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

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#                                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.
#
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#  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_cutacyc



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C36 H40 Cu N6 O2 S2'

_chemical_formula_weight         716.40



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source












C C 0.0181 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'
Cu Cu -1.9646 0.5888 '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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   C2/c



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   32.090(2)

_cell_length_b                   6.3662(4)

_cell_length_c                   18.8845(13)

_cell_angle_alpha                90.00

_cell_angle_beta                 118.786(4)

_cell_angle_gamma                90.00

_cell_volume                     3381.2(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    8245

_cell_measurement_theta_min      3.14

_cell_measurement_theta_max      62.74



_exptl_crystal_description       block

_exptl_crystal_colour            blue

_exptl_crystal_size_max          0.12

_exptl_crystal_size_mid          0.07

_exptl_crystal_size_min          0.05

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.407

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1500

_exptl_absorpt_coefficient_mu    2.404

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.7613

_exptl_absorpt_correction_T_max  0.8893

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(2)

_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            25427

_diffrn_reflns_av_R_equivalents  0.0741

_diffrn_reflns_av_sigmaI/netI    0.0341

_diffrn_reflns_limit_h_min       -36

_diffrn_reflns_limit_h_max       36

_diffrn_reflns_limit_k_min       -6

_diffrn_reflns_limit_k_max       6

_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_limit_l_max       20

_diffrn_reflns_theta_min         5.35

_diffrn_reflns_theta_max         60.00

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             2425

_reflns_number_gt                2070

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        'Bruker APEX2'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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. 

  

Elongated thermal ellipsoids of C6 and S1 indicated a possible disorder of 

C3-S1-C4-C5-C6 ring and was modeled successfully between two position. 

Constraints and Restraints were used to keept he bond distances, angles, 

and thermal ellipsoids, meaningful (SAME, EADP, and EXYZ). 

;



_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)+(0.0528P)²+1.0647P] 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         2425

_refine_ls_number_parameters     227

_refine_ls_number_restraints     10

_refine_ls_R_factor_all          0.0390

_refine_ls_R_factor_gt           0.0336

_refine_ls_wR_factor_ref         0.0887

_refine_ls_wR_factor_gt          0.0869

_refine_ls_goodness_of_fit_ref   1.089

_refine_ls_restrained_S_all      1.090

_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




















































Cu1 Cu 0.2500 0.7500 0.0000 0.01406(17) Uani 1 2 d S . .
O1 O 0.25190(5) 0.9875(2) 0.06303(9) 0.0198(4) Uani 1 1 d . A .
N1 N 0.33059(6) 0.9641(3) 0.16800(10) 0.0145(4) Uani 1 1 d . A .
N2 N 0.39007(6) 0.7424(3) 0.18587(11) 0.0180(5) Uani 1 1 d . . .
H2 H 0.4030 0.6564 0.1655 0.022 Uiso 1 1 calc R . .
N3 N 0.31959(6) 0.7221(3) 0.06332(11) 0.0141(4) Uani 1 1 d . . .
C1 C 0.34469(8) 0.8052(3) 0.13656(13) 0.0135(5) Uani 1 1 d . . .
C2 C 0.28779(7) 1.0489(3) 0.12773(12) 0.0144(5) Uani 1 1 d . . .
C3 C 0.28154(8) 1.2451(3) 0.16280(13) 0.0154(5) Uani 0.918(3) 1 d PD A 1
S1 S 0.32659(2) 1.33988(11) 0.25201(4) 0.0185(3) Uani 0.918(3) 1 d PD A 1
C4 C 0.29406(12) 1.5596(4) 0.24674(17) 0.0204(8) Uani 0.918(3) 1 d PD A 1
H4 H 0.3051 1.6683 0.2861 0.025 Uiso 0.918(3) 1 calc PR A 1
C5 C 0.25058(16) 1.5590(7) 0.1793(3) 0.0228(7) Uani 0.918(3) 1 d PD A 1
H5 H 0.2275 1.6669 0.1661 0.027 Uiso 0.918(3) 1 calc PR A 1
C6 C 0.24390(15) 1.3789(7) 0.1315(3) 0.0212(8) Uani 0.918(3) 1 d PD A 1
H6 H 0.2157 1.3536 0.0820 0.025 Uiso 0.918(3) 1 calc PR A 1
C3A C 0.28154(8) 1.2451(3) 0.16280(13) 0.0154(5) Uani 0.082(3) 1 d PD A 2
S1A S 0.2323(4) 1.399(2) 0.1155(8) 0.0185(3) Uani 0.082(3) 1 d PD A 2
C4A C 0.259(2) 1.576(8) 0.194(3) 0.0204(8) Uani 0.082(3) 1 d PD A 2
H4A H 0.2461 1.7096 0.1942 0.025 Uiso 0.082(3) 1 calc PR A 2
C5A C 0.3008(15) 1.503(6) 0.255(2) 0.0228(7) Uani 0.082(3) 1 d PD A 2
H5A H 0.3194 1.5787 0.3040 0.027 Uiso 0.082(3) 1 calc PR A 2
C6A C 0.3133(11) 1.303(5) 0.2392(12) 0.0212(8) Uani 0.082(3) 1 d PD A 2
H6A H 0.3399 1.2226 0.2759 0.025 Uiso 0.082(3) 1 calc PR A 2
C7 C 0.41924(8) 0.8062(4) 0.27018(13) 0.0166(5) Uani 1 1 d . . .
H7 H 0.3979 0.8272 0.2945 0.020 Uiso 1 1 calc R . .
C8 C 0.45347(8) 0.6276(4) 0.31471(14) 0.0230(6) Uani 1 1 d . . .
H8A H 0.4724 0.5949 0.2874 0.028 Uiso 1 1 calc R . .
H8B H 0.4351 0.5006 0.3124 0.028 Uiso 1 1 calc R . .
C9 C 0.48695(8) 0.6830(4) 0.40265(14) 0.0232(6) Uani 1 1 d . . .
H9A H 0.4684 0.6976 0.4318 0.028 Uiso 1 1 calc R . .
H9B H 0.5101 0.5675 0.4283 0.028 Uiso 1 1 calc R . .
C10 C 0.51341(9) 0.8849(4) 0.41000(14) 0.0283(6) Uani 1 1 d . . .
H10A H 0.5352 0.8643 0.3872 0.034 Uiso 1 1 calc R . .
H10B H 0.5329 0.9215 0.4678 0.034 Uiso 1 1 calc R . .
C11 C 0.47939(9) 1.0652(4) 0.36589(15) 0.0349(7) Uani 1 1 d . . .
H11A H 0.4606 1.0985 0.3934 0.042 Uiso 1 1 calc R . .
H11B H 0.4980 1.1916 0.3682 0.042 Uiso 1 1 calc R . .
C12 C 0.44569(8) 1.0102(4) 0.27786(14) 0.0242(6) Uani 1 1 d . . .
H12A H 0.4224 1.1254 0.2526 0.029 Uiso 1 1 calc R . .
H12B H 0.4641 0.9969 0.2484 0.029 Uiso 1 1 calc R . .
C13 C 0.34433(7) 0.5766(4) 0.03828(12) 0.0139(5) Uani 1 1 d . . .
C14 C 0.35880(8) 0.6403(4) -0.01679(13) 0.0178(5) Uani 1 1 d . . .
H14 H 0.3521 0.7789 -0.0381 0.021 Uiso 1 1 calc R . .
C15 C 0.38294(8) 0.5021(4) -0.04076(14) 0.0224(6) Uani 1 1 d . . .
H15 H 0.3926 0.5462 -0.0787 0.027 Uiso 1 1 calc R . .
C16 C 0.39313(8) 0.3000(4) -0.00988(14) 0.0216(6) Uani 1 1 d . . .
H16 H 0.4099 0.2061 -0.0263 0.026 Uiso 1 1 calc R . .
C17 C 0.37876(8) 0.2358(4) 0.04501(14) 0.0209(6) Uani 1 1 d . . .
H17 H 0.3857 0.0974 0.0664 0.025 Uiso 1 1 calc R . .
C18 C 0.35432(8) 0.3729(4) 0.06892(13) 0.0174(5) Uani 1 1 d . . .
H18 H 0.3443 0.3278 0.1063 0.021 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























































Cu1 O1 1.9069(15) . ?
Cu1 O1 1.9070(15) 7_565 ?
Cu1 N3 1.9688(18) 7_565 ?
Cu1 N3 1.9688(18) . ?
O1 C2 1.272(2) . ?
N1 C2 1.323(3) . ?
N1 C1 1.356(3) . ?
N2 C1 1.357(3) . ?
N2 C7 1.463(3) . ?
N2 H2 0.8800 . ?
N3 C1 1.330(3) . ?
N3 C13 1.440(3) . ?
C2 C3 1.472(3) . ?
C3 C6 1.359(4) . ?
C3 S1 1.717(2) . ?
S1 C4 1.719(3) . ?
C4 C5 1.363(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
S1A C4A 1.721(6) . ?
C4A C5A 1.363(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.411(7) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7 C12 1.520(3) . ?
C7 C8 1.522(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.510(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.388(3) . ?
C13 C18 1.393(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?



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 Cu1 O1 180.0 . 7_565 ?
O1 Cu1 N3 89.63(7) . 7_565 ?
O1 Cu1 N3 90.37(7) 7_565 7_565 ?
O1 Cu1 N3 90.37(7) . . ?
O1 Cu1 N3 89.63(7) 7_565 . ?
N3 Cu1 N3 180.0 7_565 . ?
C2 O1 Cu1 125.84(14) . . ?
C2 N1 C1 121.71(18) . . ?
C1 N2 C7 125.29(18) . . ?
C1 N2 H2 117.4 . . ?
C7 N2 H2 117.4 . . ?
C1 N3 C13 116.35(18) . . ?
C1 N3 Cu1 122.51(15) . . ?
C13 N3 Cu1 120.14(13) . . ?
N3 C1 N1 126.1(2) . . ?
N3 C1 N2 120.6(2) . . ?
N1 C1 N2 113.16(19) . . ?
O1 C2 N1 129.5(2) . . ?
O1 C2 C3 115.89(19) . . ?
N1 C2 C3 114.61(18) . . ?
C6 C3 C2 128.4(2) . . ?
C6 C3 S1 111.0(2) . . ?
C2 C3 S1 120.47(16) . . ?
C3 S1 C4 91.63(12) . . ?
C5 C4 S1 111.8(2) . . ?
C5 C4 H4 124.1 . . ?
S1 C4 H4 124.1 . . ?
C4 C5 C6 111.8(3) . . ?
C4 C5 H5 124.1 . . ?
C6 C5 H5 124.1 . . ?
C3 C6 C5 113.7(3) . . ?
C3 C6 H6 123.1 . . ?
C5 C6 H6 123.1 . . ?
C5A C4A S1A 113.0(17) . . ?
C5A C4A H4A 123.5 . . ?
S1A C4A H4A 123.5 . . ?
C4A C5A C6A 112.7(19) . . ?
C4A C5A H5A 123.7 . . ?
C6A C5A H5A 123.7 . . ?
C5A C6A H6A 125.3 . . ?
N2 C7 C12 112.10(18) . . ?
N2 C7 C8 107.88(18) . . ?
C12 C7 C8 111.37(19) . . ?
N2 C7 H7 108.5 . . ?
C12 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C7 C8 C9 111.8(2) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 111.58(19) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.6(2) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 111.6(2) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C7 C12 C11 111.7(2) . . ?
C7 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C7 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C18 119.3(2) . . ?
C14 C13 N3 119.6(2) . . ?
C18 C13 N3 121.01(19) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?



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























































O1 Cu1 O1 C2 -95(6) 7_565 . . . ?
N3 Cu1 O1 C2 169.54(18) 7_565 . . . ?
N3 Cu1 O1 C2 -10.46(18) . . . . ?
O1 Cu1 N3 C1 20.59(18) . . . . ?
O1 Cu1 N3 C1 -159.41(18) 7_565 . . . ?
N3 Cu1 N3 C1 151.4(11) 7_565 . . . ?
O1 Cu1 N3 C13 -171.25(16) . . . . ?
O1 Cu1 N3 C13 8.75(16) 7_565 . . . ?
N3 Cu1 N3 C13 -40.5(11) 7_565 . . . ?
C13 N3 C1 N1 171.0(2) . . . . ?
Cu1 N3 C1 N1 -20.5(3) . . . . ?
C13 N3 C1 N2 -4.4(3) . . . . ?
Cu1 N3 C1 N2 164.15(15) . . . . ?
C2 N1 C1 N3 2.8(3) . . . . ?
C2 N1 C1 N2 178.48(19) . . . . ?
C7 N2 C1 N3 -173.3(2) . . . . ?
C7 N2 C1 N1 10.8(3) . . . . ?
Cu1 O1 C2 N1 -2.7(3) . . . . ?
Cu1 O1 C2 C3 176.06(13) . . . . ?
C1 N1 C2 O1 10.5(4) . . . . ?
C1 N1 C2 C3 -168.33(19) . . . . ?
O1 C2 C3 C6 -6.3(4) . . . . ?
N1 C2 C3 C6 172.6(3) . . . . ?
O1 C2 C3 S1 177.68(16) . . . . ?
N1 C2 C3 S1 -3.4(3) . . . . ?
C6 C3 S1 C4 0.3(3) . . . . ?
C2 C3 S1 C4 177.0(2) . . . . ?
C3 S1 C4 C5 0.0(5) . . . . ?
S1 C4 C5 C6 -0.3(7) . . . . ?
C2 C3 C6 C5 -176.9(4) . . . . ?
S1 C3 C6 C5 -0.6(6) . . . . ?
C4 C5 C6 C3 0.6(8) . . . . ?
S1A C4A C5A C6A 2(10) . . . . ?
C1 N2 C7 C12 -87.1(3) . . . . ?
C1 N2 C7 C8 149.9(2) . . . . ?
N2 C7 C8 C9 177.60(19) . . . . ?
C12 C7 C8 C9 54.2(3) . . . . ?
C7 C8 C9 C10 -54.8(3) . . . . ?
C8 C9 C10 C11 54.7(3) . . . . ?
C9 C10 C11 C12 -54.4(3) . . . . ?
N2 C7 C12 C11 -174.8(2) . . . . ?
C8 C7 C12 C11 -53.9(3) . . . . ?
C10 C11 C12 C7 54.0(3) . . . . ?
C1 N3 C13 C14 -104.1(2) . . . . ?
Cu1 N3 C13 C14 87.0(2) . . . . ?
C1 N3 C13 C18 75.4(3) . . . . ?
Cu1 N3 C13 C18 -93.4(2) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
N3 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 0.5(3) . . . . ?
N3 C13 C18 C17 -179.1(2) . . . . ?



