# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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/access/V1 
# 
# Audit and citation data items may have 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_import
_database_code_depnum_ccdc_archive 'CCDC 1046694'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C25 H16 O2 S2), C H Cl3'
_chemical_formula_sum            '	C51 H33 Cl3 O4 S4 '
_chemical_formula_weight         944.40
_chemical_absolute_configuration unk

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'
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'
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.9757(2)
_cell_length_b                   9.3007(2)
_cell_length_c                   13.5937(3)
_cell_angle_alpha                101.4580(10)
_cell_angle_beta                 97.3160(10)
_cell_angle_gamma                106.5770(10)
_cell_volume                     1045.31(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7365
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      26.94


_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             486
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.995

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6757  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17361
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.49
_reflns_number_total             7002
_reflns_number_gt                6294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (ALtomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0480P)²+0.4343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.28(6)
_refine_ls_number_reflns         7002
_refine_ls_number_parameters     560
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.3516(4) 0.0258(4) 0.1967(2) 0.0194(7) Uani 1 1 d . . .
C2 C 0.2290(4) 0.0701(4) 0.2352(3) 0.0273(8) Uani 1 1 d . . .
H2 H 0.1667 0.0099 0.2712 0.033 Uiso 1 1 calc R . .
C3 C 0.2016(5) 0.2015(4) 0.2198(3) 0.0286(8) Uani 1 1 d . . .
H3 H 0.1194 0.2304 0.2440 0.034 Uiso 1 1 calc R . .
C4 C 0.2976(4) 0.2921(4) 0.1674(3) 0.0267(8) Uani 1 1 d . . .
H4 H 0.2801 0.3824 0.1571 0.032 Uiso 1 1 calc R . .
C5 C 0.4180(4) 0.2485(4) 0.1311(3) 0.0210(7) Uani 1 1 d . . .
H5 H 0.4812 0.3106 0.0965 0.025 Uiso 1 1 calc R . .
C6 C 0.4487(4) 0.1137(3) 0.1444(2) 0.0171(6) Uani 1 1 d . . .
C7 C 0.5847(4) 0.0751(3) 0.0993(2) 0.0156(6) Uani 1 1 d . . .
C8 C 0.6278(4) -0.0629(3) 0.1265(2) 0.0162(6) Uani 1 1 d . . .
C9 C 0.7627(4) -0.0915(4) 0.0977(2) 0.0200(7) Uani 1 1 d . . .
H9 H 0.8223 -0.0279 0.0623 0.024 Uiso 1 1 calc R . .
C10 C 0.8098(4) -0.2131(4) 0.1209(3) 0.0260(8) Uani 1 1 d . . .
H10 H 0.9000 -0.2299 0.1009 0.031 Uiso 1 1 calc R . .
C11 C 0.7225(4) -0.3094(4) 0.1737(3) 0.0255(8) Uani 1 1 d . . .
H11 H 0.7543 -0.3907 0.1890 0.031 Uiso 1 1 calc R . .
C12 C 0.5894(4) -0.2846(4) 0.2033(2) 0.0236(8) Uani 1 1 d . . .
H12 H 0.5312 -0.3481 0.2394 0.028 Uiso 1 1 calc R . .
C13 C 0.5420(4) -0.1622(3) 0.1787(2) 0.0167(6) Uani 1 1 d . . .
C14 C 0.5344(4) 0.0364(3) -0.0184(2) 0.0164(6) Uani 1 1 d . . .
C15 C 0.3826(4) -0.0653(4) -0.0632(2) 0.0246(7) Uani 1 1 d . . .
H15 H 0.3142 -0.1017 -0.0212 0.029 Uiso 1 1 calc R . .
C16 C 0.3307(4) -0.1134(4) -0.1678(3) 0.0278(8) Uani 1 1 d . . .
H16 H 0.2281 -0.1797 -0.1954 0.033 Uiso 1 1 calc R . .
C17 C 0.4316(5) -0.0630(4) -0.2316(3) 0.0287(8) Uani 1 1 d . . .
H17 H 0.3988 -0.0981 -0.3023 0.034 Uiso 1 1 calc R . .
C18 C 0.5809(5) 0.0397(4) -0.1895(3) 0.0272(8) Uani 1 1 d . . .
H18 H 0.6485 0.0749 -0.2322 0.033 Uiso 1 1 calc R . .
C19 C 0.6322(4) 0.0918(4) -0.0837(2) 0.0218(7) Uani 1 1 d . . .
C20 C 0.8369(4) 0.2915(3) 0.0885(2) 0.0181(7) Uani 1 1 d . . .
C21 C 0.9674(4) 0.4243(4) 0.1379(2) 0.0197(7) Uani 1 1 d . . .
H21 H 1.0343 0.4742 0.0996 0.024 Uiso 1 1 calc R . .
C22 C 0.9963(4) 0.4802(4) 0.2422(3) 0.0214(7) Uani 1 1 d . . .
H22 H 1.0820 0.5682 0.2742 0.026 Uiso 1 1 calc R . .
C23 C 0.8976(4) 0.4056(4) 0.3001(2) 0.0211(7) Uani 1 1 d . . .
H23 H 0.9189 0.4409 0.3710 0.025 Uiso 1 1 calc R . .
C24 C 0.7672(4) 0.2782(4) 0.2512(2) 0.0203(7) Uani 1 1 d . . .
H24 H 0.6999 0.2308 0.2902 0.024 Uiso 1 1 calc R . .
C25 C 0.7331(4) 0.2186(3) 0.1455(2) 0.0149(6) Uani 1 1 d . . .
C26 C 0.4479(4) 0.3831(3) 0.5158(2) 0.0175(7) Uani 1 1 d . . .
C27 C 0.5701(4) 0.3364(4) 0.4799(3) 0.0239(7) Uani 1 1 d . . .
H27 H 0.6344 0.3955 0.4443 0.029 Uiso 1 1 calc R . .
C28 C 0.5956(4) 0.2053(4) 0.4966(3) 0.0270(8) Uani 1 1 d . . .
H28 H 0.6778 0.1754 0.4732 0.032 Uiso 1 1 calc R . .
C29 C 0.4984(4) 0.1161(4) 0.5487(3) 0.0231(7) Uani 1 1 d . . .
H29 H 0.5152 0.0262 0.5602 0.028 Uiso 1 1 calc R . .
C30 C 0.3763(4) 0.1616(4) 0.5835(2) 0.0196(7) Uani 1 1 d . . .
H30 H 0.3120 0.1007 0.6182 0.024 Uiso 1 1 calc R . .
C31 C 0.3468(4) 0.2953(3) 0.5681(2) 0.0150(6) Uani 1 1 d . . .
C32 C 0.2073(4) 0.3346(3) 0.6086(2) 0.0147(6) Uani 1 1 d . . .
C33 C 0.1684(4) 0.4725(3) 0.5782(2) 0.0155(6) Uani 1 1 d . . .
C34 C 0.0339(4) 0.5050(4) 0.6050(2) 0.0199(7) Uani 1 1 d . . .
H34 H -0.0284 0.4420 0.6395 0.024 Uiso 1 1 calc R . .
C35 C -0.0094(4) 0.6268(4) 0.5822(3) 0.0242(8) Uani 1 1 d . . .
H35 H -0.0980 0.6463 0.6029 0.029 Uiso 1 1 calc R . .
C36 C 0.0790(4) 0.7216(4) 0.5279(3) 0.0238(7) Uani 1 1 d . . .
H36 H 0.0489 0.8029 0.5114 0.029 Uiso 1 1 calc R . .
C37 C 0.2115(4) 0.6921(3) 0.4994(2) 0.0200(7) Uani 1 1 d . . .
H37 H 0.2715 0.7539 0.4633 0.024 Uiso 1 1 calc R . .
C38 C 0.2557(4) 0.5705(3) 0.5245(2) 0.0169(7) Uani 1 1 d . . .
C39 C 0.0607(4) 0.1909(3) 0.5600(2) 0.0142(6) Uani 1 1 d . . .
C40 C 0.0110(4) 0.1538(4) 0.4535(2) 0.0190(7) Uani 1 1 d . . .
H40 H 0.0658 0.2181 0.4166 0.023 Uiso 1 1 calc R . .
C41 C -0.1157(4) 0.0261(4) 0.4011(2) 0.0220(7) Uani 1 1 d . . .
H41 H -0.1438 0.0034 0.3301 0.026 Uiso 1 1 calc R . .
C42 C -0.2016(4) -0.0690(4) 0.4564(3) 0.0209(7) Uani 1 1 d . . .
H42 H -0.2891 -0.1543 0.4227 0.025 Uiso 1 1 calc R . .
C43 C -0.1553(4) -0.0349(4) 0.5606(3) 0.0197(7) Uani 1 1 d . . .
H43 H -0.2125 -0.0978 0.5973 0.024 Uiso 1 1 calc R . .
C44 C -0.0233(4) 0.0928(3) 0.6132(2) 0.0166(6) Uani 1 1 d . . .
C45 C 0.1823(4) 0.2844(4) 0.7890(2) 0.0194(7) Uani 1 1 d . . .
C46 C 0.2346(4) 0.3305(4) 0.8950(3) 0.0267(8) Uani 1 1 d . . .
H46 H 0.1896 0.2667 0.9354 0.032 Uiso 1 1 calc R . .
C47 C 0.3521(4) 0.4692(4) 0.9407(2) 0.0259(8) Uani 1 1 d . . .
H47 H 0.3857 0.4995 1.0114 0.031 Uiso 1 1 calc R . .
