# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_indenodithipine
_database_code_depnum_ccdc_archive 'CCDC 1019959'
_audit_update_record             
;
2014-08-18 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C30 H24 S2'

_chemical_formula_sum            'C30 H24 S2'

_chemical_formula_weight         448.61



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'
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/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                   8.6410(12)

_cell_length_b                   10.6699(15)

_cell_length_c                   25.373(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 97.159(2)

_cell_angle_gamma                90.00

_cell_volume                     2321.2(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    6407

_cell_measurement_theta_min      2.38

_cell_measurement_theta_max      28.02



_exptl_crystal_description       BLOCKS

_exptl_crystal_colour            COLOURLESS

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.28

_exptl_crystal_size_min          0.23

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.284

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    0.245

_exptl_absorpt_correction_type   MULTI-SCAN

_exptl_absorpt_correction_T_min  0.9190

_exptl_absorpt_correction_T_max  0.9457

_exptl_absorpt_process_details   'BRUKER 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  'BRUKER SMART APEX CCD DIFFRACTOMETER'

_diffrn_measurement_method       'OMEGA-PHI SCAN'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            13021

_diffrn_reflns_av_R_equivalents  0.0236

_diffrn_reflns_av_sigmaI/netI    0.0298

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -31

_diffrn_reflns_limit_l_max       32

_diffrn_reflns_theta_min         1.62

_diffrn_reflns_theta_max         27.00

_reflns_number_total             5057

_reflns_number_gt                4366

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'BRUKER SMART'

_computing_cell_refinement       'BRUKER SMART'

_computing_data_reduction        'BRUKER SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    ORTEP

_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)+(0.0617P)²+0.5197P] 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         5057

