# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br2 O4'
_chemical_formula_sum            'C10 H10 Br2 O4'
_chemical_formula_weight         354.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.9370(11)
_cell_length_b                   5.0321(2)
_cell_length_c                   13.3138(12)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.958(8)
_cell_angle_gamma                90.000(6)
_cell_volume                     594.34(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2095
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      26.98

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    6.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5193
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  area_detector
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6898
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         26.98
_reflns_number_total             1286
_reflns_number_gt                965
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0082P)²+0.9730P] 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         1286
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37768(4) 0.06328(9) 0.82402(3) 0.04692(15) Uani 1 1 d . . .
O2 O 0.2061(3) 0.4232(7) 0.9480(3) 0.0727(10) Uani 1 1 d . . .
O1 O 0.6956(3) 0.1960(7) 0.9009(2) 0.0608(9) Uani 1 1 d . . .
C3 C 0.6027(4) 0.3425(8) 0.9479(3) 0.0359(9) Uani 1 1 d . . .
C2 C 0.8569(4) 0.2172(9) 0.9096(3) 0.0568(12) Uani 1 1 d . . .
H2A H 0.9012 0.1661 0.9770 0.068 Uiso 1 1 calc R . .
H2B H 0.8866 0.3985 0.8971 0.068 Uiso 1 1 calc R . .
C4 C 0.4529(4) 0.3109(7) 0.9237(3) 0.0344(8) Uani 1 1 d . . .
C5 C 0.3404(4) 0.4563(8) 0.9711(3) 0.0411(9) Uani 1 1 d . . .
C1 C 0.9083(4) 0.0350(10) 0.8327(3) 0.0599(12) Uani 1 1 d . . .
H1A H 1.0161 0.0429 0.8361 0.090 Uiso 1 1 calc R . .
H1B H 0.8638 0.0880 0.7664 0.090 Uiso 1 1 calc R . .
H1C H 0.8780 -0.1435 0.8458 0.090 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.884(4) . ?
O2 C5 1.213(4) . ?
O1 C3 1.323(4) . ?
O1 C2 1.437(4) . ?
C3 C4 1.348(5) . ?
C3 C5 1.521(5) 3_667 ?
C2 C1 1.488(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.449(5) . ?
C5 C3 1.521(5) 3_667 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 127.0(3) . . ?
O1 C3 C4 118.9(3) . . ?
O1 C3 C5 122.1(3) . 3_667 ?
C4 C3 C5 119.0(3) . 3_667 ?
O1 C2 C1 106.8(3) . . ?
O1 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C3 C4 C5 123.9(3) . . ?
C3 C4 Br1 120.4(3) . . ?
C5 C4 Br1 115.7(2) . . ?
O2 C5 C4 122.5(4) . . ?
O2 C5 C3 120.4(3) . 3_667 ?
C4 C5 C3 117.1(3) . 3_667 ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.089
_database_code_depnum_ccdc_archive 'CCDC 1015746'
#######################################################################
#
#                 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_3a
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O4 S2'
_chemical_formula_sum            'C18 H16 O4 S2'
_chemical_formula_weight         360.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   4.8906(9)
_cell_length_b                   9.361(2)
_cell_length_c                   9.693(4)
_cell_angle_alpha                104.639(19)
_cell_angle_beta                 101.792(2)
_cell_angle_gamma                100.598(2)
_cell_volume                     407.06(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    883
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      26.49

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8196
_diffrn_reflns_av_R_equivalents  0.1120
_diffrn_reflns_av_sigmaI/netI    0.1611
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.38
_diffrn_reflns_theta_max         26.49
_reflns_number_total             1676
_reflns_number_gt                799
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0507P)²+0.0808P] 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         1676
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2307(2) 0.69844(11) 0.74829(11) 0.0534(4) Uani 1 1 d . . .
O1 O 0.6543(4) 0.7437(3) 0.9880(3) 0.0505(7) Uani 1 1 d . . .
O2 O 0.8365(5) 1.1586(2) 0.8038(2) 0.0409(7) Uani 1 1 d . . .
C1 C -0.0110(7) 0.7038(4) 0.5980(4) 0.0503(11) Uani 1 1 d . . .
H1 H -0.1800 0.6282 0.5484 0.060 Uiso 1 1 calc R . .
C2 C 0.0691(8) 0.8288(4) 0.5590(4) 0.0559(11) Uani 1 1 d . . .
H2 H -0.0389 0.8488 0.4784 0.067 Uiso 1 1 calc R . .
C3 C 0.3333(7) 0.9281(4) 0.6514(4) 0.0447(10) Uani 1 1 d . . .
H3 H 0.4162 1.0202 0.6392 0.054 Uiso 1 1 calc R . .
C4 C 0.4547(6) 0.8719(3) 0.7631(3) 0.0308(8) Uani 1 1 d . . .
C5 C 0.7264(6) 0.9404(3) 0.8787(3) 0.0304(8) Uani 1 1 d . . .
C6 C 0.9009(7) 1.0787(4) 0.8980(4) 0.0323(8) Uani 1 1 d . . .
C7 C 0.8153(7) 0.8597(4) 0.9867(3) 0.0337(9) Uani 1 1 d . . .
C8 C 0.8706(7) 1.3237(4) 0.8557(4) 0.0411(9) Uani 1 1 d . . .
H15A H 1.0608 1.3771 0.8562 0.049 Uiso 1 1 calc R . .
H15B H 0.8488 1.3537 0.9554 0.049 Uiso 1 1 calc R . .
C9 C 0.6447(7) 1.3624(4) 0.7533(4) 0.0518(11) Uani 1 1 d . . .
H16A H 0.6619 1.4702 0.7853 0.078 Uiso 1 1 calc R . .
H16B H 0.4575 1.3089 0.7534 0.078 Uiso 1 1 calc R . .
H16C H 0.6693 1.3331 0.6551 0.078 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.696(3) . ?
S1 C4 1.738(3) . ?
O1 C7 1.223(4) . ?
O2 C6 1.344(4) . ?
O2 C8 1.465(4) . ?
C1 C2 1.335(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.414(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.465(4) . ?
C5 C6 1.359(4) . ?
C5 C7 1.479(4) . ?
C6 C7 1.501(4) 2_777 ?
C7 C6 1.501(4) 2_777 ?
C8 C9 1.489(4) . ?
C8 H15A 0.9700 . ?
C8 H15B 0.9700 . ?
C9 H16A 0.9600 . ?
C9 H16B 0.9600 . ?
C9 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 92.41(16) . . ?
C6 O2 C8 121.7(2) . . ?
C2 C1 S1 112.3(3) . . ?
C2 C1 H1 123.9 . . ?
S1 C1 H1 123.9 . . ?
C1 C2 C3 113.8(3) . . ?
C1 C2 H2 123.1 . . ?
C3 C2 H2 123.1 . . ?
C4 C3 C2 112.1(3) . . ?
C4 C3 H3 123.9 . . ?
C2 C3 H3 123.9 . . ?
C3 C4 C5 128.4(3) . . ?
C3 C4 S1 109.4(2) . . ?
C5 C4 S1 122.2(2) . . ?
C6 C5 C4 124.0(3) . . ?
C6 C5 C7 116.7(3) . . ?
C4 C5 C7 119.3(3) . . ?
O2 C6 C5 120.3(3) . . ?
O2 C6 C7 117.5(3) . 2_777 ?
C5 C6 C7 121.9(3) . 2_777 ?
O1 C7 C5 120.7(3) . . ?
O1 C7 C6 118.0(3) . 2_777 ?
C5 C7 C6 121.2(3) . 2_777 ?
O2 C8 C9 107.9(3) . . ?
O2 C8 H15A 110.1 . . ?
C9 C8 H15A 110.1 . . ?
O2 C8 H15B 110.1 . . ?
C9 C8 H15B 110.1 . . ?
H15A C8 H15B 108.4 . . ?
C8 C9 H16A 109.5 . . ?
C8 C9 H16B 109.5 . . ?
H16A C9 H16B 109.5 . . ?
C8 C9 H16C 109.5 . . ?
H16A C9 H16C 109.5 . . ?