_diffrn_measured_fraction_theta_max 0.967

_diffrn_reflns_theta_full        60.00

_diffrn_measured_fraction_theta_full 0.967

_refine_diff_density_max         0.304

_refine_diff_density_min         -0.521

_refine_diff_density_rms         0.079

_database_code_depnum_ccdc_archive 'CCDC 984601'
#######################################################################
#
#                 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_rkb



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C38 H32 Cu N6 O2 S2'

_chemical_formula_weight         732.36



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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


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



_cell_length_a                   8.8813(5)

_cell_length_b                   9.9783(6)

_cell_length_c                   10.5085(6)

_cell_angle_alpha                65.333(4)

_cell_angle_beta                 83.253(4)

_cell_angle_gamma                86.906(4)

_cell_volume                     840.41(8)

_cell_formula_units_Z            1

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    3231

_cell_measurement_theta_min      4.66

_cell_measurement_theta_max      62.45



_exptl_crystal_description       block

_exptl_crystal_colour            blue

_exptl_crystal_size_max          0.16

_exptl_crystal_size_mid          0.06

_exptl_crystal_size_min          0.04

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.447

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             379

_exptl_absorpt_coefficient_mu    2.438

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6963

_exptl_absorpt_correction_T_max  0.9088

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(2)

_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14731

_diffrn_reflns_av_R_equivalents  0.0467

_diffrn_reflns_av_sigmaI/netI    0.0315

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         4.66

_diffrn_reflns_theta_max         59.99

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             2447

_reflns_number_gt                2102

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        'Bruker APEX2'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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)+(0.0622P)²+0.1787P] 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     SHELXL

_refine_ls_extinction_coef       0.0137(11)

_refine_ls_extinction_expression 
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         2447

_refine_ls_number_parameters     224

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0393

_refine_ls_R_factor_gt           0.0349

_refine_ls_wR_factor_ref         0.0973

_refine_ls_wR_factor_gt          0.0956

_refine_ls_goodness_of_fit_ref   1.092

_refine_ls_restrained_S_all      1.092

_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









































Cu1 Cu 0.0000 0.0000 0.0000 0.0139(2) Uani 1 2 d S . .
S1 S 0.26193(7) 0.43060(7) -0.51349(6) 0.0260(2) Uani 1 1 d . . .
O1 O 0.0188(2) 0.13500(19) -0.19376(17) 0.0230(4) Uani 1 1 d . . .
N2 N 0.3711(2) 0.2587(2) -0.0345(2) 0.0170(5) Uani 1 1 d . . .
H2 H 0.4016 0.2105 0.0496 0.020 Uiso 1 1 calc R . .
N1 N 0.2325(2) 0.2697(2) -0.20608(19) 0.0151(4) Uani 1 1 d . . .
N3 N 0.1791(2) 0.0855(2) 0.0296(2) 0.0144(4) Uani 1 1 d . . .
C13 C 0.2344(3) 0.5331(3) -0.0500(3) 0.0203(6) Uani 1 1 d . . .
H13 H 0.1834 0.4423 0.0043 0.024 Uiso 1 1 calc R . .
C8 C 0.3727(3) 0.5336(3) -0.1265(2) 0.0151(5) Uani 1 1 d . . .
C18 C 0.3984(3) -0.1502(3) 0.3254(3) 0.0245(6) Uani 1 1 d . . .
H18 H 0.4711 -0.2277 0.3454 0.029 Uiso 1 1 calc R . .
C19 C 0.3417(3) -0.0897(3) 0.1956(3) 0.0202(6) Uani 1 1 d . . .
H19 H 0.3758 -0.1262 0.1268 0.024 Uiso 1 1 calc R . .
C6 C 0.2548(3) 0.2011(3) -0.0684(2) 0.0151(5) Uani 1 1 d . . .
C1 C 0.1236(3) 0.2300(2) -0.2584(2) 0.0150(5) Uani 1 1 d . . .
C9 C 0.4462(3) 0.6674(3) -0.2043(2) 0.0186(6) Uani 1 1 d . . .
H9 H 0.5412 0.6693 -0.2569 0.022 Uiso 1 1 calc R . .
C7 C 0.4480(3) 0.3945(3) -0.1280(2) 0.0165(5) Uani 1 1 d . . .
H7A H 0.4557 0.4014 -0.2253 0.020 Uiso 1 1 calc R . .
H7B H 0.5525 0.3896 -0.1022 0.020 Uiso 1 1 calc R . .
C14 C 0.2356(3) 0.0236(3) 0.1654(2) 0.0153(5) Uani 1 1 d . . .
C12 C 0.1693(3) 0.6634(3) -0.0517(3) 0.0263(6) Uani 1 1 d . . .
H12 H 0.0742 0.6616 0.0009 0.032 Uiso 1 1 calc R . .
C15 C 0.1853(3) 0.0759(3) 0.2677(3) 0.0205(6) Uani 1 1 d . . .
H15 H 0.1117 0.1527 0.2484 0.025 Uiso 1 1 calc R . .
C16 C 0.2426(3) 0.0159(3) 0.3965(3) 0.0268(6) Uani 1 1 d . . .
H16 H 0.2091 0.0522 0.4655 0.032 Uiso 1 1 calc R . .
C11 C 0.2430(3) 0.7957(3) -0.1299(3) 0.0288(7) Uani 1 1 d . . .
H11 H 0.1983 0.8850 -0.1316 0.035 Uiso 1 1 calc R . .
C10 C 0.3825(3) 0.7984(3) -0.2061(3) 0.0238(6) Uani 1 1 d . . .
H10 H 0.4340 0.8891 -0.2590 0.029 Uiso 1 1 calc R . .
C5 C 0.1754(3) 0.4697(3) -0.6623(3) 0.0273(6) Uani 1 1 d . . .
H5 H 0.2135 0.5387 -0.7532 0.033 Uiso 1 1 calc R . .
C3 C 0.0151(3) 0.2970(3) -0.4917(3) 0.0217(6) Uani 1 1 d . . .
H3 H -0.0706 0.2342 -0.4545 0.026 Uiso 1 1 calc R . .
C2 C 0.1218(3) 0.3067(3) -0.4118(2) 0.0168(5) Uani 1 1 d . . .
C4 C 0.0474(3) 0.3920(3) -0.6365(3) 0.0245(6) Uani 1 1 d . . .
H4 H -0.0144 0.3998 -0.7073 0.029 Uiso 1 1 calc R . .
C17 C 0.3488(3) -0.0973(3) 0.4257(3) 0.0289(7) Uani 1 1 d . . .
H17 H 0.3875 -0.1386 0.5148 0.035 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














































Cu1 O1 1.9087(16) 2 ?
Cu1 O1 1.9087(16) . ?
Cu1 N3 1.9589(19) . ?
Cu1 N3 1.9590(19) 2 ?
S1 C5 1.711(3) . ?
S1 C2 1.723(2) . ?
O1 C1 1.279(3) . ?
N2 C6 1.359(3) . ?
N2 C7 1.449(3) . ?
N2 H2 0.8800 . ?
N1 C1 1.320(3) . ?
N1 C6 1.351(3) . ?
N3 C6 1.331(3) . ?
N3 C14 1.439(3) . ?
C13 C8 1.386(4) . ?
C13 C12 1.389(4) . ?
C13 H13 0.9500 . ?
C8 C9 1.391(3) . ?
C8 C7 1.513(3) . ?
C18 C17 1.384(4) . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 C14 1.387(4) . ?
C19 H19 0.9500 . ?
C1 C2 1.470(3) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 C15 1.399(3) . ?
C12 C11 1.382(4) . ?
C12 H12 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C11 C10 1.389(4) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C5 C4 1.347(4) . ?
C5 H5 0.9500 . ?
C3 C2 1.370(4) . ?
C3 C4 1.421(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C17 H17 0.9500 . ?



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 Cu1 O1 180.0 2 . ?
O1 Cu1 N3 89.71(7) 2 . ?
O1 Cu1 N3 90.30(7) . . ?
O1 Cu1 N3 90.29(7) 2 2 ?
O1 Cu1 N3 89.70(7) . 2 ?
N3 Cu1 N3 180.00(10) . 2 ?
C5 S1 C2 91.13(13) . . ?
C1 O1 Cu1 126.97(15) . . ?
C6 N2 C7 124.21(19) . . ?
C6 N2 H2 117.9 . . ?
C7 N2 H2 117.9 . . ?
C1 N1 C6 121.9(2) . . ?
C6 N3 C14 115.72(19) . . ?
C6 N3 Cu1 124.52(16) . . ?
C14 N3 Cu1 119.75(15) . . ?
C8 C13 C12 120.9(2) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 C7 122.8(2) . . ?
C9 C8 C7 118.6(2) . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N3 C6 N1 126.8(2) . . ?
N3 C6 N2 120.0(2) . . ?
N1 C6 N2 113.2(2) . . ?
O1 C1 N1 128.9(2) . . ?
O1 C1 C2 115.6(2) . . ?
N1 C1 C2 115.5(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
N2 C7 C8 115.1(2) . . ?
N2 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
N2 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C19 C14 C15 119.4(2) . . ?
C19 C14 N3 119.5(2) . . ?
C15 C14 N3 121.0(2) . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C4 C5 S1 112.7(2) . . ?
C4 C5 H5 123.6 . . ?
S1 C5 H5 123.6 . . ?
C2 C3 C4 112.2(2) . . ?
C2 C3 H3 123.9 . . ?
C4 C3 H3 123.9 . . ?
C3 C2 C1 127.8(2) . . ?
C3 C2 S1 111.50(18) . . ?
C1 C2 S1 120.68(18) . . ?
C5 C4 C3 112.4(2) . . ?
C5 C4 H4 123.8 . . ?
C3 C4 H4 123.8 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?



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























































O1 Cu1 O1 C1 -140.8(14) 2 . . . ?
N3 Cu1 O1 C1 3.3(2) . . . . ?
N3 Cu1 O1 C1 -176.7(2) 2 . . . ?
O1 Cu1 N3 C6 -176.42(19) 2 . . . ?
O1 Cu1 N3 C6 3.58(19) . . . . ?
N3 Cu1 N3 C6 15(18) 2 . . . ?
O1 Cu1 N3 C14 2.88(17) 2 . . . ?
O1 Cu1 N3 C14 -177.12(17) . . . . ?
N3 Cu1 N3 C14 -165(18) 2 . . . ?
C12 C13 C8 C9 0.6(3) . . . . ?
C12 C13 C8 C7 -180.0(2) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C14 N3 C6 N1 173.7(2) . . . . ?
Cu1 N3 C6 N1 -7.0(3) . . . . ?
C14 N3 C6 N2 -4.1(3) . . . . ?
Cu1 N3 C6 N2 175.22(16) . . . . ?
C1 N1 C6 N3 2.8(4) . . . . ?
C1 N1 C6 N2 -179.3(2) . . . . ?
C7 N2 C6 N3 -172.0(2) . . . . ?
C7 N2 C6 N1 10.0(3) . . . . ?
Cu1 O1 C1 N1 -8.4(4) . . . . ?
Cu1 O1 C1 C2 172.23(15) . . . . ?
C6 N1 C1 O1 5.6(4) . . . . ?
C6 N1 C1 C2 -175.1(2) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 -179.7(2) . . . . ?
C6 N2 C7 C8 85.0(3) . . . . ?
C13 C8 C7 N2 -4.8(3) . . . . ?
C9 C8 C7 N2 174.63(19) . . . . ?
C18 C19 C14 C15 -0.5(4) . . . . ?
C18 C19 C14 N3 179.6(2) . . . . ?
C6 N3 C14 C19 -91.4(3) . . . . ?
Cu1 N3 C14 C19 89.3(2) . . . . ?
C6 N3 C14 C15 88.6(3) . . . . ?
Cu1 N3 C14 C15 -90.7(2) . . . . ?
C8 C13 C12 C11 -0.3(4) . . . . ?
C19 C14 C15 C16 0.8(4) . . . . ?
N3 C14 C15 C16 -179.2(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C13 C12 C11 C10 -0.4(4) . . . . ?
C12 C11 C10 C9 0.8(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C2 S1 C5 C4 -0.5(2) . . . . ?
C4 C3 C2 C1 177.5(2) . . . . ?
C4 C3 C2 S1 -0.4(3) . . . . ?
O1 C1 C2 C3 5.7(4) . . . . ?
N1 C1 C2 C3 -173.8(2) . . . . ?
O1 C1 C2 S1 -176.65(17) . . . . ?
N1 C1 C2 S1 3.9(3) . . . . ?
C5 S1 C2 C3 0.5(2) . . . . ?
C5 S1 C2 C1 -177.58(19) . . . . ?
S1 C5 C4 C3 0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C19 C18 C17 C16 0.0(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?