C48 C 0.4190(4) 0.5624(4) 0.8806(2) 0.0243(7) Uani 1 1 d . . .
H48 H 0.4969 0.6571 0.9110 0.029 Uiso 1 1 calc R . .
C49 C 0.3713(4) 0.5163(4) 0.7751(2) 0.0217(7) Uani 1 1 d . . .
H49 H 0.4201 0.5795 0.7355 0.026 Uiso 1 1 calc R . .
C50 C 0.2505(4) 0.3761(4) 0.7263(2) 0.0152(6) Uani 1 1 d . . .
C51 C -0.1833(4) 0.5889(4) 0.8580(3) 0.0302(8) Uani 1 1 d . . .
H51 H -0.2403 0.5738 0.9140 0.036 Uiso 1 1 calc R . .
O1 O 0.2370(3) -0.2724(3) 0.1376(2) 0.0390(7) Uani 1 1 d . . .
O2 O 0.3682(4) -0.1550(3) 0.3177(2) 0.0390(7) Uani 1 1 d . . .
O3 O 0.4411(4) 0.5608(3) 0.3919(2) 0.0406(7) Uani 1 1 d . . .
O4 O 0.5612(3) 0.6810(3) 0.5728(2) 0.0380(7) Uani 1 1 d . . .
S1 S 0.36260(10) -0.15324(9) 0.21221(6) 0.02201(18) Uani 1 1 d . . .
S2 S 0.82500(10) 0.22540(10) -0.04297(7) 0.0308(2) Uani 1 1 d . . .
S3 S 0.43878(9) 0.56071(8) 0.49694(6) 0.02149(18) Uani 1 1 d . . .
S4 S 0.02884(11) 0.10767(10) 0.74434(7) 0.0315(2) Uani 1 1 d . . .
Cl1 Cl -0.27761(11) 0.43092(11) 0.75210(7) 0.0367(2) Uani 1 1 d . . .
Cl2 Cl 0.01319(12) 0.59895(12) 0.89962(8) 0.0439(3) Uani 1 1 d . . .
Cl3 Cl -0.19186(14) 0.76264(11) 0.82843(9) 0.0474(3) 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 C6 1.385(4) . ?
C1 C2 1.405(5) . ?
C1 S1 1.748(3) . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.532(4) . ?
C7 C8 1.540(4) . ?
C7 C14 1.545(4) . ?
C7 C25 1.545(4) . ?
C8 C13 1.393(4) . ?
C8 C9 1.398(5) . ?
C9 C10 1.392(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.408(4) . ?
C12 H12 0.9300 . ?
C13 S1 1.748(3) . ?
C14 C19 1.395(5) . ?
C14 C15 1.395(4) . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(5) . ?
C18 H18 0.9300 . ?
C19 S2 1.761(4) . ?
C20 C25 1.401(4) . ?
C20 C21 1.412(4) . ?
C20 S2 1.749(3) . ?
C21 C22 1.373(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.389(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(4) . ?
C24 H24 0.9300 . ?
C26 C27 1.397(5) . ?
C26 C31 1.404(4) . ?
C26 S3 1.744(3) . ?
C27 C28 1.359(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.389(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.392(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.536(4) . ?
C32 C33 1.538(4) . ?
C32 C50 1.540(4) . ?
C32 C39 1.542(4) . ?
C33 C34 1.399(4) . ?
C33 C38 1.408(4) . ?
C34 C35 1.375(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.400(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.378(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.389(4) . ?
C37 H37 0.9300 . ?
C38 S3 1.754(3) . ?
C39 C44 1.390(4) . ?
C39 C40 1.401(4) . ?
C40 C41 1.378(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.401(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.370(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.403(4) . ?
C43 H43 0.9300 . ?
C44 S4 1.752(3) . ?
C45 C46 1.396(4) . ?
C45 C50 1.397(4) . ?
C45 S4 1.751(3) . ?
C46 C47 1.379(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.375(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.385(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.408(4) . ?
C49 H49 0.9300 . ?
C51 Cl2 1.752(4) . ?
C51 Cl1 1.757(4) . ?
C51 Cl3 1.761(4) . ?
C51 H51 0.9800 . ?
O1 S1 1.441(3) . ?
O2 S1 1.432(3) . ?
O3 S3 1.431(3) . ?
O4 S3 1.441(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.8(3) . . ?
C6 C1 S1 123.0(2) . . ?
C2 C1 S1 115.1(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 116.6(3) . . ?
C1 C6 C7 125.8(3) . . ?
C5 C6 C7 117.6(3) . . ?
C6 C7 C8 116.0(3) . . ?
C6 C7 C14 107.0(3) . . ?
C8 C7 C14 107.4(2) . . ?
C6 C7 C25 105.9(2) . . ?
C8 C7 C25 106.0(2) . . ?
C14 C7 C25 114.8(3) . . ?
C13 C8 C9 117.1(3) . . ?
C13 C8 C7 124.7(3) . . ?
C9 C8 C7 118.3(3) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.3(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C12 122.0(3) . . ?
C8 C13 S1 123.4(2) . . ?
C12 C13 S1 114.4(2) . . ?
C19 C14 C15 117.4(3) . . ?
C19 C14 C7 124.5(3) . . ?
C15 C14 C7 118.0(3) . . ?
C16 C15 C14 122.1(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 S2 114.9(3) . . ?
C14 C19 S2 124.7(2) . . ?
C25 C20 C21 120.0(3) . . ?
C25 C20 S2 124.9(2) . . ?
C21 C20 S2 115.1(2) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 122.4(3) . . ?
C23 C24 H24 118.8 . . ?
C25 C24 H24 118.8 . . ?
C24 C25 C20 117.7(3) . . ?
C24 C25 C7 117.8(3) . . ?
C20 C25 C7 124.5(3) . . ?
C27 C26 C31 121.3(3) . . ?
C27 C26 S3 115.3(2) . . ?
C31 C26 S3 123.3(2) . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.7(3) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 122.1(3) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C30 C31 C26 116.5(3) . . ?
C30 C31 C32 118.1(3) . . ?
C26 C31 C32 125.3(3) . . ?
C31 C32 C33 115.6(3) . . ?
C31 C32 C50 107.3(2) . . ?
C33 C32 C50 106.9(2) . . ?
C31 C32 C39 105.6(2) . . ?
C33 C32 C39 106.5(2) . . ?
C50 C32 C39 115.3(3) . . ?
C34 C33 C38 115.9(3) . . ?
C34 C33 C32 118.2(3) . . ?
C38 C33 C32 125.9(3) . . ?
C35 C34 C33 122.4(3) . . ?
C35 C34 H34 118.8 . . ?
C33 C34 H34 118.8 . . ?
C34 C35 C36 120.4(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 118.8(3) . . ?
C37 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C36 C37 C38 120.2(3) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C37 C38 C33 122.2(3) . . ?
C37 C38 S3 115.2(2) . . ?
C33 C38 S3 122.2(2) . . ?
C44 C39 C40 117.4(3) . . ?
C44 C39 C32 125.2(3) . . ?
C40 C39 C32 117.4(3) . . ?
C41 C40 C39 122.8(3) . . ?
C41 C40 H40 118.6 . . ?
C39 C40 H40 118.6 . . ?
C40 C41 C42 118.9(3) . . ?
C40 C41 H41 120.5 . . ?
C42 C41 H41 120.5 . . ?
C43 C42 C41 119.3(3) . . ?
C43 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C42 C43 C44 121.5(3) . . ?
C42 C43 H43 119.3 . . ?
C44 C43 H43 119.3 . . ?
C39 C44 C43 120.1(3) . . ?
C39 C44 S4 124.9(2) . . ?
C43 C44 S4 114.9(2) . . ?
C46 C45 C50 120.8(3) . . ?
C46 C45 S4 114.8(3) . . ?
C50 C45 S4 124.4(2) . . ?
C47 C46 C45 120.9(3) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C48 C47 C46 119.3(3) . . ?
C48 C47 H47 120.3 . . ?
C46 C47 H47 120.3 . . ?
C47 C48 C49 120.4(3) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C48 C49 C50 121.5(3) . . ?
C48 C49 H49 119.2 . . ?
C50 C49 H49 119.2 . . ?
C45 C50 C49 117.0(3) . . ?
C45 C50 C32 125.4(3) . . ?
C49 C50 C32 117.5(3) . . ?
Cl2 C51 Cl1 111.1(2) . . ?
Cl2 C51 Cl3 110.9(2) . . ?
Cl1 C51 Cl3 110.5(2) . . ?
Cl2 C51 H51 108.1 . . ?
Cl1 C51 H51 108.1 . . ?
Cl3 C51 H51 108.1 . . ?
O2 S1 O1 117.62(17) . . ?
O2 S1 C1 108.98(15) . . ?
O1 S1 C1 107.80(16) . . ?
O2 S1 C13 109.40(16) . . ?