_refine_ls_number_parameters     289

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0493

_refine_ls_R_factor_gt           0.0430

_refine_ls_wR_factor_ref         0.1155

_refine_ls_wR_factor_gt          0.1115

_refine_ls_goodness_of_fit_ref   1.039

_refine_ls_restrained_S_all      1.039

_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
























































S2 S 0.29293(5) 0.33678(4) 0.165338(17) 0.04510(13) Uani 1 1 d . . .
S1 S 0.34972(5) 0.02642(4) 0.235657(16) 0.04481(13) Uani 1 1 d . . .
C23 C 0.62366(17) -0.01767(15) 0.19457(6) 0.0368(3) Uani 1 1 d . . .
C14 C 0.41611(16) 0.10671(14) 0.13734(6) 0.0336(3) Uani 1 1 d . . .
C7 C 0.35607(17) 0.02727(15) 0.09893(6) 0.0359(3) Uani 1 1 d . . .
C15 C 0.39244(17) 0.24294(14) 0.11888(6) 0.0363(3) Uani 1 1 d . . .
C29 C 0.22212(19) 0.15973(17) 0.23918(7) 0.0455(4) Uani 1 1 d . . .
H29A H 0.1340 0.1326 0.2566 0.055 Uiso 1 1 calc R . .
H29B H 0.2782 0.2219 0.2620 0.055 Uiso 1 1 calc R . .
C22 C 0.49351(16) 0.07914(14) 0.19248(6) 0.0348(3) Uani 1 1 d . . .
H22 H 0.5395 0.1575 0.2073 0.042 Uiso 1 1 calc R . .
C6 C 0.27719(17) 0.10019(16) 0.05413(6) 0.0396(3) Uani 1 1 d . . .
C16 C 0.55284(17) 0.30189(15) 0.11335(6) 0.0383(3) Uani 1 1 d . . .
C1 C 0.29209(17) 0.22721(16) 0.06580(6) 0.0398(3) Uani 1 1 d . . .
C30 C 0.15811(18) 0.22435(16) 0.18744(7) 0.0432(4) Uani 1 1 d . . .
H30A H 0.0618 0.2669 0.1924 0.052 Uiso 1 1 calc R . .
H30B H 0.1341 0.1614 0.1601 0.052 Uiso 1 1 calc R . .
C8 C 0.36263(18) -0.11129(15) 0.09787(6) 0.0381(3) Uani 1 1 d . . .
C28 C 0.6017(2) -0.14382(17) 0.20407(7) 0.0465(4) Uani 1 1 d . . .
H28 H 0.5046 -0.1719 0.2112 0.056 Uiso 1 1 calc R . .
C13 C 0.2498(2) -0.18374(17) 0.11743(7) 0.0493(4) Uani 1 1 d . . .
H13 H 0.1673 -0.1452 0.1314 0.059 Uiso 1 1 calc R . .
C5 C 0.1950(2) 0.0593(2) 0.00672(7) 0.0519(4) Uani 1 1 d . . .
H5 H 0.1862 -0.0256 -0.0014 0.062 Uiso 1 1 calc R . .
C17 C 0.6351(2) 0.37361(17) 0.15285(7) 0.0477(4) Uani 1 1 d . . .
H17 H 0.5910 0.3921 0.1836 0.057 Uiso 1 1 calc R . .
C24 C 0.7707(2) 0.02213(18) 0.18523(8) 0.0519(4) Uani 1 1 d . . .
H24 H 0.7883 0.1066 0.1791 0.062 Uiso 1 1 calc R . .
C11 C 0.3809(3) -0.37050(19) 0.09586(8) 0.0667(6) Uani 1 1 d . . .
H11 H 0.3880 -0.4575 0.0956 0.080 Uiso 1 1 calc R . .
C12 C 0.2591(3) -0.31407(19) 0.11631(9) 0.0624(5) Uani 1 1 d . . .
H12 H 0.1829 -0.3625 0.1294 0.075 Uiso 1 1 calc R . .
C18 C 0.7833(2) 0.41829(19) 0.14696(9) 0.0585(5) Uani 1 1 d . . .
H18 H 0.8372 0.4669 0.1736 0.070 Uiso 1 1 calc R . .
C9 C 0.4829(2) -0.17081(18) 0.07638(8) 0.0550(4) Uani 1 1 d . . .
H9 H 0.5581 -0.1234 0.0622 0.066 Uiso 1 1 calc R . .
C27 C 0.7230(2) -0.22891(18) 0.20311(8) 0.0548(5) Uani 1 1 d . . .
H27 H 0.7062 -0.3136 0.2090 0.066 Uiso 1 1 calc R . .
C2 C 0.2235(2) 0.31609(19) 0.03079(7) 0.0533(4) Uani 1 1 d . . .
H2 H 0.2331 0.4012 0.0385 0.064 Uiso 1 1 calc R . .
C19 C 0.8505(2) 0.3911(2) 0.10200(9) 0.0648(6) Uani 1 1 d . . .
H19 H 0.9496 0.4211 0.0982 0.078 Uiso 1 1 calc R . .
C25 C 0.8911(2) -0.0631(2) 0.18500(9) 0.0654(6) Uani 1 1 d . . .
H25 H 0.9894 -0.0352 0.1790 0.078 Uiso 1 1 calc R . .
C26 C 0.8676(2) -0.1883(2) 0.19352(8) 0.0599(5) Uani 1 1 d . . .
H26 H 0.9490 -0.2452 0.1928 0.072 Uiso 1 1 calc R . .
C4 C 0.1266(2) 0.1489(2) -0.02807(8) 0.0650(6) Uani 1 1 d . . .
H4 H 0.0707 0.1237 -0.0600 0.078 Uiso 1 1 calc R . .
C21 C 0.6223(2) 0.2756(2) 0.06837(8) 0.0605(5) Uani 1 1 d . . .
H21 H 0.5688 0.2276 0.0414 0.073 Uiso 1 1 calc R . .
C20 C 0.7705(2) 0.3195(3) 0.06274(9) 0.0765(7) Uani 1 1 d . . .
H20 H 0.8157 0.3004 0.0323 0.092 Uiso 1 1 calc R . .
C3 C 0.1395(2) 0.2746(2) -0.01635(8) 0.0648(6) Uani 1 1 d . . .
H3 H 0.0914 0.3328 -0.0403 0.078 Uiso 1 1 calc R . .
C10 C 0.4919(3) -0.3001(2) 0.07585(9) 0.0696(6) Uani 1 1 d . . .
H10 H 0.5737 -0.3393 0.0618 0.084 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





























