H16B C9 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 1015747'
#######################################################################
#
#                 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_3b
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H32 O8 S4'
_chemical_formula_sum            'C36 H32 O8 S4'
_chemical_formula_weight         720.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/a

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

_cell_length_a                   7.6923(7)
_cell_length_b                   46.482(6)
_cell_length_c                   9.9383(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.199(11)
_cell_angle_gamma                90.00
_cell_volume                     3290.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6434
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.00

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5662
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18708
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -55
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5332
_reflns_number_gt                3524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0864P)²+3.4653P] 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         5332
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C3C C 0.6945(14) 0.00662(19) 0.5836(10) 0.071(2) Uani 0.64 1 d P A 2
H3C H 0.6137 0.0107 0.4889 0.085 Uiso 0.64 1 calc PR A 2
S1A S 0.8197(8) 0.00326(9) 0.5694(5) 0.0760(12) Uani 0.36 1 d P A 1
S1C S 0.8284(3) 0.01121(4) 0.8573(2) 0.0488(6) Uani 0.64 1 d P A 2
C3A C 0.742(2) 0.0108(4) 0.8136(18) 0.0488(6) Uani 0.36 1 d P A 1
H3A H 0.7071 0.0184 0.8863 0.059 Uiso 0.36 1 calc PR A 1
S2A S 0.78658(15) 0.16356(2) 0.89425(11) 0.0432(3) Uani 1 1 d . . .
S1B S 0.32224(17) 0.07875(2) 0.66822(11) 0.0461(3) Uani 1 1 d . . .
S2B S 0.23179(19) 0.22942(2) 0.58209(12) 0.0563(4) Uani 1 1 d . . .
O4A O 0.8122(3) 0.14893(5) 0.6380(2) 0.0329(6) Uani 1 1 d . . .
O2B O 0.3418(4) 0.18183(5) 1.0929(3) 0.0410(7) Uani 1 1 d . . .
O4B O 0.3121(4) 0.12192(5) 1.0772(2) 0.0374(6) Uani 1 1 d . . .
C10A C 0.7989(5) 0.10901(7) 0.7789(3) 0.0272(8) Uani 1 1 d . . .
O3B O 0.2455(4) 0.21651(5) 0.8566(3) 0.0388(7) Uani 1 1 d . . .
O1A O 0.8582(4) 0.06646(6) 0.9184(3) 0.0507(8) Uani 1 1 d . . .
O1B O 0.3139(4) 0.13396(5) 0.6130(3) 0.0406(7) Uani 1 1 d . . .
C9A C 0.8052(5) 0.11997(7) 0.6555(4) 0.0286(8) Uani 1 1 d . . .
C10B C 0.2410(5) 0.17609(7) 0.7144(4) 0.0284(8) Uani 1 1 d . . .
C5B C 0.2862(5) 0.12539(7) 0.8352(4) 0.0276(8) Uani 1 1 d . . .
O2A O 0.8695(5) 0.11233(6) 0.4456(3) 0.0559(8) Uani 1 1 d . . .
C12A C 0.7599(4) 0.11557(7) 1.0266(3) 0.0215(7) Uani 1 1 d . . .
H12A H 0.7564 0.0964 1.0516 0.026 Uiso 1 1 calc R . .
C7A C 0.8268(6) 0.10151(8) 0.5414(4) 0.0371(9) Uani 1 1 d . . .
C7B C 0.2966(5) 0.17009(8) 0.9744(4) 0.0313(8) Uani 1 1 d . . .
C17B C 0.2479(5) 0.13065(8) 1.1907(4) 0.0340(9) Uani 1 1 d . . .
H17A H 0.1270 0.1401 1.1489 0.041 Uiso 1 1 calc R . .
H17B H 0.3368 0.1439 1.2572 0.041 Uiso 1 1 calc R . .
C9B C 0.2511(5) 0.18745(7) 0.8418(4) 0.0293(8) Uani 1 1 d . . .
C5A C 0.7973(5) 0.05770(8) 0.6722(4) 0.0336(9) Uani 1 1 d . A .
C11A C 0.7832(5) 0.12634(7) 0.8964(3) 0.0284(8) Uani 1 1 d . . .
C3B C 0.2897(6) 0.07256(8) 0.9129(4) 0.0397(10) Uani 1 1 d . . .
H3B H 0.2792 0.0762 1.0016 0.048 Uiso 1 1 calc R . .
O3A O 0.7988(5) 0.05294(6) 0.4405(3) 0.0637(10) Uani 1 1 d . . .
C12B C 0.1512(5) 0.18199(8) 0.4388(4) 0.0365(9) Uani 1 1 d . . .
H12B H 0.1283 0.1627 0.4135 0.044 Uiso 1 1 calc R . .
C6B C 0.2893(5) 0.13818(8) 0.9601(4) 0.0293(8) Uani 1 1 d . . .
C8A C 0.8194(5) 0.07702(8) 0.7984(4) 0.0330(9) Uani 1 1 d . . .
C8B C 0.2814(5) 0.14442(8) 0.7134(4) 0.0298(8) Uani 1 1 d . . .
C6A C 0.8015(5) 0.07005(8) 0.5503(4) 0.0376(9) Uani 1 1 d . . .
C11B C 0.2075(5) 0.19246(8) 0.5823(4) 0.0316(9) Uani 1 1 d . . .
C4B C 0.2970(5) 0.09442(8) 0.8180(4) 0.0312(8) Uani 1 1 d . . .
C4A C 0.7843(6) 0.02677(8) 0.6904(4) 0.0396(10) Uani 1 1 d . . .
C2B C 0.2994(6) 0.04488(8) 0.8618(4) 0.0459(11) Uani 1 1 d . . .
H2B H 0.2926 0.0282 0.9112 0.055 Uiso 1 1 calc R . .
C17A C 0.7611(7) 0.06186(10) 0.2953(4) 0.0551(12) Uani 1 1 d . . .
H17C H 0.8680 0.0721 0.2900 0.066 Uiso 1 1 calc R . .
H17D H 0.6527 0.0745 0.2615 0.066 Uiso 1 1 calc R . .
C14A C 0.7578(5) 0.16577(9) 1.0533(4) 0.0412(10) Uani 1 1 d . . .
H14A H 0.7524 0.1831 1.0980 0.049 Uiso 1 1 calc R . .
C18A C 0.7240(7) 0.03542(10) 0.2049(4) 0.0588(13) Uani 1 1 d . . .
H18A H 0.6962 0.0406 0.1054 0.088 Uiso 1 1 calc R . .
H18B H 0.6190 0.0253 0.2122 0.088 Uiso 1 1 calc R . .
H18C H 0.8328 0.0232 0.2387 0.088 Uiso 1 1 calc R . .
C15A C 0.6649(6) 0.16143(8) 0.5123(4) 0.0421(10) Uani 1 1 d . . .
H15A H 0.5428 0.1559 0.5114 0.051 Uiso 1 1 calc R . .
H15B H 0.6753 0.1544 0.4238 0.051 Uiso 1 1 calc R . .
C2A C 0.7733(7) -0.02158(9) 0.7816(5) 0.0557(12) Uani 1 1 d . . .
H2A1 H 0.8029 -0.0366 0.8482 0.067 Uiso 0.36 1 calc PR A 1
H2A2 H 0.7593 -0.0374 0.8341 0.067 Uiso 0.64 1 d PR A 2
C13A C 0.7432(5) 0.14013(9) 1.1093(4) 0.0395(10) Uani 1 1 d . . .
H13A H 0.7237 0.1383 1.1957 0.047 Uiso 1 1 calc R . .
C13B C 0.1340(6) 0.20429(9) 0.3384(4) 0.0476(11) Uani 1 1 d . . .
H13B H 0.0980 0.2012 0.2391 0.057 Uiso 1 1 calc R . .
C1B C 0.3198(6) 0.04495(9) 0.7326(4) 0.0496(11) Uani 1 1 d . . .
H1B H 0.3312 0.0284 0.6843 0.060 Uiso 1 1 calc R . .
C18B C 0.2322(6) 0.10405(9) 1.2685(4) 0.0466(11) Uani 1 1 d . . .
H18D H 0.1881 0.1089 1.3440 0.070 Uiso 1 1 calc R . .
H18E H 0.3531 0.0950 1.3105 0.070 Uiso 1 1 calc R . .
H18F H 0.1453 0.0910 1.2012 0.070 Uiso 1 1 calc R . .
C15B C 0.1084(5) 0.22807(8) 0.9085(4) 0.0388(10) Uani 1 1 d . . .
H15C H 0.0850 0.2145 0.9738 0.047 Uiso 1 1 calc R . .
H15D H -0.0089 0.2316 0.8274 0.047 Uiso 1 1 calc R . .
C16B C 0.1827(7) 0.25554(10) 0.9866(6) 0.0731(16) Uani 1 1 d . . .
H16A H 0.0931 0.2635 1.0223 0.110 Uiso 1 1 calc R . .
H16B H 0.2042 0.2689 0.9210 0.110 Uiso 1 1 calc R . .
H16C H 0.2987 0.2519 1.0666 0.110 Uiso 1 1 calc R . .
