# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_50sd

#====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N2 O4'
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31

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'

_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                   4.8667(3)
_cell_length_b                   7.7561(4)
_cell_length_c                   18.3813(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.214(4)
_cell_angle_gamma                90
_cell_volume                     693.83(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2380
_cell_measurement_theta_min      2.216
_cell_measurement_theta_max      30.494

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            7676
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.216
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             1863
_reflns_number_gt                1346
_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0635P)²+0.1505P]
 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         1863
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_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
N1 N 0.1483(2) 0.33079(15) 0.37535(7) 0.0133(3) Uani 1 1 d . . . . .
O2 O 0.4920(2) 0.16929(13) 0.32821(6) 0.0191(3) Uani 1 1 d . . . . .
C4 C -0.1201(3) 0.22164(18) 0.47785(8) 0.0122(3) Uani 1 1 d . . . . .
O1 O -0.2004(2) 0.49065(13) 0.42179(6) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.0297(3) 0.06611(18) 0.47510(8) 0.0113(3) Uani 1 1 d . . . . .
C5 C 0.2382(3) 0.04117(18) 0.42318(8) 0.0120(3) Uani 1 1 d . . . . .
C6 C -0.0659(3) 0.35873(18) 0.42406(8) 0.0129(3) Uani 1 1 d . . . . .
C3 C 0.3795(3) -0.11260(19) 0.42070(8) 0.0142(3) Uani 1 1 d . . . . .
H3 H 0.5182 -0.1294 0.3852 0.017 Uiso 1 1 calc R U . . .
C7 C 0.3067(3) 0.18130(18) 0.37216(8) 0.0130(3) Uani 1 1 d . . . . .
C1 C -0.3199(3) 0.24438(19) 0.52966(9) 0.0141(3) Uani 1 1 d . . . . .
H1 H -0.4181 0.3501 0.5318 0.017 Uiso 1 1 calc R U . . .
C8 C 0.1992(3) 0.46240(19) 0.31894(9) 0.0161(3) Uani 1 1 d . . . . .
H8A H 0.3995 0.4740 0.3111 0.019 Uiso 1 1 calc R U . . .
H8B H 0.1282 0.5752 0.3357 0.019 Uiso 1 1 calc R U . . .
C9 C 0.0608(3) 0.4139(2) 0.24803(9) 0.0201(4) Uani 1 1 d . . . . .
H9A H 0.0979 0.5029 0.2115 0.030 Uiso 1 1 calc R U . . .
H9B H -0.1379 0.4045 0.2555 0.030 Uiso 1 1 calc R U . . .
H9C H 0.1328 0.3030 0.2311 0.030 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
N1 C6 1.3935(17) . ?
N1 C7 1.3939(18) . ?
N1 C8 1.4765(19) . ?
O2 C7 1.2164(16) . ?
C4 C1 1.3751(18) . ?
C4 C2 1.4105(19) . ?
C4 C6 1.476(2) . ?
O1 C6 1.2154(17) . ?
C2 C2 1.406(3) 3_556 ?
C2 C5 1.4088(18) . ?
C5 C3 1.378(2) . ?
C5 C7 1.475(2) . ?
C3 C1 1.401(2) 3_556 ?
C3 H3 0.9500 . ?
C1 C3 1.401(2) 3_556 ?
C1 H1 0.9500 . ?
C8 C9 1.512(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C6 N1 C7 124.86(12) . . ?
C6 N1 C8 118.13(11) . . ?
C7 N1 C8 116.82(11) . . ?
C1 C4 C2 120.10(13) . . ?
C1 C4 C6 120.00(12) . . ?
C2 C4 C6 119.89(12) . . ?
C2 C2 C5 119.45(15) 3_556 . ?
C2 C2 C4 119.53(15) 3_556 . ?
C5 C2 C4 121.02(13) . . ?
C3 C5 C2 120.14(13) . . ?
C3 C5 C7 120.20(12) . . ?
C2 C5 C7 119.65(12) . . ?
O1 C6 N1 120.86(13) . . ?
O1 C6 C4 122.13(12) . . ?
N1 C6 C4 117.01(12) . . ?
C5 C3 C1 120.36(12) . 3_556 ?
C5 C3 H3 119.8 . . ?
C1 C3 H3 119.8 3_556 . ?
O2 C7 N1 120.21(13) . . ?
O2 C7 C5 122.40(13) . . ?
N1 C7 C5 117.38(11) . . ?
C4 C1 C3 120.41(13) . 3_556 ?
C4 C1 H1 119.8 . . ?
C3 C1 H1 119.8 3_556 . ?
N1 C8 C9 110.99(12) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C1 C4 C2 C2 1.0(3) . . . 3_556 ?
C6 C4 C2 C2 -177.78(16) . . . 3_556 ?
C1 C4 C2 C5 -179.01(14) . . . . ?
C6 C4 C2 C5 2.2(2) . . . . ?
C2 C2 C5 C3 0.9(3) 3_556 . . . ?
C4 C2 C5 C3 -179.07(14) . . . . ?
C2 C2 C5 C7 -178.28(17) 3_556 . . . ?
C4 C2 C5 C7 1.7(2) . . . . ?
C7 N1 C6 O1 -177.55(14) . . . . ?
C8 N1 C6 O1 -2.6(2) . . . . ?
C7 N1 C6 C4 2.5(2) . . . . ?
C8 N1 C6 C4 177.39(13) . . . . ?
C1 C4 C6 O1 -3.0(2) . . . . ?
C2 C4 C6 O1 175.74(14) . . . . ?
C1 C4 C6 N1 176.96(13) . . . . ?
C2 C4 C6 N1 -4.3(2) . . . . ?
C2 C5 C3 C1 -0.9(2) . . . 3_556 ?
C7 C5 C3 C1 178.33(14) . . . 3_556 ?
C6 N1 C7 O2 -179.15(13) . . . . ?
C8 N1 C7 O2 5.9(2) . . . . ?
C6 N1 C7 C5 1.4(2) . . . . ?
C8 N1 C7 C5 -173.64(13) . . . . ?
C3 C5 C7 O2 -2.2(2) . . . . ?
C2 C5 C7 O2 177.00(14) . . . . ?
C3 C5 C7 N1 177.28(14) . . . . ?
C2 C5 C7 N1 -3.5(2) . . . . ?
C2 C4 C1 C3 -1.1(2) . . . 3_556 ?
C6 C4 C1 C3 177.71(14) . . . 3_556 ?
C6 N1 C8 C9 -96.41(15) . . . . ?
C7 N1 C8 C9 78.93(16) . . . . ?

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 937648'
#######################################################################
#
#                 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_mp20sd

#====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "C32 H22 N2 O8','C2 H6 O1 S1','C2 H6 O1 S1"
_chemical_formula_sum            'C36 H34 N2 O10 S2'
_chemical_formula_weight         718.77

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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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, 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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   8.953(3)
_cell_length_b                   13.508(6)
_cell_length_c                   27.663(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3345(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1106
_cell_measurement_theta_min      2.827
_cell_measurement_theta_max      20.997

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4636
_exptl_absorpt_correction_T_max  0.6688
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            8461
_diffrn_reflns_av_unetI/netI     0.1098
_diffrn_reflns_av_R_equivalents  0.1155
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.472
_diffrn_reflns_theta_max         22.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.706
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.706
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.692
_reflns_number_total             2101
_reflns_number_gt                1706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.673

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1382P)²+2.2286P]
 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 x determined using 607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.39(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2101
_refine_ls_number_parameters     113
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2233
_refine_ls_wR_factor_gt          0.2097
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.036
_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_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
O9 O 0.2567(9) 0.3168(6) 0.4730(3) 0.035(2) Uani 1 1 d . U . . .
C32 C 0.2104(15) 0.1333(9) 0.5012(5) 0.043(3) Uani 1 1 d . U . . .
H32A H 0.2276 0.1021 0.4697 0.064 Uiso 1 1 calc R U . . .
H32B H 0.1414 0.0925 0.5202 0.064 Uiso 1 1 calc R U . . .
H32C H 0.3055 0.1394 0.5185 0.064 Uiso 1 1 calc R U . . .
C33 C 0.1146(19) 0.2846(9) 0.5548(5) 0.055(4) Uani 1 1 d . U . . .
H33A H 0.0717 0.3512 0.5574 0.083 Uiso 1 1 calc R U . . .
H33B H 0.2133 0.2837 0.5701 0.083 Uiso 1 1 calc R U . . .
H33C H 0.0490 0.2370 0.5711 0.083 Uiso 1 1 calc R U . . .
S1 S 0.1323(3) 0.2519(2) 0.49269(11) 0.0344(9) Uani 1 1 d . U . . .
N1 N 0.1712(9) 0.5173(6) 0.3202(3) 0.0135(19) Uiso 1 1 d . U . . .
O1 O 0.1665(8) 0.3497(5) 0.3173(2) 0.0180(13) Uiso 1 1 d . U . . .
O2 O 0.1718(8) 0.6851(5) 0.3209(2) 0.0180(13) Uiso 1 1 d . U . . .
C6 C 0.2291(11) 0.4263(7) 0.3052(3) 0.013(2) Uiso 1 1 d . U . . .
O6 O 0.1835(8) 0.4551(5) 0.4145(3) 0.0211(19) Uiso 1 1 d . U . . .
H6 H 0.1909 0.4144 0.4373 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2320(11) 0.6088(7) 0.3074(3) 0.013(2) Uiso 1 1 d . U . . .
C2 C 0.4323(11) 0.5173(7) 0.2637(3) 0.011(2) Uiso 1 1 d . U . . .
C5 C 0.3701(11) 0.6085(7) 0.2778(3) 0.011(2) Uiso 1 1 d . U . . .
C15 C 0.0358(11) 0.5148(7) 0.3499(3) 0.014(2) Uiso 1 1 d . U . . .
H15 H 0.0235 0.5823 0.3641 0.017 Uiso 1 1 calc R U . . .
C3 C 0.4346(11) 0.6959(7) 0.2644(4) 0.014(2) Uiso 1 1 d . U . . .
H3 H 0.3915 0.7568 0.2743 0.017 Uiso 1 1 calc R U . . .
C1 C 0.4311(11) 0.3395(7) 0.2634(3) 0.011(2) Uiso 1 1 d . U . . .
H1 H 0.3839 0.2787 0.2715 0.013 Uiso 1 1 calc R U . . .
C17 C -0.1024(11) 0.4948(7) 0.3192(3) 0.014(2) Uiso 1 1 d . U . . .
H17A H -0.1038 0.4241 0.3099 0.017 Uiso 1 1 calc R U . . .
H17B H -0.0964 0.5346 0.2892 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3691(12) 0.4262(7) 0.2769(3) 0.013(2) Uiso 1 1 d . U . . .
O5 O -0.0431(8) 0.3847(5) 0.4052(2) 0.0198(18) Uiso 1 1 d . U . . .
C18 C -0.2477(6) 0.5197(4) 0.3456(2) 0.015(2) Uani 1 1 d G U . . .
C23 C -0.2825(7) 0.6186(4) 0.3538(3) 0.018(3) Uiso 1 1 d G U . . .
H23 H -0.2173 0.6692 0.3426 0.022 Uiso 1 1 calc R U . . .
C21 C -0.4126(7) 0.6435(3) 0.3783(3) 0.019(3) Uiso 1 1 d G U . . .
H21 H -0.4364 0.7111 0.3839 0.023 Uiso 1 1 calc R U . . .
C22 C -0.5079(6) 0.5695(4) 0.3947(2) 0.017(2) Uiso 1 1 d G U . . .
H22 H -0.5969 0.5865 0.4115 0.021 Uiso 1 1 calc R U . . .
C20 C -0.4732(6) 0.4707(4) 0.3865(2) 0.020(3) Uiso 1 1 d G U . . .
H20 H -0.5383 0.4201 0.3977 0.024 Uiso 1 1 calc R U . . .
C19 C -0.3431(7) 0.4458(3) 0.3619(2) 0.013(2) Uiso 1 1 d G U . . .
H19 H -0.3193 0.3782 0.3563 0.016 Uiso 1 1 calc R U . . .
C16 C 0.0543(12) 0.4424(7) 0.3923(4) 0.018(2) Uiso 1 1 d . 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
O9 S1 1.518(8) . ?
C32 S1 1.764(12) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 S1 1.782(14) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
N1 C7 1.395(13) . ?
N1 C6 1.397(12) . ?
N1 C15 1.464(13) . ?
O1 C6 1.223(11) . ?
O2 C7 1.221(11) . ?
C6 C4 1.479(15) . ?
O6 C16 1.320(13) . ?
O6 H6 0.8400 . ?
C7 C5 1.483(14) . ?
C2 C4 1.402(14) . ?
C2 C5 1.407(13) . ?
C2 C2 1.431(19) 4_655 ?
C5 C3 1.365(14) . ?
C15 C17 1.524(14) . ?
C15 C16 1.536(13) . ?
C15 H15 1.0000 . ?
C3 C3 1.41(2) 4_655 ?
C3 H3 0.9500 . ?
C1 C4 1.349(13) . ?
C1 C1 1.439(19) 4_655 ?
C1 H1 0.9500 . ?
C17 C18 1.529(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O5 C16 1.223(12) . ?
C18 C23 1.3900 . ?
C18 C19 1.3900 . ?
C23 C21 1.3900 . ?
C23 H23 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 C20 1.3900 . ?
C22 H22 0.9500 . ?
C20 C19 1.3900 . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?