S2 C30 1.8093(17) . ?
S2 C15 1.8396(16) . ?
S1 C29 1.8086(17) . ?
S1 C22 1.8439(15) . ?
C23 C28 1.385(2) . ?
C23 C24 1.388(2) . ?
C23 C22 1.523(2) . ?
C14 C7 1.346(2) . ?
C14 C22 1.502(2) . ?
C14 C15 1.533(2) . ?
C7 C6 1.473(2) . ?
C7 C8 1.480(2) . ?
C15 C1 1.517(2) . ?
C15 C16 1.544(2) . ?
C29 C30 1.524(2) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C22 H22 0.9800 . ?
C6 C5 1.389(2) . ?
C6 C1 1.390(2) . ?
C16 C21 1.383(2) . ?
C16 C17 1.385(2) . ?
C1 C2 1.382(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C8 C13 1.384(2) . ?
C8 C9 1.386(2) . ?
C28 C27 1.389(2) . ?
C28 H28 0.9300 . ?
C13 C12 1.393(3) . ?
C13 H13 0.9300 . ?
C5 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9300 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9300 . ?
C11 C10 1.365(3) . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C27 C26 1.373(3) . ?
C27 H27 0.9300 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C4 C3 1.375(3) . ?
C4 H4 0.9300 . ?
C21 C20 1.388(3) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag








































































































C30 S2 C15 102.02(8) . . ?
C29 S1 C22 104.45(8) . . ?
C28 C23 C24 118.39(15) . . ?
C28 C23 C22 123.28(14) . . ?
C24 C23 C22 118.31(15) . . ?
C7 C14 C22 129.61(14) . . ?
C7 C14 C15 110.55(13) . . ?
C22 C14 C15 119.81(13) . . ?
C14 C7 C6 109.01(14) . . ?
C14 C7 C8 129.06(14) . . ?
C6 C7 C8 121.93(13) . . ?
C1 C15 C14 101.89(12) . . ?
C1 C15 C16 112.62(12) . . ?
C14 C15 C16 109.08(12) . . ?
C1 C15 S2 111.58(11) . . ?
C14 C15 S2 112.05(10) . . ?
C16 C15 S2 109.45(11) . . ?
C30 C29 S1 118.11(12) . . ?
C30 C29 H29A 107.8 . . ?
S1 C29 H29A 107.8 . . ?
C30 C29 H29B 107.8 . . ?
S1 C29 H29B 107.8 . . ?
H29A C29 H29B 107.1 . . ?
C14 C22 C23 113.97(12) . . ?
C14 C22 S1 110.99(10) . . ?
C23 C22 S1 108.77(10) . . ?
C14 C22 H22 107.6 . . ?
C23 C22 H22 107.6 . . ?
S1 C22 H22 107.6 . . ?
C5 C6 C1 120.98(15) . . ?
C5 C6 C7 129.80(16) . . ?
C1 C6 C7 109.21(13) . . ?
C21 C16 C17 118.22(16) . . ?
C21 C16 C15 118.63(15) . . ?
C17 C16 C15 123.02(14) . . ?
C2 C1 C6 120.76(15) . . ?
C2 C1 C15 130.30(16) . . ?
C6 C1 C15 108.93(13) . . ?
C29 C30 S2 112.85(11) . . ?
C29 C30 H30A 109.0 . . ?
S2 C30 H30A 109.0 . . ?
C29 C30 H30B 109.0 . . ?
S2 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C13 C8 C9 118.78(16) . . ?
C13 C8 C7 121.41(15) . . ?
C9 C8 C7 119.81(15) . . ?
C23 C28 C27 120.81(17) . . ?
C23 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C8 C13 C12 120.34(18) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C4 C5 C6 117.85(19) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C16 C17 C18 120.51(18) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C25 C24 C23 120.32(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C10 C11 C12 120.53(19) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.71(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C19 C18 C17 120.44(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C10 C9 C8 120.45(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C26 C27 C28 120.17(18) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C1 C2 C3 118.06(19) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C20 C19 C18 119.58(18) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C26 C25 C24 120.91(19) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 119.39(18) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C3 C4 C5 121.30(18) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C16 C21 C20 121.16(19) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C4 C3 C2 121.04(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?



