# Electronic Supplementary Material (ESI) for Organic .
# 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mon

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H26 N2 O2 S'
_chemical_formula_sum            'C33 H26 N2 O2 S'
_chemical_formula_weight         514.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.8941(17)
_cell_length_b                   19.167(3)
_cell_length_c                   14.200(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.800(3)
_cell_angle_gamma                90.00
_cell_volume                     2625.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.782460
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'Bruker SADABS; Sheldrick'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14078
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5150
_reflns_number_gt                4680
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0692P)²+1.4850P] 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         5150
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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 0.50161(6) 0.15246(3) 1.06172(4) 0.02434(17) Uani 1 1 d . . .
O1 O 0.46428(18) 0.09084(9) 1.10616(12) 0.0331(4) Uani 1 1 d . . .
O2 O 0.53355(19) 0.21489(9) 1.11696(11) 0.0363(4) Uani 1 1 d . . .
N1 N 0.36360(19) 0.17247(10) 0.97385(13) 0.0225(4) Uani 1 1 d . . .
N2 N 0.33246(18) 0.11538(10) 0.90738(13) 0.0231(4) Uani 1 1 d . . .
C1 C 0.3630(2) 0.23985(12) 0.91852(15) 0.0225(5) Uani 1 1 d . . .
H1B H 0.4432 0.2689 0.9468 0.027 Uiso 1 1 calc R . .
C2 C 0.3730(2) 0.21237(11) 0.82067(15) 0.0212(5) Uani 1 1 d . . .
C17 C 0.2260(2) 0.27817(11) 0.91766(15) 0.0229(5) Uani 1 1 d . . .
C21 C 0.0758(2) 0.35092(12) 0.99385(17) 0.0284(5) Uani 1 1 d . . .
C3 C 0.3321(2) 0.13880(12) 0.82197(16) 0.0223(5) Uani 1 1 d . . .
C26 C 0.2071(2) 0.31903(12) 0.99804(16) 0.0251(5) Uani 1 1 d . . .
C18 C 0.1183(2) 0.27209(13) 0.83886(16) 0.0288(5) Uani 1 1 d . . .
H7A H 0.1305 0.2457 0.7864 0.035 Uiso 1 1 calc R . .
C4 C 0.2955(2) 0.09276(12) 0.73672(16) 0.0240(5) Uani 1 1 d . . .
C10 C 0.4284(2) 0.24076(12) 0.75184(16) 0.0251(5) Uani 1 1 d . . .
H9A H 0.4244 0.2135 0.6971 0.030 Uiso 1 1 calc R . .
C27 C 0.6425(2) 0.13366(12) 1.00973(16) 0.0244(5) Uani 1 1 d . . .
C9 C 0.3447(3) 0.02481(12) 0.74069(18) 0.0295(5) Uani 1 1 d . . .
H11A H 0.4007 0.0079 0.7975 0.035 Uiso 1 1 calc R . .
C32 C 0.6639(2) 0.06677(13) 0.98108(19) 0.0323(6) Uani 1 1 d . . .
H12A H 0.6003 0.0318 0.9852 0.039 Uiso 1 1 calc R . .
C12 C 0.4621(3) 0.36667(13) 0.80087(18) 0.0337(6) Uani 1 1 d . . .
H13A H 0.3924 0.3635 0.8351 0.040 Uiso 1 1 calc R . .
C15 C 0.6676(3) 0.37783(15) 0.6979(2) 0.0391(6) Uani 1 1 d . . .
H14A H 0.7364 0.3816 0.6629 0.047 Uiso 1 1 calc R . .
C11 C 0.4947(2) 0.30907(12) 0.75110(16) 0.0250(5) Uani 1 1 d . . .
C5 C 0.2089(2) 0.11691(13) 0.65139(17) 0.0295(5) Uani 1 1 d . . .
H16A H 0.1747 0.1622 0.6480 0.035 Uiso 1 1 calc R . .
C19 C -0.0105(3) 0.30451(14) 0.83485(18) 0.0351(6) Uani 1 1 d . . .
H17A H -0.0812 0.2998 0.7799 0.042 Uiso 1 1 calc R . .