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
S1 C32 H32A 109.5 . . ?
S1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
S1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
S1 C33 H33A 109.5 . . ?
S1 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
S1 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O9 S1 C32 106.4(6) . . ?
O9 S1 C33 105.5(6) . . ?
C32 S1 C33 97.5(7) . . ?
C7 N1 C6 124.0(8) . . ?
C7 N1 C15 119.1(8) . . ?
C6 N1 C15 116.9(8) . . ?
O1 C6 N1 119.6(9) . . ?
O1 C6 C4 122.2(9) . . ?
N1 C6 C4 118.2(8) . . ?
C16 O6 H6 109.5 . . ?
O2 C7 N1 119.9(9) . . ?
O2 C7 C5 122.5(9) . . ?
N1 C7 C5 117.6(8) . . ?
C4 C2 C5 122.5(9) . . ?
C4 C2 C2 118.7(6) . 4_655 ?
C5 C2 C2 118.8(6) . 4_655 ?
C3 C5 C2 120.9(9) . . ?
C3 C5 C7 120.1(9) . . ?
C2 C5 C7 119.0(8) . . ?
N1 C15 C17 111.4(8) . . ?
N1 C15 C16 110.7(8) . . ?
C17 C15 C16 113.6(9) . . ?
N1 C15 H15 106.9 . . ?
C17 C15 H15 106.9 . . ?
C16 C15 H15 106.9 . . ?
C5 C3 C3 120.2(6) . 4_655 ?
C5 C3 H3 119.9 . . ?
C3 C3 H3 119.9 4_655 . ?
C4 C1 C1 119.7(6) . 4_655 ?
C4 C1 H1 120.2 . . ?
C1 C1 H1 120.2 4_655 . ?
C15 C17 C18 112.8(7) . . ?
C15 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C15 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C1 C4 C2 121.6(9) . . ?
C1 C4 C6 119.7(9) . . ?
C2 C4 C6 118.6(8) . . ?
C23 C18 C19 120.0 . . ?
C23 C18 C17 118.7(5) . . ?
C19 C18 C17 121.3(5) . . ?
C21 C23 C18 120.0 . . ?
C21 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C23 C21 C22 120.0 . . ?
C23 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C22 C21 120.0 . . ?
C20 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C20 C19 120.0 . . ?
C22 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
O5 C16 O6 124.8(9) . . ?
O5 C16 C15 123.5(9) . . ?
O6 C16 C15 111.5(9) . . ?

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
C7 N1 C6 O1 -178.4(9) . . . . ?
C15 N1 C6 O1 -0.3(13) . . . . ?
C7 N1 C6 C4 4.3(14) . . . . ?
C15 N1 C6 C4 -177.6(8) . . . . ?
C6 N1 C7 O2 177.8(9) . . . . ?
C15 N1 C7 O2 -0.3(13) . . . . ?
C6 N1 C7 C5 -2.6(13) . . . . ?
C15 N1 C7 C5 179.3(8) . . . . ?
C4 C2 C5 C3 180.0(9) . . . . ?
C2 C2 C5 C3 2.1(16) 4_655 . . . ?
C4 C2 C5 C7 -0.4(14) . . . . ?
C2 C2 C5 C7 -178.3(10) 4_655 . . . ?
O2 C7 C5 C3 -0.3(14) . . . . ?
N1 C7 C5 C3 -179.9(9) . . . . ?
O2 C7 C5 C2 -179.9(9) . . . . ?
N1 C7 C5 C2 0.5(13) . . . . ?
C7 N1 C15 C17 101.0(10) . . . . ?
C6 N1 C15 C17 -77.2(11) . . . . ?
C7 N1 C15 C16 -131.5(9) . . . . ?
C6 N1 C15 C16 50.2(11) . . . . ?
C2 C5 C3 C3 0.3(17) . . . 4_655 ?
C7 C5 C3 C3 -179.3(11) . . . 4_655 ?
N1 C15 C17 C18 -164.0(7) . . . . ?
C16 C15 C17 C18 70.1(10) . . . . ?
C1 C1 C4 C2 2.8(17) 4_655 . . . ?
C1 C1 C4 C6 -178.8(11) 4_655 . . . ?
C5 C2 C4 C1 -179.4(10) . . . . ?
C2 C2 C4 C1 -1.5(17) 4_655 . . . ?
C5 C2 C4 C6 2.1(14) . . . . ?
C2 C2 C4 C6 -180.0(10) 4_655 . . . ?
O1 C6 C4 C1 0.3(14) . . . . ?
N1 C6 C4 C1 177.5(9) . . . . ?
O1 C6 C4 C2 178.8(9) . . . . ?
N1 C6 C4 C2 -4.0(13) . . . . ?
C15 C17 C18 C23 70.9(9) . . . . ?
C15 C17 C18 C19 -108.0(8) . . . . ?
C19 C18 C23 C21 0.0 . . . . ?
C17 C18 C23 C21 -178.9(7) . . . . ?
C18 C23 C21 C22 0.0 . . . . ?
C23 C21 C22 C20 0.0 . . . . ?
C21 C22 C20 C19 0.0 . . . . ?
C22 C20 C19 C18 0.0 . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
C17 C18 C19 C20 178.9(7) . . . . ?
N1 C15 C16 O5 -137.4(10) . . . . ?
C17 C15 C16 O5 -11.2(14) . . . . ?
N1 C15 C16 O6 46.6(11) . . . . ?
C17 C15 C16 O6 172.8(8) . . . . ?

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.128

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 937649'
#######################################################################
#
#                 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_mp35sd

#====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "C32 H22 N2 O8','C2 H6 O1 S1','C2 H6 O1 S1"
_chemical_formula_sum            'C36 H34 N2 O10 S2'
_chemical_formula_weight         718.77

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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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, 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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   9.104(7)
_cell_length_b                   13.550(10)
_cell_length_c                   28.20(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3479(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    413
_cell_measurement_theta_min      2.791
_cell_measurement_theta_max      19.043

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3740
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            5044
_diffrn_reflns_av_unetI/netI     0.1354
_diffrn_reflns_av_R_equivalents  0.1066
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.695
_diffrn_reflns_theta_max         21.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.626
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.626
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.616
_reflns_number_total             1944
_reflns_number_gt                1103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.602

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0936P)²+1.6694P]
 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_abs_structure_details 
;
 Flack x determined using 308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1944
_refine_ls_number_parameters     214
_refine_ls_number_restraints     302
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      0.952
_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_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 0.3618(8) -0.2442(5) 0.4964(3) 0.146(3) Uani 1 1 d . U . . .
C17 C 0.292(3) -0.3644(14) 0.5030(10) 0.185(13) Uani 1 1 d . U . . .
H17A H 0.2915 -0.3976 0.4721 0.277 Uiso 1 1 calc R U . . .
H17B H 0.1919 -0.3613 0.5155 0.277 Uiso 1 1 calc R U . . .
H17C H 0.3545 -0.4015 0.5250 0.277 Uiso 1 1 calc R U . . .
O5 O 0.2400(14) -0.1864(10) 0.4742(5) 0.119(5) Uani 1 1 d . U . . .
C18 C 0.349(4) -0.2063(16) 0.5535(10) 0.211(16) Uani 1 1 d . U . . .
H18A H 0.3833 -0.1378 0.5560 0.317 Uiso 1 1 calc R U . . .
H18B H 0.4109 -0.2486 0.5736 0.317 Uiso 1 1 calc R U . . .
H18C H 0.2471 -0.2105 0.5641 0.317 Uiso 1 1 calc R U . . .
C3 C 0.0633(11) 0.1821(9) 0.2637(5) 0.038(4) Uani 1 1 d . U . . .
H3 H 0.1055 0.2432 0.2731 0.046 Uiso 1 1 calc R U . . .
N1 N 0.3222(9) 0.0052(8) 0.3184(4) 0.039(3) Uani 1 1 d . U . . .
C2 C 0.0652(10) 0.0068(9) 0.2632(4) 0.031(3) Uani 1 1 d D U . . .
O2 O 0.3228(10) 0.1710(7) 0.3197(4) 0.057(3) Uani 1 1 d . U . . .
C5 C 0.1280(12) 0.0958(9) 0.2774(5) 0.035(4) Uani 1 1 d D U . . .
C4 C 0.1295(12) -0.0848(8) 0.2764(5) 0.032(3) Uani 1 1 d D U . . .
O1 O 0.3282(10) -0.1619(7) 0.3153(4) 0.056(3) Uani 1 1 d . U . . .
C6 C 0.2656(14) -0.0855(11) 0.3044(5) 0.041(4) Uani 1 1 d . U . . .
C8 C 0.4558(11) 0.0017(12) 0.3491(5) 0.045(3) Uani 1 1 d . U . . .
H8 H 0.4686 0.0692 0.3628 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2621(14) 0.0980(10) 0.3058(5) 0.035(4) Uani 1 1 d . U . . .
C9 C 0.5946(12) -0.0197(11) 0.3184(5) 0.052(4) Uani 1 1 d . U . . .
H9A H 0.5971 -0.0907 0.3102 0.063 Uiso 1 1 calc R U . . .
H9B H 0.5884 0.0183 0.2885 0.063 Uiso 1 1 calc R U . . .
C1 C 0.0646(13) -0.1719(9) 0.2640(5) 0.040(4) Uani 1 1 d . U . . .
H1 H 0.1062 -0.2327 0.2741 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7339(7) 0.0073(6) 0.3438(3) 0.038(3) Uani 1 1 d G U . . .
C11 C 0.8289(9) -0.0670(5) 0.3584(3) 0.050(4) Uani 1 1 d G U . . .
H11 H 0.8057 -0.1341 0.3522 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9579(8) -0.0432(7) 0.3822(3) 0.062(5) Uani 1 1 d G U . . .
H12 H 1.0228 -0.0940 0.3922 0.074 Uiso 1 1 calc R U . . .
C13 C 0.9918(7) 0.0550(8) 0.3914(3) 0.056(4) Uani 1 1 d G U . . .
H13 H 1.0799 0.0713 0.4076 0.067 Uiso 1 1 calc R U . . .
C14 C 0.8967(10) 0.1293(5) 0.3768(4) 0.067(5) Uani 1 1 d G U . . .
H14 H 0.9199 0.1964 0.3831 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7678(8) 0.1055(5) 0.3530(3) 0.048(4) Uani 1 1 d G U . . .
H15 H 0.7029 0.1563 0.3431 0.057 Uiso 1 1 calc R U . . .
O3 O 0.3084(9) -0.0562(7) 0.4110(4) 0.067(3) Uani 1 1 d . U . . .
H3A H 0.3017 -0.0974 0.4331 0.101 Uiso 1 1 calc R U . . .
O4 O 0.5293(10) -0.1215(8) 0.4045(4) 0.072(4) Uani 1 1 d . U . . .
C16 C 0.4387(12) -0.0667(10) 0.3892(5) 0.040(4) Uani 1 1 d . 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 O5 1.495(13) . ?
S1 C18 1.70(3) . ?
S1 C17 1.76(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 C5 1.366(16) . ?
C3 C3 1.39(2) 4 ?
C3 H3 0.9500 . ?
N1 C6 1.390(16) . ?
N1 C7 1.416(15) . ?
N1 C8 1.493(14) . ?
C2 C5 1.393(14) . ?
C2 C2 1.401(19) 4 ?
C2 C4 1.421(14) . ?
O2 C7 1.199(14) . ?
C5 C7 1.461(18) . ?
C4 C1 1.367(15) . ?
C4 C6 1.469(18) . ?
O1 C6 1.222(14) . ?
C8 C16 1.471(17) . ?
C8 C9 1.559(16) . ?
C8 H8 1.0000 . ?
C9 C10 1.502(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C1 C1 1.41(2) 4 ?
C1 H1 0.9500 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O3 C16 1.344(14) . ?
O3 H3A 0.8400 . ?
O4 C16 1.192(14) . ?

