .
H13 H 0.3229 0.4985 0.5185 0.089 Uiso 1 1 calc R . .
C14 C 0.3656(3) 0.5241(3) 0.1989(14) 0.0691(17) Uani 1 1 d U . .
C15 C 0.4126(3) 0.4909(4) 0.0312(12) 0.0697(17) Uani 1 1 d U . .
H15 H 0.4184 0.5193 -0.1078 0.084 Uiso 1 1 calc R . .
C16 C 0.4516(3) 0.4155(3) 0.0652(10) 0.0594(14) Uani 1 1 d U . .
H16 H 0.4835 0.3943 -0.0499 0.071 Uiso 1 1 calc R . .
C17 C 0.3249(4) 0.6075(4) 0.1679(16) 0.119(3) Uani 1 1 d U . .
H17A H 0.3560 0.6514 0.2327 0.179 Uiso 1 1 calc R . .
H17B H 0.2758 0.6059 0.2449 0.179 Uiso 1 1 calc R . .
H17C H 0.3171 0.6179 0.0066 0.179 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 O4 1.429(4) . ?
S1 O3 1.431(4) . ?
S1 N1 1.654(4) . ?
S1 C11 1.752(5) . ?
N1 C4 1.446(7) . ?
N1 C1 1.477(6) . ?
O1 C2 1.416(7) . ?
O1 C4 1.438(5) . ?
O2 C6 1.392(6) . ?
O2 C1 1.430(6) . ?
C1 C2 1.490(8) . ?
C1 H1 0.9800 . ?
C2 C3 1.310(7) . ?
C3 H3A 0.9300 . ?
C3 H3B 0.9300 . ?
C4 C5 1.509(7) . ?
C4 H4 0.9800 . ?
C5 C6 1.374(7) . ?
C5 C10 1.388(8) . ?
C6 C7 1.402(8) . ?
C7 C8 1.396(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.362(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.376(7) . ?
C11 C12 1.388(7) . ?
C12 C13 1.385(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.411(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(9) . ?
C14 C17 1.517(8) . ?
C15 C16 1.395(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O3 121.2(3) . . ?
O4 S1 N1 106.2(2) . . ?
O3 S1 N1 103.9(2) . . ?
O4 S1 C11 107.6(3) . . ?
O3 S1 C11 108.9(2) . . ?
N1 S1 C11 108.7(2) . . ?
C4 N1 C1 100.0(5) . . ?
C4 N1 S1 123.0(3) . . ?
C1 N1 S1 119.3(4) . . ?
C2 O1 C4 103.9(4) . . ?
C6 O2 C1 112.3(4) . . ?
O2 C1 N1 107.6(4) . . ?
O2 C1 C2 112.8(5) . . ?
N1 C1 C2 102.0(5) . . ?
O2 C1 H1 111.3 . . ?
N1 C1 H1 111.3 . . ?
C2 C1 H1 111.3 . . ?
C3 C2 O1 121.4(6) . . ?
C3 C2 C1 130.3(6) . . ?
O1 C2 C1 108.3(4) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
O1 C4 N1 105.3(4) . . ?
O1 C4 C5 110.0(4) . . ?
N1 C4 C5 105.9(4) . . ?
O1 C4 H4 111.8 . . ?
N1 C4 H4 111.8 . . ?
C5 C4 H4 111.8 . . ?
C6 C5 C10 119.4(5) . . ?
C6 C5 C4 115.8(5) . . ?
C10 C5 C4 124.7(6) . . ?
C5 C6 O2 123.7(5) . . ?
C5 C6 C7 121.6(6) . . ?
O2 C6 C7 114.7(6) . . ?
C8 C7 C6 117.2(7) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C9 C8 C7 121.5(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.4(6) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.9(7) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C16 C11 C12 120.3(5) . . ?
C16 C11 S1 121.0(4) . . ?
C12 C11 S1 118.7(4) . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.0(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 118.0(5) . . ?
C15 C14 C17 122.0(7) . . ?
C13 C14 C17 120.0(7) . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 119.8(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N1 C4 -169.1(4) . . . . ?
O3 S1 N1 C4 -40.3(4) . . . . ?
C11 S1 N1 C4 75.5(4) . . . . ?
O4 S1 N1 C1 63.9(5) . . . . ?
O3 S1 N1 C1 -167.3(4) . . . . ?
C11 S1 N1 C1 -51.5(5) . . . . ?
C6 O2 C1 N1 -45.4(6) . . . . ?
C6 O2 C1 C2 66.3(5) . . . . ?
C4 N1 C1 O2 80.3(5) . . . . ?
S1 N1 C1 O2 -142.5(4) . . . . ?
C4 N1 C1 C2 -38.5(5) . . . . ?
S1 N1 C1 C2 98.6(5) . . . . ?
C4 O1 C2 C3 -172.4(5) . . . . ?
C4 O1 C2 C1 8.1(5) . . . . ?
O2 C1 C2 C3 84.9(7) . . . . ?
N1 C1 C2 C3 -160.0(5) . . . . ?
O2 C1 C2 O1 -95.7(4) . . . . ?
N1 C1 C2 O1 19.5(5) . . . . ?
C2 O1 C4 N1 -33.8(5) . . . . ?
C2 O1 C4 C5 79.8(5) . . . . ?
C1 N1 C4 O1 45.6(4) . . . . ?
S1 N1 C4 O1 -89.4(5) . . . . ?
C1 N1 C4 C5 -70.8(4) . . . . ?
S1 N1 C4 C5 154.1(3) . . . . ?
O1 C4 C5 C6 -79.4(6) . . . . ?
N1 C4 C5 C6 33.8(6) . . . . ?
O1 C4 C5 C10 102.1(6) . . . . ?
N1 C4 C5 C10 -144.7(5) . . . . ?
C10 C5 C6 O2 179.6(5) . . . . ?
C4 C5 C6 O2 1.0(7) . . . . ?
C10 C5 C6 C7 1.3(8) . . . . ?
C4 C5 C6 C7 -177.4(5) . . . . ?
C1 O2 C6 C5 5.1(7) . . . . ?
C1 O2 C6 C7 -176.5(5) . . . . ?
C5 C6 C7 C8 -0.5(9) . . . . ?
O2 C6 C7 C8 -179.0(5) . . . . ?
C6 C7 C8 C9 -0.6(10) . . . . ?
C7 C8 C9 C10 0.8(10) . . . . ?
C8 C9 C10 C5 0.0(9) . . . . ?
C6 C5 C10 C9 -1.0(8) . . . . ?
C4 C5 C10 C9 177.5(5) . . . . ?
O4 S1 C11 C16 153.5(4) . . . . ?
O3 S1 C11 C16 20.6(5) . . . . ?
N1 S1 C11 C16 -91.9(4) . . . . ?
O4 S1 C11 C12 -26.7(5) . . . . ?
O3 S1 C11 C12 -159.7(4) . . . . ?
N1 S1 C11 C12 87.8(4) . . . . ?
C16 C11 C12 C13 -1.3(7) . . . . ?
S1 C11 C12 C13 178.9(4) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C13 C14 C15 2.1(8) . . . . ?
C12 C13 C14 C17 -177.9(5) . . . . ?
C13 C14 C15 C16 -2.2(8) . . . . ?
C17 C14 C15 C16 177.9(5) . . . . ?
C12 C11 C16 C15 1.2(7) . . . . ?
S1 C11 C16 C15 -179.0(4) . . . . ?
C14 C15 C16 C11 0.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 962969'