C1A C 0.7507(11) -0.02340(11) 0.6479(5) 0.107(3) Uani 1 1 d . A .
H1A1 H 0.6956 -0.0397 0.5946 0.129 Uiso 0.36 1 calc PR B 1
H1A2 H 0.7686 -0.0397 0.6006 0.129 Uiso 0.64 1 d PR B 2
C14B C 0.1744(7) 0.23025(9) 0.3995(5) 0.0585(13) Uani 1 1 d . . .
H14B H 0.1714 0.2470 0.3476 0.070 Uiso 1 1 calc R . .
C16A C 0.6834(6) 0.19305(9) 0.5189(5) 0.0618(14) Uani 1 1 d . . .
H16D H 0.5883 0.2014 0.4347 0.093 Uiso 1 1 calc R . .
H16E H 0.8052 0.1984 0.5214 0.093 Uiso 1 1 calc R . .
H16F H 0.6686 0.2000 0.6050 0.093 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3C C4A 1.388(9) . ?
C3C C1A 1.528(10) . ?
C3C H3C 0.9300 . ?
S1A C1A 1.655(7) . ?
S1A C4A 1.721(6) . ?
S1C C2A 1.682(5) . ?
S1C C4A 1.722(4) . ?
C3A C4A 1.568(18) . ?
C3A C2A 1.575(18) . ?
C3A H3A 0.9300 . ?
S2A C14A 1.680(4) . ?
S2A C11A 1.730(4) . ?
S1B C1B 1.699(4) . ?
S1B C4B 1.732(4) . ?
S2B C14B 1.698(4) . ?
S2B C11B 1.728(4) . ?
O4A C9A 1.361(4) . ?
O4A C15A 1.454(4) . ?
O2B C7B 1.223(4) . ?
O4B C6B 1.342(4) . ?
O4B C17B 1.449(4) . ?
C10A C9A 1.346(5) . ?
C10A C11A 1.460(5) . ?
C10A C8A 1.500(5) . ?
O3B C9B 1.361(4) . ?
O3B C15B 1.442(4) . ?
O1A C8A 1.218(4) . ?
O1B C8B 1.219(4) . ?
C9A C7A 1.481(5) . ?
C10B C9B 1.347(5) . ?
C10B C11B 1.454(5) . ?
C10B C8B 1.505(5) . ?
C5B C6B 1.368(5) . ?
C5B C4B 1.456(5) . ?
C5B C8B 1.488(5) . ?
O2A C7A 1.227(4) . ?
C12A C13A 1.440(5) . ?
C12A C11A 1.461(5) . ?
C12A H12A 0.9300 . ?
C7A C6A 1.482(5) . ?
C7B C9B 1.471(5) . ?
C7B C6B 1.489(5) . ?
C17B C18B 1.487(5) . ?
C17B H17A 0.9700 . ?
C17B H17B 0.9700 . ?
C5A C6A 1.352(5) . ?
C5A C4A 1.458(5) . ?
C5A C8A 1.500(5) . ?
C3B C2B 1.396(5) . ?
C3B C4B 1.403(5) . ?
C3B H3B 0.9300 . ?
O3A C6A 1.344(4) . ?
O3A C17A 1.422(5) . ?
C12B C13B 1.410(5) . ?
C12B C11B 1.411(5) . ?
C12B H12B 0.9300 . ?
C2B C1B 1.351(6) . ?
C2B H2B 0.9300 . ?
C17A C18A 1.485(6) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C14A C13A 1.338(6) . ?
C14A H14A 0.9300 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C15A C16A 1.476(5) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C2A C1A 1.277(6) . ?
C2A H2A1 0.9300 . ?
C2A H2A2 0.9300 . ?
C13A H13A 0.9300 . ?
C13B C14B 1.333(6) . ?
C13B H13B 0.9300 . ?
C1B H1B 0.9300 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C15B C16B 1.491(5) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C16B H16A 0.9600 . ?
C16B H16B 0.9600 . ?
C16B H16C 0.9600 . ?
C1A H1A1 0.9300 . ?
C1A H1A2 0.9300 . ?
C14B H14B 0.9300 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4A C3C C1A 108.4(7) . . ?
C4A C3C H3C 125.8 . . ?
C1A C3C H3C 125.8 . . ?
C1A S1A C4A 89.0(3) . . ?
C2A S1C C4A 91.4(2) . . ?
C4A C3A C2A 101.6(11) . . ?
C4A C3A H3A 129.2 . . ?
C2A C3A H3A 129.2 . . ?
C14A S2A C11A 92.39(19) . . ?
C1B S1B C4B 92.56(19) . . ?
C14B S2B C11B 92.24(19) . . ?
C9A O4A C15A 116.7(3) . . ?
C6B O4B C17B 123.1(3) . . ?
C9A C10A C11A 124.2(3) . . ?
C9A C10A C8A 117.1(3) . . ?
C11A C10A C8A 118.7(3) . . ?
C9B O3B C15B 117.7(3) . . ?
C10A C9A O4A 120.5(3) . . ?
C10A C9A C7A 122.1(3) . . ?
O4A C9A C7A 117.0(3) . . ?
C9B C10B C11B 124.8(3) . . ?
C9B C10B C8B 116.8(3) . . ?
C11B C10B C8B 118.2(3) . . ?
C6B C5B C4B 123.7(3) . . ?
C6B C5B C8B 117.8(3) . . ?
C4B C5B C8B 118.5(3) . . ?
C13A C12A C11A 107.5(3) . . ?
C13A C12A H12A 126.2 . . ?
C11A C12A H12A 126.2 . . ?
O2A C7A C9A 119.8(3) . . ?
O2A C7A C6A 122.1(3) . . ?
C9A C7A C6A 118.1(3) . . ?
O2B C7B C9B 120.2(3) . . ?
O2B C7B C6B 121.6(3) . . ?
C9B C7B C6B 118.2(3) . . ?
O4B C17B C18B 106.9(3) . . ?
O4B C17B H17A 110.3 . . ?
C18B C17B H17A 110.3 . . ?
O4B C17B H17B 110.3 . . ?
C18B C17B H17B 110.3 . . ?
H17A C17B H17B 108.6 . . ?
C10B C9B O3B 119.8(3) . . ?
C10B C9B C7B 122.5(3) . . ?
O3B C9B C7B 117.0(3) . . ?
C6A C5A C4A 123.8(3) . . ?
C6A C5A C8A 117.5(3) . . ?
C4A C5A C8A 118.6(3) . . ?
C10A C11A C12A 126.4(3) . . ?
C10A C11A S2A 122.4(3) . . ?
C12A C11A S2A 111.2(2) . . ?
C2B C3B C4B 113.7(3) . . ?
C2B C3B H3B 123.2 . . ?
C4B C3B H3B 123.2 . . ?
C6A O3A C17A 125.9(3) . . ?
C13B C12B C11B 111.9(3) . . ?
C13B C12B H12B 124.1 . . ?
C11B C12B H12B 124.1 . . ?
O4B C6B C5B 119.6(3) . . ?
O4B C6B C7B 119.3(3) . . ?
C5B C6B C7B 120.4(3) . . ?
O1A C8A C5A 119.1(3) . . ?
O1A C8A C10A 120.1(3) . . ?
C5A C8A C10A 120.8(3) . . ?
O1B C8B C5B 118.6(3) . . ?
O1B C8B C10B 120.1(3) . . ?
C5B C8B C10B 121.2(3) . . ?
O3A C6A C5A 118.5(3) . . ?
O3A C6A C7A 119.8(3) . . ?
C5A C6A C7A 121.4(3) . . ?
C12B C11B C10B 127.9(3) . . ?
C12B C11B S2B 109.5(3) . . ?
C10B C11B S2B 122.6(3) . . ?
C3B C4B C5B 128.2(3) . . ?
C3B C4B S1B 108.6(3) . . ?
C5B C4B S1B 123.2(3) . . ?
C3C C4A C5A 127.5(5) . . ?
C3C C4A C3A 95.0(8) . . ?
C5A C4A C3A 127.5(7) . . ?
C3C C4A S1A 37.0(4) . . ?
C5A C4A S1A 120.2(3) . . ?
C3A C4A S1A 112.3(7) . . ?
C3C C4A S1C 108.3(4) . . ?
C5A C4A S1C 122.4(3) . . ?
C3A C4A S1C 21.9(6) . . ?
S1A C4A S1C 112.4(3) . . ?
C1B C2B C3B 112.7(4) . . ?
C1B C2B H2B 123.7 . . ?
C3B C2B H2B 123.7 . . ?
O3A C17A C18A 107.0(4) . . ?