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
O5 S1 C18 101.0(13) . . ?
O5 S1 C17 105.2(11) . . ?
C18 S1 C17 99.0(12) . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C3 C3 121.0(7) . 4 ?
C5 C3 H3 119.5 . . ?
C3 C3 H3 119.5 4 . ?
C6 N1 C7 124.7(9) . . ?
C6 N1 C8 116.0(12) . . ?
C7 N1 C8 119.2(11) . . ?
C5 C2 C2 120.0(7) . 4 ?
C5 C2 C4 120.7(9) . . ?
C2 C2 C4 119.2(6) 4 . ?
C3 C5 C2 118.9(11) . . ?
C3 C5 C7 119.8(11) . . ?
C2 C5 C7 121.2(11) . . ?
C1 C4 C2 120.6(11) . . ?
C1 C4 C6 119.8(11) . . ?
C2 C4 C6 119.6(11) . . ?
O1 C6 N1 120.3(12) . . ?
O1 C6 C4 122.3(13) . . ?
N1 C6 C4 117.4(12) . . ?
C16 C8 N1 112.3(10) . . ?
C16 C8 C9 113.3(12) . . ?
N1 C8 C9 110.2(10) . . ?
C16 C8 H8 106.9 . . ?
N1 C8 H8 106.9 . . ?
C9 C8 H8 106.9 . . ?
O2 C7 N1 118.2(12) . . ?
O2 C7 C5 125.6(12) . . ?
N1 C7 C5 116.2(12) . . ?
C10 C9 C8 112.0(10) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C4 C1 C1 120.2(7) . 4 ?
C4 C1 H1 119.9 . . ?
C1 C1 H1 119.9 4 . ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 119.4(8) . . ?
C15 C10 C9 120.6(8) . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C16 O3 H3A 109.5 . . ?
O4 C16 O3 120.8(13) . . ?
O4 C16 C8 126.8(11) . . ?
O3 C16 C8 112.3(11) . . ?

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
C3 C3 C5 C2 0(2) 4 . . . ?
C3 C3 C5 C7 179.4(15) 4 . . . ?
C2 C2 C5 C3 -2(2) 4 . . . ?
C4 C2 C5 C3 179.7(13) . . . . ?
C2 C2 C5 C7 178.5(14) 4 . . . ?
C4 C2 C5 C7 0.6(17) . . . . ?
C5 C2 C4 C1 177.5(13) . . . . ?
C2 C2 C4 C1 0(2) 4 . . . ?
C5 C2 C4 C6 -1.5(17) . . . . ?
C2 C2 C4 C6 -179.5(13) 4 . . . ?
C7 N1 C6 O1 177.0(15) . . . . ?
C8 N1 C6 O1 -3.2(18) . . . . ?
C7 N1 C6 C4 -3.2(16) . . . . ?
C8 N1 C6 C4 176.6(11) . . . . ?
C1 C4 C6 O1 4(2) . . . . ?
C2 C4 C6 O1 -177.4(13) . . . . ?
C1 C4 C6 N1 -176.3(12) . . . . ?
C2 C4 C6 N1 2.7(18) . . . . ?
C6 N1 C8 C16 -49.2(15) . . . . ?
C7 N1 C8 C16 130.6(12) . . . . ?
C6 N1 C8 C9 78.1(14) . . . . ?
C7 N1 C8 C9 -102.1(14) . . . . ?
C6 N1 C7 O2 -179.0(14) . . . . ?
C8 N1 C7 O2 1.3(18) . . . . ?
C6 N1 C7 C5 2.2(16) . . . . ?
C8 N1 C7 C5 -177.6(11) . . . . ?
C3 C5 C7 O2 1(2) . . . . ?
C2 C5 C7 O2 -179.5(14) . . . . ?
C3 C5 C7 N1 -179.9(12) . . . . ?
C2 C5 C7 N1 -0.8(18) . . . . ?
C16 C8 C9 C10 -71.3(15) . . . . ?
N1 C8 C9 C10 161.9(11) . . . . ?
C2 C4 C1 C1 3(2) . . . 4 ?
C6 C4 C1 C1 -178.4(16) . . . 4 ?
C8 C9 C10 C11 111.2(11) . . . . ?
C8 C9 C10 C15 -68.5(13) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C12 -179.7(9) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C9 C10 C15 C14 179.7(9) . . . . ?
N1 C8 C16 O4 139.9(15) . . . . ?
C9 C8 C16 O4 14(2) . . . . ?
N1 C8 C16 O3 -45.4(16) . . . . ?
C9 C8 C16 O3 -171.0(11) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 937650'
#######################################################################
#
#                 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_tgmp23

#====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
"C36 H24 N4 O8','C2 H6 O1 S1','C2 H6 O1 S1','C2 H6 O1 S1','O1','O1"
_chemical_formula_sum            'C42 H42 N4 O13 S3'
_chemical_formula_weight         909.41

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.670(2)
_cell_length_b                   19.624(5)
_cell_length_c                   25.099(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4270.4(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    328
_cell_measurement_theta_min      2.647
_cell_measurement_theta_max      18.297

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4955
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            7766
_diffrn_reflns_av_unetI/netI     0.1818
_diffrn_reflns_av_R_equivalents  0.1149
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.317
_diffrn_reflns_theta_max         19.778
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.508
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.508
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.444
_reflns_number_total             3442
_reflns_number_gt                2045
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_max     0.755
_reflns_Friedel_fraction_full    0.363

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0489P)²]
 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 x determined using 522 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3442
_refine_ls_number_parameters     367
_refine_ls_number_restraints     424
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.922
_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_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
S3 S 0.3071(6) 0.7097(3) 0.1493(2) 0.0513(16) Uani 1 1 d . U . . .
O11 O 0.3805(15) 0.7144(7) 0.0949(5) 0.064(4) Uani 1 1 d . U . . .
C41 C 0.302(2) 0.7945(9) 0.1725(7) 0.052(6) Uiso 1 1 d . U . . .
H41A H 0.4073 0.8097 0.1806 0.077 Uiso 1 1 calc R U . . .
H41B H 0.2391 0.7970 0.2049 0.077 Uiso 1 1 calc R U . . .
H41C H 0.2575 0.8240 0.1451 0.077 Uiso 1 1 calc R U . . .
C42 C 0.105(2) 0.6990(10) 0.1387(7) 0.055(6) Uiso 1 1 d . U . . .
H42A H 0.0848 0.6529 0.1253 0.083 Uiso 1 1 calc R U . . .
H42B H 0.0687 0.7325 0.1126 0.083 Uiso 1 1 calc R U . . .
H42C H 0.0498 0.7056 0.1725 0.083 Uiso 1 1 calc R U . . .
C38 C 0.769(3) 0.8630(11) 0.0715(8) 0.090(8) Uiso 1 1 d . U . . .
H38A H 0.7156 0.8695 0.1055 0.135 Uiso 1 1 calc R U . . .
H38B H 0.8563 0.8319 0.0766 0.135 Uiso 1 1 calc R U . . .
H38C H 0.6974 0.8435 0.0454 0.135 Uiso 1 1 calc R U . . .
O2 O -0.1199(11) 0.2495(5) 0.0430(4) 0.022(2) Uani 1 1 d . U . . .
O1 O 0.5677(12) 0.4090(5) 0.2428(4) 0.022(2) Uani 1 1 d . U . . .
C14 C -0.0589(18) 0.2616(8) 0.0849(6) 0.020(3) Uiso 1 1 d . U . . .
S1 S 0.8373(6) 0.9425(3) 0.04796(19) 0.0417(14) Uani 1 1 d . U . . .
S2 S 1.2296(6) 0.9831(3) 0.0887(2) 0.0428(14) Uani 1 1 d . U . . .
O9 O 0.6966(13) 0.9832(6) 0.0321(4) 0.039(3) Uani 1 1 d . U . . .
O10 O 1.1860(14) 0.9089(6) 0.0829(5) 0.048(4) Uani 1 1 d . U . . .
C39 C 1.324(2) 1.0039(8) 0.0282(6) 0.037(5) Uani 1 1 d . U . . .
H39A H 1.2481 1.0078 -0.0005 0.055 Uiso 1 1 calc R U . . .
H39B H 1.3987 0.9680 0.0193 0.055 Uiso 1 1 calc R U . . .
H39C H 1.3787 1.0474 0.0323 0.055 Uiso 1 1 calc R U . . .
C40 C 1.3922(18) 0.9846(8) 0.1306(6) 0.034(5) Uiso 1 1 d . U . . .
H40A H 1.3604 0.9752 0.1674 0.051 Uiso 1 1 calc R U . . .
H40B H 1.4409 1.0296 0.1288 0.051 Uiso 1 1 calc R U . . .
H40C H 1.4659 0.9498 0.1190 0.051 Uiso 1 1 calc R U . . .
C37 C 0.914(2) 0.9131(10) -0.0119(7) 0.060(7) Uani 1 1 d . U . . .
H37A H 0.9585 0.9514 -0.0316 0.090 Uiso 1 1 calc R U . . .
H37B H 0.8316 0.8922 -0.0332 0.090 Uiso 1 1 calc R U . . .
H37C H 0.9939 0.8792 -0.0046 0.090 Uiso 1 1 calc R U . . .
N2 N -0.1187(13) 0.2340(6) 0.1320(4) 0.014(2) Uiso 1 1 d . U . . .
N1 N 0.5623(14) 0.4277(6) 0.1532(5) 0.014(2) Uiso 1 1 d . U . . .
O4 O -0.1355(12) 0.2291(5) 0.2225(4) 0.024(2) Uani 1 1 d . U . . .
O7 O -0.0918(11) 0.1084(5) 0.0844(4) 0.023(2) Uani 1 1 d . U . . .
O8 O -0.3467(11) 0.0979(5) 0.0750(4) 0.023(2) Uani 1 1 d . U . . .
H8 H -0.3218 0.0635 0.0569 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3577(18) 0.3609(7) 0.1960(5) 0.012(4) Uiso 1 1 d D U . . .
C11 C 0.0774(17) 0.2881(8) 0.1882(5) 0.018(4) Uiso 1 1 d D U . . .
C8 C 0.1485(17) 0.2994(7) 0.2366(6) 0.014(4) Uiso 1 1 d . U . . .
H8A H 0.1010 0.2831 0.2683 0.017 Uiso 1 1 calc R U . . .
C12 C 0.0847(16) 0.3024(7) 0.0899(5) 0.010(4) Uiso 1 1 d D U . . .
O5 O 0.5253(13) 0.5638(5) 0.1313(4) 0.027(2) Uani 1 1 d . U . . .
O6 O 0.7731(12) 0.5724(5) 0.1095(4) 0.027(2) Uani 1 1 d . U . . .
H6 H 0.7444 0.6098 0.0965 0.041 Uiso 1 1 calc R U . . .
O3 O 0.5656(12) 0.4396(5) 0.0630(4) 0.024(2) Uani 1 1 d . U . . .
N3 N 1.2160(14) 0.5239(6) 0.1606(5) 0.028(4) Uani 1 1 d . U . . .
H43 H 1.3006 0.5449 0.1504 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5016(19) 0.4002(8) 0.2005(6) 0.019(3) Uani 1 1 d . U . . .
C1 C 0.2895(18) 0.3346(7) 0.2402(6) 0.017(4) Uiso 1 1 d . U . . .
H1 H 0.3376 0.3400 0.2740 0.020 Uiso 1 1 calc R U . . .
C5 C 0.3570(17) 0.3774(7) 0.0984(5) 0.014(4) Uiso 1 1 d D U . . .
C13 C -0.0625(18) 0.2481(8) 0.1843(6) 0.020(3) Uiso 1 1 d . U . . .
C3 C 0.2924(17) 0.3653(7) 0.0490(6) 0.014(4) Uiso 1 1 d . U . . .
H3 H 0.3417 0.3815 0.0176 0.017 Uiso 1 1 calc R U . . .
N4 N -0.7817(16) 0.1489(6) 0.1101(5) 0.028(4) Uani 1 1 d . U . . .
H44 H -0.8642 0.1332 0.0938 0.034 Uiso 1 1 calc R U . . .
C9 C 0.1472(17) 0.3136(7) 0.1408(5) 0.016(4) Uiso 1 1 d D U . . .
C28 C -0.4023(17) 0.2322(8) 0.1122(6) 0.022(4) Uiso 1 1 d . U . . .
H28A H -0.4002 0.2752 0.1328 0.026 Uiso 1 1 calc R U . . .
H28B H -0.3967 0.2443 0.0739 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1538(18) 0.3290(7) 0.0454(6) 0.022(4) Uani 1 1 d . U . . .
H10 H 0.1068 0.3227 0.0116 0.026 Uiso 1 1 calc R U . . .
C29 C -0.5515(18) 0.1977(8) 0.1221(6) 0.018(4) Uiso 1 1 d . U . . .
C30 C -0.6599(18) 0.1811(8) 0.0858(6) 0.023(4) Uiso 1 1 d . U . . .
H30 H -0.6529 0.1903 0.0487 0.028 Uiso 1 1 calc R U . . .
C31 C -0.6076(19) 0.1754(8) 0.1725(6) 0.026(5) Uiso 1 1 d . U . . .
C32 C -0.552(2) 0.1802(8) 0.2260(6) 0.029(5) Uiso 1 1 d . U . . .
H32 H -0.4554 0.2003 0.2341 0.034 Uiso 1 1 calc R U . . .
C33 C -0.647(2) 0.1539(8) 0.2656(7) 0.030(5) Uiso 1 1 d . U . . .
H33 H -0.6129 0.1565 0.3015 0.036 Uiso 1 1 calc R U . . .
C34 C -0.788(2) 0.1240(8) 0.2548(7) 0.032(5) Uani 1 1 d . U . . .
H34 H -0.8475 0.1058 0.2832 0.039 Uiso 1 1 calc R U . . .
C35 C -0.844(2) 0.1203(8) 0.2035(7) 0.029(5) Uani 1 1 d . U . . .
H35 H -0.9419 0.1009 0.1963 0.035 Uiso 1 1 calc R U . . .
C36 C -0.7546(19) 0.1452(8) 0.1636(6) 0.021(4) Uiso 1 1 d . U . . .
C17 C 0.8419(18) 0.4379(8) 0.1374(6) 0.027(4) Uani 1 1 d . U . . .
H17A H 0.8437 0.4379 0.0979 0.032 Uiso 1 1 calc R U . . .
H17B H 0.8403 0.3898 0.1493 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2906(17) 0.3509(7) 0.1455(5) 0.020(4) Uiso 1 1 d D U . . .
C7 C 0.5012(19) 0.4157(8) 0.1018(6) 0.019(3) Uani 1 1 d . U . . .
C15 C 0.6941(17) 0.4722(8) 0.1559(6) 0.020(4) Uani 1 1 d . U . . .
H15 H 0.7096 0.4820 0.1946 0.024 Uiso 1 1 calc R U . . .
C18 C 0.9905(18) 0.4711(8) 0.1575(6) 0.022(4) Uiso 1 1 d . U . . .
C19 C 1.1019(19) 0.5013(8) 0.1275(7) 0.028(5) Uiso 1 1 d . U . . .
H19 H 1.1005 0.5060 0.0898 0.033 Uiso 1 1 calc R U . . .
C20 C 1.0403(18) 0.4751(8) 0.2118(6) 0.018(4) Uiso 1 1 d . U . . .
C21 C 0.980(2) 0.4505(8) 0.2598(6) 0.028(5) Uiso 1 1 d . U . . .
H21 H 0.8831 0.4275 0.2606 0.033 Uiso 1 1 calc R U . . .
C22 C 1.062(2) 0.4603(9) 0.3049(7) 0.039(5) Uiso 1 1 d . U . . .
H22 H 1.0232 0.4429 0.3376 0.046 Uiso 1 1 calc R U . . .
C23 C 1.200(2) 0.4948(9) 0.3048(8) 0.038(5) Uani 1 1 d . U . . .
H23 H 1.2527 0.5014 0.3376 0.046 Uiso 1 1 calc R U . . .
C24 C 1.2661(19) 0.5206(8) 0.2581(7) 0.033(5) Uani 1 1 d . U . . .
H24 H 1.3619 0.5440 0.2578 0.039 Uiso 1 1 calc R U . . .
C25 C 1.179(2) 0.5090(8) 0.2112(7) 0.027(5) Uiso 1 1 d . U . . .
C26 C -0.2567(16) 0.1898(7) 0.1268(6) 0.016(4) Uiso 1 1 d . U . . .
H26 H -0.2766 0.1712 0.1632 0.019 Uiso 1 1 calc R U . . .
C27 C -0.220(2) 0.1290(8) 0.0925(6) 0.017(4) Uiso 1 1 d . U . . .
C16 C 0.658(2) 0.5418(8) 0.1298(6) 0.025(5) Uani 1 1 d . U . . .
O12 O 0.7016(13) 0.6916(6) 0.0800(4) 0.043(3) Uiso 1 1 d . . . . .
O13 O 0.773(4) 0.6958(19) -0.0201(15) 0.054(18) Uiso 0.55(17) 1 d . U P . .
O14 O 0.699(15) 0.706(4) -0.025(3) 0.10(3) Uiso 0.30(9) 1 d . U P . .
O15 O 0.839(13) 0.688(3) -0.019(3) 0.08(2) Uiso 0.30(9) 1 d . U P . .