O1 S1 C13 107.42(15) . . ?
C1 S1 C13 104.88(15) . . ?
C20 S2 C19 102.87(15) . . ?
O3 S3 O4 117.20(18) . . ?
O3 S3 C26 108.94(15) . . ?
O4 S3 C26 107.80(16) . . ?
O3 S3 C38 109.62(16) . . ?
O4 S3 C38 107.49(15) . . ?
C26 S3 C38 105.12(15) . . ?
C45 S4 C44 103.82(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(5) . . . . ?
S1 C1 C2 C3 -174.7(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
S1 C1 C6 C5 175.0(2) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
S1 C1 C6 C7 -4.3(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C1 C6 C7 C8 -7.8(4) . . . . ?
C5 C6 C7 C8 172.9(3) . . . . ?
C1 C6 C7 C14 112.1(3) . . . . ?
C5 C6 C7 C14 -67.3(3) . . . . ?
C1 C6 C7 C25 -125.0(3) . . . . ?
C5 C6 C7 C25 55.7(3) . . . . ?
C6 C7 C8 C13 7.2(4) . . . . ?
C14 C7 C8 C13 -112.4(3) . . . . ?
C25 C7 C8 C13 124.4(3) . . . . ?
C6 C7 C8 C9 -172.5(3) . . . . ?
C14 C7 C8 C9 67.9(3) . . . . ?
C25 C7 C8 C9 -55.3(3) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
C7 C8 C9 C10 179.2(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C9 C8 C13 C12 1.1(4) . . . . ?
C7 C8 C13 C12 -178.6(3) . . . . ?
C9 C8 C13 S1 -175.1(2) . . . . ?
C7 C8 C13 S1 5.3(4) . . . . ?
C11 C12 C13 C8 -1.2(5) . . . . ?
C11 C12 C13 S1 175.3(3) . . . . ?
C6 C7 C14 C19 135.1(3) . . . . ?
C8 C7 C14 C19 -99.7(3) . . . . ?
C25 C7 C14 C19 17.9(4) . . . . ?
C6 C7 C14 C15 -47.2(4) . . . . ?
C8 C7 C14 C15 78.0(3) . . . . ?
C25 C7 C14 C15 -164.4(3) . . . . ?
C19 C14 C15 C16 1.6(5) . . . . ?
C7 C14 C15 C16 -176.2(3) . . . . ?
C14 C15 C16 C17 1.3(5) . . . . ?
C15 C16 C17 C18 -2.5(5) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C14 2.1(5) . . . . ?
C17 C18 C19 S2 -178.9(3) . . . . ?
C15 C14 C19 C18 -3.3(5) . . . . ?
C7 C14 C19 C18 174.4(3) . . . . ?
C15 C14 C19 S2 177.9(3) . . . . ?
C7 C14 C19 S2 -4.4(5) . . . . ?
C25 C20 C21 C22 1.9(5) . . . . ?
S2 C20 C21 C22 -175.1(2) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C21 C22 C23 C24 -2.3(5) . . . . ?
C22 C23 C24 C25 1.9(5) . . . . ?
C23 C24 C25 C20 0.4(5) . . . . ?
C23 C24 C25 C7 179.6(3) . . . . ?
C21 C20 C25 C24 -2.3(4) . . . . ?
S2 C20 C25 C24 174.3(2) . . . . ?
C21 C20 C25 C7 178.6(3) . . . . ?
S2 C20 C25 C7 -4.8(4) . . . . ?
C6 C7 C25 C24 49.9(3) . . . . ?
C8 C7 C25 C24 -73.9(3) . . . . ?
C14 C7 C25 C24 167.7(3) . . . . ?
C6 C7 C25 C20 -131.0(3) . . . . ?
C8 C7 C25 C20 105.2(3) . . . . ?
C14 C7 C25 C20 -13.2(4) . . . . ?
C31 C26 C27 C28 -1.2(5) . . . . ?
S3 C26 C27 C28 175.4(3) . . . . ?
C26 C27 C28 C29 0.7(5) . . . . ?
C27 C28 C29 C30 -0.1(6) . . . . ?
C28 C29 C30 C31 -0.1(5) . . . . ?
C29 C30 C31 C26 -0.3(5) . . . . ?
C29 C30 C31 C32 179.3(3) . . . . ?
C27 C26 C31 C30 0.9(5) . . . . ?
S3 C26 C31 C30 -175.4(2) . . . . ?
C27 C26 C31 C32 -178.7(3) . . . . ?
S3 C26 C31 C32 5.0(4) . . . . ?
C30 C31 C32 C33 -173.0(3) . . . . ?
C26 C31 C32 C33 6.6(4) . . . . ?
C30 C31 C32 C50 67.8(3) . . . . ?
C26 C31 C32 C50 -112.5(3) . . . . ?
C30 C31 C32 C39 -55.6(3) . . . . ?
C26 C31 C32 C39 124.0(3) . . . . ?
C31 C32 C33 C34 174.3(3) . . . . ?
C50 C32 C33 C34 -66.3(4) . . . . ?
C39 C32 C33 C34 57.4(3) . . . . ?
C31 C32 C33 C38 -5.2(4) . . . . ?
C50 C32 C33 C38 114.2(3) . . . . ?
C39 C32 C33 C38 -122.1(3) . . . . ?
C38 C33 C34 C35 -1.1(5) . . . . ?
C32 C33 C34 C35 179.3(3) . . . . ?
C33 C34 C35 C36 1.7(5) . . . . ?
C34 C35 C36 C37 -1.1(5) . . . . ?
C35 C36 C37 C38 -0.1(5) . . . . ?
C36 C37 C38 C33 0.6(5) . . . . ?
C36 C37 C38 S3 -172.8(2) . . . . ?
C34 C33 C38 C37 0.0(4) . . . . ?
C32 C33 C38 C37 179.5(3) . . . . ?
C34 C33 C38 S3 172.9(2) . . . . ?
C32 C33 C38 S3 -7.5(4) . . . . ?
C31 C32 C39 C44 112.6(3) . . . . ?
C33 C32 C39 C44 -124.0(3) . . . . ?
C50 C32 C39 C44 -5.6(4) . . . . ?
C31 C32 C39 C40 -65.5(3) . . . . ?
C33 C32 C39 C40 57.9(3) . . . . ?
C50 C32 C39 C40 176.3(3) . . . . ?
C44 C39 C40 C41 0.0(5) . . . . ?
C32 C39 C40 C41 178.3(3) . . . . ?
C39 C40 C41 C42 1.7(5) . . . . ?
C40 C41 C42 C43 -1.6(5) . . . . ?
C41 C42 C43 C44 -0.2(5) . . . . ?
C40 C39 C44 C43 -1.9(4) . . . . ?
C32 C39 C44 C43 -179.9(3) . . . . ?
C40 C39 C44 S4 174.1(2) . . . . ?
C32 C39 C44 S4 -4.0(4) . . . . ?
C42 C43 C44 C39 2.0(4) . . . . ?
C42 C43 C44 S4 -174.3(3) . . . . ?
C50 C45 C46 C47 1.6(5) . . . . ?
S4 C45 C46 C47 -178.3(3) . . . . ?
C45 C46 C47 C48 -0.5(5) . . . . ?
C46 C47 C48 C49 -1.2(5) . . . . ?
C47 C48 C49 C50 1.9(5) . . . . ?
C46 C45 C50 C49 -0.9(5) . . . . ?
S4 C45 C50 C49 179.0(2) . . . . ?
C46 C45 C50 C32 177.6(3) . . . . ?
S4 C45 C50 C32 -2.5(5) . . . . ?
C48 C49 C50 C45 -0.8(5) . . . . ?
C48 C49 C50 C32 -179.4(3) . . . . ?
C31 C32 C50 C45 -108.3(3) . . . . ?
C33 C32 C50 C45 127.1(3) . . . . ?
C39 C32 C50 C45 9.0(4) . . . . ?
C31 C32 C50 C49 70.2(3) . . . . ?
C33 C32 C50 C49 -54.4(4) . . . . ?
C39 C32 C50 C49 -172.5(3) . . . . ?
C6 C1 S1 O2 131.2(3) . . . . ?
C2 C1 S1 O2 -53.0(3) . . . . ?
C6 C1 S1 O1 -100.1(3) . . . . ?
C2 C1 S1 O1 75.7(3) . . . . ?
C6 C1 S1 C13 14.2(3) . . . . ?
C2 C1 S1 C13 -170.1(3) . . . . ?
C8 C13 S1 O2 -131.4(3) . . . . ?
C12 C13 S1 O2 52.1(3) . . . . ?
C8 C13 S1 O1 99.8(3) . . . . ?
C12 C13 S1 O1 -76.6(3) . . . . ?
C8 C13 S1 C1 -14.7(3) . . . . ?
C12 C13 S1 C1 168.9(2) . . . . ?
C25 C20 S2 C19 15.9(3) . . . . ?
C21 C20 S2 C19 -167.3(2) . . . . ?
C18 C19 S2 C20 169.7(3) . . . . ?
C14 C19 S2 C20 -11.4(3) . . . . ?
C27 C26 S3 O3 51.0(3) . . . . ?
C31 C26 S3 O3 -132.4(3) . . . . ?
C27 C26 S3 O4 -77.1(3) . . . . ?
C31 C26 S3 O4 99.4(3) . . . . ?
C27 C26 S3 C38 168.4(2) . . . . ?
C31 C26 S3 C38 -15.0(3) . . . . ?
C37 C38 S3 O3 -53.5(3) . . . . ?
C33 C38 S3 O3 133.1(3) . . . . ?
C37 C38 S3 O4 74.9(3) . . . . ?
C33 C38 S3 O4 -98.5(3) . . . . ?
C37 C38 S3 C26 -170.4(2) . . . . ?
C33 C38 S3 C26 16.1(3) . . . . ?
C46 C45 S4 C44 174.0(3) . . . . ?
C50 C45 S4 C44 -5.9(3) . . . . ?
C39 C44 S4 C45 9.1(3) . . . . ?
C43 C44 S4 C45 -174.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_import
_database_code_depnum_ccdc_archive 'CCDC 1046695'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 N2 S'
_chemical_formula_sum            'C23 H14 N2 S'
_chemical_formula_weight         350.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.0720(3)
_cell_length_b                   19.5933(9)
_cell_length_c                   24.3261(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3370.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5180
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.37