O3A C17A H17C 110.3 . . ?
C18A C17A H17C 110.3 . . ?
O3A C17A H17D 110.3 . . ?
C18A C17A H17D 110.3 . . ?
H17C C17A H17D 108.6 . . ?
C13A C14A S2A 113.5(3) . . ?
C13A C14A H14A 123.2 . . ?
S2A C14A H14A 123.2 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O4A C15A C16A 109.2(3) . . ?
O4A C15A H15A 109.8 . . ?
C16A C15A H15A 109.8 . . ?
O4A C15A H15B 109.8 . . ?
C16A C15A H15B 109.8 . . ?
H15A C15A H15B 108.3 . . ?
C1A C2A C3A 107.6(7) . . ?
C1A C2A S1C 116.0(4) . . ?
C3A C2A S1C 22.5(6) . . ?
C1A C2A H2A1 126.2 . . ?
C3A C2A H2A1 126.2 . . ?
S1C C2A H2A1 114.3 . . ?
C1A C2A H2A2 122.1 . . ?
C3A C2A H2A2 125.6 . . ?
S1C C2A H2A2 121.9 . . ?
H2A1 C2A H2A2 19.4 . . ?
C14A C13A C12A 115.4(3) . . ?
C14A C13A H13A 122.3 . . ?
C12A C13A H13A 122.3 . . ?
C14B C13B C12B 113.6(4) . . ?
C14B C13B H13B 123.2 . . ?
C12B C13B H13B 123.2 . . ?
C2B C1B S1B 112.4(3) . . ?
C2B C1B H1B 123.8 . . ?
S1B C1B H1B 123.8 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
O3B C15B C16B 108.5(3) . . ?
O3B C15B H15C 110.0 . . ?
C16B C15B H15C 110.0 . . ?
O3B C15B H15D 110.0 . . ?
C16B C15B H15D 110.0 . . ?
H15C C15B H15D 108.4 . . ?
C15B C16B H16A 109.5 . . ?
C15B C16B H16B 109.5 . . ?
H16A C16B H16B 109.5 . . ?
C15B C16B H16C 109.5 . . ?
H16A C16B H16C 109.5 . . ?
H16B C16B H16C 109.5 . . ?
C2A C1A C3C 106.3(5) . . ?
C2A C1A S1A 119.9(4) . . ?
C3C C1A S1A 37.8(3) . . ?
C2A C1A H1A1 120.0 . . ?
C3C C1A H1A1 120.7 . . ?
S1A C1A H1A1 120.0 . . ?
C2A C1A H1A2 126.3 . . ?
C3C C1A H1A2 127.4 . . ?
S1A C1A H1A2 103.8 . . ?
H1A1 C1A H1A2 33.9 . . ?
C13B C14B S2B 112.8(3) . . ?
C13B C14B H14B 123.6 . . ?
S2B C14B H14B 123.6 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.921
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 1015748'
#######################################################################
#
#                 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_4a
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O8 S2'
_chemical_formula_sum            'C22 H20 O8 S2'
_chemical_formula_weight         476.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   20.4414(19)
_cell_length_b                   6.6136(9)
_cell_length_c                   17.1675(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.534(6)
_cell_angle_gamma                90.00
_cell_volume                     2158.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5960
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      30.50

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13312
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         30.50
_reflns_number_total             3274
_reflns_number_gt                2507
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0594P)²+2.8921P] 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         3274
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20104(7) 0.2076(3) 0.91777(9) 0.0302(3) Uani 1 1 d . . .
C2 C 0.25496(8) 0.3716(3) 0.93335(9) 0.0300(3) Uani 1 1 d . . .
C3 C 0.19448(7) 0.0996(2) 0.98971(9) 0.0277(3) Uani 1 1 d . . .
C4 C 0.13858(8) -0.0522(3) 0.97224(10) 0.0303(3) Uani 1 1 d . . .
C5 C 0.06888(8) -0.0304(3) 0.92345(10) 0.0320(3) Uani 1 1 d . . .
C6 C 0.02952(10) -0.2119(3) 0.91631(13) 0.0440(4) Uani 1 1 d . . .
C7 C 0.06938(12) -0.3695(3) 0.95880(17) 0.0549(6) Uani 1 1 d . . .
H14 H 0.0524 -0.4993 0.9602 0.066 Uiso 1 1 calc R . .
C8 C -0.03482(13) 0.1355(5) 0.8480(3) 0.0934(12) Uani 1 1 d . . .
H16A H -0.0540 0.2133 0.8825 0.112 Uiso 1 1 calc R . .
H16B H -0.0477 0.2062 0.7949 0.112 Uiso 1 1 calc R . .
C9 C -0.06916(14) -0.0430(6) 0.8321(3) 0.130(2) Uani 1 1 d . . .
H15A H -0.0821 -0.0678 0.7726 0.156 Uiso 1 1 calc R . .
H15B H -0.1128 -0.0217 0.8412 0.156 Uiso 1 1 calc R . .
C10 C 0.19405(10) 0.5635(3) 0.80651(11) 0.0447(4) Uani 1 1 d . . .
H9A H 0.1949 0.7092 0.8134 0.054 Uiso 1 1 calc R . .
H9B H 0.1530 0.5109 0.8152 0.054 Uiso 1 1 calc R . .
C11 C 0.19085(11) 0.5116(4) 0.72084(12) 0.0494(5) Uani 1 1 d . . .
H10A H 0.1491 0.5686 0.6801 0.074 Uiso 1 1 calc R . .
H10B H 0.1900 0.3673 0.7145 0.074 Uiso 1 1 calc R . .
H10C H 0.2314 0.5655 0.7126 0.074 Uiso 1 1 calc R . .
O1 O 0.16740(7) 0.1546(2) 0.84596(8) 0.0462(4) Uani 1 1 d . . .
O2 O 0.25809(7) 0.4739(2) 0.86732(8) 0.0452(4) Uani 1 1 d . . .
O3 O 0.03933(6) 0.1465(2) 0.88664(9) 0.0463(4) Uani 1 1 d . . .
O4 O -0.04141(8) -0.2210(3) 0.87183(13) 0.0706(6) Uani 1 1 d . . .
S1 S 0.15494(3) -0.29768(7) 1.00937(4) 0.04465(16) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2220(19) . ?
C1 C3 1.475(2) . ?
C1 C2 1.499(2) . ?
C2 O2 1.342(2) . ?
C2 C3 1.359(2) 7_557 ?
C3 C2 1.359(2) 7_557 ?
C3 C4 1.467(2) . ?
C4 C5 1.370(2) . ?
C4 S1 1.7315(18) . ?
C5 O3 1.361(2) . ?
C5 C6 1.425(2) . ?
C6 C7 1.359(3) . ?
C6 O4 1.370(2) . ?
C7 S1 1.710(2) . ?
C7 H14 0.9300 . ?
C8 C9 1.350(5) . ?
C8 O3 1.416(3) . ?
C8 H16A 0.9700 . ?
C8 H16B 0.9700 . ?
C9 O4 1.374(4) . ?
C9 H15A 0.9700 . ?
C9 H15B 0.9700 . ?
C10 O2 1.467(2) . ?
C10 C11 1.488(3) . ?
C10 H9A 0.9700 . ?
C10 H9B 0.9700 . ?
C11 H10A 0.9600 . ?
C11 H10B 0.9600 . ?
C11 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C3 121.03(15) . . ?
O1 C1 C2 119.49(15) . . ?
C3 C1 C2 119.21(13) . . ?
O2 C2 C3 119.70(15) . 7_557 ?
O2 C2 C1 118.30(13) . . ?
C3 C2 C1 121.45(14) 7_557 . ?
C2 C3 C4 123.50(15) 7_557 . ?
C2 C3 C1 118.40(14) 7_557 . ?
C4 C3 C1 117.62(13) . . ?
C5 C4 C3 127.63(16) . . ?
C5 C4 S1 109.90(12) . . ?
C3 C4 S1 122.40(11) . . ?
O3 C5 C4 123.97(15) . . ?
O3 C5 C6 122.93(15) . . ?
C4 C5 C6 113.09(16) . . ?
C7 C6 O4 124.69(19) . . ?
C7 C6 C5 113.04(17) . . ?
O4 C6 C5 122.26(19) . . ?
C6 C7 S1 111.09(15) . . ?
C6 C7 H14 124.5 . . ?
S1 C7 H14 124.5 . . ?
C9 C8 O3 121.8(3) . . ?
C9 C8 H16A 106.9 . . ?
O3 C8 H16A 106.9 . . ?
C9 C8 H16B 106.9 . . ?