_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        27.00

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         0.354

_refine_diff_density_min         -0.145

_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_indenodithipine2
_database_code_depnum_ccdc_archive 'CCDC 1019960'
_audit_update_record             
;
2014-08-18 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C33 H29 Cl S2'

_chemical_formula_sum            
'C33 H29 Cl S2'

_chemical_formula_weight         525.13



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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           TRICLINIC

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   9.901(2)

_cell_length_b                   11.029(3)

_cell_length_c                   14.297(3)

_cell_angle_alpha                74.650(4)

_cell_angle_beta                 76.568(4)

_cell_angle_gamma                68.378(4)

_cell_volume                     1383.6(5)

_cell_formula_units_Z            2

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    3412

_cell_measurement_theta_min      2.24

_cell_measurement_theta_max      26.94



_exptl_crystal_description       BLOCKS

_exptl_crystal_colour            YELLOW

_exptl_crystal_size_max          0.22

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.260

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.309

_exptl_absorpt_correction_type   MULTI-SCAN

_exptl_absorpt_correction_T_min  0.9341

_exptl_absorpt_correction_T_max  0.9668

_exptl_absorpt_process_details   'BRUKER 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  'BRUKER SMART APEX CCD DIFFRACTOMETER'

_diffrn_measurement_method       'OMEGA-PHI SCAN'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            10775

_diffrn_reflns_av_R_equivalents  0.0232

_diffrn_reflns_av_sigmaI/netI    0.0389

_diffrn_reflns_limit_h_min       -12

_diffrn_reflns_limit_h_max       12

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         1.49

_diffrn_reflns_theta_max         26.00

_reflns_number_total             5447

_reflns_number_gt                4235

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'BRUKER SMART'

_computing_cell_refinement       'BRUKER SMART'

_computing_data_reduction        'BRUKER SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    ORTEP

_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)+(0.0698P)²+0.5957P] 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         5382

