# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_shelx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H10 F6 N2 S2), C4 H12 N, Cl'
_chemical_formula_sum            'C40 H32 Cl F12 N5 S4'
_chemical_formula_weight         974.40

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'
F F 0.0171 0.0103 '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'
'-x, -y, -z'

_cell_length_a                   8.0301(5)
_cell_length_b                   16.9861(11)
_cell_length_c                   17.5950(11)
_cell_angle_alpha                64.243(4)
_cell_angle_beta                 80.825(6)
_cell_angle_gamma                77.765(5)
_cell_volume                     2106.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21137
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25975
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         27.50
_reflns_number_total             9528
_reflns_number_gt                5962
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'



_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 > 2σ(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)+(0.0778P)²+1.8308P] 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         9528
_refine_ls_number_parameters     587
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Cl1 Cl 0.22447(17) 0.53325(7) 0.05681(6) 0.0410(3) Uani 1 1 d . . .
S1 S 0.18217(12) 0.53533(6) 0.43722(5) 0.0233(2) Uani 1 1 d . . .
S2 S 0.15942(13) 0.77154(7) 0.28484(6) 0.0279(2) Uani 1 1 d . . .
S3 S -0.40687(13) 0.48712(7) 0.32216(6) 0.0275(2) Uani 1 1 d . . .
S5 S -0.25790(15) 0.69871(7) 0.17312(6) 0.0343(3) Uani 1 1 d . . .
F1 F 0.0423(3) 0.09485(15) 0.46509(15) 0.0375(6) Uani 1 1 d . . .
F2 F -0.1551(3) 0.15981(16) 0.52572(15) 0.0373(6) Uani 1 1 d . . .
N2 N 0.2066(4) 0.6862(2) 0.11986(17) 0.0227(7) Uani 1 1 d . . .
H2 H 0.2086 0.6493 0.0968 0.027 Uiso 1 1 calc R . .
N1 N 0.1654(4) 0.4921(2) 0.25162(18) 0.0236(7) Uani 1 1 d . . .
H1 H 0.1886 0.4965 0.1995 0.028 Uiso 1 1 calc R . .
F3 F 0.1022(3) 0.12821(15) 0.56150(15) 0.0389(6) Uani 1 1 d . . .
N3 N -0.3297(4) 0.4307(2) 0.13583(18) 0.0245(7) Uani 1 1 d . . .
H3 H -0.3246 0.4410 0.0820 0.029 Uiso 1 1 calc R . .
N4 N -0.2337(4) 0.6148(2) 0.00944(18) 0.0250(7) Uani 1 1 d . . .
H4 H -0.2165 0.5756 -0.0122 0.030 Uiso 1 1 calc R . .
F10 F -0.3593(4) 0.02094(16) 0.31829(17) 0.0514(7) Uani 1 1 d . . .
C21 C -0.3177(5) 0.2200(3) 0.3278(2) 0.0266(8) Uani 1 1 d . . .
H21 H -0.2853 0.1948 0.3843 0.032 Uiso 1 1 calc R . .
C5 C 0.1239(5) 0.4102(2) 0.3129(2) 0.0198(7) Uani 1 1 d . . .
C4 C 0.0136(5) 0.4033(2) 0.3845(2) 0.0209(7) Uani 1 1 d . . .
H4A H -0.0362 0.4549 0.3935 0.025 Uiso 1 1 calc R . .
C16 C 0.2223(5) 0.7745(2) 0.0622(2) 0.0214(8) Uani 1 1 d . . .
C34 C -0.2133(5) 0.7018(2) -0.0485(2) 0.0232(8) Uani 1 1 d . . .
C2 C 0.0448(5) 0.2458(2) 0.4287(2) 0.0226(8) Uani 1 1 d . . .
C32 C -0.2880(5) 0.8597(3) -0.0992(2) 0.0290(9) Uani 1 1 d . . .
H32 H -0.3503 0.9104 -0.0919 0.035 Uiso 1 1 calc R . .
C11 C 0.1893(5) 0.6514(2) 0.2042(2) 0.0212(7) Uani 1 1 d . . .
C27 C -0.3432(5) 0.5263(2) 0.2216(2) 0.0220(8) Uani 1 1 d . . .
C28 C -0.2902(5) 0.6125(3) 0.1617(2) 0.0253(8) Uani 1 1 d . . .
C10 C 0.1756(4) 0.6801(2) 0.2732(2) 0.0203(7) Uani 1 1 d . . .
C22 C -0.2989(5) 0.3066(3) 0.2756(2) 0.0253(8) Uani 1 1 d . . .
H22 H -0.2519 0.3404 0.2954 0.030 Uiso 1 1 calc R . .
C35 C -0.1029(5) 0.7119(3) -0.1211(2) 0.0262(8) Uani 1 1 d . . .
H35 H -0.0395 0.6613 -0.1282 0.031 Uiso 1 1 calc R . .
N5 N 0.4010(4) 0.2765(2) 0.58441(18) 0.0229(7) Uani 1 1 d . . .
C36 C -0.0864(5) 0.7957(3) -0.1824(2) 0.0265(8) Uani 1 1 d . . .
H36 H -0.0120 0.8029 -0.2318 0.032 Uiso 1 1 calc R . .
C17 C 0.2965(6) 0.8288(3) 0.0827(2) 0.0317(9) Uani 1 1 d . . .
H17 H 0.3412 0.8069 0.1362 0.038 Uiso 1 1 calc R . .
C9 C 0.1746(5) 0.5858(2) 0.3348(2) 0.0203(7) Uani 1 1 d . . .
C23 C -0.3498(5) 0.3440(2) 0.1931(2) 0.0231(8) Uani 1 1 d . . .
C7 C 0.1515(5) 0.2528(3) 0.3561(2) 0.0260(8) Uani 1 1 d . . .
H7 H 0.1972 0.2014 0.3462 0.031 Uiso 1 1 calc R . .
C8 C 0.1734(5) 0.5637(2) 0.2633(2) 0.0198(7) Uani 1 1 d . . .
C29 C -0.2757(5) 0.5838(2) 0.0933(2) 0.0229(8) Uani 1 1 d . . .
C20 C -0.3836(5) 0.1689(3) 0.2990(2) 0.0273(8) Uani 1 1 d . . .
C33 C -0.3057(5) 0.7760(3) -0.0379(2) 0.0284(9) Uani 1 1 d . . .
H33 H -0.3807 0.7692 0.0113 0.034 Uiso 1 1 calc R . .
C26 C -0.3170(5) 0.5000(2) 0.1508(2) 0.0208(7) Uani 1 1 d . . .
F12 F -0.3101(4) 0.04200(18) 0.42357(18) 0.0590(8) Uani 1 1 d . . .
C13 C 0.2433(5) 0.9466(3) -0.0553(2) 0.0286(9) Uani 1 1 d . . .
C15 C 0.1670(5) 0.8045(3) -0.0180(2) 0.0291(9) Uani 1 1 d . . .
H15 H 0.1213 0.7661 -0.0327 0.035 Uiso 1 1 calc R . .
C6 C 0.1911(5) 0.3343(3) 0.2983(2) 0.0262(8) Uani 1 1 d . . .
H6 H 0.2638 0.3389 0.2489 0.031 Uiso 1 1 calc R . .
C3 C -0.0232(5) 0.3211(2) 0.4426(2) 0.0218(8) Uani 1 1 d . . .
H3A H -0.0954 0.3162 0.4923 0.026 Uiso 1 1 calc R . .
C31 C -0.1793(5) 0.8700(3) -0.1716(2) 0.0269(8) Uani 1 1 d . A .
F6 F 0.2063(5) 1.0600(2) -0.1933(2) 0.0780(11) Uani 1 1 d . . .
F5 F 0.4068(4) 1.06136(19) -0.1300(2) 0.0653(9) Uani 1 1 d . . .
C25 C -0.4320(5) 0.2065(3) 0.2164(2) 0.0291(9) Uani 1 1 d . . .
H25 H -0.4771 0.1724 0.1961 0.035 Uiso 1 1 calc R . .
C18 C 0.3048(6) 0.9149(3) 0.0246(2) 0.0338(10) Uani 1 1 d . . .
H18 H 0.3525 0.9528 0.0390 0.041 Uiso 1 1 calc R . .
F11 F -0.5650(4) 0.06797(19) 0.3885(2) 0.0736(11) Uani 1 1 d . . .
C1 C 0.0080(5) 0.1576(3) 0.4946(2) 0.0264(8) Uani 1 1 d . . .
C24 C -0.4147(5) 0.2930(3) 0.1639(2) 0.0263(8) Uani 1 1 d . . .
H24 H -0.4471 0.3181 0.1075 0.032 Uiso 1 1 calc R . .
C14 C 0.1784(6) 0.8906(3) -0.0769(3) 0.0344(10) Uani 1 1 d . . .
H14 H 0.1415 0.9110 -0.1320 0.041 Uiso 1 1 calc R . .
C38 C 0.2147(5) 0.2950(3) 0.6071(3) 0.0359(10) Uani 1 1 d . . .
H38A H 0.1656 0.3526 0.5651 0.054 Uiso 1 1 calc R . .
H38B H 0.1973 0.2959 0.6631 0.054 Uiso 1 1 calc R . .
H38C H 0.1585 0.2487 0.6079 0.054 Uiso 1 1 calc R . .
C30 C -0.1670(6) 0.9611(3) -0.2400(3) 0.0379(10) Uani 1 1 d . . .
C40 C 0.4763(6) 0.1891(3) 0.6485(3) 0.0366(10) Uani 1 1 d . . .
H40A H 0.5990 0.1772 0.6335 0.055 Uiso 1 1 calc R . .
H40B H 0.4206 0.1425 0.6496 0.055 Uiso 1 1 calc R . .
H40C H 0.4588 0.1903 0.7044 0.055 Uiso 1 1 calc R . .
C37 C 0.4873(5) 0.3479(3) 0.5818(3) 0.0323(9) Uani 1 1 d . . .
H37A H 0.6101 0.3352 0.5672 0.048 Uiso 1 1 calc R . .
H37B H 0.4695 0.3499 0.6373 0.048 Uiso 1 1 calc R . .
H37C H 0.4388 0.4051 0.5390 0.048 Uiso 1 1 calc R . .
F4 F 0.1484(5) 1.0976(2) -0.0920(2) 0.0978(14) Uani 1 1 d . . .