_diffrn_measured_fraction_theta_max 0.979

_diffrn_reflns_theta_full        59.99

_diffrn_measured_fraction_theta_full 0.979

_refine_diff_density_max         0.321

_refine_diff_density_min         -0.472

_refine_diff_density_rms         0.086

_database_code_depnum_ccdc_archive 'CCDC 984602'
#######################################################################
#
#                 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_rkb



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C16 H19 N3 O S'

_chemical_formula_weight         301.40



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



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)



loop_

_symmetry_equiv_pos_as_xyz


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



_cell_length_a                   7.9816(19)

_cell_length_b                   9.606(2)

_cell_length_c                   10.048(2)

_cell_angle_alpha                90.00

_cell_angle_beta                 94.281(3)

_cell_angle_gamma                90.00

_cell_volume                     768.2(3)

_cell_formula_units_Z            2

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    3439

_cell_measurement_theta_min      2.56

_cell_measurement_theta_max      27.51



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.37

_exptl_crystal_size_mid          0.27

_exptl_crystal_size_min          0.03

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.303

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             320

_exptl_absorpt_coefficient_mu    0.213

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9253

_exptl_absorpt_correction_T_max  0.9936

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(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  'APEX II'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            4488

_diffrn_reflns_av_R_equivalents  0.0568

_diffrn_reflns_av_sigmaI/netI    0.0912

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -10

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         2.03

_diffrn_reflns_theta_max         25.00

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             2641

_reflns_number_gt                2549

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  APEX-II(BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        APEX-II

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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)+(0.0948P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.039(9)

_refine_ls_extinction_expression 
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.09(10)

_refine_ls_number_reflns         2641

_refine_ls_number_parameters     205

_refine_ls_number_restraints     11

_refine_ls_R_factor_all          0.0563

_refine_ls_R_factor_gt           0.0553

_refine_ls_wR_factor_ref         0.1456

_refine_ls_wR_factor_gt          0.1435

_refine_ls_goodness_of_fit_ref   1.024

_refine_ls_restrained_S_all      1.023

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group
















































S1 S 1.00650(9) 0.50835(10) 0.75721(8) 0.0194(3) Uani 0.897(4) 1 d PD A 1
C1 C 0.9490(3) 0.5899(3) 0.8999(3) 0.0186(6) Uani 0.897(4) 1 d PD A 1
C2 C 1.0666(6) 0.6818(5) 0.9454(5) 0.0217(10) Uani 0.897(4) 1 d PD A 1
H2 H 1.0573 0.7360 1.0237 0.026 Uiso 0.897(4) 1 calc PR A 1
C3 C 1.2057(8) 0.6906(7) 0.8663(5) 0.0251(12) Uani 0.897(4) 1 d PD A 1
H3 H 1.2985 0.7513 0.8845 0.030 Uiso 0.897(4) 1 calc PR A 1
C4 C 1.1902(4) 0.6016(5) 0.7608(4) 0.0214(11) Uani 0.897(4) 1 d PD A 1
H4 H 1.2713 0.5921 0.6969 0.026 Uiso 0.897(4) 1 calc PR A 1
S1A S 1.0778(13) 0.7130(12) 0.9744(11) 0.0194(3) Uani 0.103(4) 1 d PD A 2
C1A C 0.9490(3) 0.5899(3) 0.8999(3) 0.0186(6) Uani 0.103(4) 1 d PD A 2
C2A C 1.004(4) 0.555(4) 0.781(2) 0.0217(10) Uani 0.103(4) 1 d PD A 2
H2A H 0.9435 0.4942 0.7204 0.026 Uiso 0.103(4) 1 calc PR A 2
C3A C 1.159(5) 0.616(6) 0.753(4) 0.0251(12) Uani 0.103(4) 1 d PD A 2
H3A H 1.2175 0.5957 0.6768 0.030 Uiso 0.103(4) 1 calc PR A 2
C4A C 1.214(6) 0.708(7) 0.850(4) 0.0214(11) Uani 0.103(4) 1 d PD A 2
H4A H 1.3135 0.7622 0.8487 0.026 Uiso 0.103(4) 1 calc PR A 2
O1 O 0.7596(2) 0.6091(2) 1.0665(2) 0.0226(5) Uani 1 1 d . A .
N1 N 0.6908(3) 0.4685(3) 0.8786(2) 0.0179(5) Uani 1 1 d . A .
N2 N 0.4468(3) 0.3374(3) 0.8400(2) 0.0194(5) Uani 1 1 d . A .
H2B H 0.3558 0.3020 0.8807 0.029 Uiso 1 1 d R . .
N3 N 0.4870(3) 0.4558(3) 1.0378(2) 0.0188(6) Uani 1 1 d . A .
H3B H 0.5594 0.5134 1.0835 0.028 Uiso 1 1 d R . .
C5 C 0.7885(3) 0.5561(3) 0.9571(3) 0.0171(6) Uani 1 1 d . . .
C6 C 0.5433(3) 0.4236(3) 0.9205(3) 0.0171(6) Uani 1 1 d . . .
C7 C 0.4571(3) 0.3020(3) 0.7035(3) 0.0185(6) Uani 1 1 d . . .
C8 C 0.5838(4) 0.3423(3) 0.6250(3) 0.0241(7) Uani 1 1 d . A .
H8 H 0.6742 0.3978 0.6617 0.029 Uiso 1 1 calc R . .
C9 C 0.5780(4) 0.3012(3) 0.4922(3) 0.0271(7) Uani 1 1 d . . .
H9 H 0.6651 0.3293 0.4386 0.033 Uiso 1 1 calc R A .
C10 C 0.4475(4) 0.2199(3) 0.4365(3) 0.0248(7) Uani 1 1 d . A .
H10 H 0.4454 0.1914 0.3458 0.030 Uiso 1 1 calc R . .
C11 C 0.3206(4) 0.1810(4) 0.5151(3) 0.0261(7) Uani 1 1 d . . .
H11 H 0.2302 0.1256 0.4780 0.031 Uiso 1 1 calc R A .
C12 C 0.3240(3) 0.2218(3) 0.6467(3) 0.0231(7) Uani 1 1 d . A .
H12 H 0.2352 0.1952 0.6993 0.028 Uiso 1 1 calc R . .
C13 C 0.3289(3) 0.4113(3) 1.0877(3) 0.0197(6) Uani 1 1 d . . .
H13A H 0.3348 0.3110 1.1100 0.024 Uiso 1 1 calc R A .
H13B H 0.2365 0.4250 1.0176 0.024 Uiso 1 1 calc R . .
C14 C 0.2928(3) 0.4940(3) 1.2107(3) 0.0213(6) Uani 1 1 d . A .
H14A H 0.2857 0.5941 1.1877 0.026 Uiso 1 1 calc R . .
H14B H 0.3867 0.4816 1.2799 0.026 Uiso 1 1 calc R . .
C15 C 0.1295(3) 0.4483(4) 1.2667(3) 0.0259(7) Uani 1 1 d . . .
H15A H 0.1312 0.3460 1.2789 0.031 Uiso 1 1 calc R A .
H15B H 0.0343 0.4714 1.2016 0.031 Uiso 1 1 calc R . .
C16 C 0.1019(4) 0.5178(5) 1.3999(3) 0.0372(8) Uani 1 1 d . A .
H16A H 0.0880 0.6183 1.3866 0.056 Uiso 1 1 calc R . .
H16B H 0.1992 0.5003 1.4631 0.056 Uiso 1 1 calc R . .
H16C H 0.0008 0.4793 1.4357 0.056 Uiso 1 1 calc R . .






_geom_special_details            
; 

 All esds (except the esd in the dihedral angle between two l.s. planes) 

 are estimated using the full covariance matrix.  The cell esds are taken 

 into account individually in the estimation of esds in distances, angles 

 and torsion angles; correlations between esds in cell parameters are only 

 used when they are defined by crystal symmetry.  An approximate (isotropic) 

 treatment of cell esds is used for estimating esds involving l.s. planes. 

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag















































S1 C4 1.716(4) . ?
S1 C1 1.725(3) . ?
C1 C2 1.344(6) . ?
C1 C5 1.479(4) . ?
C2 C3 1.415(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
S1A C4A 1.716(11) . ?
C2A C3A 1.416(12) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.360(10) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
O1 C5 1.248(3) . ?
N1 C6 1.350(3) . ?
N1 C5 1.359(4) . ?
N2 C6 1.357(4) . ?
N2 C7 1.421(3) . ?
N2 H2B 0.9245 . ?
N3 C6 1.329(4) . ?
N3 C13 1.457(3) . ?
N3 H3B 0.9001 . ?
C7 C8 1.383(4) . ?
C7 C12 1.399(4) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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











































































C4 S1 C1 91.45(17) . . ?
C2 C1 C5 127.9(3) . . ?
C2 C1 S1 111.0(3) . . ?
C5 C1 S1 121.0(2) . . ?
C1 C2 C3 113.9(4) . . ?
C1 C2 H2 123.1 . . ?
C3 C2 H2 123.1 . . ?
C4 C3 C2 111.8(4) . . ?
C4 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
C3 C4 S1 111.9(3) . . ?
C3 C4 H4 124.1 . . ?
S1 C4 H4 124.1 . . ?
C3A C2A H2A 122.6 . . ?
C4A C3A C2A 112(2) . . ?
C4A C3A H3A 124.2 . . ?
C2A C3A H3A 124.2 . . ?
C3A C4A S1A 110.5(17) . . ?
C3A C4A H4A 124.8 . . ?
S1A C4A H4A 124.8 . . ?
C6 N1 C5 119.5(2) . . ?
C6 N2 C7 130.6(2) . . ?
C6 N2 H2B 113.0 . . ?
C7 N2 H2B 116.3 . . ?
C6 N3 C13 126.6(2) . . ?
C6 N3 H3B 110.4 . . ?
C13 N3 H3B 123.0 . . ?
O1 C5 N1 128.9(2) . . ?
O1 C5 C1 118.3(2) . . ?
N1 C5 C1 112.7(2) . . ?
N3 C6 N1 124.2(2) . . ?
N3 C6 N2 117.2(2) . . ?
N1 C6 N2 118.6(3) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 N2 125.5(3) . . ?
C12 C7 N2 115.4(2) . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N3 C13 C14 110.4(2) . . ?
N3 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.7(2) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.5(3) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
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 . . ?



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

































C4 S1 C1 C2 -0.3(3) . . . . ?
C4 S1 C1 C5 179.7(3) . . . . ?
C5 C1 C2 C3 -179.3(4) . . . . ?
S1 C1 C2 C3 0.6(6) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 S1 0.4(7) . . . . ?
C1 S1 C4 C3 -0.1(4) . . . . ?
C2A C3A C4A S1A 2(8) . . . . ?
C6 N1 C5 O1 -3.1(4) . . . . ?
C6 N1 C5 C1 177.2(2) . . . . ?
C2 C1 C5 O1 -6.1(5) . . . . ?
S1 C1 C5 O1 174.0(2) . . . . ?
C2 C1 C5 N1 173.7(3) . . . . ?
S1 C1 C5 N1 -6.3(3) . . . . ?
C13 N3 C6 N1 179.5(2) . . . . ?
C13 N3 C6 N2 -2.1(4) . . . . ?
C5 N1 C6 N3 -2.3(4) . . . . ?
C5 N1 C6 N2 179.3(2) . . . . ?
C7 N2 C6 N3 168.6(3) . . . . ?
C7 N2 C6 N1 -12.9(4) . . . . ?
C6 N2 C7 C8 6.0(5) . . . . ?
C6 N2 C7 C12 -172.7(3) . . . . ?
C12 C7 C8 C9 -0.8(5) . . . . ?
N2 C7 C8 C9 -179.5(3) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C7 -0.8(5) . . . . ?
C8 C7 C12 C11 1.3(4) . . . . ?
N2 C7 C12 C11 -179.9(3) . . . . ?
C6 N3 C13 C14 -167.6(3) . . . . ?
N3 C13 C14 C15 -179.1(2) . . . . ?
C13 C14 C15 C16 173.0(3) . . . . ?



_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.481

_refine_diff_density_min         -0.405

_refine_diff_density_rms         0.079

_database_code_depnum_ccdc_archive 'CCDC 984603'
#######################################################################
#
#                 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_rkb



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C19 H17 N3 O S'

_chemical_formula_weight         335.42



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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/n



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   17.941(4)

_cell_length_b                   9.5618(19)

_cell_length_c                   20.779(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 107.292(2)

_cell_angle_gamma                90.00

_cell_volume                     3403.6(12)

_cell_formula_units_Z            8

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    9875

_cell_measurement_theta_min      2.36

_cell_measurement_theta_max      27.46



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.42

_exptl_crystal_size_mid          0.37

_exptl_crystal_size_min          0.27

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.309

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    0.200

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9206

_exptl_absorpt_correction_T_max  0.9479

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(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  'APEX II'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            31382

_diffrn_reflns_av_R_equivalents  0.0614

_diffrn_reflns_av_sigmaI/netI    0.0423

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       21

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -24

_diffrn_reflns_limit_l_max       24

_diffrn_reflns_theta_min         2.05

_diffrn_reflns_theta_max         25.00

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             5997

_reflns_number_gt                5380

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  APEX-II(BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        APEX-II

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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)+(0.0326P)²+1.8015P] 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         5997