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.982

#----------------------------- Remark ------------------------------------#
# SADABS output:                                                          #
# Estimated minimum and maximum transmission:  0.6671  0.7456             #
# The ratio of these values is more reliable than their absolute values!  #
#-------------------------------------------------------------------------#


_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16158
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3864
_reflns_number_gt                3128
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (ALtomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0635P)²+1.0324P] 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         3864
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.6742(2) 0.12043(8) 0.61599(6) 0.0150(3) Uani 1 1 d . . .
C2 C 0.5665(2) 0.14164(8) 0.56368(6) 0.0171(3) Uani 1 1 d . . .
C3 C 0.5690(2) 0.09973(10) 0.51713(7) 0.0231(4) Uani 1 1 d . . .
H3 H 0.6448 0.0610 0.5171 0.028 Uiso 1 1 calc R . .
C4 C 0.4610(3) 0.11467(11) 0.47104(7) 0.0317(4) Uani 1 1 d . . .
H4 H 0.4653 0.0863 0.4404 0.038 Uiso 1 1 calc R . .
C5 C 0.3466(3) 0.17213(11) 0.47085(7) 0.0351(5) Uani 1 1 d . . .
H5 H 0.2715 0.1818 0.4405 0.042 Uiso 1 1 calc R . .
C6 C 0.3445(2) 0.21500(10) 0.51581(8) 0.0295(4) Uani 1 1 d . . .
H6 H 0.2697 0.2540 0.5153 0.035 Uiso 1 1 calc R . .
C7 C 0.4542(2) 0.20019(9) 0.56214(7) 0.0203(4) Uani 1 1 d . . .
C8 C 0.6599(2) 0.24440(8) 0.64976(6) 0.0172(3) Uani 1 1 d . . .
C9 C 0.7372(2) 0.29927(9) 0.67872(6) 0.0212(4) Uani 1 1 d . . .
H9 H 0.6783 0.3417 0.6777 0.025 Uiso 1 1 calc R . .
C10 C 0.9010(2) 0.29063(9) 0.70895(7) 0.0236(4) Uani 1 1 d . . .
H10 H 0.9518 0.3271 0.7284 0.028 Uiso 1 1 calc R . .
C11 C 0.9892(2) 0.22778(9) 0.71016(7) 0.0231(4) Uani 1 1 d . . .
H11 H 1.0972 0.2214 0.7314 0.028 Uiso 1 1 calc R . .
C12 C 0.9162(2) 0.17416(9) 0.67959(6) 0.0189(3) Uani 1 1 d . . .
H12 H 0.9784 0.1323 0.6799 0.023 Uiso 1 1 calc R . .
C13 C 0.7513(2) 0.18139(8) 0.64836(6) 0.0148(3) Uani 1 1 d . . .
C14 C 0.8309(2) 0.06924(8) 0.60271(6) 0.0162(3) Uani 1 1 d . . .
C15 C 0.9938(2) 0.07792(9) 0.57167(6) 0.0209(4) Uani 1 1 d . . .
H15 H 1.0220 0.1193 0.5548 0.025 Uiso 1 1 calc R . .
C16 C 1.1128(2) 0.02172(10) 0.56702(7) 0.0253(4) Uani 1 1 d . . .
H16 H 1.2238 0.0250 0.5467 0.030 Uiso 1 1 calc R . .
C17 C 1.0661(2) -0.03932(10) 0.59276(8) 0.0266(4) Uani 1 1 d . . .
H17 H 1.1486 -0.0760 0.5888 0.032 Uiso 1 1 calc R . .
C18 C 0.7966(2) 0.00602(8) 0.62690(6) 0.0165(3) Uani 1 1 d . . .
C19 C 0.6175(2) 0.01000(8) 0.65761(6) 0.0164(3) Uani 1 1 d . . .
C20 C 0.3763(2) -0.02331(9) 0.71262(7) 0.0219(4) Uani 1 1 d . . .
H20 H 0.3150 -0.0568 0.7330 0.026 Uiso 1 1 calc R . .
C21 C 0.2960(2) 0.04139(9) 0.71086(6) 0.0209(4) Uani 1 1 d . . .
H21 H 0.1852 0.0503 0.7302 0.025 Uiso 1 1 calc R . .
C22 C 0.3811(2) 0.09291(9) 0.68018(6) 0.0180(3) Uani 1 1 d . . .
H22 H 0.3295 0.1365 0.6783 0.022 Uiso 1 1 calc R . .
C23 C 0.5461(2) 0.07625(8) 0.65259(6) 0.0152(3) Uani 1 1 d . . .
N1 N 0.9094(2) -0.04877(8) 0.62303(6) 0.0235(3) Uani 1 1 d . . .
N2 N 0.53760(19) -0.04039(7) 0.68665(6) 0.0201(3) Uani 1 1 d . . .
S1 S 0.44080(6) 0.25874(2) 0.616970(18) 0.02319(14) 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 C14 1.529(2) . ?
C1 C13 1.531(2) . ?
C1 C23 1.537(2) . ?
C1 C2 1.540(2) . ?
C2 C7 1.395(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(2) . ?
C6 H6 0.9300 . ?
C7 S1 1.7618(18) . ?
C8 C13 1.394(2) . ?
C8 C9 1.397(2) . ?
C8 S1 1.7654(16) . ?
C9 C10 1.383(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(2) . ?
C12 H12 0.9300 . ?
C14 C15 1.388(2) . ?
C14 C18 1.393(2) . ?
C15 C16 1.390(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9300 . ?
C17 N1 1.344(2) . ?
C17 H17 0.9300 . ?
C18 N1 1.340(2) . ?
C18 C19 1.473(2) . ?
C19 N2 1.339(2) . ?
C19 C23 1.398(2) . ?
C20 N2 1.346(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(2) . ?
C22 H22 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
C14 C1 C13 111.23(12) . . ?
C14 C1 C23 100.38(12) . . ?
C13 C1 C23 110.57(12) . . ?
C14 C1 C2 111.15(12) . . ?
C13 C1 C2 112.99(13) . . ?
C23 C1 C2 109.81(12) . . ?
C7 C2 C3 117.90(15) . . ?
C7 C2 C1 121.69(14) . . ?
C3 C2 C1 120.27(15) . . ?
C4 C3 C2 121.55(17) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 119.67(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 119.88(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.45(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.51(16) . . ?
C2 C7 S1 123.07(12) . . ?
C6 C7 S1 116.43(14) . . ?
C13 C8 C9 120.84(15) . . ?
C13 C8 S1 122.48(12) . . ?
C9 C8 S1 116.66(12) . . ?
C10 C9 C8 120.12(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.95(16) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.71(16) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 121.67(16) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 117.58(15) . . ?
C8 C13 C1 122.57(14) . . ?
C12 C13 C1 119.82(14) . . ?
C15 C14 C18 118.89(15) . . ?
C15 C14 C1 129.51(15) . . ?
C18 C14 C1 111.59(13) . . ?
C14 C15 C16 116.72(16) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
C17 C16 C15 120.07(15) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N1 C17 C16 124.16(16) . . ?
N1 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
N1 C18 C14 125.40(15) . . ?
N1 C18 C19 126.12(15) . . ?
C14 C18 C19 108.48(14) . . ?
N2 C19 C23 125.31(14) . . ?
N2 C19 C18 126.27(15) . . ?
C23 C19 C18 108.40(14) . . ?
N2 C20 C21 123.97(15) . . ?
N2 C20 H20 118.0 . . ?
C21 C20 H20 118.0 . . ?
C20 C21 C22 120.07(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 116.94(15) . . ?
C23 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
C22 C23 C19 118.74(14) . . ?
C22 C23 C1 130.13(15) . . ?
C19 C23 C1 111.12(13) . . ?
C18 N1 C17 114.76(15) . . ?
C19 N2 C20 114.95(14) . . ?
C7 S1 C8 101.01(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C7 -162.31(14) . . . . ?
C13 C1 C2 C7 -36.44(19) . . . . ?
C23 C1 C2 C7 87.52(18) . . . . ?
C14 C1 C2 C3 21.9(2) . . . . ?
C13 C1 C2 C3 147.81(14) . . . . ?
C23 C1 C2 C3 -88.24(17) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
C1 C2 C3 C4 174.66(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C3 C2 C7 C6 1.6(2) . . . . ?
C1 C2 C7 C6 -174.21(15) . . . . ?
C3 C2 C7 S1 -178.57(12) . . . . ?
C1 C2 C7 S1 5.6(2) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C5 C6 C7 S1 179.80(14) . . . . ?
C13 C8 C9 C10 -3.5(2) . . . . ?
S1 C8 C9 C10 175.09(12) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 2.1(2) . . . . ?
C10 C11 C12 C13 -1.7(2) . . . . ?
C9 C8 C13 C12 3.8(2) . . . . ?
S1 C8 C13 C12 -174.73(11) . . . . ?
C9 C8 C13 C1 -178.47(14) . . . . ?
S1 C8 C13 C1 3.0(2) . . . . ?
C11 C12 C13 C8 -1.2(2) . . . . ?
C11 C12 C13 C1 -179.02(14) . . . . ?
C14 C1 C13 C8 157.76(14) . . . . ?
C23 C1 C13 C8 -91.61(17) . . . . ?
C2 C1 C13 C8 31.93(19) . . . . ?
C14 C1 C13 C12 -24.52(19) . . . . ?
C23 C1 C13 C12 86.12(16) . . . . ?
C2 C1 C13 C12 -150.35(13) . . . . ?
C13 C1 C14 C15 -61.6(2) . . . . ?
C23 C1 C14 C15 -178.64(15) . . . . ?
C2 C1 C14 C15 65.2(2) . . . . ?
C13 C1 C14 C18 117.88(14) . . . . ?
C23 C1 C14 C18 0.85(16) . . . . ?
C2 C1 C14 C18 -115.27(14) . . . . ?
C18 C14 C15 C16 0.0(2) . . . . ?
C1 C14 C15 C16 179.43(15) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 N1 -0.1(3) . . . . ?
C15 C14 C18 N1 0.1(2) . . . . ?
C1 C14 C18 N1 -179.43(15) . . . . ?
C15 C14 C18 C19 179.61(13) . . . . ?
C1 C14 C18 C19 0.05(17) . . . . ?
N1 C18 C19 N2 -0.1(3) . . . . ?
C14 C18 C19 N2 -179.58(15) . . . . ?
N1 C18 C19 C23 178.41(15) . . . . ?
C14 C18 C19 C23 -1.06(17) . . . . ?
N2 C20 C21 C22 1.1(3) . . . . ?
C20 C21 C22 C23 -0.3(2) . . . . ?
C21 C22 C23 C19 -0.7(2) . . . . ?
C21 C22 C23 C1 -179.58(14) . . . . ?
N2 C19 C23 C22 1.1(2) . . . . ?
C18 C19 C23 C22 -177.40(13) . . . . ?
N2 C19 C23 C1 -179.81(14) . . . . ?
C18 C19 C23 C1 1.66(17) . . . . ?
C14 C1 C23 C22 177.39(15) . . . . ?
C13 C1 C23 C22 59.9(2) . . . . ?
C2 C1 C23 C22 -65.5(2) . . . . ?
C14 C1 C23 C19 -1.53(15) . . . . ?
C13 C1 C23 C19 -119.04(14) . . . . ?
C2 C1 C23 C19 115.60(14) . . . . ?
C14 C18 N1 C17 -0.2(2) . . . . ?
C19 C18 N1 C17 -179.60(15) . . . . ?
C16 C17 N1 C18 0.2(3) . . . . ?
C23 C19 N2 C20 -0.4(2) . . . . ?
C18 C19 N2 C20 177.88(14) . . . . ?
C21 C20 N2 C19 -0.7(2) . . . . ?
C2 C7 S1 C8 24.85(15) . . . . ?
C6 C7 S1 C8 -155.36(13) . . . . ?
C13 C8 S1 C7 -29.21(14) . . . . ?
C9 C8 S1 C7 152.25(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_squeezed
_database_code_depnum_ccdc_archive 'CCDC 1046696'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 	C31 H21 N O2 S'
_chemical_formula_sum            '	C31 H21 N O2 S'
_chemical_formula_weight         471.56

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           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                   8.8667(3)
_cell_length_b                   11.8588(3)
_cell_length_c                   15.4264(4)
_cell_angle_alpha                112.2520(10)
_cell_angle_beta                 95.2040(10)
_cell_angle_gamma                94.2860(10)
_cell_volume                     1484.57(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5721
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.38
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.972

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.7032  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#



_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray


_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13134
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.55
_reflns_number_total             6766
_reflns_number_gt                5152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (ALtomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'



_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. 
;

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.015 0.500 0.500 431.1 -5.6
_platon_squeeze_details          
; squeeze on disordered chloroform molecules
;