C12 C 0.2509(6) 1.0409(3) -0.1163(3) 0.0400(11) Uani 1 1 d . . .
C19 C -0.4047(6) 0.0755(3) 0.3575(3) 0.0360(10) Uani 1 1 d . . .
C39 C 0.4276(5) 0.2752(3) 0.4985(2) 0.0329(10) Uani 1 1 d . . .
H39A H 0.5503 0.2628 0.4837 0.049 Uiso 1 1 calc R . .
H39B H 0.3790 0.3330 0.4565 0.049 Uiso 1 1 calc R . .
H39C H 0.3710 0.2291 0.4993 0.049 Uiso 1 1 calc R . .
F7A F -0.095(2) 0.9602(5) -0.3171(7) 0.080(6) Uani 0.417(19) 1 d PD A 1
F8A F -0.3139(17) 1.0103(11) -0.2610(10) 0.079(6) Uani 0.417(19) 1 d PD A 1
F9A F -0.077(3) 1.0067(8) -0.2270(11) 0.115(11) Uani 0.417(19) 1 d PD A 1
F7B F -0.0157(9) 0.9673(4) -0.2770(6) 0.058(3) Uani 0.583(19) 1 d P A 2
F8B F -0.2754(19) 0.9878(9) -0.2937(11) 0.119(8) Uani 0.583(19) 1 d P A 2
F9B F -0.190(2) 1.0193(5) -0.2045(6) 0.095(5) Uani 0.583(19) 1 d P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.630(4) . ?
S2 C10 1.630(4) . ?
S3 C27 1.633(4) . ?
S5 C28 1.638(4) . ?
F1 C1 1.340(4) . ?
F2 C1 1.336(5) . ?
N2 C11 1.333(4) . ?
N2 C16 1.418(5) . ?
N2 H2 0.8800 . ?
N1 C8 1.335(4) . ?
N1 C5 1.408(5) . ?
N1 H1 0.8800 . ?
F3 C1 1.348(4) . ?
N3 C26 1.340(4) . ?
N3 C23 1.403(5) . ?
N3 H3 0.8800 . ?
N4 C29 1.345(4) . ?
N4 C34 1.410(5) . ?
N4 H4 0.8800 . ?
F10 C19 1.342(5) . ?
C21 C22 1.380(5) . ?
C21 C20 1.399(5) . ?
C21 H21 0.9500 . ?
C5 C4 1.396(5) . ?
C5 C6 1.403(5) . ?
C4 C3 1.386(5) . ?
C4 H4A 0.9500 . ?
C16 C17 1.388(5) . ?
C16 C15 1.389(5) . ?
C34 C33 1.392(5) . ?
C34 C35 1.401(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.393(5) . ?
C2 C1 1.498(5) . ?
C32 C33 1.382(5) . ?
C32 C31 1.389(5) . ?
C32 H32 0.9500 . ?
C11 C8 1.418(5) . ?
C11 C10 1.474(4) . ?
C27 C26 1.469(4) . ?
C27 C28 1.488(5) . ?
C28 C29 1.463(4) . ?
C10 C9 1.495(5) . ?
C22 C23 1.398(5) . ?
C22 H22 0.9500 . ?
C35 C36 1.381(5) . ?
C35 H35 0.9500 . ?
N5 C38 1.489(5) . ?
N5 C40 1.490(5) . ?
N5 C37 1.500(5) . ?
N5 C39 1.501(4) . ?
C36 C31 1.395(5) . ?
C36 H36 0.9500 . ?
C17 C18 1.381(6) . ?
C17 H17 0.9500 . ?
C9 C8 1.462(4) . ?
C23 C24 1.396(5) . ?
C7 C6 1.382(5) . ?
C7 H7 0.9500 . ?
C29 C26 1.414(5) . ?
C20 C25 1.393(5) . ?
C20 C19 1.498(6) . ?
C33 H33 0.9500 . ?
F12 C19 1.332(5) . ?
C13 C14 1.381(5) . ?
C13 C18 1.402(5) . ?
C13 C12 1.499(6) . ?
C15 C14 1.390(6) . ?
C15 H15 0.9500 . ?
C6 H6 0.9500 . ?
C3 H3A 0.9500 . ?
C31 C30 1.504(6) . ?
F6 C12 1.338(5) . ?
F5 C12 1.328(5) . ?
C25 C24 1.377(5) . ?
C25 H25 0.9500 . ?
C18 H18 0.9500 . ?
F11 C19 1.325(5) . ?
C24 H24 0.9500 . ?
C14 H14 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C30 F8B 1.257(10) . ?
C30 F9A 1.271(10) . ?
C30 F7B 1.286(7) . ?
C30 F8A 1.296(14) . ?
C30 F9B 1.349(9) . ?
C30 F7A 1.393(10) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
F4 C12 1.303(5) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
C11 N2 C16 129.0(3) . . ?
C11 N2 H2 115.5 . . ?
C16 N2 H2 115.5 . . ?
C8 N1 C5 127.7(3) . . ?
C8 N1 H1 116.1 . . ?
C5 N1 H1 116.1 . . ?
C26 N3 C23 129.7(3) . . ?
C26 N3 H3 115.2 . . ?
C23 N3 H3 115.2 . . ?
C29 N4 C34 128.8(3) . . ?
C29 N4 H4 115.6 . . ?
C34 N4 H4 115.6 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 N1 122.3(3) . . ?
C6 C5 N1 118.0(3) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 N2 122.1(3) . . ?
C15 C16 N2 117.6(3) . . ?
C33 C34 C35 120.1(4) . . ?
C33 C34 N4 122.3(3) . . ?
C35 C34 N4 117.5(3) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 118.8(3) . . ?
C7 C2 C1 121.3(3) . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
N2 C11 C8 130.2(3) . . ?
N2 C11 C10 138.8(3) . . ?
C8 C11 C10 91.0(3) . . ?
C26 C27 C28 88.3(3) . . ?
C26 C27 S3 139.3(3) . . ?
C28 C27 S3 132.4(3) . . ?
C29 C28 C27 88.7(3) . . ?
C29 C28 S5 137.6(3) . . ?
C27 C28 S5 133.6(3) . . ?
C11 C10 C9 88.3(3) . . ?
C11 C10 S2 138.7(3) . . ?
C9 C10 S2 132.9(2) . . ?
C21 C22 C23 119.3(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C38 N5 C40 109.6(3) . . ?
C38 N5 C37 109.7(3) . . ?
C40 N5 C37 109.6(3) . . ?
C38 N5 C39 109.5(3) . . ?
C40 N5 C39 109.8(3) . . ?
C37 N5 C39 108.6(3) . . ?
C35 C36 C31 119.9(4) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C8 C9 C10 88.5(3) . . ?
C8 C9 S1 138.7(3) . . ?
C10 C9 S1 132.8(2) . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 N3 117.8(3) . . ?
C22 C23 N3 122.3(3) . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N1 C8 C11 130.8(3) . . ?
N1 C8 C9 137.3(3) . . ?
C11 C8 C9 91.8(3) . . ?
N4 C29 C26 129.7(3) . . ?
N4 C29 C28 138.8(3) . . ?
C26 C29 C28 91.4(3) . . ?
C25 C20 C21 119.2(4) . . ?
C25 C20 C19 121.0(4) . . ?
C21 C20 C19 119.8(4) . . ?
C32 C33 C34 119.8(4) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
N3 C26 C29 129.3(3) . . ?
N3 C26 C27 139.2(3) . . ?
C29 C26 C27 91.4(3) . . ?
C14 C13 C18 119.7(4) . . ?
C14 C13 C12 121.2(4) . . ?
C18 C13 C12 119.1(4) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C32 C31 C36 120.1(4) . . ?
C32 C31 C30 119.9(4) . . ?
C36 C31 C30 119.9(4) . . ?
C24 C25 C20 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C17 C18 C13 120.3(4) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
F2 C1 F1 106.7(3) . . ?
F2 C1 F3 106.1(3) . . ?
F1 C1 F3 106.6(3) . . ?
F2 C1 C2 112.7(3) . . ?
F1 C1 C2 112.5(3) . . ?
F3 C1 C2 111.7(3) . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
N5 C38 H38A 109.5 . . ?
N5 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N5 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
F8B C30 F7B 110.3(8) . . ?
F9A C30 F8A 107.0(9) . . ?
F8B C30 F9B 108.0(9) . . ?
F7B C30 F9B 102.9(6) . . ?
F9A C30 F7A 103.3(9) . . ?
F8A C30 F7A 101.3(8) . . ?
F8B C30 C31 113.6(6) . . ?
F9A C30 C31 116.8(6) . . ?
F7B C30 C31 112.2(4) . . ?
F8A C30 C31 113.8(8) . . ?
F9B C30 C31 109.2(5) . . ?
F7A C30 C31 113.0(5) . . ?
N5 C40 H40A 109.5 . . ?
N5 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N5 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N5 C37 H37A 109.5 . . ?
N5 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N5 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
F4 C12 F5 107.6(4) . . ?
F4 C12 F6 105.1(4) . . ?
F5 C12 F6 104.5(4) . . ?
F4 C12 C13 112.9(4) . . ?
F5 C12 C13 112.9(4) . . ?
F6 C12 C13 113.1(4) . . ?
F11 C19 F12 106.8(4) . . ?
F11 C19 F10 106.1(4) . . ?
F12 C19 F10 106.4(3) . . ?
F11 C19 C20 112.5(3) . . ?
F12 C19 C20 112.8(4) . . ?
F10 C19 C20 111.9(3) . . ?
N5 C39 H39A 109.5 . . ?
N5 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N5 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 0.88 2.34 3.209(3) 170.8 .
N1 H1 Cl1 0.88 2.29 3.163(3) 169.9 .
N3 H3 Cl1 0.88 2.32 3.175(3) 162.7 2_565
N4 H4 Cl1 0.88 2.32 3.184(3) 168.7 2_565