_refine_ls_number_parameters     459

_refine_ls_number_restraints     20

_refine_ls_R_factor_all          0.0402

_refine_ls_R_factor_gt           0.0357

_refine_ls_wR_factor_ref         0.0921

_refine_ls_wR_factor_gt          0.0885

_refine_ls_goodness_of_fit_ref   1.027

_refine_ls_restrained_S_all      1.034

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group


































































































S1 S 0.14472(3) 0.19745(6) 0.66716(2) 0.02314(16) Uani 0.9029(19) 1 d PD A 1
C1 C 0.22816(8) 0.12569(15) 0.65559(7) 0.0190(3) Uani 0.9029(19) 1 d PD A 1
C2 C 0.26017(16) 0.0351(3) 0.70592(13) 0.0260(6) Uani 0.9029(19) 1 d PD A 1
H2 H 0.3069 -0.0145 0.7085 0.031 Uiso 0.9029(19) 1 calc PR A 1
C3 C 0.2207(4) 0.0184(7) 0.7539(3) 0.0269(7) Uani 0.9029(19) 1 d PD A 1
H3 H 0.2366 -0.0427 0.7916 0.032 Uiso 0.9029(19) 1 calc PR A 1
C4 C 0.15622(18) 0.1016(4) 0.73946(13) 0.0267(5) Uani 0.9029(19) 1 d PD A 1
H4 H 0.1216 0.1061 0.7662 0.032 Uiso 0.9029(19) 1 calc PR A 1
S1A S 0.2785(4) 0.0047(7) 0.7103(3) 0.02314(16) Uani 0.0971(19) 1 d PD A 2
C1A C 0.22816(8) 0.12569(15) 0.65559(7) 0.0190(3) Uani 0.0971(19) 1 d PD A 2
C2A C 0.1704(11) 0.186(2) 0.6732(11) 0.0260(6) Uani 0.0971(19) 1 d PD A 2
H2A H 0.1430 0.2658 0.6513 0.031 Uiso 0.0971(19) 1 calc PR A 2
C3A C 0.1542(19) 0.119(4) 0.7269(16) 0.0269(7) Uani 0.0971(19) 1 d PD A 2
H3A H 0.1084 0.1313 0.7402 0.032 Uiso 0.0971(19) 1 calc PR A 2
C4A C 0.215(3) 0.033(8) 0.757(3) 0.0267(5) Uani 0.0971(19) 1 d PD A 2
H4A H 0.2220 -0.0082 0.8003 0.032 Uiso 0.0971(19) 1 calc PR A 2
O1 O 0.30882(6) 0.09785(11) 0.58516(5) 0.0225(2) Uani 1 1 d . A .
N1 N 0.20537(7) 0.25720(13) 0.55591(6) 0.0179(3) Uani 1 1 d . A .
N2 N 0.16595(7) 0.39362(12) 0.46158(6) 0.0176(3) Uani 1 1 d . A .
H2D H 0.1734 0.4255 0.4242 0.021 Uiso 1 1 calc R . .
N3 N 0.27118(7) 0.24416(13) 0.47280(6) 0.0175(3) Uani 1 1 d . A .
H3D H 0.3033 0.1841 0.4991 0.021 Uiso 1 1 calc R . .
C5 C 0.25144(8) 0.16044(15) 0.59529(7) 0.0177(3) Uani 1 1 d . . .
C6 C 0.21508(8) 0.29746(14) 0.49702(7) 0.0155(3) Uani 1 1 d . . .
C7 C 0.09995(8) 0.44872(15) 0.48213(8) 0.0197(3) Uani 1 1 d . . .
H7A H 0.0903 0.5471 0.4671 0.024 Uiso 1 1 calc R A .
H7B H 0.1135 0.4474 0.5319 0.024 Uiso 1 1 calc R . .
C8 C 0.02648(8) 0.36426(16) 0.45271(7) 0.0188(3) Uani 1 1 d . A .
C9 C 0.01280(9) 0.24244(17) 0.48402(8) 0.0257(4) Uani 1 1 d . . .
H9 H 0.0487 0.2147 0.5257 0.031 Uiso 1 1 calc R A .
C10 C -0.05240(10) 0.16120(19) 0.45524(10) 0.0331(4) Uani 1 1 d . A .
H10 H -0.0609 0.0781 0.4771 0.040 Uiso 1 1 calc R . .
C11 C -0.10502(10) 0.2005(2) 0.39501(10) 0.0372(4) Uani 1 1 d . . .
H11 H -0.1495 0.1441 0.3750 0.045 Uiso 1 1 calc R A .
C12 C -0.09293(10) 0.3219(2) 0.36394(9) 0.0388(5) Uani 1 1 d . A .
H12 H -0.1294 0.3496 0.3226 0.047 Uiso 1 1 calc R . .
C13 C -0.02775(9) 0.40391(19) 0.39276(8) 0.0285(4) Uani 1 1 d . . .
H13 H -0.0202 0.4881 0.3712 0.034 Uiso 1 1 calc R A .
C14 C 0.28470(8) 0.27314(16) 0.40999(7) 0.0185(3) Uani 1 1 d . . .
C15 C 0.29580(10) 0.40768(17) 0.39053(9) 0.0276(4) Uani 1 1 d . A .
H15 H 0.2936 0.4847 0.4188 0.033 Uiso 1 1 calc R . .
C16 C 0.31027(11) 0.4293(2) 0.32927(9) 0.0359(4) Uani 1 1 d . . .
H16 H 0.3166 0.5219 0.3151 0.043 Uiso 1 1 calc R A .
C17 C 0.31555(10) 0.3186(2) 0.28893(9) 0.0358(4) Uani 1 1 d . A .
H17 H 0.3251 0.3346 0.2469 0.043 Uiso 1 1 calc R . .
C18 C 0.30700(11) 0.1843(2) 0.30936(10) 0.0397(5) Uani 1 1 d . . .
H18 H 0.3122 0.1073 0.2821 0.048 Uiso 1 1 calc R A .
C19 C 0.29081(10) 0.16134(19) 0.36958(9) 0.0321(4) Uani 1 1 d . A .
H19 H 0.2839 0.0686 0.3832 0.038 Uiso 1 1 calc R . .
S1B S 0.05699(4) 0.92932(6) 0.33331(3) 0.02614(19) Uani 0.878(2) 1 d PD B 1
C1B C 0.10334(9) 0.77300(16) 0.35713(7) 0.0199(3) Uani 0.878(2) 1 d PD B 1
C2B C 0.1610(2) 0.7892(3) 0.41674(16) 0.0279(7) Uani 0.878(2) 1 d PD B 1
H2B H 0.1920 0.7130 0.4391 0.034 Uiso 0.878(2) 1 calc PR B 1
C3B C 0.17149(14) 0.9234(3) 0.44239(16) 0.0282(6) Uani 0.878(2) 1 d PD B 1
H3B H 0.2110 0.9504 0.4821 0.034 Uiso 0.878(2) 1 calc PR B 1
C4B C 0.11755(17) 1.0116(3) 0.40305(12) 0.0293(6) Uani 0.878(2) 1 d PD B 1
H4B H 0.1137 1.1079 0.4129 0.035 Uiso 0.878(2) 1 calc PR B 1
S1C S 0.1743(4) 0.7654(7) 0.4278(3) 0.02614(19) Uani 0.122(2) 1 d PD B 2
C1C C 0.10334(9) 0.77300(16) 0.35713(7) 0.0199(3) Uani 0.122(2) 1 d PD B 2
C2C C 0.0684(13) 0.9001(14) 0.3419(11) 0.0279(7) Uani 0.122(2) 1 d PD B 2
H2C H 0.0245 0.9171 0.3039 0.034 Uiso 0.122(2) 1 calc PR B 2
C3C C 0.1040(15) 1.002(2) 0.3881(11) 0.0282(6) Uani 0.122(2) 1 d PD B 2
H3C H 0.0946 1.0993 0.3829 0.034 Uiso 0.122(2) 1 calc PR B 2
C4C C 0.1549(15) 0.9386(16) 0.4420(13) 0.0293(6) Uani 0.122(2) 1 d PD B 2
H4C H 0.1777 0.9850 0.4836 0.035 Uiso 0.122(2) 1 calc PR B 2
O1B O 0.11728(6) 0.53489(11) 0.33558(5) 0.0237(2) Uani 1 1 d . B .
N1B N 0.01661(7) 0.66432(13) 0.26220(6) 0.0178(3) Uani 1 1 d . B .
N2B N 0.00396(7) 0.42292(13) 0.23796(6) 0.0200(3) Uani 1 1 d . B .
H2BA H 0.0304 0.4046 0.2801 0.024 Uiso 1 1 calc R . .
N3B N -0.06857(7) 0.58459(13) 0.16266(6) 0.0184(3) Uani 1 1 d . B .
H3BA H -0.0933 0.5134 0.1389 0.022 Uiso 1 1 calc R . .
C5B C 0.07915(8) 0.64484(15) 0.31672(7) 0.0181(3) Uani 1 1 d . . .
C6B C -0.01388(8) 0.55662(15) 0.22189(7) 0.0167(3) Uani 1 1 d . . .
C7B C -0.01664(9) 0.30450(15) 0.19156(8) 0.0218(3) Uani 1 1 d . . .
H7BA H -0.0731 0.3082 0.1671 0.026 Uiso 1 1 calc R B .
H7BB H -0.0063 0.2162 0.2176 0.026 Uiso 1 1 calc R . .
C8B C 0.02912(9) 0.30532(15) 0.14134(8) 0.0213(3) Uani 1 1 d . B .
C9B C 0.10976(10) 0.29414(18) 0.16351(9) 0.0314(4) Uani 1 1 d . . .
H9B H 0.1359 0.2867 0.2104 0.038 Uiso 1 1 calc R B .
C10B C 0.15241(11) 0.2938(2) 0.11813(10) 0.0396(5) Uani 1 1 d . B .
H10B H 0.2076 0.2852 0.1339 0.047 Uiso 1 1 calc R . .
C11B C 0.11535(12) 0.3058(2) 0.05021(10) 0.0416(5) Uani 1 1 d . . .
H11B H 0.1448 0.3050 0.0190 0.050 Uiso 1 1 calc R B .
C12B C 0.03557(13) 0.3187(2) 0.02761(10) 0.0439(5) Uani 1 1 d . B .
H12B H 0.0098 0.3284 -0.0192 0.053 Uiso 1 1 calc R . .
C13B C -0.00738(11) 0.31774(19) 0.07308(9) 0.0329(4) Uani 1 1 d . . .
H13B H -0.0626 0.3257 0.0571 0.040 Uiso 1 1 calc R B .
C14B C -0.08867(9) 0.72127(15) 0.13635(7) 0.0196(3) Uani 1 1 d . . .
C15B C -0.16691(9) 0.75541(18) 0.10898(8) 0.0251(4) Uani 1 1 d . B .
H15B H -0.2062 0.6881 0.1080 0.030 Uiso 1 1 calc R . .
C16B C -0.18748(11) 0.88819(19) 0.08303(8) 0.0333(4) Uani 1 1 d . . .
H16B H -0.2410 0.9123 0.0648 0.040 Uiso 1 1 calc R B .
C17B C -0.13046(12) 0.98559(19) 0.08366(9) 0.0380(5) Uani 1 1 d . B .
H17B H -0.1447 1.0770 0.0665 0.046 Uiso 1 1 calc R . .
C18B C -0.05242(11) 0.94965(18) 0.10942(9) 0.0341(4) Uani 1 1 d . . .
H18B H -0.0132 1.0162 0.1090 0.041 Uiso 1 1 calc R B .
C19B C -0.03119(10) 0.81768(16) 0.13568(8) 0.0250(4) Uani 1 1 d . B .
H19B H 0.0224 0.7932 0.1531 0.030 Uiso 1 1 calc R . .






_geom_special_details            
; 

 All esds (except the esd in the dihedral angle between two l.s. planes) 

 are estimated using the full covariance matrix.  The cell esds are taken 

 into account individually in the estimation of esds in distances, angles 

 and torsion angles; correlations between esds in cell parameters are only 

 used when they are defined by crystal symmetry.  An approximate (isotropic) 

 treatment of cell esds is used for estimating esds involving l.s. planes. 

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag


































































































S1 C4 1.719(2) . ?
S1 C1 1.7273(15) . ?
C1 C2 1.348(3) . ?
C1 C5 1.472(2) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
S1A C4A 1.725(10) . ?
C2A C3A 1.389(11) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.365(10) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
O1 C5 1.2614(18) . ?
N1 C6 1.3427(19) . ?
N1 C5 1.3441(19) . ?
N2 C6 1.3338(19) . ?
N2 C7 1.4705(19) . ?
N2 H2D 0.8800 . ?
N3 C6 1.3517(19) . ?
N3 C14 1.4238(19) . ?
N3 H3D 0.8800 . ?
C7 C8 1.511(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.386(2) . ?
C8 C9 1.391(2) . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 C19 1.384(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S1B C1B 1.7106(16) . ?
S1B C4B 1.7215(19) . ?
C1B C2B 1.367(3) . ?
C1B C5B 1.476(2) . ?
C2B C3B 1.380(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.359(3) . ?
C3B H3B 0.9500 . ?
C4B H4B 0.9500 . ?
S1C C4C 1.735(10) . ?
C2C C3C 1.380(11) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.357(10) . ?
C3C H3C 0.9500 . ?
C4C H4C 0.9500 . ?
O1B C5B 1.2520(18) . ?
N1B C6B 1.3376(19) . ?
N1B C5B 1.3495(19) . ?
N2B C6B 1.3359(19) . ?
N2B C7B 1.4618(19) . ?
N2B H2BA 0.8800 . ?
N3B C6B 1.3532(19) . ?
N3B C14B 1.4212(19) . ?
N3B H3BA 0.8800 . ?
C7B C8B 1.507(2) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C13B 1.379(2) . ?
C8B C9B 1.386(2) . ?
C9B C10B 1.380(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.374(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.373(3) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.385(3) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C19B 1.386(2) . ?
C14B C15B 1.388(2) . ?
C15B C16B 1.386(2) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.381(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.385(3) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.383(2) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?



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






















































































































































C4 S1 C1 91.49(10) . . ?
C2 C1 C5 129.97(16) . . ?
C2 C1 S1 109.53(15) . . ?
C5 C1 S1 120.39(11) . . ?
C1 C2 C3 116.0(3) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C2 110.8(3) . . ?
C4 C3 H3 124.6 . . ?
C2 C3 H3 124.6 . . ?
C3 C4 S1 112.1(2) . . ?
C3 C4 H4 123.9 . . ?
S1 C4 H4 123.9 . . ?
C3A C2A H2A 123.5 . . ?
C4A C3A C2A 109(2) . . ?
C4A C3A H3A 125.7 . . ?
C2A C3A H3A 125.7 . . ?
C3A C4A S1A 113.8(18) . . ?
C3A C4A H4A 123.1 . . ?
S1A C4A H4A 123.1 . . ?
C6 N1 C5 121.95(13) . . ?
C6 N2 C7 122.93(13) . . ?
C6 N2 H2D 118.5 . . ?
C7 N2 H2D 118.5 . . ?
C6 N3 C14 128.06(12) . . ?
C6 N3 H3D 116.0 . . ?
C14 N3 H3D 116.0 . . ?
O1 C5 N1 127.58(14) . . ?
O1 C5 C1 119.15(13) . . ?
N1 C5 C1 113.25(13) . . ?
N2 C6 N1 117.22(13) . . ?
N2 C6 N3 119.83(13) . . ?
N1 C6 N3 122.95(13) . . ?
N2 C7 C8 111.83(12) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 118.35(15) . . ?
C13 C8 C7 120.81(14) . . ?
C9 C8 C7 120.81(14) . . ?
C10 C9 C8 120.81(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.19(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.70(16) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.29(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 120.64(16) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C19 119.85(15) . . ?
C15 C14 N3 121.91(14) . . ?
C19 C14 N3 118.15(14) . . ?
C14 C15 C16 119.34(16) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.75(17) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.87(16) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 119.98(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.15(17) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C1B S1B C4B 91.42(11) . . ?
C2B C1B C5B 128.72(18) . . ?
C2B C1B S1B 109.58(17) . . ?
C5B C1B S1B 121.69(11) . . ?
C1B C2B C3B 115.8(3) . . ?
C1B C2B H2B 122.1 . . ?
C3B C2B H2B 122.1 . . ?
C4B C3B C2B 110.7(2) . . ?
C4B C3B H3B 124.6 . . ?
C2B C3B H3B 124.6 . . ?
C3B C4B S1B 112.4(2) . . ?
C3B C4B H4B 123.8 . . ?
S1B C4B H4B 123.8 . . ?
C3C C2C H2C 123.8 . . ?
C4C C3C C2C 108.7(17) . . ?
C4C C3C H3C 125.7 . . ?
C2C C3C H3C 125.7 . . ?
C3C C4C S1C 113.8(15) . . ?
C3C C4C H4C 123.1 . . ?
S1C C4C H4C 123.1 . . ?
C6B N1B C5B 120.18(13) . . ?
C6B N2B C7B 125.56(13) . . ?
C6B N2B H2BA 117.2 . . ?
C7B N2B H2BA 117.2 . . ?
C6B N3B C14B 124.34(12) . . ?
C6B N3B H3BA 117.8 . . ?
C14B N3B H3BA 117.8 . . ?
O1B C5B N1B 128.26(14) . . ?
O1B C5B C1B 118.56(13) . . ?
N1B C5B C1B 113.18(13) . . ?
N2B C6B N1B 123.86(13) . . ?
N2B C6B N3B 118.14(13) . . ?
N1B C6B N3B 117.93(13) . . ?
N2B C7B C8B 111.69(12) . . ?
N2B C7B H7BA 109.3 . . ?
C8B C7B H7BA 109.3 . . ?
N2B C7B H7BB 109.3 . . ?
C8B C7B H7BB 109.3 . . ?
H7BA C7B H7BB 107.9 . . ?
C13B C8B C9B 118.56(16) . . ?
C13B C8B C7B 121.50(15) . . ?
C9B C8B C7B 119.94(14) . . ?
C10B C9B C8B 120.61(17) . . ?
C10B C9B H9B 119.7 . . ?
C8B C9B H9B 119.7 . . ?
C11B C10B C9B 120.28(18) . . ?
C11B C10B H10B 119.9 . . ?
C9B C10B H10B 119.9 . . ?
C12B C11B C10B 119.72(18) . . ?
C12B C11B H11B 120.1 . . ?
C10B C11B H11B 120.1 . . ?
C11B C12B C13B 120.05(18) . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C8B C13B C12B 120.77(17) . . ?
C8B C13B H13B 119.6 . . ?
C12B C13B H13B 119.6 . . ?
C19B C14B C15B 120.29(15) . . ?
C19B C14B N3B 120.72(14) . . ?
C15B C14B N3B 118.95(14) . . ?
C16B C15B C14B 119.66(16) . . ?
C16B C15B H15B 120.2 . . ?
C14B C15B H15B 120.2 . . ?
C17B C16B C15B 120.23(16) . . ?
C17B C16B H16B 119.9 . . ?
C15B C16B H16B 119.9 . . ?
C16B C17B C18B 119.82(16) . . ?
C16B C17B H17B 120.1 . . ?
C18B C17B H17B 120.1 . . ?
C19B C18B C17B 120.47(17) . . ?
C19B C18B H18B 119.8 . . ?
C17B C18B H18B 119.8 . . ?
C18B C19B C14B 119.49(16) . . ?
C18B C19B H19B 120.3 . . ?
C14B C19B H19B 120.3 . . ?