_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
S3 O11 1.508(12) . ?
S3 C41 1.764(17) . ?
S3 C42 1.787(18) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C38 S1 1.77(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O2 C14 1.201(16) . ?
O1 C6 1.218(16) . ?
C14 N2 1.401(18) . ?
C14 C12 1.48(2) . ?
S1 O9 1.512(12) . ?
S1 C37 1.740(17) . ?
S2 O10 1.511(11) . ?
S2 C40 1.759(16) . ?
S2 C39 1.775(15) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
N2 C13 1.427(18) . ?
N2 C26 1.483(17) . ?
N1 C6 1.407(18) . ?
N1 C7 1.414(18) . ?
N1 C15 1.439(18) . ?
O4 C13 1.206(17) . ?
O7 C27 1.200(16) . ?
O8 C27 1.332(17) . ?
O8 H8 0.8400 . ?
C4 C1 1.359(18) . ?
C4 C2 1.409(15) . ?
C4 C6 1.47(2) . ?
C11 C8 1.380(19) . ?
C11 C9 1.426(16) . ?
C11 C13 1.45(2) . ?
C8 C1 1.407(19) . ?
C8 H8A 0.9500 . ?
C12 C10 1.370(19) . ?
C12 C9 1.406(15) . ?
O5 C16 1.228(18) . ?
O6 C16 1.273(17) . ?
O6 H6 0.8400 . ?
O3 C7 1.218(17) . ?
N3 C25 1.342(18) . ?
N3 C19 1.366(19) . ?
N3 H43 0.8800 . ?
C1 H1 0.9500 . ?
C5 C3 1.381(18) . ?
C5 C2 1.414(15) . ?
C5 C7 1.46(2) . ?
C3 C10 1.40(2) . ?
C3 H3 0.9500 . ?
N4 C36 1.366(18) . ?
N4 C30 1.374(18) . ?
N4 H44 0.8800 . ?
C9 C2 1.448(19) . ?
C28 C29 1.48(2) . ?
C28 C26 1.556(19) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C10 H10 0.9500 . ?
C29 C30 1.350(19) . ?
C29 C31 1.42(2) . ?
C30 H30 0.9500 . ?
C31 C36 1.42(2) . ?
C31 C32 1.43(2) . ?
C32 C33 1.39(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.39(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.38(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.36(2) . ?
C35 H35 0.9500 . ?
C17 C15 1.52(2) . ?
C17 C18 1.53(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C15 C16 1.55(2) . ?
C15 H15 1.0000 . ?
C18 C19 1.36(2) . ?
C18 C20 1.43(2) . ?
C19 H19 0.9500 . ?
C20 C25 1.37(2) . ?
C20 C21 1.40(2) . ?
C21 C22 1.35(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.38(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.40(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.42(2) . ?
C24 H24 0.9500 . ?
C26 C27 1.51(2) . ?
C26 H26 1.0000 . ?
O13 O15 0.59(12) . ?
O13 O14 0.68(13) . ?
O14 O15 1.3(2) . ?

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
O11 S3 C41 104.6(8) . . ?
O11 S3 C42 106.7(9) . . ?
C41 S3 C42 97.9(9) . . ?
S3 C41 H41A 109.5 . . ?
S3 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
S3 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
S3 C42 H42A 109.5 . . ?
S3 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
S3 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
S1 C38 H38A 109.5 . . ?
S1 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
S1 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O2 C14 N2 120.0(14) . . ?
O2 C14 C12 123.4(14) . . ?
N2 C14 C12 116.6(13) . . ?
O9 S1 C37 104.8(8) . . ?
O9 S1 C38 106.5(9) . . ?
C37 S1 C38 97.1(10) . . ?
O10 S2 C40 105.9(8) . . ?
O10 S2 C39 104.8(8) . . ?
C40 S2 C39 97.8(8) . . ?
S2 C39 H39A 109.5 . . ?
S2 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
S2 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
S2 C40 H40A 109.5 . . ?
S2 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
S2 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
S1 C37 H37A 109.5 . . ?
S1 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
S1 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C14 N2 C13 125.1(13) . . ?
C14 N2 C26 116.7(12) . . ?
C13 N2 C26 118.1(12) . . ?
C6 N1 C7 124.4(13) . . ?
C6 N1 C15 119.4(12) . . ?
C7 N1 C15 116.2(12) . . ?
C27 O8 H8 109.5 . . ?
C1 C4 C2 120.2(14) . . ?
C1 C4 C6 120.3(13) . . ?
C2 C4 C6 119.5(13) . . ?
C8 C11 C9 119.3(14) . . ?
C8 C11 C13 121.4(13) . . ?
C9 C11 C13 119.3(13) . . ?
C11 C8 C1 121.5(14) . . ?
C11 C8 H8A 119.2 . . ?
C1 C8 H8A 119.2 . . ?
C10 C12 C9 120.7(13) . . ?
C10 C12 C14 120.3(13) . . ?
C9 C12 C14 119.0(13) . . ?
C16 O6 H6 109.5 . . ?
C25 N3 C19 109.4(14) . . ?
C25 N3 H43 125.3 . . ?
C19 N3 H43 125.3 . . ?
O1 C6 N1 120.3(14) . . ?
O1 C6 C4 122.7(14) . . ?
N1 C6 C4 117.0(13) . . ?
C4 C1 C8 120.8(14) . . ?
C4 C1 H1 119.6 . . ?
C8 C1 H1 119.6 . . ?
C3 C5 C2 121.5(13) . . ?
C3 C5 C7 119.3(13) . . ?
C2 C5 C7 119.1(13) . . ?
O4 C13 N2 119.4(14) . . ?
O4 C13 C11 123.6(14) . . ?
N2 C13 C11 116.9(14) . . ?
C5 C3 C10 119.5(15) . . ?
C5 C3 H3 120.2 . . ?
C10 C3 H3 120.2 . . ?
C36 N4 C30 109.2(14) . . ?
C36 N4 H44 125.4 . . ?
C30 N4 H44 125.4 . . ?
C12 C9 C11 122.7(13) . . ?
C12 C9 C2 119.0(12) . . ?
C11 C9 C2 118.3(12) . . ?
C29 C28 C26 115.2(13) . . ?
C29 C28 H28A 108.5 . . ?
C26 C28 H28A 108.5 . . ?
C29 C28 H28B 108.5 . . ?
C26 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C12 C10 C3 121.2(14) . . ?
C12 C10 H10 119.4 . . ?
C3 C10 H10 119.4 . . ?
C30 C29 C31 106.7(14) . . ?
C30 C29 C28 127.2(14) . . ?
C31 C29 C28 126.1(14) . . ?
C29 C30 N4 110.3(14) . . ?
C29 C30 H30 124.9 . . ?
N4 C30 H30 124.9 . . ?
C36 C31 C29 107.1(14) . . ?
C36 C31 C32 118.4(15) . . ?
C29 C31 C32 134.4(16) . . ?
C33 C32 C31 116.8(16) . . ?
C33 C32 H32 121.6 . . ?
C31 C32 H32 121.6 . . ?
C32 C33 C34 122.6(16) . . ?
C32 C33 H33 118.7 . . ?
C34 C33 H33 118.7 . . ?
C35 C34 C33 121.0(16) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C36 C35 C34 118.1(16) . . ?
C36 C35 H35 120.9 . . ?
C34 C35 H35 120.9 . . ?
C35 C36 N4 130.3(16) . . ?
C35 C36 C31 123.0(15) . . ?
N4 C36 C31 106.6(15) . . ?
C15 C17 C18 114.9(13) . . ?
C15 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C15 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C4 C2 C5 122.3(14) . . ?
C4 C2 C9 119.8(12) . . ?
C5 C2 C9 117.9(12) . . ?
O3 C7 N1 119.6(14) . . ?
O3 C7 C5 122.9(14) . . ?
N1 C7 C5 117.5(14) . . ?
N1 C15 C17 112.8(12) . . ?
N1 C15 C16 110.7(12) . . ?
C17 C15 C16 115.7(13) . . ?
N1 C15 H15 105.6 . . ?
C17 C15 H15 105.6 . . ?
C16 C15 H15 105.6 . . ?
C19 C18 C20 106.9(14) . . ?
C19 C18 C17 126.8(15) . . ?
C20 C18 C17 126.3(14) . . ?
C18 C19 N3 108.5(15) . . ?
C18 C19 H19 125.8 . . ?
N3 C19 H19 125.8 . . ?
C25 C20 C21 120.4(15) . . ?
C25 C20 C18 106.2(14) . . ?
C21 C20 C18 133.3(15) . . ?
C22 C21 C20 118.2(17) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C21 C22 C23 121.9(18) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C24 122.2(17) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C23 C24 C25 114.9(16) . . ?
C23 C24 H24 122.5 . . ?
C25 C24 H24 122.5 . . ?
N3 C25 C20 109.0(15) . . ?
N3 C25 C24 128.5(17) . . ?
C20 C25 C24 122.3(16) . . ?
N2 C26 C27 110.1(12) . . ?
N2 C26 C28 111.3(11) . . ?
C27 C26 C28 117.4(13) . . ?
N2 C26 H26 105.7 . . ?
C27 C26 H26 105.7 . . ?
C28 C26 H26 105.7 . . ?
O7 C27 O8 123.6(14) . . ?
O7 C27 C26 124.0(15) . . ?
O8 C27 C26 112.2(13) . . ?
O5 C16 O6 125.7(16) . . ?
O5 C16 C15 119.1(15) . . ?
O6 C16 C15 115.2(14) . . ?
O15 O13 O14 172(10) . . ?
O13 O14 O15 4(8) . . ?
O13 O15 O14 4(9) . . ?