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 1005458'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_epgs1

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H44 N2 O2, C2 H6 O S'
_chemical_formula_sum            'C34 H50 N2 O3 S'
_chemical_formula_weight         566.82

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0175(6)
_cell_length_b                   12.8086(7)
_cell_length_c                   12.9025(7)
_cell_angle_alpha                91.871(2)
_cell_angle_beta                 113.774(2)
_cell_angle_gamma                96.730(2)
_cell_volume                     1648.39(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5294
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.56

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            33121
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.607
_diffrn_reflns_theta_max         28.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8308
_reflns_number_gt                5709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-II v2013-10.0'
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_reduction        'Bruker SAINT v8.32B'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.2770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     vecmao
_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         8308
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75154(11) 0.43513(9) 0.53139(9) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.92463(10) 0.57496(9) 0.76323(9) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.48712(12) 0.40950(10) 0.60439(10) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.4354 0.4340 0.6337 0.019 Uiso 1 1 calc R U . . .
N2 N 0.64491(12) 0.57052(10) 0.81468(10) 0.0152(3) Uani 1 1 d . . . . .
H2 H 0.5608 0.5500 0.8023 0.018 Uiso 1 1 calc R U . . .
C1 C 0.61286(15) 0.45875(12) 0.64263(12) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.72705(15) 0.46658(12) 0.60988(13) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.80697(15) 0.53592(12) 0.71702(13) 0.0147(3) Uani 1 1 d . . . . .
C4 C 0.68575(15) 0.53010(11) 0.73912(12) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.42814(15) 0.32220(12) 0.52187(12) 0.0147(3) Uani 1 1 d . . . . .
C6 C 0.50345(15) 0.26809(12) 0.48129(13) 0.0161(3) Uani 1 1 d . . . . .
H6 H 0.5972 0.2897 0.5083 0.019 Uiso 1 1 calc R U . . .
C7 C 0.44222(15) 0.18174(12) 0.40077(12) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.30575(16) 0.15172(12) 0.36448(13) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.2634 0.0931 0.3093 0.021 Uiso 1 1 calc R U . . .
C9 C 0.22775(15) 0.20401(12) 0.40562(13) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.29074(15) 0.29016(12) 0.48467(13) 0.0165(3) Uani 1 1 d . . . . .
H10 H 0.2401 0.3277 0.5138 0.020 Uiso 1 1 calc R U . . .
C11 C 0.52843(16) 0.12576(12) 0.35586(13) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.64152(19) 0.08469(15) 0.45343(15) 0.0304(4) Uani 1 1 d . . . . .
H12A H 0.6978 0.1440 0.5081 0.046 Uiso 1 1 calc R U . . .
H12B H 0.6961 0.0494 0.4231 0.046 Uiso 1 1 calc R U . . .
H12C H 0.6030 0.0344 0.4915 0.046 Uiso 1 1 calc R U . . .
C13 C 0.59065(18) 0.20405(14) 0.29854(15) 0.0277(4) Uani 1 1 d . . . . .
H13A H 0.5195 0.2313 0.2360 0.042 Uiso 1 1 calc R U . . .
H13B H 0.6454 0.1686 0.2686 0.042 Uiso 1 1 calc R U . . .
H13C H 0.6471 0.2626 0.3541 0.042 Uiso 1 1 calc R U . . .
C14 C 0.44665(19) 0.03229(15) 0.27008(17) 0.0375(5) Uani 1 1 d . . . . .
H14A H 0.4060 -0.0184 0.3062 0.056 Uiso 1 1 calc R U . . .
H14B H 0.5054 -0.0020 0.2438 0.056 Uiso 1 1 calc R U . . .
H14C H 0.3760 0.0572 0.2051 0.056 Uiso 1 1 calc R U . . .
C15 C 0.07793(15) 0.16412(13) 0.36288(14) 0.0207(4) Uani 1 1 d . . . . .
C16 C 0.05997(18) 0.05101(14) 0.39458(16) 0.0308(4) Uani 1 1 d . . . . .
H16A H 0.1004 0.0057 0.3586 0.046 Uiso 1 1 calc R U . . .
H16B H -0.0358 0.0250 0.3681 0.046 Uiso 1 1 calc R U . . .
H16C H 0.1038 0.0499 0.4773 0.046 Uiso 1 1 calc R U . . .
C17 C 0.01077(17) 0.16409(14) 0.23320(14) 0.0259(4) Uani 1 1 d . . . . .
H17A H 0.0256 0.2356 0.2116 0.039 Uiso 1 1 calc R U . . .
H17B H -0.0857 0.1408 0.2065 0.039 Uiso 1 1 calc R U . . .
H17C H 0.0494 0.1158 0.1985 0.039 Uiso 1 1 calc R U . . .
C18 C 0.00781(17) 0.23184(16) 0.41416(17) 0.0350(5) Uani 1 1 d . . . . .
H18A H 0.0474 0.2306 0.4970 0.052 Uiso 1 1 calc R U . . .
H18B H -0.0878 0.2039 0.3839 0.052 Uiso 1 1 calc R U . . .
H18C H 0.0187 0.3046 0.3946 0.052 Uiso 1 1 calc R U . . .
C19 C 0.71956(15) 0.64188(11) 0.91162(12) 0.0145(3) Uani 1 1 d . . . . .
C20 C 0.64748(15) 0.69182(12) 0.96031(13) 0.0159(3) Uani 1 1 d . . . . .
H20 H 0.5525 0.6769 0.9281 0.019 Uiso 1 1 calc R U . . .
C21 C 0.71286(16) 0.76320(12) 1.05541(13) 0.0169(3) Uani 1 1 d . . . . .
C22 C 0.85232(16) 0.78094(12) 1.10134(13) 0.0185(3) Uani 1 1 d . . . . .
H22 H 0.8985 0.8302 1.1661 0.022 Uiso 1 1 calc R U . . .
C23 C 0.92676(15) 0.72942(12) 1.05627(13) 0.0158(3) Uani 1 1 d . . . . .
C24 C 0.85809(15) 0.65945(12) 0.95951(13) 0.0155(3) Uani 1 1 d . . . . .
H24 H 0.9064 0.6238 0.9264 0.019 Uiso 1 1 calc R U . . .
C25 C 0.63834(16) 0.82417(12) 1.10932(14) 0.0202(4) Uani 1 1 d . . . . .
C26 C 0.48758(18) 0.79023(16) 1.05299(17) 0.0359(5) Uani 1 1 d . . . . .
H26A H 0.4543 0.8016 0.9720 0.054 Uiso 1 1 calc R U . . .
H26B H 0.4440 0.8320 1.0892 0.054 Uiso 1 1 calc R U . . .
H26C H 0.4673 0.7152 1.0614 0.054 Uiso 1 1 calc R U . . .
C27 C 0.68732(19) 0.80693(15) 1.23537(15) 0.0306(4) Uani 1 1 d . . . . .
H27A H 0.6690 0.7317 1.2439 0.046 Uiso 1 1 calc R U . . .
H27B H 0.6404 0.8472 1.2696 0.046 Uiso 1 1 calc R U . . .
H27C H 0.7839 0.8308 1.2735 0.046 Uiso 1 1 calc R U . . .
C28 C 0.66751(19) 0.94138(13) 1.09513(16) 0.0304(4) Uani 1 1 d . . . . .
H28A H 0.7642 0.9649 1.1329 0.046 Uiso 1 1 calc R U . . .
H28B H 0.6212 0.9824 1.1293 0.046 Uiso 1 1 calc R U . . .
H28C H 0.6358 0.9519 1.0140 0.046 Uiso 1 1 calc R U . . .
C29 C 1.07968(15) 0.75178(13) 1.11200(13) 0.0190(3) Uani 1 1 d . . . . .
C30 C 1.12981(17) 0.74136(15) 1.24009(14) 0.0284(4) Uani 1 1 d . . . . .
H30A H 1.0965 0.7943 1.2744 0.043 Uiso 1 1 calc R U . . .
H30B H 1.2280 0.7525 1.2748 0.043 Uiso 1 1 calc R U . . .
H30C H 1.0969 0.6706 1.2529 0.043 Uiso 1 1 calc R U . . .
C31 C 1.12435(18) 0.86411(14) 1.09232(16) 0.0298(4) Uani 1 1 d . . . . .
H31A H 1.0908 0.8714 1.0105 0.045 Uiso 1 1 calc R U . . .
H31B H 1.2224 0.8787 1.1265 0.045 Uiso 1 1 calc R U . . .
H31C H 1.0884 0.9143 1.1274 0.045 Uiso 1 1 calc R U . . .
C32 C 1.14351(16) 0.67527(14) 1.06336(15) 0.0269(4) Uani 1 1 d . . . . .
H32A H 1.1100 0.6026 1.0701 0.040 Uiso 1 1 calc R U . . .
H32B H 1.2411 0.6883 1.1057 0.040 Uiso 1 1 calc R U . . .
H32C H 1.1204 0.6858 0.9831 0.040 Uiso 1 1 calc R U . . .
S1 S 0.25688(4) 0.54268(3) 0.74208(4) 0.02125(11) Uani 1 1 d . . . . .
O3 O 0.37556(11) 0.48901(9) 0.75117(9) 0.0236(3) Uani 1 1 d . . . . .
C33 C 0.11424(17) 0.46148(16) 0.64149(14) 0.0288(4) Uani 1 1 d . . . . .