C28 C 0.7362(3) 0.18597(14) 1.0030(2) 0.0399(6) Uani 1 1 d . . .
H18A H 0.7208 0.2314 1.0211 0.048 Uiso 1 1 calc R . .
C30 C 0.8773(3) 0.10308(16) 0.94143(18) 0.0375(6) Uani 1 1 d . . .
C31 C 0.7805(3) 0.05192(15) 0.94616(19) 0.0375(6) Uani 1 1 d . . .
H20A H 0.7940 0.0069 0.9256 0.045 Uiso 1 1 calc R . .
C6 C 0.1742(3) 0.07337(14) 0.57198(19) 0.0363(6) Uani 1 1 d . . .
H21A H 0.1158 0.0893 0.5155 0.044 Uiso 1 1 calc R . .
C16 C 0.5971(3) 0.31611(13) 0.69797(18) 0.0326(6) Uani 1 1 d . . .
H22A H 0.6178 0.2785 0.6622 0.039 Uiso 1 1 calc R . .
C22 C 0.0551(3) 0.39048(14) 1.0734(2) 0.0375(6) Uani 1 1 d . . .
H23A H -0.0309 0.4109 1.0710 0.045 Uiso 1 1 calc R . .
C25 C 0.3127(3) 0.33093(14) 1.08150(19) 0.0353(6) Uani 1 1 d . . .
H24A H 0.4003 0.3121 1.0851 0.042 Uiso 1 1 calc R . .
C13 C 0.5327(3) 0.42889(14) 0.8000(2) 0.0414(7) Uani 1 1 d . . .
H25A H 0.5102 0.4673 0.8334 0.050 Uiso 1 1 calc R . .
C14 C 0.6365(3) 0.43399(15) 0.7494(2) 0.0423(7) Uani 1 1 d . . .
H26A H 0.6855 0.4755 0.7502 0.051 Uiso 1 1 calc R . .
C20 C -0.0318(3) 0.34249(14) 0.91036(19) 0.0337(6) Uani 1 1 d . . .
H27A H -0.1176 0.3632 0.9075 0.040 Uiso 1 1 calc R . .
C8 C 0.3106(3) -0.01790(13) 0.6603(2) 0.0378(6) Uani 1 1 d . . .
H28A H 0.3450 -0.0632 0.6630 0.045 Uiso 1 1 calc R . .
C24 C 0.2885(3) 0.36953(17) 1.1570(2) 0.0477(7) Uani 1 1 d . . .
H29A H 0.3593 0.3761 1.2115 0.057 Uiso 1 1 calc R . .
C23 C 0.1578(3) 0.39927(16) 1.1531(2) 0.0463(7) Uani 1 1 d . . .
H30A H 0.1418 0.4249 1.2052 0.056 Uiso 1 1 calc R . .
C29 C 0.8528(3) 0.17007(16) 0.9691(2) 0.0472(7) Uani 1 1 d . . .
H31A H 0.9161 0.2052 0.9647 0.057 Uiso 1 1 calc R . .
C7 C 0.2261(3) 0.00630(14) 0.57627(19) 0.0381(6) Uani 1 1 d . . .
H32A H 0.2039 -0.0225 0.5224 0.046 Uiso 1 1 calc R . .
C33 C 1.0101(3) 0.0868(2) 0.9106(2) 0.0543(9) Uani 1 1 d . . .
H33A H 1.0115 0.0383 0.8940 0.081 Uiso 1 1 calc R . .
H33B H 1.0876 0.0969 0.9627 0.081 Uiso 1 1 calc R . .
H33C H 1.0159 0.1147 0.8556 0.081 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 O1 1.4257(18) . ?
S1 O2 1.4273(18) . ?
S1 N1 1.6774(19) . ?
S1 C27 1.754(2) . ?
N1 N2 1.433(3) . ?
N1 C1 1.511(3) . ?
N2 C3 1.293(3) . ?
C1 C2 1.510(3) . ?
C1 C17 1.539(3) . ?
C2 C10 1.338(3) . ?
C2 C3 1.468(3) . ?
C17 C18 1.369(3) . ?
C17 C26 1.430(3) . ?
C21 C22 1.413(3) . ?
C21 C20 1.416(4) . ?