O3 C8 H16B 106.9 . . ?
H16A C8 H16B 106.7 . . ?
C8 C9 O4 124.0(2) . . ?
C8 C9 H15A 106.3 . . ?
O4 C9 H15A 106.3 . . ?
C8 C9 H15B 106.3 . . ?
O4 C9 H15B 106.3 . . ?
H15A C9 H15B 106.4 . . ?
O2 C10 C11 108.31(17) . . ?
O2 C10 H9A 110.0 . . ?
C11 C10 H9A 110.0 . . ?
O2 C10 H9B 110.0 . . ?
C11 C10 H9B 110.0 . . ?
H9A C10 H9B 108.4 . . ?
C10 C11 H10A 109.5 . . ?
C10 C11 H10B 109.5 . . ?
H10A C11 H10B 109.5 . . ?
C10 C11 H10C 109.5 . . ?
H10A C11 H10C 109.5 . . ?
H10B C11 H10C 109.5 . . ?
C2 O2 C10 119.88(14) . . ?
C5 O3 C8 112.95(18) . . ?
C6 O4 C9 113.50(18) . . ?
C7 S1 C4 92.87(10) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 1015749'
#######################################################################
#
#                 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_4b
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O8 S2'
_chemical_formula_sum            'C22 H20 O8 S2'
_chemical_formula_weight         476.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.7823(13)
_cell_length_b                   14.5562(6)
_cell_length_c                   15.4932(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.14(11)
_cell_angle_gamma                90.00
_cell_volume                     2183.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1572
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8697
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10651
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0996
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4783
_reflns_number_gt                2364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1102P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4783
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2166
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C20 C 1.1030(6) 0.5819(4) 0.4505(3) 0.0785(15) Uani 1 1 d . . .
H25A H 1.1346 0.5575 0.5073 0.118 Uiso 1 1 calc R . .
H25B H 1.0429 0.5382 0.4178 0.118 Uiso 1 1 calc R . .
H25C H 1.0536 0.6381 0.4560 0.118 Uiso 1 1 calc R . .
C22 C 1.8203(6) 0.5968(5) 0.2273(5) 0.114(2) Uani 1 1 d . . .
H23A H 1.9090 0.6245 0.2261 0.171 Uiso 1 1 calc R . .
H23B H 1.8166 0.5388 0.1975 0.171 Uiso 1 1 calc R . .
H23C H 1.8060 0.5872 0.2867 0.171 Uiso 1 1 calc R . .
S1 S 0.98938(12) 0.86211(9) 0.18009(7) 0.0616(4) Uani 1 1 d . . .
S2 S 1.55179(12) 0.88539(7) 0.05849(7) 0.0554(3) Uani 1 1 d . . .
O3 O 1.1704(3) 0.63659(17) 0.31976(16) 0.0449(6) Uani 1 1 d . . .
O4 O 1.5806(2) 0.61271(18) 0.18835(19) 0.0512(7) Uani 1 1 d . . .
C4 C 1.3745(4) 0.6215(2) 0.2483(2) 0.0358(8) Uani 1 1 d . . .
O9 O 1.4881(3) 0.63051(17) -0.00418(16) 0.0469(7) Uani 1 1 d . . .
C6 C 1.2282(3) 0.7598(2) 0.2349(2) 0.0368(8) Uani 1 1 d . . .
O2 O 1.3904(3) 0.54123(18) 0.27094(17) 0.0524(7) Uani 1 1 d . . .
C2 C 1.4327(3) 0.7428(2) 0.1474(2) 0.0341(8) Uani 1 1 d . . .
O6 O 1.1669(3) 0.8100(2) 0.41387(16) 0.0566(8) Uani 1 1 d . . .
C14 C 1.5211(4) 0.7210(2) 0.0035(2) 0.0378(8) Uani 1 1 d . . .
C1 C 1.3150(4) 0.7967(3) 0.1714(2) 0.0407(8) Uani 1 1 d . . .
C5 C 1.2571(3) 0.6766(2) 0.2704(2) 0.0357(8) Uani 1 1 d . . .
O7 O 1.6085(3) 0.7303(2) -0.13679(17) 0.0655(9) Uani 1 1 d . . .
C13 C 1.4978(4) 0.7742(2) 0.0726(2) 0.0375(8) Uani 1 1 d . . .
O1 O 1.2925(4) 0.8739(2) 0.1409(2) 0.0740(10) Uani 1 1 d . . .
C3 C 1.4685(3) 0.6650(2) 0.1919(2) 0.0351(8) Uani 1 1 d . . .
O5 O 0.9216(3) 0.9207(2) 0.41456(19) 0.0701(9) Uani 1 1 d . . .
C15 C 1.5812(4) 0.7706(3) -0.0609(2) 0.0457(9) Uani 1 1 d . . .
C7 C 1.1142(4) 0.8152(3) 0.2575(2) 0.0415(9) Uani 1 1 d . . .
C19 C 1.2230(4) 0.6002(3) 0.4045(2) 0.0525(10) Uani 1 1 d . . .
H19A H 1.2846 0.6442 0.4370 0.063 Uiso 1 1 calc R . .
H19B H 1.2739 0.5439 0.3986 0.063 Uiso 1 1 calc R . .
C8 C 1.0855(4) 0.8361(3) 0.3390(2) 0.0439(9) Uani 1 1 d . . .
C16 C 1.6061(5) 0.8591(3) -0.0386(3) 0.0578(11) Uani 1 1 d . . .
H15 H 1.6479 0.9008 -0.0721 0.069 Uiso 1 1 calc R . .
C9 C 0.9649(4) 0.8898(3) 0.3382(3) 0.0504(10) Uani 1 1 d . . .
C10 C 0.9016(4) 0.9073(3) 0.2576(3) 0.0577(11) Uani 1 1 d . . .
H10 H 0.8196 0.9401 0.2454 0.069 Uiso 1 1 calc R . .
C21 C 1.7128(4) 0.6571(4) 0.1841(3) 0.0668(13) Uani 1 1 d . . .
H21A H 1.7163 0.7162 0.2132 0.080 Uiso 1 1 calc R . .
H21B H 1.7257 0.6668 0.1239 0.080 Uiso 1 1 calc R . .
C18 C 1.5747(6) 0.6375(4) -0.1417(3) 0.0794(16) Uani 1 1 d . . .
H18A H 1.5221 0.6279 -0.1989 0.095 Uiso 1 1 calc R . .
H18B H 1.6610 0.6045 -0.1412 0.095 Uiso 1 1 calc R . .
C12 C 0.9831(6) 0.8684(4) 0.4880(3) 0.0834(17) Uani 1 1 d . . .
H12A H 0.9417 0.8077 0.4859 0.100 Uiso 1 1 calc R . .
H12B H 0.9647 0.8981 0.5412 0.100 Uiso 1 1 calc R . .
C11 C 1.1348(6) 0.8594(4) 0.4895(3) 0.0797(16) Uani 1 1 d . . .
H11A H 1.1760 0.9200 0.4908 0.096 Uiso 1 1 calc R . .
H11B H 1.1741 0.8271 0.5419 0.096 Uiso 1 1 calc R . .
C23 C 1.5067(12) 0.5950(5) -0.0855(5) 0.179(5) Uani 1 1 d . . .
H23D H 1.5510 0.5357 -0.0744 0.215 Uiso 1 1 calc R . .
H23E H 1.4150 0.5828 -0.1162 0.215 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C20 C19 1.480(6) . ?
C20 H25A 0.9600 . ?
C20 H25B 0.9600 . ?
C20 H25C 0.9600 . ?
C22 C21 1.457(7) . ?
C22 H23A 0.9600 . ?
C22 H23B 0.9600 . ?
C22 H23C 0.9600 . ?
S1 C10 1.704(4) . ?
S1 C7 1.727(4) . ?
S2 C16 1.709(4) . ?
S2 C13 1.726(4) . ?
O3 C5 1.352(4) . ?
O3 C19 1.442(4) . ?
O4 C3 1.342(4) . ?
O4 C21 1.456(5) . ?
C4 O2 1.223(4) . ?
C4 C5 1.481(5) . ?
C4 C3 1.495(5) . ?
O9 C14 1.357(4) . ?
O9 C23 1.398(6) . ?
C6 C5 1.343(5) . ?
C6 C7 1.458(5) . ?
C6 C1 1.489(5) . ?
C2 C3 1.345(5) . ?
C2 C13 1.473(5) . ?
C2 C1 1.484(5) . ?
O6 C8 1.365(4) . ?
O6 C11 1.446(5) . ?
C14 C13 1.366(5) . ?
C14 C15 1.424(5) . ?