_refine_ls_number_parameters     327

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0794

_refine_ls_R_factor_gt           0.0619

_refine_ls_wR_factor_ref         0.1546

_refine_ls_wR_factor_gt          0.1434

_refine_ls_goodness_of_fit_ref   1.078

_refine_ls_restrained_S_all      1.078

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

































































S1 S 0.09893(8) 1.11409(8) 0.16052(6) 0.0582(2) Uani 1 1 d . . .
S2 S 0.21444(9) 0.72913(7) 0.26976(6) 0.0578(2) Uani 1 1 d . . .
Cl1 Cl 0.71035(11) 1.32055(10) 0.01479(6) 0.0807(3) Uani 1 1 d . . .
C1 C 0.3475(3) 1.2295(3) 0.1447(2) 0.0558(7) Uani 1 1 d . . .
H1 H 0.2520 1.2738 0.1708 0.067 Uiso 1 1 calc R . .
C2 C 0.4458(4) 1.2992(3) 0.1052(2) 0.0617(8) Uani 1 1 d . . .
H2 H 0.4166 1.3897 0.1048 0.074 Uiso 1 1 calc R . .
C3 C 0.5862(4) 1.2335(3) 0.0667(2) 0.0551(8) Uani 1 1 d . . .
C4 C 0.6320(3) 1.0995(3) 0.0684(2) 0.0572(8) Uani 1 1 d . . .
H4 H 0.7283 1.0555 0.0434 0.069 Uiso 1 1 calc R . .
C5 C 0.5332(3) 1.0310(3) 0.1078(2) 0.0510(7) Uani 1 1 d . . .
H5 H 0.5638 0.9402 0.1088 0.061 Uiso 1 1 calc R . .
C6 C 0.3901(3) 1.0943(3) 0.14571(18) 0.0430(6) Uani 1 1 d . . .
C7 C 0.2874(3) 1.0127(3) 0.18458(19) 0.0415(6) Uani 1 1 d . . .
H7 H 0.3209 0.9437 0.1452 0.050 Uiso 1 1 calc R . .
C8 C 0.2949(3) 0.9398(2) 0.28951(18) 0.0371(5) Uani 1 1 d . . .
C9 C 0.3371(3) 0.7874(2) 0.31262(19) 0.0414(6) Uani 1 1 d . . .
C10 C 0.0352(3) 0.8433(3) 0.3084(2) 0.0611(8) Uani 1 1 d . . .
H10A H -0.0217 0.7933 0.3563 0.073 Uiso 1 1 calc R . .
H10B H 0.0480 0.9053 0.3399 0.073 Uiso 1 1 calc R . .
C11 C -0.0493(3) 0.9207(3) 0.2235(3) 0.0640(8) Uani 1 1 d . . .
H11A H -0.0765 0.8594 0.1999 0.077 Uiso 1 1 calc R . .
H11B H -0.1395 0.9849 0.2479 0.077 Uiso 1 1 calc R . .
C12 C 0.0313(4) 0.9938(3) 0.1377(2) 0.0630(8) Uani 1 1 d . . .
H12A H -0.0338 1.0398 0.0889 0.076 Uiso 1 1 calc R . .
H12B H 0.1146 0.9278 0.1087 0.076 Uiso 1 1 calc R . .
C13 C 0.2720(3) 0.9857(2) 0.37174(18) 0.0367(5) Uani 1 1 d . . .
C14 C 0.2896(3) 0.8732(2) 0.45670(18) 0.0364(5) Uani 1 1 d . . .
C15 C 0.3216(3) 0.7568(2) 0.42278(19) 0.0388(6) Uani 1 1 d . . .
C16 C 0.2338(3) 1.1245(2) 0.38542(18) 0.0386(6) Uani 1 1 d . . .
C17 C 0.0920(3) 1.2112(3) 0.3873(2) 0.0555(7) Uani 1 1 d . . .
H17 H 0.0184 1.1840 0.3780 0.067 Uiso 1 1 calc R . .
C18 C 0.0578(4) 1.3385(3) 0.4028(3) 0.0704(10) Uani 1 1 d . . .
H18 H -0.0384 1.3963 0.4035 0.085 Uiso 1 1 calc R . .
C19 C 0.1641(4) 1.3800(3) 0.4170(3) 0.0697(10) Uani 1 1 d . . .
H19 H 0.1409 1.4662 0.4262 0.084 Uiso 1 1 calc R . .
C20 C 0.3043(4) 1.2944(3) 0.4175(3) 0.0744(10) Uani 1 1 d . . .
H20 H 0.3768 1.3216 0.4283 0.089 Uiso 1 1 calc R . .
C21 C 0.3390(3) 1.1673(3) 0.4019(3) 0.0614(8) Uani 1 1 d . . .
H21 H 0.4351 1.1095 0.4026 0.074 Uiso 1 1 calc R . .
C22 C 0.2818(3) 0.8687(3) 0.55550(19) 0.0416(6) Uani 1 1 d . . .
H22 H 0.2610 0.9465 0.5779 0.050 Uiso 1 1 calc R . .
C23 C 0.3054(3) 0.7469(3) 0.62118(19) 0.0451(6) Uani 1 1 d . . .
C24 C 0.3328(3) 0.6331(3) 0.5862(2) 0.0476(7) Uani 1 1 d . . .
H24 H 0.3463 0.5521 0.6302 0.057 Uiso 1 1 calc R . .
C25 C 0.3408(3) 0.6366(3) 0.4879(2) 0.0463(6) Uani 1 1 d . . .
H25 H 0.3588 0.5591 0.4659 0.056 Uiso 1 1 calc R . .
C26 C 0.3041(4) 0.7364(3) 0.7287(2) 0.0694(9) Uani 1 1 d . . .
H26A H 0.2084 0.7386 0.7641 0.104 Uiso 1 1 calc R . .
H26B H 0.3273 0.8096 0.7371 0.104 Uiso 1 1 calc R . .
H26C H 0.3758 0.6542 0.7532 0.104 Uiso 1 1 calc R . .
C27 C 0.4960(3) 0.7259(2) 0.26563(19) 0.0424(6) Uani 1 1 d . . .
C28 C 0.6096(3) 0.7260(3) 0.3070(2) 0.0481(7) Uani 1 1 d . . .
H28 H 0.5876 0.7610 0.3633 0.058 Uiso 1 1 calc R . .
C29 C 0.7543(3) 0.6755(3) 0.2663(2) 0.0573(8) Uani 1 1 d . . .
H29 H 0.8278 0.6759 0.2965 0.069 Uiso 1 1 calc R . .
C30 C 0.7932(4) 0.6244(3) 0.1824(3) 0.0651(9) Uani 1 1 d . . .
C31 C 0.6806(4) 0.6252(3) 0.1410(2) 0.0705(9) Uani 1 1 d . . .
H31 H 0.7035 0.5915 0.0841 0.085 Uiso 1 1 calc R . .
C32 C 0.5344(4) 0.6742(3) 0.1810(2) 0.0577(8) Uani 1 1 d . . .
H32 H 0.4615 0.6725 0.1509 0.069 Uiso 1 1 calc R . .
C33 C 0.9525(5) 0.5692(5) 0.1382(3) 0.1078(15) Uani 1 1 d . . .
H33A H 0.9732 0.4797 0.1309 0.162 Uiso 1 1 calc R . .
H33B H 1.0147 0.5695 0.1805 0.162 Uiso 1 1 calc R . .
H33C H 0.9706 0.6233 0.0750 0.162 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 C12 1.816(3) . ?
S1 C7 1.846(3) . ?
S2 C10 1.818(3) . ?
S2 C9 1.842(3) . ?
Cl1 C3 1.747(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.390(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.517(4) . ?
C7 C8 1.507(3) . ?
C7 H7 0.9800 . ?
C8 C13 1.341(3) . ?
C8 C9 1.536(3) . ?
C9 C15 1.504(4) . ?
C9 C27 1.533(4) . ?
C10 C11 1.516(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.513(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.479(3) . ?
C13 C16 1.490(3) . ?
C14 C22 1.385(4) . ?
C14 C15 1.394(3) . ?
C15 C25 1.380(3) . ?
C16 C17 1.376(4) . ?
C16 C21 1.378(4) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.361(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.394(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(4) . ?
C23 C26 1.508(4) . ?
C24 C25 1.381(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.388(4) . ?
C27 C32 1.388(4) . ?
C28 C29 1.377(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.374(5) . ?
C30 C33 1.514(5) . ?
C31 C32 1.385(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 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


























































































