H33A H 0.1141 0.4654 0.5657 0.043 Uiso 1 1 calc R U . . .
H33B H 0.0331 0.4857 0.6414 0.043 Uiso 1 1 calc R U . . .
H33C H 0.1164 0.3884 0.6615 0.043 Uiso 1 1 calc R U . . .
C34 C 0.23001(17) 0.51313(15) 0.86527(14) 0.0265(4) Uani 1 1 d . . . . .
H34A H 0.2233 0.4367 0.8710 0.040 Uiso 1 1 calc R U . . .
H34B H 0.1467 0.5373 0.8600 0.040 Uiso 1 1 calc R U . . .
H34C H 0.3052 0.5491 0.9329 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2165(17) . ?
O2 C3 1.2213(17) . ?
N1 C1 1.3358(18) . ?
N1 C5 1.4144(18) . ?
N1 H1 0.8800 . ?
N2 C4 1.3402(18) . ?
N2 C19 1.4128(18) . ?
N2 H2 0.8800 . ?
C1 C4 1.406(2) . ?
C1 C2 1.474(2) . ?
C2 C3 1.493(2) . ?
C3 C4 1.468(2) . ?
C5 C6 1.380(2) . ?
C5 C10 1.395(2) . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 C11 1.526(2) . ?
C8 C9 1.396(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 C15 1.530(2) . ?
C10 H10 0.9500 . ?
C11 C13 1.523(2) . ?
C11 C14 1.525(2) . ?
C11 C12 1.532(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C18 1.523(2) . ?
C15 C16 1.530(2) . ?
C15 C17 1.533(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.383(2) . ?
C19 C20 1.389(2) . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(2) . ?
C21 C25 1.531(2) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(2) . ?
C23 C29 1.528(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.521(2) . ?
C25 C27 1.526(2) . ?
C25 C28 1.531(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C32 1.525(2) . ?
C29 C31 1.528(2) . ?
C29 C30 1.533(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
S1 O3 1.5128(12) . ?
S1 C33 1.7664(18) . ?
S1 C34 1.7746(17) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C1 N1 C5 127.02(13) . . ?
C1 N1 H1 116.5 . . ?
C5 N1 H1 116.5 . . ?
C4 N2 C19 128.33(13) . . ?
C4 N2 H2 115.8 . . ?
C19 N2 H2 115.8 . . ?
N1 C1 C4 129.71(14) . . ?
N1 C1 C2 138.78(14) . . ?
C4 C1 C2 91.50(12) . . ?
O1 C2 C1 138.38(14) . . ?
O1 C2 C3 133.48(14) . . ?
C1 C2 C3 88.12(11) . . ?
O2 C3 C4 138.36(14) . . ?
O2 C3 C2 133.24(14) . . ?
C4 C3 C2 88.35(11) . . ?
N2 C4 C1 128.96(14) . . ?
N2 C4 C3 139.29(14) . . ?
C1 C4 C3 91.75(12) . . ?
C6 C5 C10 120.61(14) . . ?
C6 C5 N1 121.68(13) . . ?
C10 C5 N1 117.68(13) . . ?
C5 C6 C7 120.16(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 118.29(14) . . ?
C8 C7 C11 123.18(13) . . ?
C6 C7 C11 118.53(13) . . ?
C7 C8 C9 122.66(14) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C10 C9 C8 117.91(14) . . ?
C10 C9 C15 122.80(14) . . ?
C8 C9 C15 119.30(13) . . ?
C9 C10 C5 120.36(14) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C13 C11 C14 108.92(14) . . ?
C13 C11 C7 108.87(13) . . ?
C14 C11 C7 111.85(13) . . ?
C13 C11 C12 108.47(14) . . ?
C14 C11 C12 108.04(15) . . ?
C7 C11 C12 110.61(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C15 C9 112.30(13) . . ?
C18 C15 C16 108.63(14) . . ?
C9 C15 C16 108.90(13) . . ?
C18 C15 C17 108.41(14) . . ?
C9 C15 C17 109.79(13) . . ?
C16 C15 C17 108.74(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 120.66(14) . . ?
C24 C19 N2 122.39(13) . . ?
C20 C19 N2 116.90(13) . . ?
C21 C20 C19 120.63(14) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 117.76(14) . . ?
C20 C21 C25 122.84(14) . . ?
C22 C21 C25 119.38(13) . . ?
C23 C22 C21 122.64(14) . . ?
C23 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C22 C23 C24 118.23(14) . . ?
C22 C23 C29 119.80(13) . . ?
C24 C23 C29 121.97(13) . . ?
C19 C24 C23 120.02(14) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C27 108.41(15) . . ?
C26 C25 C28 108.54(15) . . ?
C27 C25 C28 109.88(14) . . ?
C26 C25 C21 112.28(13) . . ?
C27 C25 C21 109.91(13) . . ?
C28 C25 C21 107.80(13) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C29 C23 112.03(13) . . ?
C32 C29 C31 108.74(14) . . ?
C23 C29 C31 108.90(13) . . ?
C32 C29 C30 108.00(14) . . ?
C23 C29 C30 109.81(13) . . ?
C31 C29 C30 109.33(14) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O3 S1 C33 105.77(8) . . ?
O3 S1 C34 104.96(8) . . ?
C33 S1 C34 97.70(8) . . ?
S1 C33 H33A 109.5 . . ?
S1 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
S1 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
S1 C34 H34A 109.5 . . ?
S1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
S1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C5 N1 C1 C4 -165.23(15) . . . . ?
C5 N1 C1 C2 16.0(3) . . . . ?
N1 C1 C2 O1 4.6(4) . . . . ?
C4 C1 C2 O1 -174.5(2) . . . . ?
N1 C1 C2 C3 -176.99(19) . . . . ?
C4 C1 C2 C3 3.95(12) . . . . ?
O1 C2 C3 O2 -7.4(3) . . . . ?
C1 C2 C3 O2 174.06(18) . . . . ?
O1 C2 C3 C4 174.80(18) . . . . ?
C1 C2 C3 C4 -3.79(11) . . . . ?
C19 N2 C4 C1 179.70(15) . . . . ?
C19 N2 C4 C3 -0.6(3) . . . . ?
N1 C1 C4 N2 -3.4(3) . . . . ?
C2 C1 C4 N2 175.81(16) . . . . ?
N1 C1 C4 C3 176.79(16) . . . . ?
C2 C1 C4 C3 -4.02(12) . . . . ?
O2 C3 C4 N2 6.5(4) . . . . ?
C2 C3 C4 N2 -175.8(2) . . . . ?
O2 C3 C4 C1 -173.7(2) . . . . ?
C2 C3 C4 C1 3.97(12) . . . . ?
C1 N1 C5 C6 8.9(2) . . . . ?
C1 N1 C5 C10 -172.90(14) . . . . ?
C10 C5 C6 C7 1.2(2) . . . . ?
N1 C5 C6 C7 179.37(14) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C5 C6 C7 C11 178.48(14) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C11 C7 C8 C9 -179.54(14) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C8 C9 C15 -178.65(14) . . . . ?
C8 C9 C10 C5 -0.5(2) . . . . ?
C15 C9 C10 C5 179.08(14) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
N1 C5 C10 C9 -178.78(14) . . . . ?
C8 C7 C11 C13 118.76(16) . . . . ?
C6 C7 C11 C13 -60.47(19) . . . . ?
C8 C7 C11 C14 -1.7(2) . . . . ?
C6 C7 C11 C14 179.11(15) . . . . ?
C8 C7 C11 C12 -122.14(17) . . . . ?
C6 C7 C11 C12 58.63(19) . . . . ?
C10 C9 C15 C18 1.9(2) . . . . ?
C8 C9 C15 C18 -178.55(15) . . . . ?
C10 C9 C15 C16 -118.49(17) . . . . ?
C8 C9 C15 C16 61.09(19) . . . . ?
C10 C9 C15 C17 122.56(16) . . . . ?
C8 C9 C15 C17 -57.86(19) . . . . ?
C4 N2 C19 C24 -17.7(2) . . . . ?
C4 N2 C19 C20 164.58(15) . . . . ?
C24 C19 C20 C21 2.4(2) . . . . ?
N2 C19 C20 C21 -179.83(14) . . . . ?
C19 C20 C21 C22 -1.4(2) . . . . ?
C19 C20 C21 C25 177.17(14) . . . . ?
C20 C21 C22 C23 -0.7(2) . . . . ?
C25 C21 C22 C23 -179.28(14) . . . . ?
C21 C22 C23 C24 1.7(2) . . . . ?
C21 C22 C23 C29 -179.23(14) . . . . ?
C20 C19 C24 C23 -1.3(2) . . . . ?
N2 C19 C24 C23 -178.94(14) . . . . ?
C22 C23 C24 C19 -0.7(2) . . . . ?
C29 C23 C24 C19 -179.75(14) . . . . ?
C20 C21 C25 C26 4.9(2) . . . . ?
C22 C21 C25 C26 -176.53(15) . . . . ?
C20 C21 C25 C27 125.66(16) . . . . ?
C22 C21 C25 C27 -55.78(19) . . . . ?
C20 C21 C25 C28 -114.59(17) . . . . ?
C22 C21 C25 C28 63.96(19) . . . . ?
C22 C23 C29 C32 170.47(15) . . . . ?
C24 C23 C29 C32 -10.5(2) . . . . ?
C22 C23 C29 C31 -69.21(18) . . . . ?
C24 C23 C29 C31 109.81(16) . . . . ?
C22 C23 C29 C30 50.47(19) . . . . ?
C24 C23 C29 C30 -130.51(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.88 2.02 2.8598(16) 159.7 .
N2 H2 O3 0.88 1.93 2.7974(16) 169.2 .
C6 H6 O1 0.95 2.29 3.0953(18) 141.7 .