C1 O1 1.226(5) . ?
O7 C15 1.374(4) . ?
O7 C18 1.390(6) . ?
O5 C9 1.387(5) . ?
O5 C12 1.429(6) . ?
C15 C16 1.346(6) . ?
C7 C8 1.366(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C8 C9 1.414(5) . ?
C16 H15 0.9300 . ?
C9 C10 1.337(5) . ?
C10 H10 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C18 C23 1.321(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C12 C11 1.486(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C23 H23D 0.9700 . ?
C23 H23E 0.9700 . ?

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
C19 C20 H25A 109.5 . . ?
C19 C20 H25B 109.5 . . ?
H25A C20 H25B 109.5 . . ?
C19 C20 H25C 109.5 . . ?
H25A C20 H25C 109.5 . . ?
H25B C20 H25C 109.5 . . ?
C21 C22 H23A 109.5 . . ?
C21 C22 H23B 109.5 . . ?
H23A C22 H23B 109.5 . . ?
C21 C22 H23C 109.5 . . ?
H23A C22 H23C 109.5 . . ?
H23B C22 H23C 109.5 . . ?
C10 S1 C7 92.28(18) . . ?
C16 S2 C13 92.30(19) . . ?
C5 O3 C19 120.2(3) . . ?
C3 O4 C21 119.1(3) . . ?
O2 C4 C5 121.5(3) . . ?
O2 C4 C3 120.6(3) . . ?
C5 C4 C3 117.8(3) . . ?
C14 O9 C23 112.2(3) . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 C1 119.3(3) . . ?
C7 C6 C1 119.1(3) . . ?
C3 C2 C13 123.7(3) . . ?
C3 C2 C1 118.2(3) . . ?
C13 C2 C1 118.0(3) . . ?
C8 O6 C11 112.4(3) . . ?
O9 C14 C13 123.7(3) . . ?
O9 C14 C15 123.2(3) . . ?
C13 C14 C15 113.1(3) . . ?
O1 C1 C2 119.5(3) . . ?
O1 C1 C6 119.8(3) . . ?
C2 C1 C6 120.6(3) . . ?
C6 C5 O3 120.5(3) . . ?
C6 C5 C4 121.3(3) . . ?
O3 C5 C4 117.8(3) . . ?
C15 O7 C18 112.8(3) . . ?
C14 C13 C2 125.4(3) . . ?
C14 C13 S2 110.2(3) . . ?
C2 C13 S2 124.4(2) . . ?
O4 C3 C2 127.7(3) . . ?
O4 C3 C4 110.9(3) . . ?
C2 C3 C4 121.2(3) . . ?
C9 O5 C12 111.2(3) . . ?
C16 C15 O7 125.3(3) . . ?
C16 C15 C14 112.6(3) . . ?
O7 C15 C14 122.2(3) . . ?
C8 C7 C6 127.6(3) . . ?
C8 C7 S1 109.7(3) . . ?
C6 C7 S1 122.8(3) . . ?
O3 C19 C20 107.4(4) . . ?
O3 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O3 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
O6 C8 C7 123.5(3) . . ?
O6 C8 C9 123.2(3) . . ?
C7 C8 C9 113.3(3) . . ?
C15 C16 S2 111.9(3) . . ?
C15 C16 H15 124.1 . . ?
S2 C16 H15 124.1 . . ?
C10 C9 O5 125.3(4) . . ?
C10 C9 C8 112.9(4) . . ?
O5 C9 C8 121.8(4) . . ?
C9 C10 S1 111.8(3) . . ?
C9 C10 H10 124.1 . . ?
S1 C10 H10 124.1 . . ?
O4 C21 C22 107.5(4) . . ?
O4 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O4 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C23 C18 O7 123.9(4) . . ?
C23 C18 H18A 106.4 . . ?
O7 C18 H18A 106.4 . . ?
C23 C18 H18B 106.4 . . ?
O7 C18 H18B 106.4 . . ?
H18A C18 H18B 106.4 . . ?
O5 C12 C11 111.4(4) . . ?
O5 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
O5 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O6 C11 C12 111.3(4) . . ?
O6 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
O6 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C18 C23 O9 124.2(5) . . ?
C18 C23 H23D 106.3 . . ?
O9 C23 H23D 106.3 . . ?
C18 C23 H23E 106.3 . . ?
O9 C23 H23E 106.3 . . ?
H23D C23 H23E 106.4 . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 1015750'
#######################################################################
#
#                 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_7
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 Cu N2 O6 S2'
_chemical_formula_sum            'C32 H32 Cu N2 O6 S2'
_chemical_formula_weight         668.26

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   6.878
_cell_length_b                   17.926
_cell_length_c                   24.286
_cell_angle_alpha                90.00
_cell_angle_beta                 92.51
_cell_angle_gamma                90.00
_cell_volume                     2991.5
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3691
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.20

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1388
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5019
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24472
_diffrn_reflns_av_R_equivalents  0.1197
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         24.20
_reflns_number_total             4727
_reflns_number_gt                2890
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SIR 2004'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4727
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.9220(6) -0.1837(3) 0.66817(17) 0.0248(11) Uani 0.574(5) 1 d P A 1
S1 S 0.5480(6) -0.2136(3) 0.35876(17) 0.0304(10) Uani 0.574(5) 1 d P A 1
C26 C 0.487(3) -0.0711(10) 0.3613(8) 0.026(6) Uiso 0.574(5) 1 d P A 1
H26 H 0.4736 -0.0219 0.3727 0.031 Uiso 0.574(5) 1 calc PR A 1
C30 C 0.993(3) -0.0475(11) 0.6462(9) 0.053(9) Uiso 0.574(5) 1 d P A 1
H30 H 1.0063 -0.0022 0.6282 0.064 Uiso 0.574(5) 1 calc PR A 1
S1' S 0.5054(10) -0.0520(4) 0.3564(2) 0.0264(14) Uani 0.426(5) 1 d P A 2
S2' S 0.9978(9) -0.0245(4) 0.6502(2) 0.0352(14) Uani 0.426(5) 1 d P A 2
C26' C 0.540(4) -0.1920(15) 0.3624(13) 0.057(13) Uiso 0.426(5) 1 d P A 2
H26' H 0.5721 -0.2399 0.3743 0.068 Uiso 0.426(5) 1 calc PR A 2
C30' C 0.929(3) -0.1648(11) 0.6612(9) 0.014(7) Uiso 0.426(5) 1 d P A 2
H30' H 0.8900 -0.2138 0.6551 0.017 Uiso 0.426(5) 1 calc PR A 2
O2 O 0.8387(4) 0.01634(17) 0.54771(12) 0.0204(8) Uani 1 1 d . . .
O1 O 0.6656(4) 0.00646(16) 0.45243(12) 0.0202(8) Uani 1 1 d . . .
Cu1 Cu 0.75439(8) 0.09037(3) 0.49509(2) 0.0195(2) Uani 1 1 d . . .
N2 N 0.8324(5) 0.1790(2) 0.53786(15) 0.0194(9) Uiso 1 1 d . . .
O3 O 0.8070(5) -0.24524(18) 0.56742(13) 0.0305(9) Uani 1 1 d . A .
O4 O 0.6662(5) -0.25563(18) 0.46447(13) 0.0287(8) Uani 1 1 d . . .
N1 N 0.6816(5) 0.1652(2) 0.43944(15) 0.0188(9) Uiso 1 1 d . . .
C20 C 0.7965(6) -0.0517(2) 0.53272(18) 0.0149(11) Uani 1 1 d . . .
C19 C 0.6996(6) -0.0567(3) 0.47589(18) 0.0174(11) Uani 1 1 d . . .
C24 C 0.6529(6) -0.1252(2) 0.45086(19) 0.0182(11) Uani 1 1 d . A .
C10 C 0.9063(6) 0.1800(3) 0.59008(19) 0.0216(11) Uani 1 1 d . . .
H7 H 0.9316 0.1350 0.6081 0.026 Uiso 1 1 calc R . .
C6 C 0.7970(6) 0.2453(3) 0.51223(19) 0.0194(11) Uani 1 1 d . . .
C1 C 0.6120(6) 0.1511(3) 0.38770(19) 0.0218(12) Uani 1 1 d . . .
H9 H 0.5850 0.1021 0.3773 0.026 Uiso 1 1 calc R . .
C29 C 0.9150(7) -0.1079(3) 0.62277(19) 0.0195(11) Uani 1 1 d . . .
C23 C 0.6971(6) -0.1919(3) 0.48245(19) 0.0205(11) Uani 1 1 d . A .
C25 C 0.5701(7) -0.1301(3) 0.3941(2) 0.0226(12) Uani 1 1 d . . .