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 C14 N2 C13 -175.8(14) . . . . ?
C12 C14 N2 C13 7(2) . . . . ?
O2 C14 N2 C26 0(2) . . . . ?
C12 C14 N2 C26 -176.4(12) . . . . ?
C9 C11 C8 C1 -1(2) . . . . ?
C13 C11 C8 C1 175.9(14) . . . . ?
O2 C14 C12 C10 1(2) . . . . ?
N2 C14 C12 C10 177.5(13) . . . . ?
O2 C14 C12 C9 -179.9(15) . . . . ?
N2 C14 C12 C9 -3(2) . . . . ?
C7 N1 C6 O1 174.6(14) . . . . ?
C15 N1 C6 O1 -6(2) . . . . ?
C7 N1 C6 C4 -5(2) . . . . ?
C15 N1 C6 C4 173.9(13) . . . . ?
C1 C4 C6 O1 2(2) . . . . ?
C2 C4 C6 O1 -177.8(15) . . . . ?
C1 C4 C6 N1 -177.9(14) . . . . ?
C2 C4 C6 N1 2(2) . . . . ?
C2 C4 C1 C8 -2(2) . . . . ?
C6 C4 C1 C8 177.2(14) . . . . ?
C11 C8 C1 C4 2(2) . . . . ?
C14 N2 C13 O4 169.8(14) . . . . ?
C26 N2 C13 O4 -6(2) . . . . ?
C14 N2 C13 C11 -7(2) . . . . ?
C26 N2 C13 C11 176.6(13) . . . . ?
C8 C11 C13 O4 9(3) . . . . ?
C9 C11 C13 O4 -174.0(15) . . . . ?
C8 C11 C13 N2 -174.2(13) . . . . ?
C9 C11 C13 N2 3(2) . . . . ?
C2 C5 C3 C10 3(2) . . . . ?
C7 C5 C3 C10 -179.6(13) . . . . ?
C10 C12 C9 C11 178.6(14) . . . . ?
C14 C12 C9 C11 -1(2) . . . . ?
C10 C12 C9 C2 -3(2) . . . . ?
C14 C12 C9 C2 177.5(13) . . . . ?
C8 C11 C9 C12 177.9(14) . . . . ?
C13 C11 C9 C12 1(2) . . . . ?
C8 C11 C9 C2 0(2) . . . . ?
C13 C11 C9 C2 -177.3(14) . . . . ?
C9 C12 C10 C3 3(2) . . . . ?
C14 C12 C10 C3 -177.5(13) . . . . ?
C5 C3 C10 C12 -3(2) . . . . ?
C26 C28 C29 C30 -118.0(18) . . . . ?
C26 C28 C29 C31 62(2) . . . . ?
C31 C29 C30 N4 -0.4(18) . . . . ?
C28 C29 C30 N4 179.3(14) . . . . ?
C36 N4 C30 C29 1.0(18) . . . . ?
C30 C29 C31 C36 -0.3(19) . . . . ?
C28 C29 C31 C36 180.0(15) . . . . ?
C30 C29 C31 C32 -176.9(17) . . . . ?
C28 C29 C31 C32 3(3) . . . . ?
C36 C31 C32 C33 1(2) . . . . ?
C29 C31 C32 C33 177.1(18) . . . . ?
C31 C32 C33 C34 0(2) . . . . ?
C32 C33 C34 C35 -1(3) . . . . ?
C33 C34 C35 C36 2(2) . . . . ?
C34 C35 C36 N4 -179.0(17) . . . . ?
C34 C35 C36 C31 -1(3) . . . . ?
C30 N4 C36 C35 177.4(17) . . . . ?
C30 N4 C36 C31 -1.1(18) . . . . ?
C29 C31 C36 C35 -177.8(16) . . . . ?
C32 C31 C36 C35 -1(3) . . . . ?
C29 C31 C36 N4 0.9(19) . . . . ?
C32 C31 C36 N4 178.2(13) . . . . ?
C1 C4 C2 C5 179.9(14) . . . . ?
C6 C4 C2 C5 0(2) . . . . ?
C1 C4 C2 C9 1(2) . . . . ?
C6 C4 C2 C9 -178.6(13) . . . . ?
C3 C5 C2 C4 177.8(14) . . . . ?
C7 C5 C2 C4 1(2) . . . . ?
C3 C5 C2 C9 -3(2) . . . . ?
C7 C5 C2 C9 179.6(13) . . . . ?
C12 C9 C2 C4 -178.0(14) . . . . ?
C11 C9 C2 C4 0(2) . . . . ?
C12 C9 C2 C5 3(2) . . . . ?
C11 C9 C2 C5 -178.5(14) . . . . ?
C6 N1 C7 O3 -177.1(14) . . . . ?
C15 N1 C7 O3 4(2) . . . . ?
C6 N1 C7 C5 6(2) . . . . ?
C15 N1 C7 C5 -172.9(13) . . . . ?
C3 C5 C7 O3 2(2) . . . . ?
C2 C5 C7 O3 179.5(14) . . . . ?
C3 C5 C7 N1 179.2(13) . . . . ?
C2 C5 C7 N1 -4(2) . . . . ?
C6 N1 C15 C17 105.4(16) . . . . ?
C7 N1 C15 C17 -75.5(17) . . . . ?
C6 N1 C15 C16 -123.2(14) . . . . ?
C7 N1 C15 C16 55.9(17) . . . . ?
C18 C17 C15 N1 -158.7(13) . . . . ?
C18 C17 C15 C16 72.4(17) . . . . ?
C15 C17 C18 C19 -116.3(18) . . . . ?
C15 C17 C18 C20 65(2) . . . . ?
C20 C18 C19 N3 -0.4(18) . . . . ?
C17 C18 C19 N3 -179.4(14) . . . . ?
C25 N3 C19 C18 -0.4(18) . . . . ?
C19 C18 C20 C25 1.0(18) . . . . ?
C17 C18 C20 C25 180.0(15) . . . . ?
C19 C18 C20 C21 -176.4(17) . . . . ?
C17 C18 C20 C21 3(3) . . . . ?
C25 C20 C21 C22 -1(2) . . . . ?
C18 C20 C21 C22 176.4(17) . . . . ?
C20 C21 C22 C23 2(3) . . . . ?
C21 C22 C23 C24 -2(3) . . . . ?
C22 C23 C24 C25 1(2) . . . . ?
C19 N3 C25 C20 1.0(18) . . . . ?
C19 N3 C25 C24 177.4(17) . . . . ?
C21 C20 C25 N3 176.5(14) . . . . ?
C18 C20 C25 N3 -1.3(18) . . . . ?
C21 C20 C25 C24 0(2) . . . . ?
C18 C20 C25 C24 -177.9(15) . . . . ?
C23 C24 C25 N3 -175.8(16) . . . . ?
C23 C24 C25 C20 0(2) . . . . ?
C14 N2 C26 C27 60.9(16) . . . . ?
C13 N2 C26 C27 -122.6(14) . . . . ?
C14 N2 C26 C28 -71.1(16) . . . . ?
C13 N2 C26 C28 105.4(14) . . . . ?
C29 C28 C26 N2 -162.0(12) . . . . ?
C29 C28 C26 C27 69.9(18) . . . . ?
N2 C26 C27 O7 21(2) . . . . ?
C28 C26 C27 O7 149.6(15) . . . . ?
N2 C26 C27 O8 -163.4(12) . . . . ?
C28 C26 C27 O8 -34.6(19) . . . . ?
N1 C15 C16 O5 31(2) . . . . ?
C17 C15 C16 O5 160.7(14) . . . . ?
N1 C15 C16 O6 -151.0(13) . . . . ?
C17 C15 C16 O6 -21.1(19) . . . . ?

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
C41 H41B O4 0.98 2.43 3.27(2) 143.3 4
C41 H41C O10 0.98 2.37 3.33(2) 169.6 1_455
C39 H39A O3 0.98 2.46 3.392(19) 159.5 3_565
C39 H39B O9 0.98 2.62 3.25(2) 122.6 1_655
C40 H40B O8 0.98 2.65 3.466(19) 141.2 1_765
C37 H37A O5 0.98 2.59 3.18(2) 119.3 3_565
C37 H37A O3 0.98 2.46 3.43(2) 167.8 3_565
C37 H37B O11 0.98 2.64 3.27(2) 122.4 3_565
C37 H37C O14 0.98 2.55 3.53(9) 174.0 3_565
O8 H8 S1 0.84 2.76 3.507(11) 149.8 1_445
O8 H8 O9 0.84 1.70 2.521(15) 164.5 1_445
O6 H6 O12 0.84 1.70 2.531(15) 169.9 .
C28 H28B O2 0.99 2.52 3.021(18) 110.8 .
C30 H30 O2 0.95 2.60 3.525(19) 163.6 3_455
C41 H41B O4 0.98 2.43 3.27(2) 143.3 4
C41 H41C O10 0.98 2.37 3.33(2) 169.6 1_455
C39 H39A O3 0.98 2.46 3.392(19) 159.5 3_565
C39 H39B O9 0.98 2.62 3.25(2) 122.6 1_655
C40 H40B O8 0.98 2.65 3.466(19) 141.2 1_765
C37 H37A O5 0.98 2.59 3.18(2) 119.3 3_565
C37 H37A O3 0.98 2.46 3.43(2) 167.8 3_565
C37 H37B O11 0.98 2.64 3.27(2) 122.4 3_565
C37 H37C O14 0.98 2.55 3.53(9) 174.0 3_565
O8 H8 S1 0.84 2.76 3.507(11) 149.8 1_445
O8 H8 O9 0.84 1.70 2.521(15) 164.5 1_445
O6 H6 O12 0.84 1.70 2.531(15) 169.9 .
N3 H43 O5 0.88 2.04 2.888(17) 161.7 1_655
N4 H44 O7 0.88 2.05 2.877(16) 157.0 1_455
C28 H28B O2 0.99 2.52 3.021(18) 110.8 .
C30 H30 O2 0.95 2.60 3.525(19) 163.6 3_455

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 937651'
#######################################################################
#
#                 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.
# 
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#  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_tgmp68

#====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "C20 H14 O8 N2','C2 H6 O1 S1','C2 H6 O1 S1"
_chemical_formula_sum            'C24 H26 N2 O10 S2'
_chemical_formula_weight         566.59

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.2349(5)
_cell_length_b                   7.02890(10)
_cell_length_c                   14.7664(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.8260(10)
_cell_angle_gamma                90
_cell_volume                     2515.12(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8958
_cell_measurement_theta_min      2.759
_cell_measurement_theta_max      30.370

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.274
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            30969
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.681
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             4361
_reflns_number_gt                4076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.936