_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)+(0.0815P)²+1.2350P] 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         6766
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1868
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 0.7022(2) 0.22600(19) 0.78863(15) 0.0219(4) Uani 1 1 d . . .
C2 C 0.6925(3) 0.1102(2) 0.69781(16) 0.0249(5) Uani 1 1 d . . .
C3 C 0.6151(3) 0.0017(2) 0.69745(17) 0.0296(5) Uani 1 1 d . . .
H3 H 0.5718 0.0037 0.7507 0.035 Uiso 1 1 calc R . .
C4 C 0.6023(3) -0.1078(2) 0.61967(19) 0.0372(6) Uani 1 1 d . . .
H4 H 0.5480 -0.1777 0.6202 0.045 Uiso 1 1 calc R . .
C5 C 0.6707(4) -0.1134(3) 0.5406(2) 0.0453(7) Uani 1 1 d . . .
H5 H 0.6662 -0.1881 0.4896 0.054 Uiso 1 1 calc R . .
C6 C 0.7443(4) -0.0104(3) 0.53725(19) 0.0455(7) Uani 1 1 d . . .
H6 H 0.7879 -0.0136 0.4839 0.055 Uiso 1 1 calc R . .
C7 C 0.7530(3) 0.1015(2) 0.61635(16) 0.0301(5) Uani 1 1 d . . .
C8 C 0.8625(3) 0.3472(2) 0.71225(15) 0.0239(4) Uani 1 1 d . . .
C9 C 0.9523(3) 0.4542(2) 0.71910(18) 0.0294(5) Uani 1 1 d . . .
H9 H 0.9895 0.4587 0.6659 0.035 Uiso 1 1 calc R . .
C10 C 0.9846(3) 0.5516(2) 0.80418(19) 0.0324(5) Uani 1 1 d . . .
H10 H 1.0449 0.6219 0.8091 0.039 Uiso 1 1 calc R . .
C11 C 0.9267(3) 0.5451(2) 0.88392(18) 0.0318(5) Uani 1 1 d . . .
H11 H 0.9487 0.6109 0.9419 0.038 Uiso 1 1 calc R . .
C12 C 0.8362(3) 0.4398(2) 0.87605(17) 0.0265(5) Uani 1 1 d . . .
H12 H 0.7976 0.4366 0.9293 0.032 Uiso 1 1 calc R . .
C13 C 0.8016(2) 0.3379(2) 0.78971(16) 0.0224(4) Uani 1 1 d . . .
C14 C 0.5408(2) 0.2625(2) 0.80352(16) 0.0233(4) Uani 1 1 d . . .
C15 C 0.4558(3) 0.2847(2) 0.73185(17) 0.0297(5) Uani 1 1 d . . .
H15 H 0.4984 0.2769 0.6773 0.036 Uiso 1 1 calc R . .
C16 C 0.3104(3) 0.3179(2) 0.74019(19) 0.0353(6) Uani 1 1 d . . .
H16 H 0.2549 0.3316 0.6917 0.042 Uiso 1 1 calc R . .
C17 C 0.2477(3) 0.3307(2) 0.82351(19) 0.0325(5) Uani 1 1 d . . .
H17 H 0.1506 0.3549 0.8309 0.039 Uiso 1 1 calc R . .
C18 C 0.3292(3) 0.3078(2) 0.89435(18) 0.0292(5) Uani 1 1 d . . .
H18 H 0.2858 0.3153 0.9486 0.035 Uiso 1 1 calc R . .
C19 C 0.4765(3) 0.2734(2) 0.88549(16) 0.0232(4) Uani 1 1 d . . .
N1 N 0.5561(2) 0.24856(19) 0.95783(14) 0.0289(4) Uani 1 1 d . . .
C21 C 0.7023(2) 0.20774(19) 0.94897(16) 0.0227(4) Uani 1 1 d . . .
C22 C 0.7763(3) 0.1807(2) 1.02246(17) 0.0263(5) Uani 1 1 d . . .
H22 H 0.7292 0.1893 1.0757 0.032 Uiso 1 1 calc R . .
C23 C 0.9195(3) 0.1411(2) 1.01473(17) 0.0255(5) Uani 1 1 d . . .
H23 H 0.9688 0.1245 1.0636 0.031 Uiso 1 1 calc R . .
C25 C 0.9901(3) 0.1260(2) 0.93543(17) 0.0276(5) Uani 1 1 d . . .
H25 H 1.0855 0.0982 0.9303 0.033 Uiso 1 1 calc R . .
C26 C 0.9170(3) 0.1528(2) 0.86380(17) 0.0252(5) Uani 1 1 d . . .
H26 H 0.9642 0.1432 0.8104 0.030 Uiso 1 1 calc R . .
C27 C 0.7733(2) 0.19414(19) 0.87027(16) 0.0222(4) Uani 1 1 d . . .
C28 C 0.4930(3) 0.3667(2) 1.11560(19) 0.0348(6) Uani 1 1 d . . .
H28 H 0.5460 0.4369 1.1148 0.042 Uiso 1 1 calc R . .
C29 C 0.4229(3) 0.3714(3) 1.1933(2) 0.0408(6) Uani 1 1 d . . .
H29 H 0.4287 0.4454 1.2451 0.049 Uiso 1 1 calc R . .
C30 C 0.3446(3) 0.2677(3) 1.1946(2) 0.0391(6) Uani 1 1 d . . .
H30 H 0.2979 0.2721 1.2472 0.047 Uiso 1 1 calc R . .
C31 C 0.3346(3) 0.1572(3) 1.1185(2) 0.0353(6) Uani 1 1 d . . .
H31 H 0.2818 0.0874 1.1202 0.042 Uiso 1 1 calc R . .
C32 C 0.4033(3) 0.1496(2) 1.03896(18) 0.0308(5) Uani 1 1 d . . .
H32 H 0.3961 0.0755 0.9871 0.037 Uiso 1 1 calc R . .
C20 C 0.4832(3) 0.2554(2) 1.03870(17) 0.0275(5) Uani 1 1 d . . .
O1 O 0.7163(3) 0.2624(2) 0.54248(15) 0.0566(7) Uani 1 1 d . . .
O2 O 0.9735(3) 0.2071(2) 0.56235(17) 0.0640(7) Uani 1 1 d . . .
S1 S 0.83069(8) 0.23019(6) 0.59864(4) 0.0371(2) 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 C13 1.531(3) . ?
C1 C2 1.536(3) . ?
C1 C14 1.538(3) . ?
C1 C27 1.542(3) . ?
C2 C7 1.382(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(4) . ?
C6 H6 0.9300 . ?
C7 S1 1.753(2) . ?
C8 C13 1.393(3) . ?
C8 C9 1.410(3) . ?
C8 S1 1.757(2) . ?
C9 C10 1.368(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.401(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.407(3) . ?
C12 H12 0.9300 . ?
C14 C19 1.399(3) . ?
C14 C15 1.400(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(3) . ?
C18 H18 0.9300 . ?
C19 N1 1.402(3) . ?
N1 C21 1.418(3) . ?
N1 C20 1.435(3) . ?
C21 C27 1.379(3) . ?
C21 C22 1.411(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9300 . ?
C23 C25 1.382(3) . ?
C23 H23 0.9300 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.397(3) . ?
C26 H26 0.9300 . ?
C28 C29 1.384(4) . ?
C28 C20 1.391(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.379(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.395(4) . ?
C31 H31 0.9300 . ?
C32 C20 1.395(3) . ?
C32 H32 0.9300 . ?
O1 S1 1.440(2) . ?
O2 S1 1.434(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C1 C2 115.11(18) . . ?
C13 C1 C14 107.41(17) . . ?
C2 C1 C14 108.94(17) . . ?
C13 C1 C27 107.12(17) . . ?
C2 C1 C27 107.03(17) . . ?
C14 C1 C27 111.26(18) . . ?
C7 C2 C3 116.6(2) . . ?
C7 C2 C1 126.5(2) . . ?
C3 C2 C1 117.0(2) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 122.7(2) . . ?
C2 C7 S1 122.64(18) . . ?
C6 C7 S1 114.4(2) . . ?
C13 C8 C9 121.9(2) . . ?
C13 C8 S1 123.40(17) . . ?
C9 C8 S1 114.70(17) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C12 116.8(2) . . ?
C8 C13 C1 125.4(2) . . ?
C12 C13 C1 117.7(2) . . ?
C19 C14 C15 119.3(2) . . ?
C19 C14 C1 122.36(19) . . ?
C15 C14 C1 118.3(2) . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 119.2(2) . . ?
C14 C19 N1 121.2(2) . . ?
C18 C19 N1 119.7(2) . . ?
C19 N1 C21 121.04(19) . . ?
C19 N1 C20 119.31(19) . . ?
C21 N1 C20 119.47(18) . . ?
C27 C21 C22 119.6(2) . . ?
C27 C21 N1 121.38(19) . . ?
C22 C21 N1 119.1(2) . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C25 C23 C22 121.0(2) . . ?
C25 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C26 C25 C23 119.1(2) . . ?
C26 C25 H25 120.4 . . ?
C23 C25 H25 120.4 . . ?
C25 C26 C27 121.1(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C21 C27 C26 119.7(2) . . ?
C21 C27 C1 122.58(19) . . ?
C26 C27 C1 117.7(2) . . ?
C29 C28 C20 119.1(2) . . ?
C29 C28 H28 120.5 . . ?
C20 C28 H28 120.5 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 120.6(2) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C32 120.2(2) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C20 118.7(2) . . ?
C31 C32 H32 120.7 . . ?
C20 C32 H32 120.7 . . ?
C28 C20 C32 120.9(2) . . ?
C28 C20 N1 119.8(2) . . ?
C32 C20 N1 119.2(2) . . ?
O2 S1 O1 116.50(16) . . ?
O2 S1 C7 109.50(14) . . ?
O1 S1 C7 108.14(13) . . ?
O2 S1 C8 109.48(13) . . ?
O1 S1 C8 108.25(13) . . ?
C7 S1 C8 104.26(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 C7 -5.8(3) . . . . ?
C14 C1 C2 C7 114.8(3) . . . . ?
C27 C1 C2 C7 -124.8(2) . . . . ?
C13 C1 C2 C3 173.69(19) . . . . ?
C14 C1 C2 C3 -65.6(2) . . . . ?
C27 C1 C2 C3 54.8(3) . . . . ?
C7 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 C6 -3.2(5) . . . . ?
C4 C5 C6 C7 1.5(5) . . . . ?
C3 C2 C7 C6 -2.4(4) . . . . ?
C1 C2 C7 C6 177.2(2) . . . . ?
C3 C2 C7 S1 171.54(18) . . . . ?
C1 C2 C7 S1 -8.9(4) . . . . ?
C5 C6 C7 C2 1.3(5) . . . . ?
C5 C6 C7 S1 -173.0(2) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
S1 C8 C9 C10 179.98(19) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C9 C8 C13 C12 -1.2(3) . . . . ?
S1 C8 C13 C12 -179.48(17) . . . . ?
C9 C8 C13 C1 179.5(2) . . . . ?
S1 C8 C13 C1 1.2(3) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C11 C12 C13 C1 179.5(2) . . . . ?
C2 C1 C13 C8 9.9(3) . . . . ?
C14 C1 C13 C8 -111.6(2) . . . . ?
C27 C1 C13 C8 128.7(2) . . . . ?
C2 C1 C13 C12 -169.41(19) . . . . ?
C14 C1 C13 C12 69.1(2) . . . . ?
C27 C1 C13 C12 -50.5(2) . . . . ?
C13 C1 C14 C19 -112.3(2) . . . . ?
C2 C1 C14 C19 122.4(2) . . . . ?
C27 C1 C14 C19 4.7(3) . . . . ?
C13 C1 C14 C15 68.1(2) . . . . ?
C2 C1 C14 C15 -57.2(3) . . . . ?
C27 C1 C14 C15 -175.0(2) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
C1 C14 C15 C16 -179.9(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C15 C14 C19 C18 -0.8(3) . . . . ?
C1 C14 C19 C18 179.6(2) . . . . ?
C15 C14 C19 N1 178.2(2) . . . . ?
C1 C14 C19 N1 -1.5(3) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C17 C18 C19 N1 -178.9(2) . . . . ?
C14 C19 N1 C21 -2.0(3) . . . . ?
C18 C19 N1 C21 176.9(2) . . . . ?
C14 C19 N1 C20 -177.1(2) . . . . ?
C18 C19 N1 C20 1.8(3) . . . . ?
C19 N1 C21 C27 1.8(3) . . . . ?
C20 N1 C21 C27 176.8(2) . . . . ?
C19 N1 C21 C22 -178.3(2) . . . . ?
C20 N1 C21 C22 -3.2(3) . . . . ?
C27 C21 C22 C23 0.2(3) . . . . ?
N1 C21 C22 C23 -179.8(2) . . . . ?
C21 C22 C23 C25 -1.0(3) . . . . ?
C22 C23 C25 C26 1.0(3) . . . . ?
C23 C25 C26 C27 -0.3(3) . . . . ?
C22 C21 C27 C26 0.5(3) . . . . ?
N1 C21 C27 C26 -179.5(2) . . . . ?
C22 C21 C27 C1 -177.90(19) . . . . ?
N1 C21 C27 C1 2.1(3) . . . . ?
C25 C26 C27 C21 -0.5(3) . . . . ?
C25 C26 C27 C1 178.0(2) . . . . ?
C13 C1 C27 C21 112.2(2) . . . . ?
C2 C1 C27 C21 -123.9(2) . . . . ?
C14 C1 C27 C21 -5.0(3) . . . . ?
C13 C1 C27 C26 -66.3(2) . . . . ?
C2 C1 C27 C26 57.7(2) . . . . ?
C14 C1 C27 C26 176.60(18) . . . . ?
C20 C28 C29 C30 0.0(4) . . . . ?
C28 C29 C30 C31 0.0(4) . . . . ?
C29 C30 C31 C32 -0.4(4) . . . . ?
C30 C31 C32 C20 0.7(4) . . . . ?
C29 C28 C20 C32 0.3(4) . . . . ?
C29 C28 C20 N1 -179.6(2) . . . . ?
C31 C32 C20 C28 -0.7(4) . . . . ?
C31 C32 C20 N1 179.2(2) . . . . ?
C19 N1 C20 C28 -87.8(3) . . . . ?
C21 N1 C20 C28 97.0(3) . . . . ?
C19 N1 C20 C32 92.3(3) . . . . ?
C21 N1 C20 C32 -82.9(3) . . . . ?
C2 C7 S1 O2 134.1(2) . . . . ?
C6 C7 S1 O2 -51.6(3) . . . . ?
C2 C7 S1 O1 -98.0(2) . . . . ?
C6 C7 S1 O1 76.3(3) . . . . ?
C2 C7 S1 C8 17.0(2) . . . . ?
C6 C7 S1 C8 -168.6(2) . . . . ?
C13 C8 S1 O2 -130.5(2) . . . . ?
C9 C8 S1 O2 51.1(2) . . . . ?
C13 C8 S1 O1 101.6(2) . . . . ?
C9 C8 S1 O1 -76.9(2) . . . . ?
C13 C8 S1 C7 -13.4(2) . . . . ?
C9 C8 S1 C7 168.17(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_import
_database_code_depnum_ccdc_archive 'CCDC 1046697'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H19 N3, 2(C H Cl3)'
_chemical_formula_sum            'C31 H21 Cl6 N3'
_chemical_formula_weight         648.21