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


















































































C4 S1 C1 C2 -0.2(2) . . . . ?
C4 S1 C1 C5 176.28(18) . . . . ?
C5 C1 C2 C3 -175.5(4) . . . . ?
S1 C1 C2 C3 0.5(5) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C3 C4 S1 0.5(8) . . . . ?
C1 S1 C4 C3 -0.2(5) . . . . ?
C2A C3A C4A S1A -14(8) . . . . ?
C6 N1 C5 O1 1.8(2) . . . . ?
C6 N1 C5 C1 -176.72(12) . . . . ?
C2 C1 C5 O1 1.6(3) . . . . ?
S1 C1 C5 O1 -174.10(11) . . . . ?
C2 C1 C5 N1 -179.79(19) . . . . ?
S1 C1 C5 N1 4.53(18) . . . . ?
C7 N2 C6 N1 -4.1(2) . . . . ?
C7 N2 C6 N3 175.32(12) . . . . ?
C5 N1 C6 N2 179.63(13) . . . . ?
C5 N1 C6 N3 0.2(2) . . . . ?
C14 N3 C6 N2 -2.8(2) . . . . ?
C14 N3 C6 N1 176.59(13) . . . . ?
C6 N2 C7 C8 -90.49(16) . . . . ?
N2 C7 C8 C13 -94.12(17) . . . . ?
N2 C7 C8 C9 83.86(17) . . . . ?
C13 C8 C9 C10 1.5(2) . . . . ?
C7 C8 C9 C10 -176.56(15) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C9 C8 C13 C12 -1.7(2) . . . . ?
C7 C8 C13 C12 176.34(15) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C6 N3 C14 C15 55.4(2) . . . . ?
C6 N3 C14 C19 -128.11(16) . . . . ?
C19 C14 C15 C16 2.3(2) . . . . ?
N3 C14 C15 C16 178.74(15) . . . . ?
C14 C15 C16 C17 -1.6(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 1.9(3) . . . . ?
C17 C18 C19 C14 -1.3(3) . . . . ?
C15 C14 C19 C18 -0.8(3) . . . . ?
N3 C14 C19 C18 -177.44(15) . . . . ?
C4B S1B C1B C2B 1.1(2) . . . . ?
C4B S1B C1B C5B 179.80(17) . . . . ?
C5B C1B C2B C3B 178.7(2) . . . . ?
S1B C1B C2B C3B -2.7(4) . . . . ?
C1B C2B C3B C4B 3.2(4) . . . . ?
C2B C3B C4B S1B -2.3(4) . . . . ?
C1B S1B C4B C3B 0.7(3) . . . . ?
C2C C3C C4C S1C 14(3) . . . . ?
C6B N1B C5B O1B 2.7(2) . . . . ?
C6B N1B C5B C1B -177.69(13) . . . . ?
C2B C1B C5B O1B -4.1(3) . . . . ?
S1B C1B C5B O1B 177.41(11) . . . . ?
C2B C1B C5B N1B 176.2(2) . . . . ?
S1B C1B C5B N1B -2.24(18) . . . . ?
C7B N2B C6B N1B -168.37(14) . . . . ?
C7B N2B C6B N3B 14.7(2) . . . . ?
C5B N1B C6B N2B 12.9(2) . . . . ?
C5B N1B C6B N3B -170.12(13) . . . . ?
C14B N3B C6B N2B -174.43(14) . . . . ?
C14B N3B C6B N1B 8.5(2) . . . . ?
C6B N2B C7B C8B 70.39(19) . . . . ?
N2B C7B C8B C13B -117.69(16) . . . . ?
N2B C7B C8B C9B 61.98(18) . . . . ?
C13B C8B C9B C10B -0.8(3) . . . . ?
C7B C8B C9B C10B 179.56(16) . . . . ?
C8B C9B C10B C11B 0.6(3) . . . . ?
C9B C10B C11B C12B 0.3(3) . . . . ?
C10B C11B C12B C13B -0.9(3) . . . . ?
C9B C8B C13B C12B 0.1(3) . . . . ?
C7B C8B C13B C12B 179.81(16) . . . . ?
C11B C12B C13B C8B 0.7(3) . . . . ?
C6B N3B C14B C19B 46.6(2) . . . . ?
C6B N3B C14B C15B -135.79(15) . . . . ?
C19B C14B C15B C16B -2.2(2) . . . . ?
N3B C14B C15B C16B -179.91(14) . . . . ?
C14B C15B C16B C17B 0.8(2) . . . . ?
C15B C16B C17B C18B 1.0(3) . . . . ?
C16B C17B C18B C19B -1.2(3) . . . . ?
C17B C18B C19B C14B -0.3(3) . . . . ?
C15B C14B C19B C18B 2.0(2) . . . . ?
N3B C14B C19B C18B 179.63(14) . . . . ?



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.404

_refine_diff_density_min         -0.333

_refine_diff_density_rms         0.042

_database_code_depnum_ccdc_archive 'CCDC 984604'
#######################################################################
#
#                 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_rkb



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C19 H17 N3 O S'

_chemical_formula_weight         335.42



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'
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           Tetragonal

_symmetry_space_group_name_H-M   P-4



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   19.258(5)

_cell_length_b                   19.258(5)

_cell_length_c                   9.374(2)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     3476.6(14)

_cell_formula_units_Z            8

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    9978

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      27.25



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.60

_exptl_crystal_size_mid          0.50

_exptl_crystal_size_min          0.20

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.282

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    0.196

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.8914

_exptl_absorpt_correction_T_max  0.9618

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(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  'APEX II'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            38915

_diffrn_reflns_av_R_equivalents  0.0327

_diffrn_reflns_av_sigmaI/netI    0.0239

_diffrn_reflns_limit_h_min       -24

_diffrn_reflns_limit_h_max       24

_diffrn_reflns_limit_k_min       -24

_diffrn_reflns_limit_k_max       24

_diffrn_reflns_limit_l_min       -12

_diffrn_reflns_limit_l_max       12

_diffrn_reflns_theta_min         1.06

_diffrn_reflns_theta_max         27.50

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             7889

_reflns_number_gt                7440

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  APEX-II(BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        APEX-II

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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. 



 The thiophenyl groups (S1, C1-C4) and (S1D, C1D-C4D) were found disordered 

 between two positions which was successfully modeled with a ratio 

 of (0.79:0.21) and (0.88:0.12) respectively. Constraints (EADP, EXYZ) and 

 were used to keep the thermal ellipsoids of the disordered atoms meaningful.

 (SAME) was used to keep the bond distances and angle between the disordered

 group similar	

;



_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)+(0.0323P)²+1.3218P] 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   0.03(6)

_refine_ls_number_reflns         7889

_refine_ls_number_parameters     467

_refine_ls_number_restraints     26

_refine_ls_R_factor_all          0.0436

_refine_ls_R_factor_gt           0.0403

_refine_ls_wR_factor_ref         0.0939

_refine_ls_wR_factor_gt          0.0917

_refine_ls_goodness_of_fit_ref   1.092

_refine_ls_restrained_S_all      1.093

_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




































































































C6 C 0.65199(10) 0.65202(10) 0.0444(2) 0.0293(4) Uani 1 1 d . A .
C7 C 0.63401(10) 0.58852(10) -0.1832(2) 0.0311(4) Uani 1 1 d . A .
C8 C 0.59313(12) 0.53136(12) -0.2147(3) 0.0463(6) Uani 1 1 d . . .
H8 H 0.5551 0.5196 -0.1549 0.056 Uiso 1 1 calc R . .
C9 C 0.60811(13) 0.49136(12) -0.3343(3) 0.0547(7) Uani 1 1 d . . .
H9 H 0.5796 0.4526 -0.3564 0.066 Uiso 1 1 calc R . .
C10 C 0.66323(12) 0.50692(13) -0.4207(3) 0.0491(6) Uani 1 1 d . . .
C11 C 0.70448(11) 0.56377(12) -0.3865(3) 0.0448(5) Uani 1 1 d . . .
H11 H 0.7431 0.5749 -0.4452 0.054 Uiso 1 1 calc R . .
C12 C 0.69014(10) 0.60431(11) -0.2686(2) 0.0352(5) Uani 1 1 d . . .
H12 H 0.7189 0.6429 -0.2464 0.042 Uiso 1 1 calc R . .
C13 C 0.67859(16) 0.46390(18) -0.5512(4) 0.0804(11) Uani 1 1 d . . .
H13D H 0.7289 0.4581 -0.5611 0.121 Uiso 1 1 calc R . .
H13E H 0.6602 0.4874 -0.6359 0.121 Uiso 1 1 calc R . .
H13F H 0.6566 0.4182 -0.5415 0.121 Uiso 1 1 calc R . .
C14 C 0.76000(10) 0.62466(9) 0.1786(2) 0.0304(4) Uani 1 1 d . A .
C15 C 0.79771(11) 0.56677(10) 0.2221(2) 0.0357(5) Uani 1 1 d . . .
H15 H 0.7880 0.5226 0.1814 0.043 Uiso 1 1 calc R . .
C16 C 0.84899(12) 0.57305(11) 0.3238(3) 0.0437(5) Uani 1 1 d . . .
H16 H 0.8744 0.5332 0.3527 0.052 Uiso 1 1 calc R . .
C17 C 0.86373(12) 0.63653(12) 0.3839(3) 0.0470(6) Uani 1 1 d . . .
H17 H 0.8980 0.6406 0.4563 0.056 Uiso 1 1 calc R . .
C18 C 0.82789(13) 0.69395(12) 0.3373(3) 0.0561(7) Uani 1 1 d . . .
H18 H 0.8387 0.7381 0.3766 0.067 Uiso 1 1 calc R . .
C19 C 0.77637(12) 0.68901(11) 0.2346(3) 0.0498(7) Uani 1 1 d . . .
H19 H 0.7526 0.7294 0.2030 0.060 Uiso 1 1 calc R . .
N1 N 0.63492(8) 0.70392(8) 0.13189(18) 0.0304(3) Uani 1 1 d . . .
N2 N 0.61422(8) 0.63341(9) -0.06924(18) 0.0348(4) Uani 1 1 d . . .
H2 H 0.5721 0.6510 -0.0742 0.042 Uiso 1 1 calc R A .
N3 N 0.71038(8) 0.61470(8) 0.06946(19) 0.0325(4) Uani 1 1 d . . .
H3 H 0.7184 0.5800 0.0106 0.039 Uiso 1 1 calc R A .
O1 O 0.52994(7) 0.72900(7) 0.01633(15) 0.0341(3) Uani 1 1 d . . .
S1 S 0.62276(4) 0.81683(6) 0.34128(10) 0.0449(3) Uani 0.794(2) 1 d PD A 1
C1 C 0.5718(2) 0.8836(3) 0.4014(5) 0.0510(11) Uani 0.794(2) 1 d PD A 1
H1 H 0.5819 0.9095 0.4851 0.061 Uiso 0.794(2) 1 calc PR A 1
C2 C 0.5158(3) 0.8957(3) 0.3177(5) 0.0496(12) Uani 0.794(2) 1 d PD A 1
H2A H 0.4839 0.9328 0.3309 0.059 Uiso 0.794(2) 1 calc PR A 1
C3 C 0.5115(2) 0.84664(19) 0.2107(5) 0.0410(8) Uani 0.794(2) 1 d PD A 1
H3A H 0.4748 0.8466 0.1430 0.049 Uiso 0.794(2) 1 calc PR A 1
C4 C 0.5636(2) 0.7980(3) 0.2083(7) 0.0320(10) Uani 0.794(2) 1 d PD A 1
C5 C 0.57573(10) 0.74018(10) 0.1087(2) 0.0303(4) Uani 0.794(2) 1 d PD A 1
S1A S 0.4949(2) 0.8482(3) 0.1770(5) 0.0449(3) Uani 0.206(2) 1 d PD A 2
C1A C 0.5118(12) 0.8898(15) 0.335(2) 0.0510(11) Uani 0.206(2) 1 d PD A 2
H1A H 0.4782 0.9158 0.3861 0.061 Uiso 0.206(2) 1 calc PR A 2
C2A C 0.5785(10) 0.8816(10) 0.378(3) 0.0496(12) Uani 0.206(2) 1 d PD A 2
H2AA H 0.6046 0.9136 0.4331 0.059 Uiso 0.206(2) 1 calc PR A 2
C3A C 0.6019(7) 0.8184(8) 0.3267(16) 0.0410(8) Uani 0.206(2) 1 d PD A 2
H3AA H 0.6349 0.7899 0.3740 0.049 Uiso 0.206(2) 1 calc PR A 2
C4A C 0.5712(10) 0.8024(12) 0.199(3) 0.0320(10) Uani 0.206(2) 1 d PD A 2
C5A C 0.57573(10) 0.74018(10) 0.1087(2) 0.0303(4) Uani 0.206(2) 1 d PD A 2
C6D C 0.86616(9) 0.16341(9) 0.4614(2) 0.0273(4) Uani 1 1 d . B .
C7D C 0.91755(10) 0.13915(9) 0.6986(2) 0.0288(4) Uani 1 1 d . B .
C8D C 0.97540(10) 0.10211(10) 0.7404(2) 0.0327(4) Uani 1 1 d . . .
H8D H 0.9949 0.0682 0.6786 0.039 Uiso 1 1 calc R . .
C9D C 1.00500(10) 0.11448(10) 0.8726(2) 0.0354(4) Uani 1 1 d . . .
H9D H 1.0448 0.0888 0.9011 0.043 Uiso 1 1 calc R . .
C10D C 0.97732(11) 0.16372(11) 0.9637(2) 0.0351(4) Uani 1 1 d . . .
C11D C 0.91999(11) 0.20202(11) 0.9185(2) 0.0361(5) Uani 1 1 d . . .
H11D H 0.9013 0.2369 0.9789 0.043 Uiso 1 1 calc R . .
C12D C 0.89016(10) 0.19000(10) 0.7875(2) 0.0346(4) Uani 1 1 d . . .
H12D H 0.8510 0.2163 0.7580 0.041 Uiso 1 1 calc R . .
C13D C 1.00876(14) 0.17602(13) 1.1081(3) 0.0516(6) Uani 1 1 d . . .
H13A H 0.9780 0.1571 1.1818 0.077 Uiso 1 1 calc R . .
H13B H 1.0147 0.2260 1.1234 0.077 Uiso 1 1 calc R . .
H13C H 1.0541 0.1530 1.1134 0.077 Uiso 1 1 calc R . .
C14D C 0.89171(10) 0.27860(9) 0.3550(2) 0.0297(4) Uani 1 1 d . B .
C15D C 0.95008(11) 0.31716(10) 0.3168(2) 0.0362(4) Uani 1 1 d . . .
H15D H 0.9945 0.3049 0.3531 0.043 Uiso 1 1 calc R . .
C16D C 0.94312(13) 0.37360(12) 0.2254(3) 0.0460(5) Uani 1 1 d . . .
H16D H 0.9829 0.3998 0.1994 0.055 Uiso 1 1 calc R . .
C17D C 0.87881(15) 0.39181(12) 0.1723(3) 0.0514(6) Uani 1 1 d . . .
H17D H 0.8743 0.4300 0.1089 0.062 Uiso 1 1 calc R . .
C18D C 0.82118(13) 0.35391(11) 0.2125(3) 0.0465(6) Uani 1 1 d . . .
H18D H 0.7769 0.3664 0.1759 0.056 Uiso 1 1 calc R . .
C19D C 0.82663(11) 0.29796(11) 0.3050(2) 0.0370(5) Uani 1 1 d . . .
H19D H 0.7863 0.2732 0.3339 0.044 Uiso 1 1 calc R . .
N1D N 0.81898(8) 0.14858(8) 0.36161(17) 0.0290(3) Uani 1 1 d . . .
N2D N 0.88210(9) 0.12093(8) 0.57011(18) 0.0334(4) Uani 1 1 d . . .
H2D H 0.8694 0.0773 0.5613 0.040 Uiso 1 1 calc R B .
N3D N 0.90210(8) 0.22349(8) 0.45317(18) 0.0297(3) Uani 1 1 d . . .
H3D H 0.9357 0.2291 0.5157 0.036 Uiso 1 1 calc R B .
O1D O 0.78137(7) 0.04582(7) 0.46990(15) 0.0331(3) Uani 1 1 d . . .
S1D S 0.72396(4) 0.13867(3) 0.11652(9) 0.0420(2) Uani 0.885(3) 1 d PD B 1
C1D C 0.6587(2) 0.08944(18) 0.0386(4) 0.0489(8) Uani 0.885(3) 1 d PD B 1
H1D H 0.6379 0.1002 -0.0506 0.059 Uiso 0.885(3) 1 calc PR B 1
C2D C 0.6408(6) 0.0337(5) 0.1195(7) 0.0503(7) Uani 0.885(3) 1 d PD B 1
H2DA H 0.6054 0.0013 0.0956 0.060 Uiso 0.885(3) 1 calc PR B 1
C3D C 0.68103(17) 0.03066(19) 0.2412(4) 0.0416(7) Uani 0.885(3) 1 d PD B 1
H3DA H 0.6753 -0.0051 0.3100 0.050 Uiso 0.885(3) 1 calc PR B 1
C4D C 0.72907(14) 0.08132(14) 0.2574(3) 0.0312(7) Uani 0.885(3) 1 d PD B 1
C5D C 0.77940(9) 0.09089(9) 0.3732(2) 0.0289(4) Uani 0.885(3) 1 d PD B 1
S1E S 0.6724(4) 0.0157(4) 0.2771(8) 0.0420(2) Uani 0.115(3) 1 d PD B 2
C1E C 0.644(5) 0.040(4) 0.108(5) 0.0489(8) Uani 0.115(3) 1 d PD B 2
H1E H 0.6125 0.0122 0.0548 0.059 Uiso 0.115(3) 1 calc PR B 2
C2E C 0.6705(18) 0.1003(17) 0.057(3) 0.0503(7) Uani 0.115(3) 1 d PD B 2
H2E H 0.6534 0.1251 -0.0235 0.060 Uiso 0.115(3) 1 calc PR B 2
C3E C 0.7262(14) 0.1199(13) 0.140(2) 0.0416(7) Uani 0.115(3) 1 d PD B 2
H3E H 0.7623 0.1503 0.1105 0.050 Uiso 0.115(3) 1 calc PR B 2
C4E C 0.7222(12) 0.0899(10) 0.270(3) 0.0312(7) Uani 0.115(3) 1 d PD B 2
C5E C 0.77940(9) 0.09089(9) 0.3732(2) 0.0289(4) Uani 0.115(3) 1 d PD B 2