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 1005459'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kaj13pt12

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 S2, C2 H6 O S'
_chemical_formula_sum            'C18 H18 N2 O S3'
_chemical_formula_weight         374.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.04880(10)
_cell_length_b                   11.62330(10)
_cell_length_c                   19.21040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.8830(10)
_cell_angle_gamma                90
_cell_volume                     1796.99(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19292
_cell_measurement_theta_min      4.4250
_cell_measurement_theta_max      76.1820

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    3.826
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            40089
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.446
_diffrn_reflns_theta_max         76.402
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3762
_reflns_number_gt                3519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.39705(5) 0.34007(3) 0.16088(2) 0.03444(14) Uani 1 1 d . . . . .
S14 S 0.17065(4) 0.32295(3) -0.00331(2) 0.03055(14) Uani 1 1 d . . . . .
S23 S 0.38799(4) -0.30912(3) 0.09457(2) 0.02594(13) Uani 1 1 d . . . . .
O24 O 0.38573(14) -0.18229(7) 0.07626(5) 0.0303(2) Uani 1 1 d . . . . .
N5 N 0.27135(13) 0.00988(9) 0.00027(5) 0.0205(2) Uani 1 1 d . . . . .
H5N H 0.297(2) -0.0472(15) 0.0148(9) 0.027(4) Uiso 1 1 d . . . . .
N6 N 0.44963(13) 0.02369(9) 0.14454(5) 0.0212(2) Uani 1 1 d . . . . .
H6N H 0.432(2) -0.0361(15) 0.1303(9) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.27955(15) 0.22565(11) 0.03935(6) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.31114(14) 0.10211(10) 0.03782(6) 0.0196(2) Uani 1 1 d . . . . .
C3 C 0.39559(14) 0.10827(10) 0.10396(6) 0.0195(2) Uani 1 1 d . . . . .
C4 C 0.36967(15) 0.23233(11) 0.10661(6) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.17822(14) 0.00378(10) -0.06280(6) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.16936(17) 0.09477(11) -0.10975(6) 0.0258(3) Uani 1 1 d . . . . .
H8 H 0.2288 0.1640 -0.1008 0.031 Uiso 1 1 calc R U . . .
C9 C 0.07279(18) 0.08338(12) -0.16978(7) 0.0290(3) Uani 1 1 d . . . . .
H9 H 0.0635 0.1462 -0.2013 0.035 Uiso 1 1 calc R U . . .
C10 C -0.01038(16) -0.01836(12) -0.18440(6) 0.0268(3) Uani 1 1 d . . . . .
H10 H -0.0772 -0.0250 -0.2254 0.032 Uiso 1 1 calc R U . . .
C11 C 0.00460(16) -0.11061(12) -0.13873(7) 0.0261(3) Uani 1 1 d . . . . .
H11 H -0.0493 -0.1814 -0.1492 0.031 Uiso 1 1 calc R U . . .
C12 C 0.09825(16) -0.09956(11) -0.07777(6) 0.0229(3) Uani 1 1 d . . . . .
H12 H 0.1077 -0.1624 -0.0464 0.027 Uiso 1 1 calc R U . . .
C15 C 0.53392(15) 0.03026(10) 0.20986(6) 0.0210(3) Uani 1 1 d . . . . .
C16 C 0.52082(19) -0.06519(12) 0.25378(7) 0.0315(3) Uani 1 1 d . . . . .
H16 H 0.4523 -0.1285 0.2409 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6091(2) -0.06646(14) 0.31650(7) 0.0376(3) Uani 1 1 d . . . . .
H17 H 0.6015 -0.1313 0.3464 0.045 Uiso 1 1 calc R U . . .
C18 C 0.70807(19) 0.02606(13) 0.33580(7) 0.0330(3) Uani 1 1 d . . . . .
H18 H 0.7680 0.0248 0.3788 0.040 Uiso 1 1 calc R U . . .
C19 C 0.71915(16) 0.12040(12) 0.29204(7) 0.0281(3) Uani 1 1 d . . . . .
H19 H 0.7862 0.1841 0.3055 0.034 Uiso 1 1 calc R U . . .
C20 C 0.63319(15) 0.12293(11) 0.22852(6) 0.0240(3) Uani 1 1 d . . . . .
H20 H 0.6426 0.1874 0.1984 0.029 Uiso 1 1 calc R U . . .
C25 C 0.3313(2) -0.38248(13) 0.01680(8) 0.0373(3) Uani 1 1 d . . . . .
H25A H 0.3130 -0.4641 0.0270 0.056 Uiso 1 1 calc R U . . .
H25B H 0.4206 -0.3750 -0.0170 0.056 Uiso 1 1 calc R U . . .
H25C H 0.2289 -0.3489 -0.0026 0.056 Uiso 1 1 calc R U . . .
C26 C 0.2036(2) -0.33541(15) 0.14207(9) 0.0426(4) Uani 1 1 d . . . . .
H26A H 0.2086 -0.2931 0.1862 0.064 Uiso 1 1 calc R U . . .
H26B H 0.1937 -0.4180 0.1515 0.064 Uiso 1 1 calc R U . . .
H26C H 0.1069 -0.3096 0.1147 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C4 1.6422(13) . ?
S14 C1 1.6422(13) . ?
S23 O24 1.5157(9) . ?
S23 C25 1.7738(15) . ?
S23 C26 1.7809(16) . ?
N5 C2 1.3286(15) . ?
N5 C7 1.4166(14) . ?
N5 H5N 0.748(18) . ?
N6 C3 1.3240(16) . ?
N6 C15 1.4192(14) . ?
N6 H6N 0.759(18) . ?
C1 C2 1.4587(17) . ?
C1 C4 1.4740(16) . ?
C2 C3 1.4334(15) . ?
C3 C4 1.4580(17) . ?
C7 C12 1.3907(17) . ?
C7 C8 1.3911(17) . ?
C8 C9 1.3870(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3855(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3896(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3888(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C15 C20 1.3851(17) . ?
C15 C16 1.3988(18) . ?
C16 C17 1.3893(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3938(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
O24 S23 C25 105.67(7) . . ?
O24 S23 C26 106.18(7) . . ?
C25 S23 C26 98.24(8) . . ?
C2 N5 C7 128.66(11) . . ?
C2 N5 H5N 116.6(13) . . ?
C7 N5 H5N 114.6(13) . . ?
C3 N6 C15 128.97(11) . . ?
C3 N6 H6N 114.2(13) . . ?
C15 N6 H6N 116.8(13) . . ?
C2 C1 C4 89.19(9) . . ?
C2 C1 S14 139.45(10) . . ?
C4 C1 S14 130.75(10) . . ?
N5 C2 C3 128.95(11) . . ?
N5 C2 C1 139.87(11) . . ?
C3 C2 C1 90.77(9) . . ?
N6 C3 C2 129.19(11) . . ?
N6 C3 C4 139.43(11) . . ?
C2 C3 C4 90.81(9) . . ?
C3 C4 C1 89.20(9) . . ?
C3 C4 S13 139.33(9) . . ?
C1 C4 S13 131.00(10) . . ?
C12 C7 C8 120.24(11) . . ?
C12 C7 N5 117.20(11) . . ?
C8 C7 N5 122.52(11) . . ?
C9 C8 C7 119.27(12) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.85(12) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.58(11) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.11(12) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.85(12) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C20 C15 C16 120.61(11) . . ?
C20 C15 N6 122.45(11) . . ?
C16 C15 N6 116.83(11) . . ?
C17 C16 C15 119.30(13) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 120.53(13) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.61(12) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.82(13) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.13(12) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
S23 C25 H25A 109.5 . . ?
S23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
S23 C26 H26A 109.5 . . ?
S23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
S23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C7 N5 C2 C3 175.34(11) . . . . ?
C7 N5 C2 C1 5.0(2) . . . . ?
C4 C1 C2 N5 173.68(15) . . . . ?
S14 C1 C2 N5 2.7(3) . . . . ?
C4 C1 C2 C3 1.18(9) . . . . ?
S14 C1 C2 C3 -169.82(13) . . . . ?
C15 N6 C3 C2 179.67(11) . . . . ?
C15 N6 C3 C4 -11.7(2) . . . . ?
N5 C2 C3 N6 -2.4(2) . . . . ?
C1 C2 C3 N6 171.43(13) . . . . ?
N5 C2 C3 C4 -174.98(12) . . . . ?
C1 C2 C3 C4 -1.20(9) . . . . ?
N6 C3 C4 C1 -170.01(15) . . . . ?
C2 C3 C4 C1 1.19(9) . . . . ?
N6 C3 C4 S13 2.1(3) . . . . ?
C2 C3 C4 S13 173.34(13) . . . . ?
C2 C1 C4 C3 -1.16(9) . . . . ?
S14 C1 C4 C3 171.12(11) . . . . ?
C2 C1 C4 S13 -174.39(11) . . . . ?
S14 C1 C4 S13 -2.11(19) . . . . ?
C2 N5 C7 C12 -155.22(12) . . . . ?
C2 N5 C7 C8 26.79(19) . . . . ?
C12 C7 C8 C9 3.42(18) . . . . ?
N5 C7 C8 C9 -178.64(12) . . . . ?
C7 C8 C9 C10 -2.0(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 1.98(19) . . . . ?
C10 C11 C12 C7 -0.54(19) . . . . ?
C8 C7 C12 C11 -2.18(18) . . . . ?
N5 C7 C12 C11 179.78(11) . . . . ?
C3 N6 C15 C20 -27.94(19) . . . . ?
C3 N6 C15 C16 155.87(13) . . . . ?
C20 C15 C16 C17 -0.2(2) . . . . ?
N6 C15 C16 C17 176.05(13) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C16 C15 C20 C19 -0.51(18) . . . . ?
N6 C15 C20 C19 -176.56(11) . . . . ?
C18 C19 C20 C15 0.93(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5N O24 0.748(18) 2.083(19) 2.8153(15) 166.2(18) .
C25 H25A S14 0.98 2.79 3.6781(15) 151.7 1_545
N6 H6N O24 0.759(18) 2.023(18) 2.7743(14) 170.3(17) .
C8 H8 S14 0.95 2.68 3.3489(13) 128.2 .
C20 H20 S13 0.95 2.74 3.4051(13) 127.3 .

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 1005460'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_s1361

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H44 N2 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C36 H56 N2 O2 S4'
_chemical_formula_weight         677.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic

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

_cell_length_a                   18.2073(6)
_cell_length_b                   11.9379(2)
_cell_length_c                   19.5492(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.355(4)
_cell_angle_gamma                90.00
_cell_volume                     3839.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12339
_cell_measurement_theta_min      4.4260
_cell_measurement_theta_max      76.0020