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'
Cl Cl 0.1484 0.1585 '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                   7.7816(5)
_cell_length_b                   17.2667(11)
_cell_length_c                   21.6500(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.164(3)
_cell_angle_gamma                90.00
_cell_volume                     2906.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7193
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.08

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.964

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6340  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#



_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  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25701
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6660
_reflns_number_gt                5039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0599P)²+2.1297P] 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         6660
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.9293(3) -0.00163(11) 0.30251(9) 0.0162(4) Uani 1 1 d . . .
C2 C 0.7598(3) -0.04375(11) 0.31182(9) 0.0164(4) Uani 1 1 d . . .
C3 C 0.6118(3) -0.04751(11) 0.27454(9) 0.0193(4) Uani 1 1 d . . .
H3 H 0.6028 -0.0215 0.2370 0.023 Uiso 1 1 calc R . .
C4 C 0.4766(3) -0.09208(12) 0.29572(10) 0.0219(4) Uani 1 1 d . . .
H4 H 0.3741 -0.0958 0.2724 0.026 Uiso 1 1 calc R . .
C5 C 0.4953(3) -0.13091(12) 0.35180(10) 0.0234(5) Uani 1 1 d . . .
H5 H 0.4035 -0.1607 0.3645 0.028 Uiso 1 1 calc R . .
C6 C 0.7640(3) -0.08428(11) 0.36782(9) 0.0182(4) Uani 1 1 d . . .
C7 C 0.9304(3) -0.06985(11) 0.39992(9) 0.0189(4) Uani 1 1 d . . .
C8 C 1.1341(3) -0.07364(14) 0.47658(10) 0.0274(5) Uani 1 1 d . . .
H8 H 1.1738 -0.0916 0.5150 0.033 Uiso 1 1 calc R . .
C9 C 1.2397(3) -0.02415(14) 0.44497(10) 0.0275(5) Uani 1 1 d . . .
H9 H 1.3457 -0.0094 0.4624 0.033 Uiso 1 1 calc R . .
C10 C 1.1865(3) 0.00346(12) 0.38676(10) 0.0223(4) Uani 1 1 d . . .
H10 H 1.2549 0.0367 0.3645 0.027 Uiso 1 1 calc R . .
C11 C 1.0275(3) -0.02087(11) 0.36379(9) 0.0176(4) Uani 1 1 d . . .
C12 C 0.9072(3) 0.08571(11) 0.29578(9) 0.0163(4) Uani 1 1 d . . .
C13 C 0.7851(3) 0.12478(12) 0.32944(9) 0.0202(4) Uani 1 1 d . . .
H13 H 0.7095 0.0962 0.3527 0.024 Uiso 1 1 calc R . .
C14 C 0.7726(3) 0.20482(12) 0.32938(10) 0.0235(5) Uani 1 1 d . . .
H14 H 0.6896 0.2297 0.3520 0.028 Uiso 1 1 calc R . .
C15 C 0.8865(3) 0.24731(12) 0.29479(10) 0.0234(5) Uani 1 1 d . . .
H15 H 0.8805 0.3011 0.2947 0.028 Uiso 1 1 calc R . .
C16 C 1.0087(3) 0.21033(12) 0.26056(10) 0.0208(4) Uani 1 1 d . . .
H16 H 1.0840 0.2394 0.2376 0.025 Uiso 1 1 calc R . .
C17 C 1.0197(3) 0.12906(11) 0.26032(9) 0.0172(4) Uani 1 1 d . . .
C18 C 1.1313(3) 0.01215(11) 0.21305(9) 0.0174(4) Uani 1 1 d . . .
C19 C 1.2271(3) -0.02130(12) 0.16648(9) 0.0207(4) Uani 1 1 d . . .
H19 H 1.2997 0.0096 0.1438 0.025 Uiso 1 1 calc R . .
C20 C 1.2151(3) -0.09975(13) 0.15374(10) 0.0234(5) Uani 1 1 d . . .
H20 H 1.2789 -0.1211 0.1225 0.028 Uiso 1 1 calc R . .
C21 C 1.1079(3) -0.14655(12) 0.18747(10) 0.0239(5) Uani 1 1 d . . .
H21 H 1.0991 -0.1992 0.1789 0.029 Uiso 1 1 calc R . .
C22 C 1.0140(3) -0.11391(12) 0.23423(10) 0.0208(4) Uani 1 1 d . . .
H22 H 0.9427 -0.1454 0.2570 0.025 Uiso 1 1 calc R . .
C23 C 1.0242(3) -0.03510(11) 0.24778(9) 0.0169(4) Uani 1 1 d . . .
C24 C 1.2586(3) 0.13796(11) 0.18983(10) 0.0200(4) Uani 1 1 d . . .
C25 C 1.4225(3) 0.15284(13) 0.21347(11) 0.0270(5) Uani 1 1 d . . .
H25 H 1.4570 0.1340 0.2522 0.032 Uiso 1 1 calc R . .
C26 C 1.5354(3) 0.19595(14) 0.17930(13) 0.0361(6) Uani 1 1 d . . .
H26 H 1.6460 0.2059 0.1951 0.043 Uiso 1 1 calc R . .
C27 C 1.4844(4) 0.22404(14) 0.12205(13) 0.0391(7) Uani 1 1 d . . .
H27 H 1.5605 0.2530 0.0993 0.047 Uiso 1 1 calc R . .
C28 C 1.3205(4) 0.20930(14) 0.09836(12) 0.0359(6) Uani 1 1 d . . .
H28 H 1.2864 0.2285 0.0597 0.043 Uiso 1 1 calc R . .
C29 C 1.2057(3) 0.16585(13) 0.13210(10) 0.0276(5) Uani 1 1 d . . .
H29 H 1.0954 0.1557 0.1162 0.033 Uiso 1 1 calc R . .
C30 C 0.7901(4) -0.03853(16) 0.06765(12) 0.0391(6) Uani 1 1 d . . .
H30 H 0.9107 -0.0501 0.0786 0.047 Uiso 1 1 calc R . .
C31 C 1.1980(3) -0.29136(13) 0.02241(10) 0.0264(5) Uani 1 1 d . . .
H31 H 1.2426 -0.3228 -0.0111 0.032 Uiso 1 1 calc R . .
N1 N 0.6372(2) -0.12818(10) 0.38871(8) 0.0227(4) Uani 1 1 d . . .
N2 N 0.9784(2) -0.09762(11) 0.45560(8) 0.0243(4) Uani 1 1 d . . .
N3 N 1.1436(2) 0.09180(9) 0.22529(8) 0.0190(4) Uani 1 1 d . . .
Cl1 Cl 0.72592(13) 0.04083(5) 0.11201(3) 0.0566(2) Uani 1 1 d . . .
Cl2 Cl 0.77364(13) -0.01581(5) -0.01146(3) 0.0589(2) Uani 1 1 d . . .
Cl3 Cl 0.66707(12) -0.12045(5) 0.08286(4) 0.0642(3) Uani 1 1 d . . .
Cl4 Cl 1.00867(10) -0.33438(5) 0.04751(4) 0.0597(2) Uani 1 1 d . . .
Cl5 Cl 1.35321(10) -0.28766(4) 0.08282(3) 0.0492(2) Uani 1 1 d . . .
Cl6 Cl 1.15564(11) -0.19759(4) -0.00572(3) 0.0511(2) 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 C12 1.524(3) . ?
C1 C2 1.526(3) . ?
C1 C23 1.533(3) . ?
C1 C11 1.542(3) . ?
C2 C3 1.383(3) . ?
C2 C6 1.399(3) . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.339(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.336(3) . ?
C6 C7 1.467(3) . ?
C7 N2 1.337(3) . ?
C7 C11 1.394(3) . ?
C8 N2 1.344(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.393(3) . ?
C12 C17 1.402(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.406(3) . ?
C16 H16 0.9300 . ?
C17 N3 1.405(3) . ?
C18 C19 1.401(3) . ?
C18 N3 1.403(3) . ?
C18 C23 1.405(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(3) . ?
C22 H22 0.9300 . ?
C24 C25 1.380(3) . ?
C24 C29 1.387(3) . ?
C24 N3 1.442(3) . ?
C25 C26 1.387(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.394(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 Cl3 1.746(3) . ?