_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






































































































C6 N1 1.334(3) . ?
C6 N2 1.339(2) . ?
C6 N3 1.355(2) . ?
C7 C12 1.379(3) . ?
C7 C8 1.385(3) . ?
C7 N2 1.426(3) . ?
C8 C9 1.390(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 C13 1.507(4) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C14 C19 1.382(3) . ?
C14 C15 1.392(3) . ?
C14 N3 1.413(2) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 C5 1.354(2) . ?
N2 H2 0.8800 . ?
N3 H3 0.8800 . ?
O1 C5 1.254(2) . ?
S1 C1 1.712(4) . ?
S1 C4 1.728(4) . ?
C1 C2 1.355(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.471(3) . ?
S1A C1A 1.712(7) . ?
S1A C4A 1.727(7) . ?
C1A C2A 1.355(6) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.382(8) . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.373(7) . ?
C3A H3AA 0.9500 . ?
C6D N1D 1.335(2) . ?
C6D N2D 1.342(2) . ?
C6D N3D 1.350(2) . ?
C7D C8D 1.380(3) . ?
C7D C12D 1.390(3) . ?
C7D N2D 1.428(3) . ?
C8D C9D 1.385(3) . ?
C8D H8D 0.9500 . ?
C9D C10D 1.382(3) . ?
C9D H9D 0.9500 . ?
C10D C11D 1.394(3) . ?
C10D C13D 1.502(3) . ?
C11D C12D 1.375(3) . ?
C11D H11D 0.9500 . ?
C12D H12D 0.9500 . ?
C13D H13A 0.9800 . ?
C13D H13B 0.9800 . ?
C13D H13C 0.9800 . ?
C14D C19D 1.389(3) . ?
C14D C15D 1.394(3) . ?
C14D N3D 1.419(2) . ?
C15D C16D 1.390(3) . ?
C15D H15D 0.9500 . ?
C16D C17D 1.380(4) . ?
C16D H16D 0.9500 . ?
C17D C18D 1.381(4) . ?
C17D H17D 0.9500 . ?
C18D C19D 1.387(3) . ?
C18D H18D 0.9500 . ?
C19D H19D 0.9500 . ?
N1D C5D 1.352(2) . ?
N2D H2D 0.8800 . ?
N3D H3D 0.8800 . ?
O1D C5D 1.256(2) . ?
S1D C4D 1.724(3) . ?
S1D C1D 1.736(3) . ?
C1D C2D 1.359(4) . ?
C1D H1D 0.9500 . ?
C2D C3D 1.381(5) . ?
C2D H2DA 0.9500 . ?
C3D C4D 1.353(4) . ?
C3D H3DA 0.9500 . ?
C4D C5D 1.467(3) . ?
S1E C4E 1.723(6) . ?
S1E C1E 1.738(6) . ?
C1E C2E 1.361(6) . ?
C1E H1E 0.9500 . ?
C2E C3E 1.381(7) . ?
C2E H2E 0.9500 . ?
C3E C4E 1.352(7) . ?
C3E H3E 0.9500 . ?



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






























































































































































N1 C6 N2 123.78(18) . . ?
N1 C6 N3 119.68(17) . . ?
N2 C6 N3 116.54(18) . . ?
C12 C7 C8 119.8(2) . . ?
C12 C7 N2 120.70(17) . . ?
C8 C7 N2 119.31(19) . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 118.7(2) . . ?
C9 C10 C13 120.8(2) . . ?
C11 C10 C13 120.5(3) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C7 C12 C11 119.77(19) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C10 C13 H13D 109.5 . . ?
C10 C13 H13E 109.5 . . ?
H13D C13 H13E 109.5 . . ?
C10 C13 H13F 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C19 C14 C15 119.19(18) . . ?
C19 C14 N3 123.45(17) . . ?
C15 C14 N3 117.15(16) . . ?
C16 C15 C14 120.43(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 121.7(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C18 119.27(19) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C6 N1 C5 119.67(16) . . ?
C6 N2 C7 127.82(17) . . ?
C6 N2 H2 116.1 . . ?
C7 N2 H2 116.1 . . ?
C6 N3 C14 127.94(17) . . ?
C6 N3 H3 116.0 . . ?
C14 N3 H3 116.0 . . ?
C1 S1 C4 91.02(19) . . ?
C2 C1 S1 113.3(4) . . ?
C2 C1 H1 123.4 . . ?
S1 C1 H1 123.4 . . ?
C1 C2 C3 110.6(5) . . ?
C1 C2 H2A 124.7 . . ?
C3 C2 H2A 124.7 . . ?
C4 C3 C2 115.8(4) . . ?
C4 C3 H3A 122.1 . . ?
C2 C3 H3A 122.1 . . ?
C3 C4 C5 130.0(4) . . ?
C3 C4 S1 109.0(2) . . ?
C5 C4 S1 120.8(2) . . ?
O1 C5 N1 127.87(19) . . ?
O1 C5 C4 117.1(2) . . ?
N1 C5 C4 115.0(2) . . ?
C1A S1A C4A 88.6(8) . . ?
C2A C1A S1A 112.5(14) . . ?
C2A C1A H1A 123.7 . . ?
S1A C1A H1A 123.7 . . ?
C1A C2A C3A 108.0(17) . . ?
C1A C2A H2AA 126.0 . . ?
C3A C2A H2AA 126.0 . . ?
C4A C3A C2A 111.1(12) . . ?
C4A C3A H3AA 124.5 . . ?
C2A C3A H3AA 124.5 . . ?
C3A C4A S1A 110.8(8) . . ?
N1D C6D N2D 123.87(17) . . ?
N1D C6D N3D 119.48(17) . . ?
N2D C6D N3D 116.63(17) . . ?
C8D C7D C12D 120.04(19) . . ?
C8D C7D N2D 119.89(18) . . ?
C12D C7D N2D 119.82(17) . . ?
C7D C8D C9D 119.83(19) . . ?
C7D C8D H8D 120.1 . . ?
C9D C8D H8D 120.1 . . ?
C10D C9D C8D 120.77(18) . . ?
C10D C9D H9D 119.6 . . ?
C8D C9D H9D 119.6 . . ?
C9D C10D C11D 118.7(2) . . ?
C9D C10D C13D 120.6(2) . . ?
C11D C10D C13D 120.6(2) . . ?
C12D C11D C10D 120.9(2) . . ?
C12D C11D H11D 119.6 . . ?
C10D C11D H11D 119.6 . . ?
C11D C12D C7D 119.69(18) . . ?
C11D C12D H12D 120.2 . . ?
C7D C12D H12D 120.2 . . ?
C10D C13D H13A 109.5 . . ?
C10D C13D H13B 109.5 . . ?
H13A C13D H13B 109.5 . . ?
C10D C13D H13C 109.5 . . ?
H13A C13D H13C 109.5 . . ?
H13B C13D H13C 109.5 . . ?
C19D C14D C15D 119.88(18) . . ?
C19D C14D N3D 123.13(18) . . ?
C15D C14D N3D 116.83(17) . . ?
C16D C15D C14D 119.8(2) . . ?
C16D C15D H15D 120.1 . . ?
C14D C15D H15D 120.1 . . ?
C17D C16D C15D 120.5(2) . . ?
C17D C16D H16D 119.8 . . ?
C15D C16D H16D 119.8 . . ?
C16D C17D C18D 119.3(2) . . ?
C16D C17D H17D 120.4 . . ?
C18D C17D H17D 120.4 . . ?
C17D C18D C19D 121.3(2) . . ?
C17D C18D H18D 119.3 . . ?
C19D C18D H18D 119.3 . . ?
C18D C19D C14D 119.2(2) . . ?
C18D C19D H19D 120.4 . . ?
C14D C19D H19D 120.4 . . ?
C6D N1D C5D 120.23(16) . . ?
C6D N2D C7D 126.86(16) . . ?
C6D N2D H2D 116.6 . . ?
C7D N2D H2D 116.6 . . ?
C6D N3D C14D 127.27(16) . . ?
C6D N3D H3D 116.4 . . ?
C14D N3D H3D 116.4 . . ?
C4D S1D C1D 90.80(15) . . ?
C2D C1D S1D 112.4(3) . . ?
C2D C1D H1D 123.8 . . ?
S1D C1D H1D 123.8 . . ?
C1D C2D C3D 110.6(4) . . ?
C1D C2D H2DA 124.7 . . ?
C3D C2D H2DA 124.7 . . ?
C4D C3D C2D 116.5(4) . . ?
C4D C3D H3DA 121.7 . . ?
C2D C3D H3DA 121.7 . . ?
C3D C4D C5D 128.7(3) . . ?
C3D C4D S1D 109.7(2) . . ?
C5D C4D S1D 121.59(19) . . ?
O1D C5D N1D 127.51(18) . . ?
O1D C5D C4D 117.86(19) . . ?
N1D C5D C4D 114.63(19) . . ?
C4E S1E C1E 85.4(10) . . ?
C2E C1E S1E 115.7(17) . . ?
C2E C1E H1E 122.1 . . ?
S1E C1E H1E 122.1 . . ?
C1E C2E C3E 109(2) . . ?
C1E C2E H2E 125.6 . . ?
C3E C2E H2E 125.6 . . ?
C4E C3E C2E 110.6(15) . . ?
C4E C3E H3E 124.7 . . ?
C2E C3E H3E 124.7 . . ?
C3E C4E S1E 114.8(12) . . ?