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_min  0.62272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60156
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         76.47
_reflns_number_total             8007
_reflns_number_gt                6044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0842P)²+11.9295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8007
_refine_ls_number_parameters     391
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.2305
_refine_ls_wR_factor_gt          0.2098
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.005
_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
C18A C 0.9150(8) 0.8378(11) 0.5515(8) 0.0581(12) Uiso 0.488(7) 1 d P A 1
H18A H 0.9510 0.7979 0.5959 0.087 Uiso 0.488(7) 1 calc PR A 1
H18B H 0.8902 0.8987 0.5660 0.087 Uiso 0.488(7) 1 calc PR A 1
H18C H 0.9453 0.8668 0.5255 0.087 Uiso 0.488(7) 1 calc PR A 1
C19A C 0.8979(8) 0.6697(10) 0.4716(7) 0.0581(12) Uiso 0.488(7) 1 d P A 1
H19A H 0.8589 0.6179 0.4378 0.087 Uiso 0.488(7) 1 calc PR A 1
H19B H 0.9371 0.6296 0.5142 0.087 Uiso 0.488(7) 1 calc PR A 1
H19C H 0.9250 0.7074 0.4456 0.087 Uiso 0.488(7) 1 calc PR A 1
C20A C 0.7924(7) 0.8149(10) 0.4289(7) 0.0581(12) Uiso 0.488(7) 1 d P A 1
H20A H 0.7530 0.7604 0.3988 0.087 Uiso 0.488(7) 1 calc PR A 1
H20B H 0.8211 0.8428 0.4011 0.087 Uiso 0.488(7) 1 calc PR A 1
H20C H 0.7652 0.8758 0.4406 0.087 Uiso 0.488(7) 1 calc PR A 1
C18B C 0.9372(8) 0.8019(11) 0.5556(7) 0.0581(12) Uiso 0.512(7) 1 d P A 2
H18D H 0.9343 0.8415 0.5971 0.087 Uiso 0.512(7) 1 calc PR A 2
H18E H 0.9579 0.8509 0.5291 0.087 Uiso 0.512(7) 1 calc PR A 2
H18F H 0.9727 0.7385 0.5745 0.087 Uiso 0.512(7) 1 calc PR A 2
C19B C 0.8488(7) 0.7000(10) 0.4367(7) 0.0581(12) Uiso 0.512(7) 1 d P A 2
H19D H 0.8743 0.7431 0.4114 0.087 Uiso 0.512(7) 1 calc PR A 2
H19E H 0.7932 0.6857 0.4024 0.087 Uiso 0.512(7) 1 calc PR A 2
H19F H 0.8770 0.6301 0.4533 0.087 Uiso 0.512(7) 1 calc PR A 2
C20B C 0.8022(7) 0.8744(10) 0.4703(7) 0.0581(12) Uiso 0.512(7) 1 d P A 2
H20D H 0.8033 0.9178 0.5121 0.087 Uiso 0.512(7) 1 calc PR A 2
H20E H 0.7470 0.8571 0.4367 0.087 Uiso 0.512(7) 1 calc PR A 2
H20F H 0.8266 0.9167 0.4437 0.087 Uiso 0.512(7) 1 calc PR A 2
C32A C 0.1651(10) 0.6083(13) 0.5071(10) 0.0423(9) Uiso 0.50(4) 1 d P B 1
H32A H 0.1381 0.6010 0.5397 0.063 Uiso 0.50(4) 1 calc PR B 1
H32B H 0.2159 0.5689 0.5288 0.063 Uiso 0.50(4) 1 calc PR B 1
H32C H 0.1314 0.5773 0.4584 0.063 Uiso 0.50(4) 1 calc PR B 1
C30A C 0.1019(8) 0.7999(18) 0.4726(9) 0.0423(9) Uiso 0.50(4) 1 d P B 1
H30A H 0.1141 0.8769 0.4679 0.063 Uiso 0.50(4) 1 calc PR B 1
H30B H 0.0800 0.7937 0.5093 0.063 Uiso 0.50(4) 1 calc PR B 1
H30C H 0.0628 0.7728 0.4246 0.063 Uiso 0.50(4) 1 calc PR B 1
C31A C 0.2389(9) 0.7773(13) 0.5794(9) 0.0423(9) Uiso 0.50(4) 1 d P B 1
H31A H 0.2483 0.8556 0.5751 0.063 Uiso 0.50(4) 1 calc PR B 1
H31B H 0.2897 0.7378 0.5983 0.063 Uiso 0.50(4) 1 calc PR B 1
H31C H 0.2142 0.7675 0.6136 0.063 Uiso 0.50(4) 1 calc PR B 1
C32B C 0.1784(10) 0.6017(13) 0.5170(10) 0.0423(9) Uiso 0.50(4) 1 d PD B 2
H32D H 0.1511 0.5921 0.5490 0.063 Uiso 0.50(4) 1 calc PR B 2
H32E H 0.2331 0.5740 0.5424 0.063 Uiso 0.50(4) 1 calc PR B 2
H32F H 0.1500 0.5610 0.4707 0.063 Uiso 0.50(4) 1 calc PR B 2
C30B C 0.0921(8) 0.7684(18) 0.4611(9) 0.0423(9) Uiso 0.50(4) 1 d PD B 2
H30D H 0.0897 0.8430 0.4419 0.063 Uiso 0.50(4) 1 calc PR B 2
H30E H 0.0698 0.7680 0.4976 0.063 Uiso 0.50(4) 1 calc PR B 2
H30F H 0.0612 0.7188 0.4202 0.063 Uiso 0.50(4) 1 calc PR B 2
C31B C 0.2260(10) 0.7939(13) 0.5713(9) 0.0423(9) Uiso 0.50(4) 1 d PD B 2
H31D H 0.2257 0.8722 0.5601 0.063 Uiso 0.50(4) 1 calc PR B 2
H31E H 0.2811 0.7677 0.5954 0.063 Uiso 0.50(4) 1 calc PR B 2
H31F H 0.2003 0.7827 0.6046 0.063 Uiso 0.50(4) 1 calc PR B 2
S1 S 0.61173(6) 0.55337(9) 0.33755(6) 0.0369(3) Uani 1 1 d . . .
S2 S 0.57905(7) 0.58786(9) 0.94708(6) 0.0376(3) Uani 1 1 d . . .
S3 S 0.39037(7) 0.63594(10) 0.24957(6) 0.0403(3) Uani 1 1 d . . .
S4 S 0.53533(7) 0.76711(9) 0.15935(6) 0.0358(3) Uani 1 1 d . . .
O3 O 0.51882(18) 0.8614(2) 0.10209(16) 0.0358(6) Uani 1 1 d . . .