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0264P)²+5.6420P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dirdif
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1741 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4361
_refine_ls_number_parameters     378
_refine_ls_number_restraints     208
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.061
_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_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 0.40653(4) 0.07226(17) 0.52526(7) 0.0270(2) Uani 1 1 d . U . . .
N1 N 0.40982(11) -0.4417(5) 0.18522(19) 0.0158(6) Uani 1 1 d . U . . .
C9 C 0.02781(13) -0.4355(6) 0.0152(2) 0.0138(7) Uani 1 1 d . U . . .
N2 N 0.13896(11) -0.4374(6) 0.07506(19) 0.0173(6) Uani 1 1 d . U . . .
C12 C 0.03981(14) -0.4289(6) 0.1088(2) 0.0146(7) Uani 1 1 d . U . . .
C4 C 0.50420(14) -0.4417(6) 0.1261(2) 0.0145(7) Uani 1 1 d . U . . .
C2 C 0.48201(14) -0.4406(6) 0.0373(2) 0.0131(7) Uani 1 1 d . U . . .
C11 C 0.07040(14) -0.4405(6) -0.0490(2) 0.0147(7) Uani 1 1 d . U . . .
C5 C 0.42463(14) -0.4398(6) 0.0209(2) 0.0149(7) Uani 1 1 d . U . . .
C7 C 0.38590(14) -0.4434(6) 0.0983(2) 0.0167(7) Uani 1 1 d . U . . .
C1 C 0.56043(14) -0.4388(6) 0.1404(2) 0.0160(7) Uani 1 1 d . U . . .
H1 H 0.5751 -0.4388 0.2005 0.019 Uiso 1 1 calc R U . . .
C13 C 0.12876(14) -0.4464(6) -0.0185(2) 0.0166(7) Uani 1 1 d . U . . .
O2 O 0.33631(10) -0.4499(5) 0.08739(17) 0.0236(6) Uani 1 1 d . U . . .
C3 C 0.40366(14) -0.4359(6) -0.0663(2) 0.0163(7) Uani 1 1 d . U . . .
H3 H 0.3649 -0.4312 -0.0764 0.020 Uiso 1 1 calc R U . . .
O1 O 0.48305(10) -0.4692(4) 0.28198(17) 0.0225(7) Uani 1 1 d . U . . .
O3 O 0.16666(10) -0.4566(5) -0.07142(18) 0.0250(7) Uani 1 1 d . U . . .
C8 C 0.05735(14) -0.4418(6) -0.1401(2) 0.0177(7) Uani 1 1 d . U . . .
H8 H 0.0861 -0.4486 -0.1830 0.021 Uiso 1 1 calc R U . . .
O9 O 0.43854(11) 0.0587(5) 0.43756(17) 0.0272(6) Uani 1 1 d . U . . .
C18 C 0.19740(14) -0.4309(7) 0.1068(2) 0.0197(7) Uani 1 1 d . U . . .
H18 H 0.2200 -0.4890 0.0579 0.024 Uiso 1 1 calc R U . . .
C6 C 0.46645(14) -0.4521(6) 0.2045(2) 0.0149(7) Uani 1 1 d . U . . .
C14 C 0.09784(14) -0.4150(6) 0.1400(2) 0.0170(8) Uani 1 1 d . U . . .
O4 O 0.11084(11) -0.3876(4) 0.21852(18) 0.0233(7) Uani 1 1 d . U . . .
C10 C -0.00236(14) -0.4334(6) 0.1705(2) 0.0174(7) Uani 1 1 d . U . . .
H10 H 0.0059 -0.4307 0.2336 0.021 Uiso 1 1 calc R U . . .
O7 O 0.23443(11) -0.5039(4) 0.25487(19) 0.0253(7) Uani 1 1 d . U . . .
O8 O 0.18090(13) -0.7186(5) 0.1839(2) 0.0289(7) Uani 1 1 d . U . . .
H8A H 0.180(2) -0.777(8) 0.236(4) 0.047(17) Uiso 1 1 d . . . . .
O6 O 0.40597(12) -0.1560(4) 0.31062(19) 0.0225(6) Uani 1 1 d . U . . .
H6 H 0.419(2) -0.085(8) 0.361(4) 0.043(15) Uiso 1 1 d . . . . .
C15 C 0.37130(14) -0.4545(6) 0.2624(2) 0.0183(8) Uani 1 1 d . U . . .
H15 H 0.3345 -0.4096 0.2395 0.022 Uiso 1 1 calc R U . . .
C16 C 0.38799(16) -0.3226(6) 0.3394(3) 0.0197(8) Uani 1 1 d . U . . .
O5 O 0.38020(12) -0.3631(4) 0.41781(18) 0.0261(7) Uani 1 1 d . U . . .
C21 C 0.4350(2) 0.2742(7) 0.5804(3) 0.0380(12) Uani 1 1 d . U . . .
H21A H 0.4233 0.3897 0.5483 0.057 Uiso 1 1 calc R U . . .
H21B H 0.4754 0.2657 0.5804 0.057 Uiso 1 1 calc R U . . .
H21C H 0.4222 0.2790 0.6429 0.057 Uiso 1 1 calc R U . . .
C20 C 0.21705(16) -0.2266(6) 0.1181(3) 0.0229(9) Uani 1 1 d . U . . .
H20A H 0.2108 -0.1570 0.0613 0.034 Uiso 1 1 calc R U . . .
H20B H 0.2565 -0.2259 0.1335 0.034 Uiso 1 1 calc R U . . .
H20C H 0.1965 -0.1653 0.1667 0.034 Uiso 1 1 calc R U . . .
C17 C 0.36370(18) -0.6592(6) 0.2929(3) 0.0245(9) Uani 1 1 d . U . . .
H17A H 0.3529 -0.7377 0.2407 0.037 Uiso 1 1 calc R U . . .
H17B H 0.3349 -0.6649 0.3386 0.037 Uiso 1 1 calc R U . . .
H17C H 0.3985 -0.7069 0.3189 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4336(2) -0.1111(7) 0.5967(3) 0.0291(10) Uani 1 1 d . U . . .
H22A H 0.4213 -0.2353 0.5739 0.044 Uiso 1 1 calc R U . . .
H22B H 0.4204 -0.0929 0.6585 0.044 Uiso 1 1 calc R U . . .
H22C H 0.4740 -0.1060 0.5968 0.044 Uiso 1 1 calc R U . . .
C19 C 0.20523(16) -0.5544(6) 0.1904(3) 0.0218(9) Uani 1 1 d . U . . .
S2A S 0.20307(6) -1.0095(2) 0.39038(10) 0.0258(5) Uani 0.773(5) 1 d . U P A 1
O10A O 0.16514(13) -0.9414(6) 0.3150(2) 0.0256(9) Uani 0.773(5) 1 d . U P A 1
C23A C 0.2260(3) -0.7994(12) 0.4482(5) 0.0331(15) Uani 0.773(5) 1 d . U P A 1
H23A H 0.1964 -0.7518 0.4866 0.050 Uiso 0.773(5) 1 calc R U P A 1
H23B H 0.2357 -0.7019 0.4037 0.050 Uiso 0.773(5) 1 calc R U P A 1
H23C H 0.2585 -0.8296 0.4858 0.050 Uiso 0.773(5) 1 calc R U P A 1
C24A C 0.2697(3) -1.0461(12) 0.3309(5) 0.0369(17) Uani 0.773(5) 1 d . U P A 1
H24A H 0.2671 -1.1595 0.2926 0.055 Uiso 0.773(5) 1 calc R U P A 1
H24B H 0.2995 -1.0631 0.3758 0.055 Uiso 0.773(5) 1 calc R U P A 1
H24C H 0.2776 -0.9348 0.2933 0.055 Uiso 0.773(5) 1 calc R U P A 1
S2B S 0.2381(2) -0.9102(8) 0.4211(3) 0.0241(17) Uani 0.227(5) 1 d . U P A 2
O10B O 0.2391(6) -0.699(2) 0.4066(10) 0.028(3) Uani 0.227(5) 1 d . U P A 2
C23B C 0.1709(11) -0.995(3) 0.3837(15) 0.033(5) Uiso 0.227(5) 1 d . U P A 2
H23D H 0.1420 -0.9175 0.4113 0.049 Uiso 0.227(5) 1 calc R U P A 2
H23E H 0.1664 -1.1281 0.4020 0.049 Uiso 0.227(5) 1 calc R U P A 2
H23F H 0.1679 -0.9855 0.3176 0.049 Uiso 0.227(5) 1 calc R U P A 2
C24B C 0.2642(12) -1.107(4) 0.3584(18) 0.032(7) Uiso 0.227(5) 1 d . U P A 2
H24D H 0.3046 -1.1061 0.3618 0.048 Uiso 0.227(5) 1 calc R U P A 2
H24E H 0.2521 -1.0961 0.2950 0.048 Uiso 0.227(5) 1 calc R U P A 2
H24F H 0.2503 -1.2256 0.3841 0.048 Uiso 0.227(5) 1 calc R U P A 2


_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 O9 1.522(3) . ?
S1 C21 1.772(5) . ?
S1 C22 1.784(5) . ?
N1 C6 1.399(4) . ?
N1 C7 1.401(4) . ?
N1 C15 1.487(4) . ?
C9 C12 1.410(5) . ?
C9 C11 1.412(5) . ?
C9 C9 1.415(7) 2 ?
N2 C13 1.402(4) . ?
N2 C14 1.402(5) . ?
N2 C18 1.486(4) . ?
C12 C10 1.379(5) . ?
C12 C14 1.477(5) . ?
C4 C1 1.376(5) . ?
C4 C2 1.411(5) . ?
C4 C6 1.487(5) . ?
C2 C5 1.408(5) . ?
C2 C2 1.414(7) 2_655 ?
C11 C8 1.377(5) . ?
C11 C13 1.479(5) . ?
C5 C3 1.378(5) . ?
C5 C7 1.489(5) . ?
C7 O2 1.211(4) . ?
C1 C3 1.409(5) 2_655 ?
C1 H1 0.9500 . ?
C13 O3 1.216(4) . ?
C3 C1 1.409(5) 2_655 ?
C3 H3 0.9500 . ?
O1 C6 1.214(4) . ?
C8 C10 1.401(5) 2 ?
C8 H8 0.9500 . ?
C18 C19 1.519(6) . ?
C18 C20 1.522(6) . ?
C18 H18 1.0000 . ?
C14 O4 1.212(4) . ?
C10 C8 1.401(5) 2 ?
C10 H10 0.9500 . ?
O7 C19 1.231(5) . ?
O8 C19 1.299(5) . ?
O8 H8A 0.87(6) . ?
O6 C16 1.322(5) . ?
O6 H6 0.94(6) . ?
C15 C16 1.517(6) . ?
C15 C17 1.519(6) . ?
C15 H15 1.0000 . ?
C16 O5 1.210(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S2A O10A 1.511(4) . ?
S2A C23A 1.790(7) . ?
S2A C24A 1.867(7) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
S2B O10B 1.499(15) . ?
S2B C24B 1.78(3) . ?
S2B C23B 1.81(3) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?