C22 C 0.7838(7) -0.1855(3) 0.54253(19) 0.0208(11) Uani 1 1 d . . .
C3 C 0.6214(6) 0.2812(3) 0.36323(19) 0.0230(12) Uani 1 1 d . . .
C9 C 0.9454(7) 0.2455(3) 0.61740(19) 0.0226(12) Uani 1 1 d . . .
H16 H 0.9992 0.2441 0.6532 0.027 Uiso 1 1 calc R . .
C5 C 0.7185(6) 0.2371(2) 0.45419(18) 0.0178(11) Uani 1 1 d . . .
C7 C 0.8324(6) 0.3124(3) 0.53871(19) 0.0216(12) Uani 1 1 d . . .
H18 H 0.8064 0.3569 0.5202 0.026 Uiso 1 1 calc R . .
C8 C 0.9063(7) 0.3139(3) 0.5927(2) 0.0230(12) Uani 1 1 d . . .
C21 C 0.8346(6) -0.1136(2) 0.56566(19) 0.0182(11) Uani 1 1 d . A .
C11 C 0.5975(7) 0.3451(3) 0.3220(2) 0.0278(13) Uani 1 1 d . . .
C15 C 0.9467(8) 0.3867(3) 0.6242(2) 0.0303(13) Uani 1 1 d . . .
C4 C 0.6889(6) 0.2952(3) 0.41757(19) 0.0219(12) Uani 1 1 d . . .
H23 H 0.7138 0.3439 0.4290 0.026 Uiso 1 1 calc R . .
C2 C 0.5802(6) 0.2072(3) 0.3500(2) 0.0230(12) Uani 1 1 d . . .
H24 H 0.5300 0.1955 0.3148 0.028 Uiso 1 1 calc R . .
C27 C 0.4225(8) -0.1011(3) 0.3049(2) 0.0380(14) Uani 1 1 d . . .
H27 H 0.3744 -0.0729 0.2753 0.046 Uiso 1 1 calc R A 1
C12 C 0.5630(8) 0.3168(3) 0.2629(2) 0.0386(14) Uani 1 1 d . . .
H26A H 0.4448 0.2883 0.2603 0.058 Uiso 1 1 calc R . .
H26B H 0.6701 0.2858 0.2532 0.058 Uiso 1 1 calc R . .
H26C H 0.5526 0.3585 0.2381 0.058 Uiso 1 1 calc R . .
C14 C 0.7844(8) 0.3931(3) 0.3246(2) 0.0428(15) Uani 1 1 d . . .
H27A H 0.8072 0.4117 0.3614 0.064 Uiso 1 1 calc R . .
H27B H 0.7690 0.4342 0.2995 0.064 Uiso 1 1 calc R . .
H27C H 0.8930 0.3631 0.3146 0.064 Uiso 1 1 calc R . .
C28 C 0.4469(7) -0.1750(3) 0.3052(2) 0.0364(14) Uani 1 1 d . A .
H28 H 0.4059 -0.2036 0.2749 0.044 Uiso 1 1 calc R B 1
C13 C 0.4213(9) 0.3924(3) 0.3373(2) 0.0492(17) Uani 1 1 d . . .
H30A H 0.3060 0.3622 0.3352 0.074 Uiso 1 1 calc R . .
H30B H 0.4063 0.4335 0.3121 0.074 Uiso 1 1 calc R . .
H30C H 0.4415 0.4111 0.3741 0.074 Uiso 1 1 calc R . .
C18 C 1.1639(8) 0.3905(3) 0.6408(2) 0.0455(16) Uani 1 1 d . . .
H31A H 1.2387 0.3898 0.6084 0.068 Uiso 1 1 calc R . .
H31B H 1.1988 0.3483 0.6636 0.068 Uiso 1 1 calc R . .
H31C H 1.1904 0.4357 0.6610 0.068 Uiso 1 1 calc R . .
C32 C 1.0226(7) -0.1338(3) 0.7169(2) 0.0368(14) Uani 1 1 d . . .
H32 H 1.0539 -0.1547 0.7512 0.044 Uiso 1 1 calc R A 1
C17 C 0.8237(10) 0.3869(3) 0.6751(2) 0.061(2) Uani 1 1 d . . .
H33A H 0.8454 0.4325 0.6951 0.092 Uiso 1 1 calc R . .
H33B H 0.8601 0.3453 0.6982 0.092 Uiso 1 1 calc R . .
H33C H 0.6886 0.3830 0.6638 0.092 Uiso 1 1 calc R . .
C16 C 0.8952(8) 0.4561(3) 0.5900(2) 0.0431(16) Uani 1 1 d . . .
H34A H 0.9694 0.4564 0.5574 0.065 Uiso 1 1 calc R . .
H34B H 0.9249 0.4999 0.6114 0.065 Uiso 1 1 calc R . .
H34C H 0.7588 0.4555 0.5797 0.065 Uiso 1 1 calc R . .
C31 C 1.0605(8) -0.0614(3) 0.7071(2) 0.0392(15) Uani 1 1 d . A .
H31 H 1.1156 -0.0269 0.7318 0.047 Uiso 1 1 calc R C 1
O1W O 0.7075(11) -0.3949(3) 0.5146(3) 0.0595(18) Uani 1 1 d . . .
O2W O 0.6499(8) 0.4660(3) 0.4605(2) 0.0952(18) Uani 1 1 d . . .
H1W H 0.710(10) -0.363(4) 0.508(3) 0.04(3) Uiso 1 1 d . . .
H2W H 0.792(10) -0.388(5) 0.535(3) 0.08(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C32 1.615(7) . ?
S2 C29 1.749(6) . ?
S1 C28 1.604(7) . ?
S1 C25 1.728(7) . ?
C26 C25 1.428(18) . ?
C26 C27 1.52(2) . ?
C26 H26 0.9300 . ?
C30 C29 1.326(19) . ?
C30 C31 1.55(2) . ?
C30 H30 0.9300 . ?
S1' C27 1.613(8) . ?
S1' C25 1.719(8) . ?
S2' C31 1.577(8) . ?
S2' C29 1.724(8) . ?
C26' C25 1.36(3) . ?
C26' C28 1.53(3) . ?
C26' H26' 0.9300 . ?
C30' C29 1.382(19) . ?
C30' C32 1.57(2) . ?
C30' H30' 0.9300 . ?
O2 C20 1.302(5) . ?
O2 Cu1 1.914(3) . ?
O1 C19 1.285(5) . ?
O1 Cu1 1.911(3) . ?
Cu1 N1 1.954(4) . ?
Cu1 N2 1.961(4) . ?
N2 C10 1.346(5) . ?
N2 C6 1.358(5) . ?
O3 C22 1.236(5) . ?
O4 C23 1.238(5) . ?
N1 C1 1.349(6) . ?
N1 C5 1.359(5) . ?
C20 C21 1.387(6) . ?
C20 C19 1.509(6) . ?
C19 C24 1.401(6) . ?
C24 C23 1.445(6) . ?
C24 C25 1.472(6) . ?
C10 C9 1.370(6) . ?
C10 H7 0.9300 . ?
C6 C7 1.381(6) . ?
C6 C5 1.494(6) . ?
C1 C2 1.371(6) . ?
C1 H9 0.9300 . ?
C29 C21 1.474(6) . ?
C23 C22 1.556(7) . ?
C22 C21 1.443(6) . ?
C3 C2 1.392(6) . ?
C3 C4 1.402(6) . ?
C3 C11 1.525(6) . ?
C9 C8 1.386(6) . ?
C9 H16 0.9300 . ?
C5 C4 1.379(6) . ?
C7 C8 1.385(6) . ?
C7 H18 0.9300 . ?
C8 C15 1.532(6) . ?
C11 C12 1.532(7) . ?
C11 C13 1.538(7) . ?
C11 C14 1.546(7) . ?
C15 C16 1.528(7) . ?
C15 C17 1.528(7) . ?
C15 C18 1.532(7) . ?
C4 H23 0.9300 . ?
C2 H24 0.9300 . ?
C27 C28 1.334(7) . ?
C27 H27 0.9300 . ?
C12 H26A 0.9600 . ?
C12 H26B 0.9600 . ?
C12 H26C 0.9600 . ?
C14 H27A 0.9600 . ?
C14 H27B 0.9600 . ?
C14 H27C 0.9600 . ?
C28 H28 0.9300 . ?
C13 H30A 0.9600 . ?
C13 H30B 0.9600 . ?
C13 H30C 0.9600 . ?
C18 H31A 0.9600 . ?
C18 H31B 0.9600 . ?