N1 N 0.60488(19) 0.6063(3) 0.51717(19) 0.0276(7) Uani 1 1 d D . .
N2 N 0.41957(19) 0.6626(3) 0.44859(19) 0.0282(7) Uani 1 1 d D . .
C2 C 0.5510(2) 0.6158(3) 0.4454(2) 0.0263(7) Uani 1 1 d . . .
O1 O 0.5632(2) 0.6333(3) 1.0108(2) 0.0480(8) Uani 1 1 d . . .
C3 C 0.4663(2) 0.6425(3) 0.4135(2) 0.0279(8) Uani 1 1 d . . .
C11 C 0.3401(2) 0.7093(3) 0.4212(2) 0.0268(8) Uani 1 1 d . . .
C16 C 0.2985(2) 0.6930(3) 0.4662(2) 0.0282(8) Uani 1 1 d . . .
H16 H 0.3208 0.6477 0.5089 0.034 Uiso 1 1 calc R . .
C12 C 0.3078(2) 0.7768(3) 0.3566(2) 0.0275(8) Uani 1 1 d . . .
H12 H 0.3355 0.7856 0.3266 0.033 Uiso 1 1 calc R . .
C4 C 0.4615(2) 0.6289(3) 0.3376(2) 0.0283(8) Uani 1 1 d . . .
C14 C 0.1927(2) 0.8127(3) 0.3830(2) 0.0304(8) Uani 1 1 d . . .
H14 H 0.1429 0.8477 0.3699 0.036 Uiso 1 1 calc R . .
C10 C 0.7365(2) 0.5696(3) 0.6176(2) 0.0296(8) Uani 1 1 d . . .
H10 H 0.7112 0.5284 0.6418 0.036 Uiso 1 1 calc R . .
C25 C 0.1975(2) 0.9102(3) 0.2694(2) 0.0308(8) Uani 1 1 d . . .
C28 C 0.2565(3) 0.9328(4) 0.2346(3) 0.0378(9) Uani 1 1 d . . .
H28A H 0.3052 0.9659 0.2719 0.057 Uiso 1 1 calc R . .
H28B H 0.2319 0.9831 0.1926 0.057 Uiso 1 1 calc R . .
H28C H 0.2696 0.8636 0.2174 0.057 Uiso 1 1 calc R . .
C6 C 0.7271(2) 0.6781(3) 0.5098(2) 0.0319(8) Uani 1 1 d . . .
H6 H 0.6954 0.7096 0.4627 0.038 Uiso 1 1 calc R . .
C1 C 0.5484(2) 0.5989(3) 0.3714(2) 0.0295(8) Uani 1 1 d . . .
C5 C 0.6909(2) 0.6157(3) 0.5466(2) 0.0284(8) Uani 1 1 d . . .
C13 C 0.2340(2) 0.8305(3) 0.3375(2) 0.0285(8) Uani 1 1 d . . .
C29 C 0.1804(2) 0.7294(4) 0.4987(2) 0.0346(9) Uani 1 1 d . . .
C26 C 0.1196(3) 0.8577(4) 0.2091(3) 0.0421(10) Uani 1 1 d . . .
H26A H 0.0821 0.8432 0.2307 0.063 Uiso 1 1 calc R . .
H26B H 0.1328 0.7887 0.1917 0.063 Uiso 1 1 calc R . .
H26C H 0.0953 0.9085 0.1673 0.063 Uiso 1 1 calc R . .
C15 C 0.2237(2) 0.7448(3) 0.4467(2) 0.0299(8) Uani 1 1 d . B .
C9 C 0.8205(2) 0.5853(3) 0.6524(2) 0.0335(9) Uani 1 1 d . . .
C7 C 0.8108(2) 0.6939(4) 0.5431(2) 0.0350(9) Uani 1 1 d . A .
C34 C 0.6161(3) 0.4483(4) 0.9735(3) 0.0496(12) Uani 1 1 d . . .
H34A H 0.6696 0.4509 1.0143 0.074 Uiso 1 1 calc R . .
H34B H 0.6183 0.4109 0.9309 0.074 Uiso 1 1 calc R . .
H34C H 0.5804 0.4082 0.9893 0.074 Uiso 1 1 calc R . .
C22 C 0.8239(3) 0.4787(5) 0.7665(3) 0.0476(12) Uani 1 1 d . . .
H22A H 0.7926 0.4193 0.7340 0.071 Uiso 1 1 calc R . .
H22B H 0.7880 0.5320 0.7731 0.071 Uiso 1 1 calc R . .
H22C H 0.8598 0.4483 0.8148 0.071 Uiso 1 1 calc R . .
C21 C 0.8741(3) 0.5371(4) 0.7306(2) 0.0388(10) Uani 1 1 d . . .
C27 C 0.1771(3) 1.0232(4) 0.2947(3) 0.0459(11) Uani 1 1 d . . .
H27A H 0.1397 1.0115 0.3168 0.069 Uiso 1 1 calc R . .
H27B H 0.1529 1.0719 0.2517 0.069 Uiso 1 1 calc R . .
H27C H 0.2260 1.0567 0.3315 0.069 Uiso 1 1 calc R . .
C8 C 0.8560(2) 0.6472(4) 0.6134(2) 0.0356(9) Uani 1 1 d . . .
H8 H 0.9120 0.6572 0.6357 0.043 Uiso 1 1 calc R . .
C37 C 0.4832(3) 0.5482(4) 0.8740(3) 0.0423(10) Uani 1 1 d . . .
H37A H 0.4524 0.6142 0.8511 0.063 Uiso 1 1 calc R . .
H37B H 0.4541 0.5039 0.8952 0.063 Uiso 1 1 calc R . .
H37C H 0.4916 0.5052 0.8365 0.063 Uiso 1 1 calc R . .
C23 C 0.9229(3) 0.6321(5) 0.7842(3) 0.0548(14) Uani 1 1 d . . .
H23A H 0.9547 0.6702 0.7629 0.082 Uiso 1 1 calc R . .
H23B H 0.9584 0.6011 0.8325 0.082 Uiso 1 1 calc R . .
H23C H 0.8862 0.6841 0.7906 0.082 Uiso 1 1 calc R . .
C24 C 0.9331(3) 0.4510(5) 0.7237(3) 0.0531(13) Uani 1 1 d . . .
H24A H 0.9652 0.4859 0.7016 0.080 Uiso 1 1 calc R . .
H24B H 0.9028 0.3901 0.6922 0.080 Uiso 1 1 calc R . .
H24C H 0.9681 0.4230 0.7731 0.080 Uiso 1 1 calc R . .
C36 C 0.6380(3) 0.7266(4) 0.1858(3) 0.0472(11) Uani 1 1 d . . .
H36A H 0.6417 0.6867 0.1448 0.071 Uiso 1 1 calc R . .
H36B H 0.6559 0.6790 0.2296 0.071 Uiso 1 1 calc R . .
H36C H 0.6717 0.7921 0.1974 0.071 Uiso 1 1 calc R . .
C33 C 0.5486(4) 0.8355(4) 0.2439(3) 0.0511(13) Uani 1 1 d . . .
H33A H 0.4972 0.8637 0.2391 0.077 Uiso 1 1 calc R . .
H33B H 0.5859 0.8967 0.2534 0.077 Uiso 1 1 calc R . .
H33C H 0.5698 0.7835 0.2853 0.077 Uiso 1 1 calc R . .
C17 C 0.8516(3) 0.7614(4) 0.5011(3) 0.0451(11) Uani 1 1 d . . .