C30 Cl2 1.757(3) . ?
C30 Cl1 1.757(3) . ?
C30 H30 0.9800 . ?
C31 Cl5 1.748(2) . ?
C31 Cl4 1.755(2) . ?
C31 Cl6 1.757(2) . ?
C31 H31 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 112.89(16) . . ?
C12 C1 C23 110.80(16) . . ?
C2 C1 C23 111.48(16) . . ?
C12 C1 C11 110.24(16) . . ?
C2 C1 C11 100.74(15) . . ?
C23 C1 C11 110.28(16) . . ?
C3 C2 C6 118.29(19) . . ?
C3 C2 C1 130.57(18) . . ?
C6 C2 C1 111.14(17) . . ?
C2 C3 C4 117.13(19) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 124.1(2) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N1 C6 C2 125.72(19) . . ?
N1 C6 C7 125.82(18) . . ?
C2 C6 C7 108.47(18) . . ?
N2 C7 C11 125.8(2) . . ?
N2 C7 C6 125.28(19) . . ?
C11 C7 C6 108.94(17) . . ?
N2 C8 C9 124.6(2) . . ?
N2 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 H10 121.6 . . ?
C9 C10 H10 121.6 . . ?
C10 C11 C7 118.67(19) . . ?
C10 C11 C1 130.70(19) . . ?
C7 C11 C1 110.62(17) . . ?
C13 C12 C17 118.69(18) . . ?
C13 C12 C1 120.38(18) . . ?
C17 C12 C1 120.66(17) . . ?
C14 C13 C12 122.1(2) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 118.7(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.65(19) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.38(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 N3 120.42(17) . . ?
C12 C17 C16 119.43(19) . . ?
N3 C17 C16 120.15(18) . . ?
C19 C18 N3 120.38(18) . . ?
C19 C18 C23 119.23(18) . . ?
N3 C18 C23 120.38(18) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 119.33(19) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 121.4(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 119.00(18) . . ?
C22 C23 C1 120.37(18) . . ?
C18 C23 C1 120.50(17) . . ?
C25 C24 C29 120.5(2) . . ?
C25 C24 N3 119.29(19) . . ?
C29 C24 N3 120.2(2) . . ?
C24 C25 C26 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.0(2) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.4(2) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 119.0(2) . . ?
C24 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
Cl3 C30 Cl2 110.15(16) . . ?
Cl3 C30 Cl1 111.08(15) . . ?
Cl2 C30 Cl1 110.31(15) . . ?
Cl3 C30 H30 108.4 . . ?
Cl2 C30 H30 108.4 . . ?
Cl1 C30 H30 108.4 . . ?
Cl5 C31 Cl4 110.38(13) . . ?
Cl5 C31 Cl6 109.95(12) . . ?
Cl4 C31 Cl6 110.41(13) . . ?
Cl5 C31 H31 108.7 . . ?
Cl4 C31 H31 108.7 . . ?
Cl6 C31 H31 108.7 . . ?
C6 N1 C5 114.86(18) . . ?
C7 N2 C8 114.33(19) . . ?
C18 N3 C17 120.51(17) . . ?
C18 N3 C24 118.72(16) . . ?
C17 N3 C24 119.14(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 59.9(3) . . . . ?
C23 C1 C2 C3 -65.6(3) . . . . ?
C11 C1 C2 C3 177.5(2) . . . . ?
C12 C1 C2 C6 -120.52(18) . . . . ?
C23 C1 C2 C6 114.00(18) . . . . ?
C11 C1 C2 C6 -3.0(2) . . . . ?
C6 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 179.37(19) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 N1 0.8(3) . . . . ?
C3 C2 C6 N1 1.2(3) . . . . ?
C1 C2 C6 N1 -178.45(18) . . . . ?
C3 C2 C6 C7 -178.32(17) . . . . ?
C1 C2 C6 C7 2.1(2) . . . . ?
N1 C6 C7 N2 -1.3(3) . . . . ?
C2 C6 C7 N2 178.24(19) . . . . ?
N1 C6 C7 C11 -179.56(19) . . . . ?
C2 C6 C7 C11 -0.1(2) . . . . ?
N2 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C7 0.9(3) . . . . ?
C9 C10 C11 C1 179.4(2) . . . . ?
N2 C7 C11 C10 -1.4(3) . . . . ?
C6 C7 C11 C10 176.86(18) . . . . ?
N2 C7 C11 C1 179.78(19) . . . . ?
C6 C7 C11 C1 -1.9(2) . . . . ?
C12 C1 C11 C10 -56.2(3) . . . . ?
C2 C1 C11 C10 -175.7(2) . . . . ?
C23 C1 C11 C10 66.5(3) . . . . ?
C12 C1 C11 C7 122.39(18) . . . . ?
C2 C1 C11 C7 2.9(2) . . . . ?
C23 C1 C11 C7 -114.94(18) . . . . ?
C2 C1 C12 C13 35.7(3) . . . . ?
C23 C1 C12 C13 161.58(18) . . . . ?
C11 C1 C12 C13 -76.1(2) . . . . ?
C2 C1 C12 C17 -150.34(18) . . . . ?
C23 C1 C12 C17 -24.5(2) . . . . ?
C11 C1 C12 C17 97.9(2) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
C1 C12 C13 C14 173.42(19) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C13 C12 C17 N3 -179.40(18) . . . . ?
C1 C12 C17 N3 6.6(3) . . . . ?
C13 C12 C17 C16 1.2(3) . . . . ?
C1 C12 C17 C16 -172.80(18) . . . . ?
C15 C16 C17 C12 -0.9(3) . . . . ?
C15 C16 C17 N3 179.74(19) . . . . ?
N3 C18 C19 C20 -179.57(19) . . . . ?
C23 C18 C19 C20 1.1(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C18 0.4(3) . . . . ?
C21 C22 C23 C1 -175.62(19) . . . . ?
C19 C18 C23 C22 -1.1(3) . . . . ?
N3 C18 C23 C22 179.60(18) . . . . ?
C19 C18 C23 C1 174.89(18) . . . . ?
N3 C18 C23 C1 -4.4(3) . . . . ?
C12 C1 C23 C22 -160.66(18) . . . . ?
C2 C1 C23 C22 -34.0(3) . . . . ?
C11 C1 C23 C22 77.0(2) . . . . ?
C12 C1 C23 C18 23.4(3) . . . . ?
C2 C1 C23 C18 150.05(18) . . . . ?
C11 C1 C23 C18 -98.9(2) . . . . ?
C29 C24 C25 C26 -0.1(3) . . . . ?
N3 C24 C25 C26 178.8(2) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
C25 C24 C29 C28 -0.1(3) . . . . ?
N3 C24 C29 C28 -178.99(19) . . . . ?
C27 C28 C29 C24 0.2(3) . . . . ?
C2 C6 N1 C5 -1.1(3) . . . . ?
C7 C6 N1 C5 178.26(19) . . . . ?
C4 C5 N1 C6 0.2(3) . . . . ?
C11 C7 N2 C8 0.8(3) . . . . ?
C6 C7 N2 C8 -177.24(19) . . . . ?
C9 C8 N2 C7 0.3(3) . . . . ?
C19 C18 N3 C17 164.22(18) . . . . ?
C23 C18 N3 C17 -16.5(3) . . . . ?
C19 C18 N3 C24 -1.1(3) . . . . ?
C23 C18 N3 C24 178.23(18) . . . . ?
C12 C17 N3 C18 15.4(3) . . . . ?
C16 C17 N3 C18 -165.20(18) . . . . ?
C12 C17 N3 C24 -179.33(18) . . . . ?
C16 C17 N3 C24 0.0(3) . . . . ?
C25 C24 N3 C18 -95.5(2) . . . . ?
C29 C24 N3 C18 83.4(2) . . . . ?
C25 C24 N3 C17 99.0(2) . . . . ?
C29 C24 N3 C17 -82.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_import
_database_code_depnum_ccdc_archive 'CCDC 1046704'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 N3 O'
_chemical_formula_sum            'C29 H21 N3 O'
_chemical_formula_weight         427.49