C12 S1 C7 102.62(14) . . ?
C10 S2 C9 101.43(13) . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 Cl1 119.9(2) . . ?
C4 C3 Cl1 119.0(3) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 118.1(2) . . ?
C1 C6 C7 123.7(3) . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 S1 113.49(18) . . ?
C6 C7 S1 110.64(17) . . ?
C8 C7 H7 105.9 . . ?
C6 C7 H7 105.9 . . ?
S1 C7 H7 105.9 . . ?
C13 C8 C7 130.5(2) . . ?
C13 C8 C9 110.5(2) . . ?
C7 C8 C9 119.0(2) . . ?
C15 C9 C27 111.7(2) . . ?
C15 C9 C8 101.9(2) . . ?
C27 C9 C8 109.6(2) . . ?
C15 C9 S2 111.37(18) . . ?
C27 C9 S2 109.49(17) . . ?
C8 C9 S2 112.59(17) . . ?
C11 C10 S2 112.5(2) . . ?
C11 C10 H10A 109.1 . . ?
S2 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
S2 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 115.5(3) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 S1 118.3(2) . . ?
C11 C12 H12A 107.7 . . ?
S1 C12 H12A 107.7 . . ?
C11 C12 H12B 107.7 . . ?
S1 C12 H12B 107.7 . . ?
H12A C12 H12B 107.1 . . ?
C8 C13 C14 109.3(2) . . ?
C8 C13 C16 129.9(2) . . ?
C14 C13 C16 120.8(2) . . ?
C22 C14 C15 120.4(2) . . ?
C22 C14 C13 131.3(2) . . ?
C15 C14 C13 108.3(2) . . ?
C25 C15 C14 120.2(2) . . ?
C25 C15 C9 130.1(2) . . ?
C14 C15 C9 109.6(2) . . ?
C17 C16 C21 118.0(2) . . ?
C17 C16 C13 121.4(2) . . ?
C21 C16 C13 120.5(2) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 121.2(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C14 C22 C23 119.6(2) . . ?
C14 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 119.0(2) . . ?
C24 C23 C26 119.5(3) . . ?
C22 C23 C26 121.5(3) . . ?
C25 C24 C23 121.8(2) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C15 C25 C24 119.0(3) . . ?
C15 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 117.1(3) . . ?
C28 C27 C9 118.8(2) . . ?
C32 C27 C9 124.0(3) . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C30 C29 C28 121.9(3) . . ?
C30 C29 H29 119.1 . . ?
C28 C29 H29 119.1 . . ?
C31 C30 C29 116.8(3) . . ?
C31 C30 C33 121.7(3) . . ?
C29 C30 C33 121.5(4) . . ?
C30 C31 C32 122.5(3) . . ?
C30 C31 H31 118.8 . . ?
C32 C31 H31 118.8 . . ?
C31 C32 C27 120.4(3) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?



_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        26.00

_diffrn_measured_fraction_theta_full 0.988

_refine_diff_density_max         0.376

_refine_diff_density_min         -0.230

_refine_diff_density_rms         0.051







#===END





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