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
O9 S1 C21 103.9(2) . . ?
O9 S1 C22 105.7(2) . . ?
C21 S1 C22 99.8(2) . . ?
C6 N1 C7 125.2(3) . . ?
C6 N1 C15 117.8(3) . . ?
C7 N1 C15 116.5(3) . . ?
C12 C9 C11 121.1(3) . . ?
C12 C9 C9 119.5(4) . 2 ?
C11 C9 C9 119.3(4) . 2 ?
C13 N2 C14 124.2(3) . . ?
C13 N2 C18 117.8(3) . . ?
C14 N2 C18 117.7(3) . . ?
C10 C12 C9 120.2(3) . . ?
C10 C12 C14 120.5(3) . . ?
C9 C12 C14 119.3(3) . . ?
C1 C4 C2 120.4(3) . . ?
C1 C4 C6 120.0(3) . . ?
C2 C4 C6 119.6(3) . . ?
C5 C2 C4 121.4(3) . . ?
C5 C2 C2 119.1(4) . 2_655 ?
C4 C2 C2 119.5(4) . 2_655 ?
C8 C11 C9 119.7(3) . . ?
C8 C11 C13 120.2(3) . . ?
C9 C11 C13 120.1(3) . . ?
C3 C5 C2 120.7(3) . . ?
C3 C5 C7 119.3(3) . . ?
C2 C5 C7 120.1(3) . . ?
O2 C7 N1 121.2(3) . . ?
O2 C7 C5 122.3(3) . . ?
N1 C7 C5 116.5(3) . . ?
C4 C1 C3 120.2(3) . 2_655 ?
C4 C1 H1 119.9 . . ?
C3 C1 H1 119.9 2_655 . ?
O3 C13 N2 120.8(3) . . ?
O3 C13 C11 122.3(3) . . ?
N2 C13 C11 116.9(3) . . ?
C5 C3 C1 120.2(3) . 2_655 ?
C5 C3 H3 119.9 . . ?
C1 C3 H3 119.9 2_655 . ?
C11 C8 C10 121.1(3) . 2 ?
C11 C8 H8 119.5 . . ?
C10 C8 H8 119.5 2 . ?
N2 C18 C19 110.3(3) . . ?
N2 C18 C20 111.0(3) . . ?
C19 C18 C20 114.5(3) . . ?
N2 C18 H18 106.9 . . ?
C19 C18 H18 106.9 . . ?
C20 C18 H18 106.9 . . ?
O1 C6 N1 120.5(3) . . ?
O1 C6 C4 122.6(3) . . ?
N1 C6 C4 116.9(3) . . ?
O4 C14 N2 119.6(3) . . ?
O4 C14 C12 122.8(3) . . ?
N2 C14 C12 117.5(3) . . ?
C12 C10 C8 120.0(3) . 2 ?
C12 C10 H10 120.0 . . ?
C8 C10 H10 120.0 2 . ?
C19 O8 H8A 111(4) . . ?
C16 O6 H6 109(3) . . ?
N1 C15 C16 112.0(3) . . ?
N1 C15 C17 111.4(3) . . ?
C16 C15 C17 112.9(3) . . ?
N1 C15 H15 106.7 . . ?
C16 C15 H15 106.7 . . ?
C17 C15 H15 106.7 . . ?
O5 C16 O6 124.9(4) . . ?
O5 C16 C15 122.0(4) . . ?
O6 C16 C15 112.7(3) . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O7 C19 O8 124.7(4) . . ?
O7 C19 C18 121.9(4) . . ?
O8 C19 C18 113.4(4) . . ?
O10A S2A C23A 105.7(3) . . ?
O10A S2A C24A 102.6(3) . . ?
C23A S2A C24A 94.2(3) . . ?
S2A C23A H23A 109.5 . . ?
S2A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
S2A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
S2A C24A H24A 109.5 . . ?
S2A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
S2A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
O10B S2B C24B 133.3(11) . . ?
O10B S2B C23B 107.4(10) . . ?
C24B S2B C23B 84.9(12) . . ?
S2B C23B H23D 109.5 . . ?
S2B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
S2B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
S2B C24B H24D 109.5 . . ?
S2B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
S2B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C9 C12 C10 -176.9(4) . . . . ?
C9 C9 C12 C10 3.7(5) 2 . . . ?
C11 C9 C12 C14 3.8(6) . . . . ?
C9 C9 C12 C14 -175.6(3) 2 . . . ?
C1 C4 C2 C5 -178.8(4) . . . . ?
C6 C4 C2 C5 3.1(6) . . . . ?
C1 C4 C2 C2 1.3(5) . . . 2_655 ?
C6 C4 C2 C2 -176.8(3) . . . 2_655 ?
C12 C9 C11 C8 -178.3(4) . . . . ?
C9 C9 C11 C8 1.2(5) 2 . . . ?
C12 C9 C11 C13 2.4(6) . . . . ?
C9 C9 C11 C13 -178.2(3) 2 . . . ?
C4 C2 C5 C3 179.0(4) . . . . ?
C2 C2 C5 C3 -1.1(5) 2_655 . . . ?
C4 C2 C5 C7 -1.0(6) . . . . ?
C2 C2 C5 C7 178.9(3) 2_655 . . . ?
C6 N1 C7 O2 173.7(4) . . . . ?
C15 N1 C7 O2 1.8(6) . . . . ?
C6 N1 C7 C5 -5.3(6) . . . . ?
C15 N1 C7 C5 -177.2(3) . . . . ?
C3 C5 C7 O2 2.8(6) . . . . ?
C2 C5 C7 O2 -177.2(4) . . . . ?
C3 C5 C7 N1 -178.2(4) . . . . ?
C2 C5 C7 N1 1.8(6) . . . . ?
C2 C4 C1 C3 -0.4(6) . . . 2_655 ?
C6 C4 C1 C3 177.7(4) . . . 2_655 ?
C14 N2 C13 O3 176.4(4) . . . . ?
C18 N2 C13 O3 3.0(7) . . . . ?
C14 N2 C13 C11 -2.9(6) . . . . ?
C18 N2 C13 C11 -176.2(4) . . . . ?
C8 C11 C13 O3 -1.6(7) . . . . ?
C9 C11 C13 O3 177.7(4) . . . . ?
C8 C11 C13 N2 177.7(4) . . . . ?
C9 C11 C13 N2 -3.0(6) . . . . ?
C2 C5 C3 C1 2.1(7) . . . 2_655 ?
C7 C5 C3 C1 -177.9(4) . . . 2_655 ?
C9 C11 C8 C10 1.7(7) . . . 2 ?
C13 C11 C8 C10 -179.0(4) . . . 2 ?
C13 N2 C18 C19 -139.6(4) . . . . ?
C14 N2 C18 C19 46.6(5) . . . . ?
C13 N2 C18 C20 92.4(4) . . . . ?
C14 N2 C18 C20 -81.4(4) . . . . ?
C7 N1 C6 O1 -172.5(4) . . . . ?
C15 N1 C6 O1 -0.7(6) . . . . ?
C7 N1 C6 C4 7.4(6) . . . . ?
C15 N1 C6 C4 179.2(3) . . . . ?
C1 C4 C6 O1 -4.3(6) . . . . ?
C2 C4 C6 O1 173.8(4) . . . . ?
C1 C4 C6 N1 175.9(4) . . . . ?
C2 C4 C6 N1 -6.0(6) . . . . ?
C13 N2 C14 O4 -171.9(4) . . . . ?
C18 N2 C14 O4 1.5(6) . . . . ?
C13 N2 C14 C12 9.0(6) . . . . ?
C18 N2 C14 C12 -177.7(4) . . . . ?
C10 C12 C14 O4 -7.7(7) . . . . ?
C9 C12 C14 O4 171.6(4) . . . . ?
C10 C12 C14 N2 171.4(4) . . . . ?
C9 C12 C14 N2 -9.3(6) . . . . ?
C9 C12 C10 C8 -0.9(6) . . . 2 ?
C14 C12 C10 C8 178.4(4) . . . 2 ?
C6 N1 C15 C16 48.4(5) . . . . ?
C7 N1 C15 C16 -139.0(4) . . . . ?
C6 N1 C15 C17 -79.1(4) . . . . ?
C7 N1 C15 C17 93.5(4) . . . . ?
N1 C15 C16 O5 -146.8(4) . . . . ?
C17 C15 C16 O5 -20.2(5) . . . . ?
N1 C15 C16 O6 39.7(4) . . . . ?
C17 C15 C16 O6 166.4(3) . . . . ?
N2 C18 C19 O7 -139.4(4) . . . . ?
C20 C18 C19 O7 -13.3(5) . . . . ?
N2 C18 C19 O8 44.2(5) . . . . ?
C20 C18 C19 O8 170.3(3) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 937652'
#######################################################################
#
#                 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_tgmp69

#====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "C20 H14 O8 N2','C2 H6 O1 S1','C2 H6 O1 S1"
_chemical_formula_sum            'C24 H26 N2 O10 S2'
_chemical_formula_weight         566.59

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.302(2)
_cell_length_b                   7.0441(6)
_cell_length_c                   14.8026(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.782(5)
_cell_angle_gamma                90
_cell_volume                     2533.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1887
_cell_measurement_theta_min      3.011
_cell_measurement_theta_max      30.201

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.272
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6008
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            6939
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.902
_reflns_number_total             4157
_reflns_number_gt                3462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.849
_reflns_Friedel_fraction_full    0.822

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0433P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4157
_refine_ls_number_parameters     388
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.009
_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 0.09360(5) 0.1953(2) 0.47479(7) 0.0343(3) Uani 1 1 d . U . . .
N1 N 0.09002(12) 0.7088(6) 0.81482(19) 0.0199(7) Uani 1 1 d . U . . .
C3 C 0.07541(15) 0.7067(7) 0.9790(2) 0.0176(8) Uani 1 1 d . U . . .
C1 C 0.11386(15) 0.7094(7) 0.9016(2) 0.0207(8) Uani 1 1 d . U . . .
C6 C 0.01812(15) 0.7079(7) 0.9628(2) 0.0169(8) Uani 1 1 d . U . . .
N2 N 0.36121(12) 0.7049(6) 0.9248(2) 0.0219(7) Uani 1 1 d . U . . .
C13 C 0.47227(14) 0.7032(7) 0.9849(2) 0.0162(7) Uani 1 1 d . U . . .
C4 C -0.00406(15) 0.7089(7) 0.8739(2) 0.0176(8) Uani 1 1 d . U . . .
O2 O 0.16345(11) 0.7183(5) 0.91278(17) 0.0288(7) Uani 1 1 d . U . . .
C11 C 0.46018(15) 0.6974(7) 0.8913(2) 0.0184(8) Uani 1 1 d . U . . .
C10 C 0.42977(15) 0.7079(7) 1.0490(2) 0.0188(8) Uani 1 1 d . U . . .
C5 C 0.09623(15) 0.7034(7) 1.0662(2) 0.0210(8) Uani 1 1 d . U . . .
H5 H 0.1349 0.6985 1.0762 0.025 Uiso 1 1 calc R U . . .
C7 C -0.06058(15) 0.7071(7) 0.8594(2) 0.0204(8) Uani 1 1 d . U . . .
H7 H -0.0752 0.7083 0.7996 0.024 Uiso 1 1 calc R U . . .
O1 O 0.01691(11) 0.7357(5) 0.71811(17) 0.0290(8) Uani 1 1 d . U . . .
C8 C 0.37119(16) 0.7144(7) 1.0185(2) 0.0223(9) Uani 1 1 d . U . . .
C2 C 0.03346(15) 0.7192(7) 0.7954(2) 0.0202(9) Uani 1 1 d . U . . .
O3 O 0.33367(11) 0.7247(5) 1.07124(18) 0.0311(8) Uani 1 1 d . U . . .
C9 C 0.40191(15) 0.6838(7) 0.8601(3) 0.0216(9) Uani 1 1 d . U . . .
C12 C 0.44265(15) 0.7090(7) 1.1393(2) 0.0218(9) Uani 1 1 d . U . . .
H12 H 0.4139 0.7152 1.1821 0.026 Uiso 1 1 calc R U . . .
O9 O 0.06187(13) 0.2092(5) 0.56258(18) 0.0345(7) Uani 1 1 d . U . . .
O4 O 0.38931(12) 0.6551(5) 0.78151(18) 0.0297(8) Uani 1 1 d . U . . .
C18 C 0.30298(15) 0.6993(8) 0.8932(3) 0.0259(9) Uani 1 1 d . U . . .
H18 H 0.2804 0.7577 0.9420 0.031 Uiso 1 1 calc R U . . .
O7 O 0.26603(12) 0.7715(5) 0.74529(19) 0.0304(8) Uani 1 1 d . U . . .
C14 C 0.50236(15) 0.7011(7) 0.8299(2) 0.0214(9) Uani 1 1 d . U . . .
H14 H 0.4943 0.6983 0.7670 0.026 Uiso 1 1 calc R U . . .
O6 O 0.09386(13) 0.4243(5) 0.6892(2) 0.0280(8) Uani 1 1 d . U . . .
H6 H 0.082(2) 0.354(8) 0.640(3) 0.047(16) Uiso 1 1 d . . . . .
C15 C 0.12832(16) 0.7227(7) 0.7377(2) 0.0229(10) Uani 1 1 d . U . . .
H15 H 0.1650 0.6777 0.7605 0.028 Uiso 1 1 calc R U . . .
O8 O 0.31935(14) 0.9865(5) 0.8156(2) 0.0365(8) Uani 1 1 d . U . . .
H8 H 0.322(3) 1.065(12) 0.762(5) 0.11(3) Uiso 1 1 d . . . . .
O5 O 0.11953(13) 0.6306(5) 0.58272(19) 0.0334(8) Uani 1 1 d . U . . .
C17 C 0.11160(18) 0.5900(7) 0.6610(3) 0.0253(10) Uani 1 1 d . U . . .
C19 C 0.28323(18) 0.4948(7) 0.8822(3) 0.0300(11) Uani 1 1 d . U . . .
H19A H 0.2892 0.4258 0.9389 0.045 Uiso 1 1 calc R U . . .
H19B H 0.3039 0.4331 0.8339 0.045 Uiso 1 1 calc R U . . .
H19C H 0.2439 0.4942 0.8665 0.045 Uiso 1 1 calc R U . . .
C22 C 0.0644(3) -0.0058(8) 0.4193(3) 0.0471(15) Uani 1 1 d . U . . .
H22A H 0.0757 -0.1217 0.4511 0.071 Uiso 1 1 calc R U . . .
H22B H 0.0772 -0.0107 0.3568 0.071 Uiso 1 1 calc R U . . .
H22C H 0.0242 0.0043 0.4193 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1361(2) 0.9250(7) 0.7075(3) 0.0290(11) Uani 1 1 d . U . . .
H16A H 0.1469 1.0034 0.7596 0.044 Uiso 1 1 calc R U . . .
H16B H 0.1016 0.9732 0.6814 0.044 Uiso 1 1 calc R U . . .
H16C H 0.1650 0.9302 0.6620 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0666(2) 0.3767(8) 0.4037(3) 0.0359(13) Uani 1 1 d . U . . .
H21A H 0.0794 0.5006 0.4255 0.054 Uiso 1 1 calc R U . . .
H21B H 0.0263 0.3727 0.4045 0.054 Uiso 1 1 calc R U . . .
H21C H 0.0792 0.3568 0.3418 0.054 Uiso 1 1 calc R U . . .
C20 C 0.29537(18) 0.8223(7) 0.8097(3) 0.0280(11) Uani 1 1 d . U . . .
S2A S 0.29669(8) 1.2775(2) 0.60956(12) 0.0335(6) Uani 0.762(5) 1 d . U P A 1
O10A O 0.33415(16) 1.2082(7) 0.6855(3) 0.0318(11) Uani 0.762(5) 1 d . U P A 1
C23A C 0.2303(5) 1.3097(14) 0.6692(7) 0.044(2) Uani 0.762(5) 1 d . U P A 1
H23A H 0.2326 1.4225 0.7079 0.067 Uiso 0.762(5) 1 calc R U P A 1
H23B H 0.2230 1.1977 0.7064 0.067 Uiso 0.762(5) 1 calc R U P A 1
H23C H 0.2005 1.3259 0.6247 0.067 Uiso 0.762(5) 1 calc R U P A 1
C24A C 0.2741(3) 1.0682(15) 0.5514(5) 0.0415(19) Uani 0.762(5) 1 d . U P A 1
H24A H 0.3035 1.0220 0.5126 0.062 Uiso 0.762(5) 1 calc R U P A 1
H24B H 0.2415 1.0980 0.5143 0.062 Uiso 0.762(5) 1 calc R U P A 1
H24C H 0.2648 0.9700 0.5956 0.062 Uiso 0.762(5) 1 calc R U P A 1
S2B S 0.2621(2) 1.1757(10) 0.5795(4) 0.033(2) Uani 0.238(5) 1 d . U P A 2
O10B O 0.2613(5) 0.968(2) 0.5946(9) 0.026(3) Uani 0.238(5) 1 d . U P A 2
C23B C 0.3271(12) 1.256(4) 0.622(2) 0.046(6) Uani 0.238(5) 1 d . U P A 2
H23D H 0.3563 1.1756 0.5972 0.070 Uiso 0.238(5) 1 calc R U P A 2
H23E H 0.3277 1.2479 0.6877 0.070 Uiso 0.238(5) 1 calc R U P A 2
H23F H 0.3329 1.3876 0.6030 0.070 Uiso 0.238(5) 1 calc R U P A 2
C24B C 0.2353(17) 1.382(5) 0.645(2) 0.044(8) Uani 0.238(5) 1 d . U P A 2
H24D H 0.1953 1.3893 0.6369 0.067 Uiso 0.238(5) 1 calc R U P A 2
H24E H 0.2521 1.4991 0.6224 0.067 Uiso 0.238(5) 1 calc R U P A 2
H24F H 0.2446 1.3656 0.7088 0.067 Uiso 0.238(5) 1 calc R U P A 2