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 C7 C8 C9 -1.6(3) . . . . ?
N2 C7 C8 C9 173.6(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C8 C9 C10 C13 -179.2(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C13 C10 C11 C12 178.8(2) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
N2 C7 C12 C11 -173.86(19) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C19 C14 C15 C16 2.5(4) . . . . ?
N3 C14 C15 C16 177.3(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 -2.0(4) . . . . ?
C16 C17 C18 C19 1.7(5) . . . . ?
C15 C14 C19 C18 -2.8(4) . . . . ?
N3 C14 C19 C18 -177.3(2) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
N2 C6 N1 C5 1.1(3) . . . . ?
N3 C6 N1 C5 -178.48(17) . . . . ?
N1 C6 N2 C7 166.94(19) . . . . ?
N3 C6 N2 C7 -13.5(3) . . . . ?
C12 C7 N2 C6 -60.3(3) . . . . ?
C8 C7 N2 C6 124.6(2) . . . . ?
N1 C6 N3 C14 -2.4(3) . . . . ?
N2 C6 N3 C14 178.03(18) . . . . ?
C19 C14 N3 C6 -31.8(3) . . . . ?
C15 C14 N3 C6 153.5(2) . . . . ?
C4 S1 C1 C2 -5.5(6) . . . . ?
S1 C1 C2 C3 4.9(7) . . . . ?
C1 C2 C3 C4 -1.3(8) . . . . ?
C2 C3 C4 C5 -178.5(6) . . . . ?
C2 C3 C4 S1 -2.8(7) . . . . ?
C1 S1 C4 C3 4.5(5) . . . . ?
C1 S1 C4 C5 -179.2(6) . . . . ?
C6 N1 C5 O1 4.6(3) . . . . ?
C6 N1 C5 C4 -177.6(4) . . . . ?
C3 C4 C5 O1 -5.7(9) . . . . ?
S1 C4 C5 O1 179.0(4) . . . . ?
C3 C4 C5 N1 176.3(6) . . . . ?
S1 C4 C5 N1 1.0(7) . . . . ?
C4A S1A C1A C2A 15(3) . . . . ?
S1A C1A C2A C3A -29(3) . . . . ?
C1A C2A C3A C4A 32(3) . . . . ?
C2A C3A C4A S1A -21(3) . . . . ?
C1A S1A C4A C3A 4(3) . . . . ?
C12D C7D C8D C9D 1.7(3) . . . . ?
N2D C7D C8D C9D -172.61(17) . . . . ?
C7D C8D C9D C10D -0.1(3) . . . . ?
C8D C9D C10D C11D -1.6(3) . . . . ?
C8D C9D C10D C13D 178.8(2) . . . . ?
C9D C10D C11D C12D 1.7(3) . . . . ?
C13D C10D C11D C12D -178.7(2) . . . . ?
C10D C11D C12D C7D -0.2(3) . . . . ?
C8D C7D C12D C11D -1.5(3) . . . . ?
N2D C7D C12D C11D 172.77(18) . . . . ?
C19D C14D C15D C16D -1.9(3) . . . . ?
N3D C14D C15D C16D -177.45(19) . . . . ?
C14D C15D C16D C17D 0.1(3) . . . . ?
C15D C16D C17D C18D 0.9(4) . . . . ?
C16D C17D C18D C19D 0.0(4) . . . . ?
C17D C18D C19D C14D -1.8(4) . . . . ?
C15D C14D C19D C18D 2.8(3) . . . . ?
N3D C14D C19D C18D 178.0(2) . . . . ?
N2D C6D N1D C5D 6.1(3) . . . . ?
N3D C6D N1D C5D -175.71(16) . . . . ?
N1D C6D N2D C7D -162.76(18) . . . . ?
N3D C6D N2D C7D 19.0(3) . . . . ?
C8D C7D N2D C6D -126.9(2) . . . . ?
C12D C7D N2D C6D 58.8(3) . . . . ?
N1D C6D N3D C14D 6.4(3) . . . . ?
N2D C6D N3D C14D -175.34(17) . . . . ?
C19D C14D N3D C6D 35.2(3) . . . . ?
C15D C14D N3D C6D -149.4(2) . . . . ?
C4D S1D C1D C2D 2.0(7) . . . . ?
S1D C1D C2D C3D -1.4(12) . . . . ?
C1D C2D C3D C4D -0.1(12) . . . . ?
C2D C3D C4D C5D -178.9(7) . . . . ?
C2D C3D C4D S1D 1.6(8) . . . . ?
C1D S1D C4D C3D -2.0(3) . . . . ?
C1D S1D C4D C5D 178.5(3) . . . . ?
C6D N1D C5D O1D -1.0(3) . . . . ?
C6D N1D C5D C4D 179.2(2) . . . . ?
C3D C4D C5D O1D 2.7(4) . . . . ?
S1D C4D C5D O1D -177.94(17) . . . . ?
C3D C4D C5D N1D -177.5(3) . . . . ?
S1D C4D C5D N1D 1.9(3) . . . . ?
C4E S1E C1E C2E -1(7) . . . . ?
S1E C1E C2E C3E 14(9) . . . . ?
C1E C2E C3E C4E -22(6) . . . . ?
C2E C3E C4E S1E 22(4) . . . . ?
C1E S1E C4E C3E -12(5) . . . . ?



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        27.50

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.232

_refine_diff_density_min         -0.262

_refine_diff_density_rms         0.038

_database_code_depnum_ccdc_archive 'CCDC 984605'
#######################################################################
#
#                 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_tatuan



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C18 H15 N3 O S'

_chemical_formula_weight         321.39



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



loop_

_symmetry_equiv_pos_as_xyz


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



_cell_length_a                   6.4059(9)

_cell_length_b                   10.8648(16)

_cell_length_c                   12.1262(17)

_cell_angle_alpha                79.907(2)

_cell_angle_beta                 82.063(2)

_cell_angle_gamma                73.721(2)

_cell_volume                     794.1(2)

_cell_formula_units_Z            2

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    6035

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      27.42



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.44

_exptl_crystal_size_min          0.38

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.344

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             336

_exptl_absorpt_coefficient_mu    0.211

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9108

_exptl_absorpt_correction_T_max  0.9240

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(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  'APEX II'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            8598

_diffrn_reflns_av_R_equivalents  0.0141

_diffrn_reflns_av_sigmaI/netI    0.0186

_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         2.42

_diffrn_reflns_theta_max         27.44

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             3538

_reflns_number_gt                3287

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  APEX-II(BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        APEX-II

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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)+(0.0338P)²+0.5463P] 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         3538

_refine_ls_number_parameters     208

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0381

_refine_ls_R_factor_gt           0.0354

_refine_ls_wR_factor_ref         0.0898

_refine_ls_wR_factor_gt          0.0882

_refine_ls_goodness_of_fit_ref   1.063

_refine_ls_restrained_S_all      1.063

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group






































S1 S 0.52111(6) 0.60447(3) 0.84496(3) 0.02372(11) Uani 1 1 d . . .
O1 O 0.44347(16) 0.89443(9) 0.59793(8) 0.0181(2) Uani 1 1 d . . .
N1 N 0.60874(18) 0.85545(11) 0.76574(9) 0.0165(2) Uani 1 1 d . . .
N2 N 0.78304(19) 0.98643(11) 0.82551(9) 0.0188(2) Uani 1 1 d . . .
H2 H 0.8261 1.0582 0.8121 0.023 Uiso 1 1 calc R . .
N3 N 0.66515(18) 1.04519(11) 0.64838(9) 0.0168(2) Uani 1 1 d . . .
H3 H 0.5832 1.0371 0.5989 0.020 Uiso 1 1 calc R . .
C1 C 0.6838(2) 0.96067(13) 0.74396(11) 0.0156(3) Uani 1 1 d . . .
C2 C 0.4953(2) 0.82954(12) 0.69017(11) 0.0144(2) Uani 1 1 d . . .
C3 C 0.4256(2) 0.70915(13) 0.72815(11) 0.0160(3) Uani 1 1 d . . .
C4 C 0.3660(3) 0.50408(14) 0.83193(13) 0.0259(3) Uani 1 1 d . . .
H4 H 0.3652 0.4259 0.8812 0.031 Uiso 1 1 calc R . .
C5 C 0.2435(3) 0.54887(14) 0.74289(12) 0.0240(3) Uani 1 1 d . . .
H5 H 0.1461 0.5057 0.7240 0.029 Uiso 1 1 calc R . .
C6 C 0.2767(2) 0.66753(13) 0.68088(11) 0.0182(3) Uani 1 1 d . . .
H6 H 0.2061 0.7121 0.6159 0.022 Uiso 1 1 calc R . .
C7 C 0.8239(2) 0.90741(13) 0.93115(11) 0.0166(3) Uani 1 1 d . . .
C8 C 0.7627(2) 0.96526(14) 1.02813(11) 0.0194(3) Uani 1 1 d . . .
H8 H 0.6864 1.0543 1.0239 0.023 Uiso 1 1 calc R . .
C9 C 0.8140(2) 0.89195(15) 1.13141(11) 0.0226(3) Uani 1 1 d . . .
H9 H 0.7720 0.9309 1.1981 0.027 Uiso 1 1 calc R . .
C10 C 0.9262(2) 0.76212(16) 1.13754(12) 0.0247(3) Uani 1 1 d . . .
H10 H 0.9626 0.7124 1.2082 0.030 Uiso 1 1 calc R . .
C11 C 0.9852(2) 0.70481(15) 1.03994(13) 0.0248(3) Uani 1 1 d . . .
H11 H 1.0605 0.6156 1.0442 0.030 Uiso 1 1 calc R . .
C12 C 0.9348(2) 0.77719(14) 0.93645(12) 0.0206(3) Uani 1 1 d . . .
H12 H 0.9758 0.7381 0.8698 0.025 Uiso 1 1 calc R . .
C13 C 0.7716(2) 1.14780(12) 0.62264(10) 0.0153(3) Uani 1 1 d . . .
C14 C 0.6537(2) 1.27473(13) 0.63177(11) 0.0195(3) Uani 1 1 d . . .
H14 H 0.5019 1.2941 0.6555 0.023 Uiso 1 1 calc R . .
C15 C 0.7599(3) 1.37316(14) 0.60594(12) 0.0227(3) Uani 1 1 d . . .
H15 H 0.6806 1.4602 0.6119 0.027 Uiso 1 1 calc R . .
C16 C 0.9817(2) 1.34395(14) 0.57150(11) 0.0220(3) Uani 1 1 d . . .
H16 H 1.0541 1.4112 0.5541 0.026 Uiso 1 1 calc R . .
C17 C 1.0984(2) 1.21733(14) 0.56238(11) 0.0204(3) Uani 1 1 d . . .
H17 H 1.2501 1.1980 0.5384 0.024 Uiso 1 1 calc R . .
C18 C 0.9937(2) 1.11858(13) 0.58832(11) 0.0174(3) Uani 1 1 d . . .
H18 H 1.0735 1.0315 0.5826 0.021 Uiso 1 1 calc R . .






_geom_special_details            
; 

 All esds (except the esd in the dihedral angle between two l.s. planes) 

 are estimated using the full covariance matrix.  The cell esds are taken 

 into account individually in the estimation of esds in distances, angles 

 and torsion angles; correlations between esds in cell parameters are only 

 used when they are defined by crystal symmetry.  An approximate (isotropic) 

 treatment of cell esds is used for estimating esds involving l.s. planes. 

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag








































S1 C4 1.7069(15) . ?
S1 C3 1.7201(13) . ?
O1 C2 1.2463(16) . ?
N1 C1 1.3322(17) . ?
N1 C2 1.3552(16) . ?
N2 C1 1.3532(17) . ?
N2 C7 1.4240(17) . ?
N2 H2 0.8800 . ?
N3 C1 1.3433(16) . ?
N3 C13 1.4322(16) . ?
N3 H3 0.8800 . ?
C2 C3 1.4771(18) . ?
C3 C6 1.3880(18) . ?
C4 C5 1.362(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4291(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3876(19) . ?
C7 C12 1.389(2) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3860(19) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.3881(19) . ?
C13 C14 1.3896(19) . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3881(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?



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






























































C4 S1 C3 91.78(7) . . ?
C1 N1 C2 120.08(11) . . ?
C1 N2 C7 125.62(11) . . ?
C1 N2 H2 117.2 . . ?
C7 N2 H2 117.2 . . ?
C1 N3 C13 123.50(11) . . ?
C1 N3 H3 118.3 . . ?
C13 N3 H3 118.3 . . ?
N1 C1 N3 125.41(12) . . ?
N1 C1 N2 117.54(12) . . ?
N3 C1 N2 117.04(12) . . ?
O1 C2 N1 128.29(12) . . ?
O1 C2 C3 119.08(11) . . ?
N1 C2 C3 112.62(11) . . ?
C6 C3 C2 126.84(12) . . ?
C6 C3 S1 111.83(10) . . ?
C2 C3 S1 121.30(10) . . ?
C5 C4 S1 112.30(11) . . ?
C5 C4 H4 123.8 . . ?
S1 C4 H4 123.8 . . ?
C4 C5 C6 112.98(13) . . ?
C4 C5 H5 123.5 . . ?
C6 C5 H5 123.5 . . ?
C3 C6 C5 111.10(13) . . ?
C3 C6 H6 124.5 . . ?
C5 C6 H6 124.5 . . ?
C8 C7 C12 120.71(12) . . ?
C8 C7 N2 118.48(12) . . ?
C12 C7 N2 120.69(12) . . ?
C7 C8 C9 119.48(13) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.27(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.80(13) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.36(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 119.38(13) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C18 C13 C14 120.63(12) . . ?
C18 C13 N3 119.06(12) . . ?
C14 C13 N3 120.31(12) . . ?
C13 C14 C15 119.47(13) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 119.89(13) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.41(13) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.02(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 119.58(13) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?