H102 H 0.444(3) 0.657(4) 0.5010(11) 0.034(12) Uiso 1 1 d D . .
H101 H 0.588(3) 0.619(4) 0.554(2) 0.042(14) Uiso 1 1 d 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
C18A C17 1.471(14) . ?
C19A C17 1.631(13) . ?
C20A C17 1.503(13) . ?
C18B C17 1.542(13) . ?
C19B C17 1.440(12) . ?
C20B C17 1.590(12) . ?
C32A C29 1.494(16) . ?
C30A C29 1.544(12) . ?
C31A C29 1.585(15) . ?
C32B C29 1.570(16) . ?
C30B C29 1.526(11) . ?
C31B C29 1.513(15) . ?
S1 C1 1.649(4) . ?
S2 O1 1.495(4) . ?
S2 C37 1.781(5) . ?
S2 C34 1.789(5) . ?
S3 C4 1.655(4) . ?
S4 O3 1.524(3) . ?
S4 C33 1.766(5) . ?
S4 C36 1.780(5) . ?
N1 C2 1.328(5) . ?
N1 C5 1.423(5) . ?
N2 C3 1.323(5) . ?
N2 C11 1.424(5) . ?
C2 C3 1.430(5) . ?
C2 C1 1.441(5) . ?
C3 C4 1.458(6) . ?
C11 C16 1.397(5) . ?
C11 C12 1.397(5) . ?
C16 C15 1.392(5) . ?
C12 C13 1.388(5) . ?
C4 C1 1.473(5) . ?
C14 C15 1.388(6) . ?
C14 C13 1.404(5) . ?
C10 C5 1.390(6) . ?
C10 C9 1.395(6) . ?
C25 C28 1.521(6) . ?
C25 C27 1.536(6) . ?
C25 C26 1.536(6) . ?
C25 C13 1.537(5) . ?
C6 C5 1.384(6) . ?
C6 C7 1.390(6) . ?
C29 C15 1.542(5) . ?
C9 C8 1.401(6) . ?
C9 C21 1.532(6) . ?
C7 C8 1.382(6) . ?
C7 C17 1.548(6) . ?
C22 C21 1.537(6) . ?
C21 C24 1.532(7) . ?
C21 C23 1.541(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S2 C37 107.0(2) . . ?
O1 S2 C34 106.3(2) . . ?
C37 S2 C34 95.9(2) . . ?
O3 S4 C33 104.5(2) . . ?
O3 S4 C36 105.5(2) . . ?
C33 S4 C36 98.5(3) . . ?
C2 N1 C5 127.4(3) . . ?
C3 N2 C11 130.7(3) . . ?
N1 C2 C3 130.6(4) . . ?
N1 C2 C1 137.8(4) . . ?
C3 C2 C1 91.6(3) . . ?
N2 C3 C2 128.9(4) . . ?
N2 C3 C4 140.9(4) . . ?
C2 C3 C4 90.2(3) . . ?
C16 C11 C12 121.1(3) . . ?
C16 C11 N2 116.5(3) . . ?
C12 C11 N2 122.1(3) . . ?
C15 C16 C11 119.7(4) . . ?
C13 C12 C11 119.6(4) . . ?
C3 C4 C1 89.2(3) . . ?
C3 C4 S3 137.1(3) . . ?
C1 C4 S3 133.7(3) . . ?
C15 C14 C13 122.3(4) . . ?
C5 C10 C9 119.7(4) . . ?
C28 C25 C27 107.6(4) . . ?
C28 C25 C26 109.0(3) . . ?
C27 C25 C26 109.5(4) . . ?
C28 C25 C13 111.7(3) . . ?
C27 C25 C13 109.8(3) . . ?
C26 C25 C13 109.1(3) . . ?
C5 C6 C7 120.0(4) . . ?
C2 C1 C4 89.1(3) . . ?
C2 C1 S1 136.1(3) . . ?
C4 C1 S1 134.6(3) . . ?
C6 C5 C10 121.3(4) . . ?
C6 C5 N1 121.3(4) . . ?
C10 C5 N1 117.1(3) . . ?
C12 C13 C14 118.6(4) . . ?
C12 C13 C25 122.0(3) . . ?
C14 C13 C25 119.5(3) . . ?
C31B C29 C30B 109.8(7) . . ?
C31B C29 C32A 116.2(9) . . ?
C30B C29 C32A 98.1(8) . . ?
C31B C29 C32B 109.7(8) . . ?
C30B C29 C32B 106.5(7) . . ?
C32A C29 C32B 8.9(9) . . ?
C31B C29 C15 109.1(6) . . ?
C30B C29 C15 112.2(5) . . ?
C32A C29 C15 111.1(7) . . ?
C32B C29 C15 109.5(7) . . ?
C31B C29 C30A 95.2(7) . . ?
C30B C29 C30A 16.3(5) . . ?
C32A C29 C30A 112.0(7) . . ?
C32B C29 C30A 119.8(8) . . ?
C15 C29 C30A 112.4(5) . . ?
C31B C29 C31A 10.6(7) . . ?
C30B C29 C31A 119.4(7) . . ?
C32A C29 C31A 108.4(8) . . ?
C32B C29 C31A 101.2(8) . . ?
C15 C29 C31A 107.3(6) . . ?
C30A C29 C31A 105.3(7) . . ?
C14 C15 C16 118.6(4) . . ?
C14 C15 C29 122.3(3) . . ?
C16 C15 C29 119.0(4) . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 C21 122.2(4) . . ?
C8 C9 C21 119.8(4) . . ?
C8 C7 C6 118.5(4) . . ?
C8 C7 C17 121.4(4) . . ?
C6 C7 C17 120.1(4) . . ?
C9 C21 C24 109.6(4) . . ?
C9 C21 C22 112.1(4) . . ?
C24 C21 C22 108.2(4) . . ?
C9 C21 C23 109.7(4) . . ?
C24 C21 C23 109.4(4) . . ?
C22 C21 C23 107.8(4) . . ?
C7 C8 C9 122.5(4) . . ?
C19B C17 C18A 128.7(8) . . ?
C19B C17 C20A 69.7(7) . . ?
C18A C17 C20A 114.0(8) . . ?
C19B C17 C18B 114.3(7) . . ?
C18A C17 C18B 21.7(6) . . ?
C20A C17 C18B 128.4(8) . . ?
C19B C17 C7 110.7(6) . . ?
C18A C17 C7 112.7(6) . . ?
C20A C17 C7 113.9(6) . . ?
C18B C17 C7 111.7(6) . . ?
C19B C17 C20B 107.4(7) . . ?
C18A C17 C20B 83.2(7) . . ?
C20A C17 C20B 38.9(6) . . ?
C18B C17 C20B 103.6(7) . . ?
C7 C17 C20B 108.7(5) . . ?
C19B C17 C19A 34.8(6) . . ?
C18A C17 C19A 106.0(8) . . ?
C20A C17 C19A 103.0(7) . . ?
C18B C17 C19A 86.1(7) . . ?
C7 C17 C19A 106.0(6) . . ?
C20B C17 C19A 136.9(7) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        76.47
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 1005461'