_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 O9 1.523(3) . ?
S1 C21 1.775(5) . ?
S1 C22 1.780(5) . ?
N1 C2 1.403(5) . ?
N1 C1 1.402(4) . ?
N1 C15 1.486(5) . ?
C3 C5 1.381(5) . ?
C3 C6 1.410(5) . ?
C3 C1 1.487(5) . ?
C1 O2 1.216(5) . ?
C6 C4 1.415(5) . ?
C6 C6 1.420(7) 2_557 ?
N2 C9 1.394(5) . ?
N2 C8 1.406(5) . ?
N2 C18 1.485(5) . ?
C13 C11 1.412(5) . ?
C13 C10 1.412(5) . ?
C13 C13 1.415(7) 2_657 ?
C4 C7 1.387(5) . ?
C4 C2 1.489(5) . ?
C11 C14 1.380(5) . ?
C11 C9 1.487(5) . ?
C10 C12 1.370(5) . ?
C10 C8 1.488(5) . ?
C5 C7 1.410(5) 2_557 ?
C5 H5 0.9500 . ?
C7 C5 1.410(5) 2_557 ?
C7 H7 0.9500 . ?
O1 C2 1.213(4) . ?
C8 O3 1.211(5) . ?
C9 O4 1.216(5) . ?
C12 C14 1.407(5) 2_657 ?
C12 H12 0.9500 . ?
C18 C20 1.519(6) . ?
C18 C19 1.527(7) . ?
C18 H18 1.0000 . ?
O7 C20 1.236(5) . ?
C14 C12 1.407(5) 2_657 ?
C14 H14 0.9500 . ?
O6 C17 1.314(5) . ?
O6 H6 0.93(5) . ?
C15 C16 1.506(7) . ?
C15 C17 1.522(6) . ?
C15 H15 1.0000 . ?
O8 C20 1.297(6) . ?
O8 H8 0.97(8) . ?
O5 C17 1.211(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
S2A O10A 1.518(4) . ?
S2A C24A 1.790(9) . ?
S2A C23A 1.863(11) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
S2B O10B 1.481(16) . ?
S2B C23B 1.78(3) . ?
S2B C24B 1.86(4) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?

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
O9 S1 C21 105.8(2) . . ?
O9 S1 C22 104.0(2) . . ?
C21 S1 C22 99.1(2) . . ?
C2 N1 C1 125.4(3) . . ?
C2 N1 C15 117.5(3) . . ?
C1 N1 C15 116.7(3) . . ?
C5 C3 C6 120.5(3) . . ?
C5 C3 C1 119.6(3) . . ?
C6 C3 C1 119.9(3) . . ?
O2 C1 N1 121.4(3) . . ?
O2 C1 C3 121.9(3) . . ?
N1 C1 C3 116.7(3) . . ?
C3 C6 C4 121.4(3) . . ?
C3 C6 C6 119.3(4) . 2_557 ?
C4 C6 C6 119.3(4) . 2_557 ?
C9 N2 C8 124.6(3) . . ?
C9 N2 C18 117.6(3) . . ?
C8 N2 C18 117.5(3) . . ?
C11 C13 C10 121.0(3) . . ?
C11 C13 C13 119.7(4) . 2_657 ?
C10 C13 C13 119.3(4) . 2_657 ?
C7 C4 C6 120.5(3) . . ?
C7 C4 C2 119.7(3) . . ?
C6 C4 C2 119.8(3) . . ?
C14 C11 C13 119.9(3) . . ?
C14 C11 C9 120.6(3) . . ?
C13 C11 C9 119.4(3) . . ?
C12 C10 C13 119.8(3) . . ?
C12 C10 C8 120.1(3) . . ?
C13 C10 C8 120.1(3) . . ?
C3 C5 C7 120.6(3) . 2_557 ?
C3 C5 H5 119.7 . . ?
C7 C5 H5 119.7 2_557 . ?
C4 C7 C5 119.8(3) . 2_557 ?
C4 C7 H7 120.1 . . ?
C5 C7 H7 120.1 2_557 . ?
O3 C8 N2 121.2(4) . . ?
O3 C8 C10 122.1(3) . . ?
N2 C8 C10 116.7(3) . . ?
O1 C2 N1 120.7(3) . . ?
O1 C2 C4 122.8(3) . . ?
N1 C2 C4 116.5(3) . . ?
O4 C9 N2 120.2(3) . . ?
O4 C9 C11 122.3(3) . . ?
N2 C9 C11 117.5(3) . . ?
C10 C12 C14 121.3(3) . 2_657 ?
C10 C12 H12 119.4 . . ?
C14 C12 H12 119.4 2_657 . ?
N2 C18 C20 110.2(4) . . ?
N2 C18 C19 110.8(4) . . ?
C20 C18 C19 114.6(4) . . ?
N2 C18 H18 106.9 . . ?
C20 C18 H18 106.9 . . ?
C19 C18 H18 106.9 . . ?
C11 C14 C12 119.9(3) . 2_657 ?
C11 C14 H14 120.0 . . ?
C12 C14 H14 120.0 2_657 . ?
C17 O6 H6 109(3) . . ?
N1 C15 C16 111.9(4) . . ?
N1 C15 C17 111.7(3) . . ?
C16 C15 C17 113.2(3) . . ?
N1 C15 H15 106.5 . . ?
C16 C15 H15 106.5 . . ?
C17 C15 H15 106.5 . . ?
C20 O8 H8 120(5) . . ?
O5 C17 O6 124.8(4) . . ?
O5 C17 C15 121.6(4) . . ?
O6 C17 C15 113.2(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C20 O8 124.3(4) . . ?
O7 C20 C18 121.7(4) . . ?
O8 C20 C18 113.9(4) . . ?
O10A S2A C24A 105.5(4) . . ?
O10A S2A C23A 101.7(3) . . ?
C24A S2A C23A 93.8(4) . . ?
S2A C23A H23A 109.5 . . ?
S2A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
S2A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
S2A C24A H24A 109.5 . . ?
S2A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
S2A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
O10B S2B C23B 105.9(12) . . ?
O10B S2B C24B 133.4(12) . . ?
C23B S2B C24B 83.5(16) . . ?
S2B C23B H23D 109.5 . . ?
S2B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
S2B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
S2B C24B H24D 109.5 . . ?
S2B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
S2B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O2 -172.8(5) . . . . ?
C15 N1 C1 O2 -1.0(7) . . . . ?
C2 N1 C1 C3 4.7(7) . . . . ?
C15 N1 C1 C3 176.6(4) . . . . ?
C5 C3 C1 O2 -3.8(7) . . . . ?
C6 C3 C1 O2 176.2(5) . . . . ?
C5 C3 C1 N1 178.7(4) . . . . ?
C6 C3 C1 N1 -1.4(7) . . . . ?
C5 C3 C6 C4 -179.2(5) . . . . ?
C1 C3 C6 C4 0.9(7) . . . . ?
C5 C3 C6 C6 0.8(6) . . . 2_557 ?
C1 C3 C6 C6 -179.2(3) . . . 2_557 ?
C3 C6 C4 C7 179.0(5) . . . . ?
C6 C6 C4 C7 -1.0(6) 2_557 . . . ?
C3 C6 C4 C2 -3.2(7) . . . . ?
C6 C6 C4 C2 176.8(3) 2_557 . . . ?
C10 C13 C11 C14 177.2(5) . . . . ?
C13 C13 C11 C14 -3.1(6) 2_657 . . . ?
C10 C13 C11 C9 -3.9(7) . . . . ?
C13 C13 C11 C9 175.7(3) 2_657 . . . ?
C11 C13 C10 C12 178.5(5) . . . . ?
C13 C13 C10 C12 -1.1(6) 2_657 . . . ?
C11 C13 C10 C8 -2.4(7) . . . . ?
C13 C13 C10 C8 178.0(3) 2_657 . . . ?
C6 C3 C5 C7 -2.0(8) . . . 2_557 ?
C1 C3 C5 C7 177.9(5) . . . 2_557 ?
C6 C4 C7 C5 -0.2(7) . . . 2_557 ?
C2 C4 C7 C5 -178.0(4) . . . 2_557 ?
C9 N2 C8 O3 -176.8(5) . . . . ?
C18 N2 C8 O3 -2.7(7) . . . . ?
C9 N2 C8 C10 2.2(7) . . . . ?
C18 N2 C8 C10 176.4(4) . . . . ?
C12 C10 C8 O3 1.6(8) . . . . ?
C13 C10 C8 O3 -177.6(5) . . . . ?
C12 C10 C8 N2 -177.4(5) . . . . ?
C13 C10 C8 N2 3.4(7) . . . . ?
C1 N1 C2 O1 173.1(5) . . . . ?
C15 N1 C2 O1 1.3(7) . . . . ?
C1 N1 C2 C4 -7.0(7) . . . . ?
C15 N1 C2 C4 -178.8(4) . . . . ?
C7 C4 C2 O1 3.7(7) . . . . ?
C6 C4 C2 O1 -174.0(5) . . . . ?
C7 C4 C2 N1 -176.2(5) . . . . ?
C6 C4 C2 N1 6.0(7) . . . . ?
C8 N2 C9 O4 171.6(5) . . . . ?
C18 N2 C9 O4 -2.6(7) . . . . ?
C8 N2 C9 C11 -8.3(7) . . . . ?
C18 N2 C9 C11 177.5(5) . . . . ?
C14 C11 C9 O4 8.0(8) . . . . ?
C13 C11 C9 O4 -170.9(4) . . . . ?
C14 C11 C9 N2 -172.1(4) . . . . ?
C13 C11 C9 N2 9.1(7) . . . . ?
C13 C10 C12 C14 -1.5(8) . . . 2_657 ?
C8 C10 C12 C14 179.4(5) . . . 2_657 ?
C9 N2 C18 C20 -45.9(6) . . . . ?
C8 N2 C18 C20 139.6(4) . . . . ?
C9 N2 C18 C19 82.1(5) . . . . ?
C8 N2 C18 C19 -92.5(5) . . . . ?
C13 C11 C14 C12 0.5(7) . . . 2_657 ?
C9 C11 C14 C12 -178.3(5) . . . 2_657 ?
C2 N1 C15 C16 79.1(5) . . . . ?
C1 N1 C15 C16 -93.4(5) . . . . ?
C2 N1 C15 C17 -48.9(5) . . . . ?
C1 N1 C15 C17 138.6(4) . . . . ?
N1 C15 C17 O5 147.4(4) . . . . ?
C16 C15 C17 O5 20.0(6) . . . . ?
N1 C15 C17 O6 -39.4(5) . . . . ?
C16 C15 C17 O6 -166.8(4) . . . . ?
N2 C18 C20 O7 139.4(4) . . . . ?
C19 C18 C20 O7 13.5(6) . . . . ?
N2 C18 C20 O8 -44.7(5) . . . . ?
C19 C18 C20 O8 -170.6(4) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 937653'