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







































C2 N1 C1 N3 -2.9(2) . . . . ?
C2 N1 C1 N2 175.65(12) . . . . ?
C13 N3 C1 N1 -171.85(12) . . . . ?
C13 N3 C1 N2 9.61(19) . . . . ?
C7 N2 C1 N1 3.2(2) . . . . ?
C7 N2 C1 N3 -178.19(12) . . . . ?
C1 N1 C2 O1 -1.4(2) . . . . ?
C1 N1 C2 C3 179.85(11) . . . . ?
O1 C2 C3 C6 -11.0(2) . . . . ?
N1 C2 C3 C6 167.89(13) . . . . ?
O1 C2 C3 S1 171.36(10) . . . . ?
N1 C2 C3 S1 -9.79(16) . . . . ?
C4 S1 C3 C6 0.31(11) . . . . ?
C4 S1 C3 C2 178.31(11) . . . . ?
C3 S1 C4 C5 -0.73(13) . . . . ?
S1 C4 C5 C6 0.96(17) . . . . ?
C2 C3 C6 C5 -177.70(12) . . . . ?
S1 C3 C6 C5 0.16(15) . . . . ?
C4 C5 C6 C3 -0.72(18) . . . . ?
C1 N2 C7 C8 -130.21(14) . . . . ?
C1 N2 C7 C12 53.86(19) . . . . ?
C12 C7 C8 C9 0.2(2) . . . . ?
N2 C7 C8 C9 -175.72(12) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C8 C7 C12 C11 -0.2(2) . . . . ?
N2 C7 C12 C11 175.64(12) . . . . ?
C1 N3 C13 C18 76.16(17) . . . . ?
C1 N3 C13 C14 -103.97(15) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
N3 C13 C14 C15 -179.73(12) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C13 0.41(19) . . . . ?
C14 C13 C18 C17 -0.31(19) . . . . ?
N3 C13 C18 C17 179.55(11) . . . . ?



_diffrn_measured_fraction_theta_max 0.973

_diffrn_reflns_theta_full        27.44

_diffrn_measured_fraction_theta_full 0.973

_refine_diff_density_max         0.385

_refine_diff_density_min         -0.377

_refine_diff_density_rms         0.046

_database_code_depnum_ccdc_archive 'CCDC 984606'
#######################################################################
#
#                 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_rkb



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C18 H21 N3 O S'

_chemical_formula_weight         327.44



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           Orthorhombic

_symmetry_space_group_name_H-M   Pna2(1)



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   11.0663(16)

_cell_length_b                   10.4930(15)

_cell_length_c                   14.541(2)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1688.5(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    110(2)

_cell_measurement_reflns_used    8437

_cell_measurement_theta_min      2.39

_cell_measurement_theta_max      27.50



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.56

_exptl_crystal_size_mid          0.33

_exptl_crystal_size_min          0.32

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.288

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    0.200

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.8963

_exptl_absorpt_correction_T_max  0.9388

_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      110(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  'APEX II'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13429

_diffrn_reflns_av_R_equivalents  0.0285

_diffrn_reflns_av_sigmaI/netI    0.0231

_diffrn_reflns_limit_h_min       -13

_diffrn_reflns_limit_h_max       13

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         2.39

_diffrn_reflns_theta_max         25.00

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_decay_%        0

_reflns_number_total             2952

_reflns_number_gt                2886

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'

_computing_cell_refinement       
; 

  APEX-II(BRUKER-NONIUS, 2003) 

;

_computing_data_reduction        APEX-II

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    Olex2

_computing_publication_material  'Bruker SHELXTL'



_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)+(0.0367P)²+0.2365P] 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   -0.04(6)

_refine_ls_number_reflns         2952

_refine_ls_number_parameters     215

_refine_ls_number_restraints     13

_refine_ls_R_factor_all          0.0256

_refine_ls_R_factor_gt           0.0250

_refine_ls_wR_factor_ref         0.0633

_refine_ls_wR_factor_gt          0.0627

_refine_ls_goodness_of_fit_ref   1.053

_refine_ls_restrained_S_all      1.055

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group




















































S1 S 0.07171(7) 0.18366(7) 0.04108(8) 0.0250(2) Uani 0.6879(16) 1 d PD A 1
C1 C 0.20531(12) 0.12064(13) 0.00601(9) 0.0173(3) Uani 0.6879(16) 1 d PD A 1
C2 C 0.2709(3) 0.2129(3) -0.0416(3) 0.0252(10) Uani 0.6879(16) 1 d PD A 1
H2 H 0.3490 0.1969 -0.0661 0.030 Uiso 0.6879(16) 1 calc PR A 1
C3 C 0.2158(4) 0.3257(5) -0.0502(4) 0.0251(4) Uani 0.6879(16) 1 d PD A 1
H3 H 0.2503 0.3959 -0.0820 0.030 Uiso 0.6879(16) 1 calc PR A 1
C4 C 0.1053(5) 0.3302(4) -0.0087(3) 0.0251(4) Uani 0.6879(16) 1 d PD A 1
H4 H 0.0541 0.4029 -0.0073 0.030 Uiso 0.6879(16) 1 calc PR A 1
S1A S 0.2981(2) 0.2100(2) -0.0568(2) 0.0250(2) Uani 0.3121(16) 1 d PD A 2
C1A C 0.20531(12) 0.12064(13) 0.00601(9) 0.0173(3) Uani 0.3121(16) 1 d PD A 2
C2A C 0.1014(7) 0.1881(7) 0.0298(7) 0.0252(10) Uani 0.3121(16) 1 d PD A 2
H2A H 0.0375 0.1519 0.0649 0.030 Uiso 0.3121(16) 1 calc PR A 2
C3A C 0.0995(11) 0.3079(10) -0.0009(7) 0.0251(4) Uani 0.3121(16) 1 d PD A 2
H3A H 0.0338 0.3641 0.0102 0.030 Uiso 0.3121(16) 1 calc PR A 2
C4A C 0.2003(8) 0.3435(12) -0.0499(9) 0.0251(4) Uani 0.3121(16) 1 d PD A 2
H4A H 0.2149 0.4253 -0.0756 0.030 Uiso 0.3121(16) 1 calc PR A 2
O1 O 0.15448(8) -0.07943(9) 0.06730(7) 0.0189(2) Uani 1 1 d . A .
N1 N 0.34908(10) -0.04589(10) 0.00973(8) 0.0152(2) Uani 1 1 d . A .
N2 N 0.34444(10) -0.22501(11) 0.10688(8) 0.0174(2) Uani 1 1 d . A .
H2B H 0.2791 -0.1921 0.1320 0.021 Uiso 1 1 calc R . .
N3 N 0.49785(10) -0.20015(10) 0.00084(8) 0.0162(2) Uani 1 1 d . A .
H3B H 0.5352 -0.2626 0.0295 0.019 Uiso 1 1 calc R . .
C5 C 0.23481(12) -0.01204(12) 0.03045(9) 0.0154(3) Uani 1 1 d . . .
C6 C 0.39401(11) -0.15719(11) 0.03953(9) 0.0139(3) Uani 1 1 d . . .
C7 C 0.38421(13) -0.34731(13) 0.14487(10) 0.0178(3) Uani 1 1 d . . .
H7 H 0.4330 -0.3925 0.0970 0.021 Uiso 1 1 calc R A .
C8 C 0.27396(13) -0.42806(13) 0.16683(11) 0.0222(3) Uani 1 1 d . A .
H8A H 0.2252 -0.4403 0.1104 0.027 Uiso 1 1 calc R . .
H8B H 0.2232 -0.3838 0.2129 0.027 Uiso 1 1 calc R . .
C9 C 0.31312(15) -0.55778(14) 0.20453(11) 0.0265(4) Uani 1 1 d . . .
H9A H 0.2407 -0.6078 0.2216 0.032 Uiso 1 1 calc R A .
H9B H 0.3571 -0.6053 0.1561 0.032 Uiso 1 1 calc R . .
C10 C 0.39385(16) -0.54265(16) 0.28802(11) 0.0308(4) Uani 1 1 d . A .
H10A H 0.4232 -0.6276 0.3075 0.037 Uiso 1 1 calc R . .
H10B H 0.3462 -0.5061 0.3392 0.037 Uiso 1 1 calc R . .
C11 C 0.50155(15) -0.45683(15) 0.26851(12) 0.0297(4) Uani 1 1 d . . .
H11A H 0.5473 -0.4429 0.3262 0.036 Uiso 1 1 calc R A .
H11B H 0.5560 -0.4996 0.2242 0.036 Uiso 1 1 calc R . .
C12 C 0.46275(14) -0.32877(14) 0.22951(11) 0.0245(3) Uani 1 1 d . A .
H12A H 0.4170 -0.2808 0.2767 0.029 Uiso 1 1 calc R . .
H12B H 0.5352 -0.2783 0.2130 0.029 Uiso 1 1 calc R . .
C13 C 0.55259(13) -0.15464(12) -0.08139(9) 0.0153(3) Uani 1 1 d . . .
C14 C 0.67626(13) -0.17425(12) -0.09024(10) 0.0183(3) Uani 1 1 d . A .
H14 H 0.7207 -0.2100 -0.0407 0.022 Uiso 1 1 calc R . .
C15 C 0.73497(14) -0.14178(13) -0.17122(10) 0.0223(3) Uani 1 1 d . . .
H15 H 0.8195 -0.1554 -0.1769 0.027 Uiso 1 1 calc R A .
C16 C 0.67104(15) -0.08982(15) -0.24346(11) 0.0272(3) Uani 1 1 d . A .
H16 H 0.7111 -0.0681 -0.2991 0.033 Uiso 1 1 calc R . .
C17 C 0.54785(15) -0.06959(15) -0.23433(11) 0.0286(4) Uani 1 1 d . . .
H17 H 0.5040 -0.0327 -0.2838 0.034 Uiso 1 1 calc R A .
C18 C 0.48771(14) -0.10245(14) -0.15414(10) 0.0215(3) Uani 1 1 d . A .
H18 H 0.4030 -0.0895 -0.1489 0.026 Uiso 1 1 calc R . .






_geom_special_details            
; 

 All esds (except the esd in the dihedral angle between two l.s. planes) 

 are estimated using the full covariance matrix.  The cell esds are taken 

 into account individually in the estimation of esds in distances, angles 

 and torsion angles; correlations between esds in cell parameters are only 

 used when they are defined by crystal symmetry.  An approximate (isotropic) 

 treatment of cell esds is used for estimating esds involving l.s. planes. 

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag




















































S1 C1 1.6980(15) . ?
S1 C4 1.740(3) . ?
C1 C2 1.394(4) . ?
C1 C5 1.4734(18) . ?
C2 C3 1.337(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
S1A C4A 1.773(8) . ?
C2A C3A 1.335(10) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.375(8) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
O1 C5 1.2560(16) . ?
N1 C6 1.3413(17) . ?
N1 C5 1.3476(17) . ?
N2 C6 1.3290(18) . ?
N2 C7 1.4648(17) . ?
N2 H2B 0.8800 . ?
N3 C6 1.3566(18) . ?
N3 C13 1.4230(18) . ?
N3 H3B 0.8800 . ?
C7 C12 1.519(2) . ?
C7 C8 1.519(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.530(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(2) . ?
C13 C18 1.391(2) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag























































































C1 S1 C4 91.89(19) . . ?
C2 C1 C5 131.35(19) . . ?
C2 C1 S1 109.39(17) . . ?
C5 C1 S1 119.24(10) . . ?
C3 C2 C1 115.1(3) . . ?
C3 C2 H2 122.5 . . ?
C1 C2 H2 122.5 . . ?
C2 C3 C4 113.5(6) . . ?
C2 C3 H3 123.3 . . ?
C4 C3 H3 123.3 . . ?
C3 C4 S1 110.2(5) . . ?
C3 C4 H4 124.9 . . ?
S1 C4 H4 124.9 . . ?
C3A C2A H2A 123.0 . . ?
C2A C3A C4A 114.6(14) . . ?
C2A C3A H3A 122.7 . . ?
C4A C3A H3A 122.7 . . ?
C3A C4A S1A 108.0(13) . . ?
C3A C4A H4A 126.0 . . ?
S1A C4A H4A 126.0 . . ?
C6 N1 C5 120.34(11) . . ?
C6 N2 C7 128.54(11) . . ?
C6 N2 H2B 115.7 . . ?
C7 N2 H2B 115.7 . . ?
C6 N3 C13 126.70(11) . . ?
C6 N3 H3B 116.6 . . ?
C13 N3 H3B 116.6 . . ?
O1 C5 N1 127.67(12) . . ?
O1 C5 C1 118.56(12) . . ?
N1 C5 C1 113.77(11) . . ?
N2 C6 N1 123.46(12) . . ?
N2 C6 N3 118.51(11) . . ?
N1 C6 N3 117.99(12) . . ?
N2 C7 C12 111.42(12) . . ?
N2 C7 C8 109.06(11) . . ?
C12 C7 C8 111.13(12) . . ?
N2 C7 H7 108.4 . . ?
C12 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C7 C8 C9 110.12(11) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 111.15(13) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 112.00(13) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.82(13) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C7 C12 C11 110.52(13) . . ?
C7 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C18 119.75(13) . . ?
C14 C13 N3 116.57(12) . . ?
C18 C13 N3 123.47(13) . . ?
C15 C14 C13 120.22(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.23(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.48(14) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.98(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.34(14) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?



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








































C4 S1 C1 C2 0.4(3) . . . . ?
C4 S1 C1 C5 178.78(19) . . . . ?
C5 C1 C2 C3 -179.1(3) . . . . ?
S1 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 S1 -0.8(7) . . . . ?
C1 S1 C4 C3 0.2(5) . . . . ?
C2A C3A C4A S1A 1.4(16) . . . . ?
C6 N1 C5 O1 -9.1(2) . . . . ?
C6 N1 C5 C1 170.58(11) . . . . ?
C2 C1 C5 O1 -173.9(3) . . . . ?
S1 C1 C5 O1 8.16(17) . . . . ?
C2 C1 C5 N1 6.4(3) . . . . ?
S1 C1 C5 N1 -171.59(11) . . . . ?
C7 N2 C6 N1 179.56(13) . . . . ?
C7 N2 C6 N3 -2.8(2) . . . . ?
C5 N1 C6 N2 -16.78(19) . . . . ?
C5 N1 C6 N3 165.59(12) . . . . ?
C13 N3 C6 N2 168.08(12) . . . . ?
C13 N3 C6 N1 -14.17(19) . . . . ?
C6 N2 C7 C12 95.10(16) . . . . ?
C6 N2 C7 C8 -141.85(14) . . . . ?
N2 C7 C8 C9 178.65(12) . . . . ?
C12 C7 C8 C9 -58.13(16) . . . . ?
C7 C8 C9 C10 56.18(17) . . . . ?
C8 C9 C10 C11 -54.12(17) . . . . ?
C9 C10 C11 C12 53.51(18) . . . . ?
N2 C7 C12 C11 179.24(12) . . . . ?
C8 C7 C12 C11 57.38(16) . . . . ?
C10 C11 C12 C7 -54.62(17) . . . . ?
C6 N3 C13 C14 155.85(13) . . . . ?
C6 N3 C13 C18 -29.5(2) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
N3 C13 C14 C15 174.98(12) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 C13 1.0(2) . . . . ?
C14 C13 C18 C17 -0.6(2) . . . . ?
N3 C13 C18 C17 -175.11(13) . . . . ?



_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.123

_refine_diff_density_min         -0.161

_refine_diff_density_rms         0.032

_database_code_depnum_ccdc_archive 'CCDC 984607'
