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

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#                                CCDC 
# 
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#  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
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data_094

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-(4-amino-5-cyano-3-phenylpyridin-2-yl)-4-methyl-N-phenylbenzenesulfonamide 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C25 H21 N4 O3 S), C H4 O'
_chemical_formula_sum            'C25.50 H23 N4 O3.50 S'
_chemical_formula_weight         473.55

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   P21/c

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

_cell_length_a                   18.9964(13)
_cell_length_b                   14.4609(10)
_cell_length_c                   19.8858(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.723(5)
_cell_angle_gamma                90.00
_cell_volume                     4696.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3121
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.55

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9173
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21986
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.1117
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.05
_reflns_number_total             7132
_reflns_number_gt                3914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0300P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7132
_refine_ls_number_parameters     616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
S4 S -0.13164(5) -0.69382(6) -0.61529(5) 0.0284(2) Uani 1 1 d . . .
O5 O -0.17394(14) -0.60811(16) -0.62742(13) 0.0385(6) Uani 1 1 d . . .
O6 O -0.16543(13) -0.77293(17) -0.59705(13) 0.0367(6) Uani 1 1 d . . .
O10 O 0.19033(16) -0.55799(19) -0.57220(14) 0.0473(7) Uani 1 1 d . . .
N1 N -0.03597(16) -0.67595(19) -0.55034(15) 0.0282(7) Uani 1 1 d . . .
N2 N -0.01323(17) -0.81016(19) -0.47249(15) 0.0305(7) Uani 1 1 d . . .
H2N H -0.0646 -0.8259 -0.4978 0.037 Uiso 1 1 d R . .
N6 N 0.1139(2) -0.8613(2) -0.56294(18) 0.0479(9) Uani 1 1 d . . .
N8 N 0.15048(17) -0.5565(2) -0.45978(16) 0.0359(8) Uani 1 1 d . . .
H8A H 0.1686 -0.5377 -0.4828 0.043 Uiso 1 1 d R . .
C6 C 0.0389(2) -0.8681(2) -0.4067(2) 0.0333(9) Uani 1 1 d . . .
C9 C 0.0090(2) -0.7311(2) -0.49174(19) 0.0263(8) Uani 1 1 d . . .
C10 C 0.1259(2) -0.7839(3) -0.5500(2) 0.0336(9) Uani 1 1 d . . .
C13 C 0.09552(19) -0.6416(2) -0.36997(18) 0.0255(8) Uani 1 1 d . . .
C18 C 0.1415(2) -0.6885(2) -0.53509(19) 0.0295(8) Uani 1 1 d . . .
C19 C -0.1301(2) -0.7195(2) -0.70115(18) 0.0277(8) Uani 1 1 d . . .
C21 C 0.09593(19) -0.6963(2) -0.43564(18) 0.0264(8) Uani 1 1 d . . .
H21 H 0.1308 -0.7506 -0.4119 0.032 Uiso 1 1 calc R . .
C32 C -0.1399(2) -0.7714(3) -0.8404(2) 0.0328(9) Uani 1 1 d . . .
C34 C 0.12950(19) -0.6437(2) -0.47924(19) 0.0272(8) Uani 1 1 d . . .
C35 C -0.1833(2) -0.6965(2) -0.8378(2) 0.0362(9) Uani 1 1 d . . .
H35 H -0.2163 -0.6633 -0.8834 0.043 Uiso 1 1 calc R . .