C21 C26 1.425(3) . ?
C3 C4 1.477(3) . ?
C26 C25 1.414(3) . ?
C18 C19 1.407(3) . ?
C4 C9 1.387(3) . ?
C4 C5 1.399(3) . ?
C10 C11 1.465(3) . ?
C27 C32 1.376(3) . ?
C27 C28 1.383(3) . ?
C9 C8 1.385(4) . ?
C32 C31 1.383(3) . ?
C12 C13 1.384(4) . ?
C12 C11 1.387(3) . ?
C15 C16 1.374(4) . ?
C15 C14 1.374(4) . ?
C11 C16 1.398(3) . ?
C5 C6 1.384(3) . ?
C19 C20 1.351(4) . ?
C28 C29 1.379(4) . ?
C30 C29 1.380(4) . ?
C30 C31 1.383(4) . ?
C30 C33 1.507(4) . ?
C6 C7 1.380(4) . ?
C22 C23 1.354(4) . ?
C25 C24 1.367(4) . ?
C13 C14 1.381(4) . ?
C8 C7 1.377(4) . ?
C24 C23 1.402(4) . ?

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 S1 O2 119.92(11) . . ?
O1 S1 N1 105.70(10) . . ?
O2 S1 N1 105.17(10) . . ?
O1 S1 C27 108.92(11) . . ?
O2 S1 C27 107.68(11) . . ?
N1 S1 C27 109.03(10) . . ?
N2 N1 C1 109.56(16) . . ?
N2 N1 S1 109.63(13) . . ?
C1 N1 S1 119.42(14) . . ?
C3 N2 N1 107.95(18) . . ?
C2 C1 N1 100.77(17) . . ?
C2 C1 C17 113.38(17) . . ?
N1 C1 C17 108.32(17) . . ?
C10 C2 C3 123.9(2) . . ?
C10 C2 C1 130.7(2) . . ?
C3 C2 C1 104.41(18) . . ?
C18 C17 C26 118.9(2) . . ?
C18 C17 C1 119.4(2) . . ?
C26 C17 C1 121.72(19) . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 C26 119.3(2) . . ?
C20 C21 C26 119.7(2) . . ?
N2 C3 C2 113.7(2) . . ?
N2 C3 C4 120.7(2) . . ?
C2 C3 C4 125.58(19) . . ?
C25 C26 C21 117.6(2) . . ?
C25 C26 C17 123.6(2) . . ?
C21 C26 C17 118.7(2) . . ?
C17 C18 C19 122.0(2) . . ?
C9 C4 C5 119.2(2) . . ?
C9 C4 C3 120.5(2) . . ?
C5 C4 C3 120.3(2) . . ?
C2 C10 C11 128.7(2) . . ?
C32 C27 C28 120.4(2) . . ?
C32 C27 S1 120.30(18) . . ?
C28 C27 S1 119.2(2) . . ?
C8 C9 C4 120.2(2) . . ?
C27 C32 C31 119.5(2) . . ?
C13 C12 C11 120.5(2) . . ?
C16 C15 C14 120.0(2) . . ?
C12 C11 C16 118.4(2) . . ?
C12 C11 C10 123.6(2) . . ?
C16 C11 C10 118.0(2) . . ?
C6 C5 C4 120.0(2) . . ?
C20 C19 C18 120.4(2) . . ?
C29 C28 C27 119.3(3) . . ?
C29 C30 C31 118.6(2) . . ?
C29 C30 C33 119.7(3) . . ?
C31 C30 C33 121.7(3) . . ?
C32 C31 C30 120.9(3) . . ?
C7 C6 C5 120.2(2) . . ?
C15 C16 C11 120.9(2) . . ?
C23 C22 C21 121.4(2) . . ?
C24 C25 C26 121.3(2) . . ?
C14 C13 C12 120.1(3) . . ?
C15 C14 C13 120.1(2) . . ?
C19 C20 C21 120.3(2) . . ?
C7 C8 C9 120.4(2) . . ?
C25 C24 C23 120.6(3) . . ?
C22 C23 C24 119.8(2) . . ?
C28 C29 C30 121.2(3) . . ?
C8 C7 C6 120.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 960118'