C18 H31C 0.9600 . ?
C32 C31 1.346(7) . ?
C32 H32 0.9300 . ?
C17 H33A 0.9600 . ?
C17 H33B 0.9600 . ?
C17 H33C 0.9600 . ?
C16 H34A 0.9600 . ?
C16 H34B 0.9600 . ?
C16 H34C 0.9600 . ?
C31 H31 0.9300 . ?
O1W H1W 0.59(6) . ?
O1W H2W 0.76(7) . ?

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
C32 S2 C29 91.7(3) . . ?
C28 S1 C25 93.1(4) . . ?
C25 C26 C27 109.5(12) . . ?
C25 C26 H26 125.2 . . ?
C27 C26 H26 125.2 . . ?
C29 C30 C31 112.1(14) . . ?
C29 C30 H30 123.9 . . ?
C31 C30 H30 123.9 . . ?
C27 S1' C25 92.4(4) . . ?
C31 S2' C29 92.7(4) . . ?
C25 C26' C28 113.4(19) . . ?
C25 C26' H26' 123.3 . . ?
C28 C26' H26' 123.3 . . ?
C29 C30' C32 109.6(14) . . ?
C29 C30' H30' 125.2 . . ?
C32 C30' H30' 125.2 . . ?
C20 O2 Cu1 113.9(3) . . ?
C19 O1 Cu1 114.0(3) . . ?
O1 Cu1 O2 84.06(12) . . ?
O1 Cu1 N1 95.68(14) . . ?
O2 Cu1 N1 176.90(15) . . ?
O1 Cu1 N2 176.99(14) . . ?
O2 Cu1 N2 98.08(14) . . ?
N1 Cu1 N2 82.29(16) . . ?
C10 N2 C6 118.3(4) . . ?
C10 N2 Cu1 126.4(3) . . ?
C6 N2 Cu1 115.3(3) . . ?
C1 N1 C5 118.5(4) . . ?
C1 N1 Cu1 125.9(3) . . ?
C5 N1 Cu1 115.4(3) . . ?
O2 C20 C21 123.7(4) . . ?
O2 C20 C19 113.3(4) . . ?
C21 C20 C19 123.0(4) . . ?
O1 C19 C24 123.1(4) . . ?
O1 C19 C20 114.6(4) . . ?
C24 C19 C20 122.2(4) . . ?
C19 C24 C23 117.1(4) . . ?
C19 C24 C25 122.0(4) . . ?
C23 C24 C25 120.8(4) . . ?
N2 C10 C9 121.7(4) . . ?
N2 C10 H7 119.1 . . ?
C9 C10 H7 119.1 . . ?
N2 C6 C7 121.6(4) . . ?
N2 C6 C5 113.4(4) . . ?
C7 C6 C5 125.0(4) . . ?
N1 C1 C2 121.7(4) . . ?
N1 C1 H9 119.1 . . ?
C2 C1 H9 119.1 . . ?
C30 C29 C30' 107.2(14) . . ?
C30 C29 C21 126.1(10) . . ?
C30' C29 C21 126.7(10) . . ?
C30 C29 S2' 5.7(11) . . ?
C30' C29 S2' 111.5(10) . . ?
C21 C29 S2' 121.8(4) . . ?
C30 C29 S2 111.3(10) . . ?
C30' C29 S2 4.2(11) . . ?
C21 C29 S2 122.6(4) . . ?
S2' C29 S2 115.5(3) . . ?
O4 C23 C24 123.2(4) . . ?
O4 C23 C22 116.8(4) . . ?
C24 C23 C22 120.0(4) . . ?
C26' C25 C26 103.9(15) . . ?
C26' C25 C24 128.4(13) . . ?
C26 C25 C24 127.5(9) . . ?
C26' C25 S1' 109.5(13) . . ?
C26 C25 S1' 9.3(9) . . ?
C24 C25 S1' 122.0(4) . . ?
C26' C25 S1 6.0(14) . . ?
C26 C25 S1 109.9(8) . . ?
C24 C25 S1 122.6(4) . . ?
S1' C25 S1 115.2(4) . . ?
O3 C22 C21 124.0(4) . . ?
O3 C22 C23 115.5(4) . . ?
C21 C22 C23 120.4(4) . . ?
C2 C3 C4 116.4(4) . . ?
C2 C3 C11 123.3(4) . . ?
C4 C3 C11 120.3(4) . . ?
C10 C9 C8 121.2(4) . . ?
C10 C9 H16 119.4 . . ?
C8 C9 H16 119.4 . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 C6 113.4(4) . . ?
C4 C5 C6 124.8(4) . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H18 119.7 . . ?
C8 C7 H18 119.7 . . ?
C9 C8 C7 116.7(4) . . ?
C9 C8 C15 120.6(4) . . ?
C7 C8 C15 122.7(4) . . ?
C20 C21 C22 117.0(4) . . ?
C20 C21 C29 122.7(4) . . ?
C22 C21 C29 120.2(4) . . ?
C3 C11 C12 112.0(4) . . ?
C3 C11 C13 108.6(4) . . ?
C12 C11 C13 108.5(4) . . ?
C3 C11 C14 109.0(4) . . ?
C12 C11 C14 108.5(4) . . ?
C13 C11 C14 110.2(4) . . ?
C16 C15 C17 108.3(5) . . ?
C16 C15 C8 112.9(4) . . ?
C17 C15 C8 108.1(4) . . ?
C16 C15 C18 107.9(4) . . ?
C17 C15 C18 110.7(5) . . ?
C8 C15 C18 108.9(4) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H23 119.8 . . ?
C3 C4 H23 119.8 . . ?
C1 C2 C3 121.3(4) . . ?
C1 C2 H24 119.4 . . ?
C3 C2 H24 119.4 . . ?
C28 C27 C26 108.4(8) . . ?
C28 C27 S1' 119.8(5) . . ?
C26 C27 S1' 13.7(8) . . ?
C28 C27 H27 125.8 . . ?
C26 C27 H27 125.8 . . ?
S1' C27 H27 113.9 . . ?
C11 C12 H26A 109.5 . . ?
C11 C12 H26B 109.5 . . ?
H26A C12 H26B 109.5 . . ?
C11 C12 H26C 109.5 . . ?
H26A C12 H26C 109.5 . . ?
H26B C12 H26C 109.5 . . ?
C11 C14 H27A 109.5 . . ?
C11 C14 H27B 109.5 . . ?
H27A C14 H27B 109.5 . . ?
C11 C14 H27C 109.5 . . ?
H27A C14 H27C 109.5 . . ?
H27B C14 H27C 109.5 . . ?
C27 C28 C26' 104.4(11) . . ?
C27 C28 S1 118.8(5) . . ?
C26' C28 S1 14.5(11) . . ?
C27 C28 H28 120.6 . . ?
C26' C28 H28 135.0 . . ?
S1 C28 H28 120.6 . . ?
C11 C13 H30A 109.5 . . ?
C11 C13 H30B 109.5 . . ?
H30A C13 H30B 109.5 . . ?
C11 C13 H30C 109.5 . . ?
H30A C13 H30C 109.5 . . ?
H30B C13 H30C 109.5 . . ?
C15 C18 H31A 109.5 . . ?
C15 C18 H31B 109.5 . . ?
H31A C18 H31B 109.5 . . ?
C15 C18 H31C 109.5 . . ?
H31A C18 H31C 109.5 . . ?
H31B C18 H31C 109.5 . . ?
C31 C32 C30' 105.3(8) . . ?
C31 C32 S2 119.0(5) . . ?
C30' C32 S2 13.8(7) . . ?
C31 C32 H32 120.5 . . ?
C30' C32 H32 134.2 . . ?
S2 C32 H32 120.5 . . ?
C15 C17 H33A 109.5 . . ?
C15 C17 H33B 109.5 . . ?
H33A C17 H33B 109.5 . . ?
C15 C17 H33C 109.5 . . ?
H33A C17 H33C 109.5 . . ?
H33B C17 H33C 109.5 . . ?
C15 C16 H34A 109.5 . . ?
C15 C16 H34B 109.5 . . ?
H34A C16 H34B 109.5 . . ?
C15 C16 H34C 109.5 . . ?
H34A C16 H34C 109.5 . . ?
H34B C16 H34C 109.5 . . ?
C32 C31 C30 105.7(8) . . ?
C32 C31 S2' 120.7(5) . . ?
C30 C31 S2' 15.6(8) . . ?
C32 C31 H31 127.2 . . ?
C30 C31 H31 127.2 . . ?
S2' C31 H31 112.0 . . ?
H1W O1W H2W 89(8) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        24.20
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 1015751'