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.5755(6)
_cell_length_b                   10.4262(6)
_cell_length_c                   11.8511(8)
_cell_angle_alpha                82.589(3)
_cell_angle_beta                 88.377(3)
_cell_angle_gamma                89.054(3)
_cell_volume                     1050.24(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3549
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.43


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.998

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6804  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13095
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4803
_reflns_number_gt                3606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (ALtomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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+0.1315P] 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         4803
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
C1 C 0.03293(18) 0.95738(14) -0.26171(13) 0.0166(3) Uani 1 1 d . . .
C2 C 0.10124(19) 1.06296(15) -0.32833(14) 0.0210(4) Uani 1 1 d . . .
H2 H 0.0413 1.1132 -0.3818 0.025 Uiso 1 1 calc R . .
C3 C 0.25465(19) 1.09487(15) -0.31718(15) 0.0228(4) Uani 1 1 d . . .
H3 H 0.2970 1.1666 -0.3617 0.027 Uiso 1 1 calc R . .
C4 C 0.34542(19) 1.01899(15) -0.23891(15) 0.0228(4) Uani 1 1 d . . .
H4 H 0.4502 1.0376 -0.2323 0.027 Uiso 1 1 calc R . .
C5 C 0.27903(19) 0.91553(15) -0.17085(14) 0.0208(4) Uani 1 1 d . . .
H5 H 0.3407 0.8659 -0.1181 0.025 Uiso 1 1 calc R . .
C6 C 0.12175(18) 0.88255(14) -0.17846(13) 0.0163(3) Uani 1 1 d . . .
C7 C 0.06541(18) 0.76482(14) -0.09792(13) 0.0171(3) Uani 1 1 d . . .
C8 C 0.09618(18) 0.63860(14) -0.14851(13) 0.0173(3) Uani 1 1 d . . .
C9 C 0.2309(2) 0.59274(15) -0.19760(15) 0.0233(4) Uani 1 1 d . . .
H9 H 0.3211 0.6417 -0.2072 0.028 Uiso 1 1 calc R . .
C10 C 0.2256(2) 0.47025(16) -0.23194(15) 0.0274(4) Uani 1 1 d . . .
H10 H 0.3122 0.4364 -0.2674 0.033 Uiso 1 1 calc R . .
C11 C 0.0903(2) 0.39904(16) -0.21296(15) 0.0275(4) Uani 1 1 d . . .
H11 H 0.0906 0.3168 -0.2353 0.033 Uiso 1 1 calc R . .
C12 C -0.03546(19) 0.56089(14) -0.13568(13) 0.0180(3) Uani 1 1 d . . .
C13 C -0.16344(19) 0.63171(14) -0.08402(13) 0.0181(3) Uani 1 1 d . . .
C14 C -0.4037(2) 0.67039(16) -0.01220(15) 0.0255(4) Uani 1 1 d . . .
H14 H -0.5052 0.6442 0.0071 0.031 Uiso 1 1 calc R . .
C15 C -0.3608(2) 0.79343(17) 0.00825(15) 0.0254(4) Uani 1 1 d . . .
H15 H -0.4332 0.8469 0.0398 0.031 Uiso 1 1 calc R . .
C16 C -0.2100(2) 0.83646(15) -0.01845(14) 0.0229(4) Uani 1 1 d . . .
H16 H -0.1786 0.9176 -0.0041 0.027 Uiso 1 1 calc R . .
C17 C -0.10876(18) 0.75345(14) -0.06719(13) 0.0178(3) Uani 1 1 d . . .
C18 C -0.15407(18) 0.81500(14) -0.33338(13) 0.0169(3) Uani 1 1 d . . .
C19 C -0.03893(19) 0.75963(15) -0.39781(14) 0.0209(4) Uani 1 1 d . . .
H19 H 0.0597 0.7959 -0.4068 0.025 Uiso 1 1 calc R . .
C20 C -0.0710(2) 0.65078(15) -0.44850(16) 0.0266(4) Uani 1 1 d . . .
H20 H 0.0060 0.6149 -0.4921 0.032 Uiso 1 1 calc R . .
C21 C -0.2171(2) 0.59502(15) -0.43474(16) 0.0284(4) Uani 1 1 d . . .
H21 H -0.2384 0.5223 -0.4693 0.034 Uiso 1 1 calc R . .
C22 C -0.3310(2) 0.64836(15) -0.36921(16) 0.0260(4) Uani 1 1 d . . .
H22 H -0.4285 0.6102 -0.3588 0.031 Uiso 1 1 calc R . .
C23 C -0.30111(19) 0.75807(15) -0.31892(14) 0.0210(4) Uani 1 1 d . . .
H23 H -0.3787 0.7937 -0.2757 0.025 Uiso 1 1 calc R . .
C24 C -0.22436(17) 1.03944(14) -0.31435(14) 0.0173(3) Uani 1 1 d . . .
C25 C -0.23596(19) 1.13545(15) -0.24305(15) 0.0226(4) Uani 1 1 d . . .
H25 H -0.1877 1.1240 -0.1731 0.027 Uiso 1 1 calc R . .
C26 C -0.3200(2) 1.24875(15) -0.27669(17) 0.0271(4) Uani 1 1 d . . .
H26 H -0.3271 1.3133 -0.2294 0.032 Uiso 1 1 calc R . .
C27 C -0.3932(2) 1.26566(15) -0.38059(17) 0.0273(4) Uani 1 1 d . . .
H27 H -0.4483 1.3417 -0.4033 0.033 Uiso 1 1 calc R . .
C28 C -0.3839(2) 1.16917(16) -0.45026(15) 0.0250(4) Uani 1 1 d . . .
H28 H -0.4347 1.1798 -0.5192 0.030 Uiso 1 1 calc R . .
C29 C -0.29921(18) 1.05625(15) -0.41798(14) 0.0203(4) Uani 1 1 d . . .
H29 H -0.2926 0.9920 -0.4656 0.024 Uiso 1 1 calc R . .
N1 N -0.04135(17) 0.44087(12) -0.16438(12) 0.0228(3) Uani 1 1 d . . .
N2 N -0.30730(16) 0.58730(13) -0.05807(12) 0.0227(3) Uani 1 1 d . . .
N3 N -0.12629(15) 0.92861(12) -0.28179(11) 0.0176(3) Uani 1 1 d . . .
O001 O 0.15249(13) 0.76639(10) 0.00377(9) 0.0218(3) Uani 1 1 d . . .
H001 H 0.1305 0.7027 0.0493 0.033 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
C1 C2 1.396(2) . ?
C1 C6 1.409(2) . ?
C1 N3 1.436(2) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.530(2) . ?
C7 O001 1.4377(18) . ?
C7 C17 1.530(2) . ?
C7 C8 1.531(2) . ?
C8 C9 1.385(2) . ?
C8 C12 1.394(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.345(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.3405(19) . ?
C12 C13 1.475(2) . ?
C13 N2 1.338(2) . ?
C13 C17 1.400(2) . ?
C14 N2 1.342(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9300 . ?
C18 C19 1.394(2) . ?
C18 C23 1.399(2) . ?
C18 N3 1.4277(19) . ?
C19 C20 1.386(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.391(2) . ?
C24 C29 1.392(2) . ?
C24 N3 1.4362(19) . ?
C25 C26 1.393(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.390(2) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O001 H001 0.8200 . ?

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
C2 C1 C6 119.42(14) . . ?
C2 C1 N3 118.18(14) . . ?
C6 C1 N3 122.40(13) . . ?
C3 C2 C1 121.97(15) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.30(15) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.50(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 122.41(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.32(14) . . ?
C5 C6 C7 116.34(13) . . ?
C1 C6 C7 126.30(13) . . ?
O001 C7 C17 109.69(13) . . ?
O001 C7 C6 104.99(11) . . ?
C17 C7 C6 118.80(12) . . ?
O001 C7 C8 110.55(12) . . ?
C17 C7 C8 101.05(12) . . ?
C6 C7 C8 111.77(13) . . ?
C9 C8 C12 119.04(14) . . ?
C9 C8 C7 130.17(14) . . ?
C12 C8 C7 110.73(14) . . ?
C8 C9 C10 117.15(15) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C11 C10 C9 119.52(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 124.41(15) . . ?
N1 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
N1 C12 C8 124.75(15) . . ?
N1 C12 C13 126.50(14) . . ?
C8 C12 C13 108.75(13) . . ?
N2 C13 C17 125.89(15) . . ?
N2 C13 C12 125.81(14) . . ?
C17 C13 C12 108.30(14) . . ?
N2 C14 C15 123.94(15) . . ?
N2 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C16 C15 C14 120.11(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 117.18(15) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C13 118.19(15) . . ?
C16 C17 C7 130.83(14) . . ?
C13 C17 C7 110.70(13) . . ?
C19 C18 C23 119.25(14) . . ?
C19 C18 N3 121.79(14) . . ?
C23 C18 N3 118.95(14) . . ?
C20 C19 C18 120.21(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.46(17) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.53(15) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.66(16) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 119.87(16) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
C25 C24 C29 119.75(14) . . ?
C25 C24 N3 118.56(14) . . ?
C29 C24 N3 121.56(14) . . ?
C24 C25 C26 119.85(16) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.21(16) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 119.81(15) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 120.44(16) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 119.93(15) . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?
C12 N1 C11 115.06(14) . . ?
C13 N2 C14 114.69(14) . . ?
C18 N3 C1 117.27(12) . . ?
C18 N3 C24 117.15(12) . . ?
C1 N3 C24 115.01(12) . . ?
C7 O001 H001 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.6(2) . . . . ?
N3 C1 C2 C3 -177.91(15) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 1.9(2) . . . . ?
C4 C5 C6 C7 179.60(15) . . . . ?
C2 C1 C6 C5 -3.0(2) . . . . ?
N3 C1 C6 C5 176.49(14) . . . . ?
C2 C1 C6 C7 179.57(15) . . . . ?
N3 C1 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 O001 33.46(18) . . . . ?
C1 C6 C7 O001 -149.06(15) . . . . ?
C5 C6 C7 C17 156.49(14) . . . . ?
C1 C6 C7 C17 -26.0(2) . . . . ?
C5 C6 C7 C8 -86.43(16) . . . . ?
C1 C6 C7 C8 91.05(18) . . . . ?
O001 C7 C8 C9 -67.3(2) . . . . ?
C17 C7 C8 C9 176.65(16) . . . . ?
C6 C7 C8 C9 49.3(2) . . . . ?
O001 C7 C8 C12 109.83(14) . . . . ?
C17 C7 C8 C12 -6.27(16) . . . . ?
C6 C7 C8 C12 -133.61(14) . . . . ?
C12 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 C10 177.19(15) . . . . ?
C8 C9 C10 C11 -1.9(2) . . . . ?
C9 C10 C11 N1 1.3(3) . . . . ?
C9 C8 C12 N1 2.2(2) . . . . ?
C7 C8 C12 N1 -175.24(14) . . . . ?
C9 C8 C12 C13 -178.83(14) . . . . ?
C7 C8 C12 C13 3.72(17) . . . . ?
N1 C12 C13 N2 -0.5(3) . . . . ?
C8 C12 C13 N2 -179.41(15) . . . . ?
N1 C12 C13 C17 179.74(15) . . . . ?
C8 C12 C13 C17 0.80(17) . . . . ?
N2 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 1.2(2) . . . . ?
C15 C16 C17 C13 -1.3(2) . . . . ?
C15 C16 C17 C7 -174.53(15) . . . . ?
N2 C13 C17 C16 0.7(2) . . . . ?
C12 C13 C17 C16 -179.53(14) . . . . ?
N2 C13 C17 C7 175.20(14) . . . . ?
C12 C13 C17 C7 -5.01(17) . . . . ?
O001 C7 C17 C16 63.7(2) . . . . ?
C6 C7 C17 C16 -57.0(2) . . . . ?
C8 C7 C17 C16 -179.62(16) . . . . ?
O001 C7 C17 C13 -109.96(14) . . . . ?
C6 C7 C17 C13 129.37(14) . . . . ?
C8 C7 C17 C13 6.77(16) . . . . ?
C23 C18 C19 C20 1.1(2) . . . . ?
N3 C18 C19 C20 -178.73(14) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C22 C23 C18 -0.6(2) . . . . ?
C19 C18 C23 C22 -0.5(2) . . . . ?
N3 C18 C23 C22 179.40(14) . . . . ?
C29 C24 C25 C26 -1.2(2) . . . . ?
N3 C24 C25 C26 174.83(15) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
C25 C26 C27 C28 0.7(3) . . . . ?
C26 C27 C28 C29 -1.2(3) . . . . ?
C27 C28 C29 C24 0.6(2) . . . . ?
C25 C24 C29 C28 0.6(2) . . . . ?
N3 C24 C29 C28 -175.28(14) . . . . ?
C8 C12 N1 C11 -2.8(2) . . . . ?
C13 C12 N1 C11 178.40(15) . . . . ?
C10 C11 N1 C12 1.0(2) . . . . ?
C17 C13 N2 C14 0.1(2) . . . . ?
C12 C13 N2 C14 -179.63(14) . . . . ?
C15 C14 N2 C13 -0.3(2) . . . . ?
C19 C18 N3 C1 -22.4(2) . . . . ?
C23 C18 N3 C1 157.78(14) . . . . ?
C19 C18 N3 C24 120.67(16) . . . . ?
C23 C18 N3 C24 -59.19(19) . . . . ?
C2 C1 N3 C18 109.31(16) . . . . ?
C6 C1 N3 C18 -70.16(19) . . . . ?
C2 C1 N3 C24 -34.5(2) . . . . ?
C6 C1 N3 C24 146.05(15) . . . . ?
C25 C24 N3 C18 160.05(14) . . . . ?
C29 C24 N3 C18 -24.0(2) . . . . ?
C25 C24 N3 C1 -56.10(19) . . . . ?
C29 C24 N3 C1 119.81(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.075