C37 C 0.1503(2) -0.6660(3) -0.2921(2) 0.0350(9) Uani 1 1 d . . .
H37 H 0.1875 -0.7137 -0.2807 0.042 Uiso 1 1 calc R . .
C38 C 0.0943(2) -0.5480(3) -0.2483(2) 0.0419(10) Uani 1 1 d . . .
H38 H 0.0932 -0.5173 -0.2078 0.050 Uiso 1 1 calc R . .
C41 C 0.0375(3) -0.8574(3) -0.3383(2) 0.0584(13) Uani 1 1 d . . .
H41 H 0.0039 -0.8137 -0.3345 0.070 Uiso 1 1 calc R . .
C44 C 0.0410(2) -0.5221(3) -0.3253(2) 0.0382(10) Uani 1 1 d . . .
H44 H 0.0050 -0.4731 -0.3363 0.046 Uiso 1 1 calc R . .
C46 C 0.1491(2) -0.6193(3) -0.2319(2) 0.0423(10) Uani 1 1 d . . .
H46 H 0.1853 -0.6361 -0.1802 0.051 Uiso 1 1 calc R . .
C48 C 0.1739(2) -0.6417(3) -0.5769(2) 0.0392(10) Uani 1 1 d . . .
H48 H 0.1835 -0.6771 -0.6105 0.047 Uiso 1 1 calc R . .
C49 C 0.0415(2) -0.5695(2) -0.3858(2) 0.0307(8) Uani 1 1 d . . .
H49 H 0.0052 -0.5526 -0.4374 0.037 Uiso 1 1 calc R . .
C50 C -0.0852(2) -0.7939(2) -0.7019(2) 0.0372(9) Uani 1 1 d . . .
H50 H -0.0520 -0.8269 -0.6562 0.045 Uiso 1 1 calc R . .
C54 C -0.1793(2) -0.6692(2) -0.7687(2) 0.0340(9) Uani 1 1 d . . .
H54 H -0.2088 -0.6184 -0.7679 0.041 Uiso 1 1 calc R . .
C55 C -0.0899(2) -0.8192(3) -0.7716(2) 0.0400(10) Uani 1 1 d . . .
H55 H -0.0590 -0.8689 -0.7721 0.048 Uiso 1 1 calc R . .
C58 C 0.0880(4) -0.9143(4) -0.2753(3) 0.088(2) Uani 1 1 d . . .
H58 H 0.0879 -0.9083 -0.2288 0.105 Uiso 1 1 calc R . .
C62 C 0.1385(3) -0.9797(4) -0.2803(3) 0.090(2) Uani 1 1 d . . .
H62 H 0.1728 -1.0163 -0.2374 0.108 Uiso 1 1 calc R . .
C63 C 0.0867(3) -0.9339(3) -0.4125(3) 0.0542(12) Uani 1 1 d . . .
H63 H 0.0855 -0.9416 -0.4595 0.065 Uiso 1 1 calc R . .
C64 C -0.1474(2) -0.8037(3) -0.9166(2) 0.0467(11) Uani 1 1 d . . .
H64A H -0.1796 -0.8592 -0.9340 0.070 Uiso 1 1 calc R . .
H64B H -0.0939 -0.8159 -0.9083 0.070 Uiso 1 1 calc R . .
H64C H -0.1735 -0.7564 -0.9556 0.070 Uiso 1 1 calc R . .
C67 C 0.1370(3) -0.9896(3) -0.3491(4) 0.0791(17) Uani 1 1 d . . .
H67 H 0.1699 -1.0338 -0.3535 0.095 Uiso 1 1 calc R . .
S5 S 0.63509(5) -0.30898(6) -0.37705(5) 0.0292(2) Uani 1 1 d . . .
O7 O 0.66604(14) -0.22876(18) -0.39697(13) 0.0391(6) Uani 1 1 d . . .
O8 O 0.67826(14) -0.39358(17) -0.36645(13) 0.0422(7) Uani 1 1 d . . .
O9 O 0.31583(17) -0.4609(2) -0.41539(16) 0.0532(8) Uani 1 1 d . . .
N3 N 0.53899(17) -0.32889(18) -0.43984(15) 0.0278(7) Uani 1 1 d . . .
N4 N 0.51001(18) -0.1887(2) -0.51140(16) 0.0378(8) Uani 1 1 d . . .
H4N H 0.5610 -0.1741 -0.4830 0.045 Uiso 1 1 d R . .
N5 N 0.4009(2) -0.1564(3) -0.4091(2) 0.0566(10) Uani 1 1 d . . .
N7 N 0.34920(17) -0.4509(2) -0.53279(16) 0.0354(7) Uani 1 1 d . . .
H7A H 0.3322 -0.4725 -0.5098 0.042 Uiso 1 1 d R . .
C23 C 0.37323(19) -0.3660(2) -0.50793(19) 0.0287(8) Uani 1 1 d . . .
C24 C 0.4584(2) -0.4263(2) -0.60788(19) 0.0310(9) Uani 1 1 d . . .
H24 H 0.4959 -0.4456 -0.5573 0.037 Uiso 1 1 calc R . .
C25 C 0.6360(2) -0.2837(2) -0.29008(18) 0.0272(8) Uani 1 1 d . . .
C27 C 0.3653(2) -0.3278(3) -0.4473(2) 0.0341(9) Uani 1 1 d . . .
C28 C 0.40405(19) -0.3077(2) -0.55066(18) 0.0263(8) Uani 1 1 d . . .
H28 H 0.3678 -0.2539 -0.5719 0.032 Uiso 1 1 calc R . .
C29 C 0.4031(2) -0.4384(3) -0.7462(2) 0.0391(10) Uani 1 1 d . . .
H29 H 0.4038 -0.4650 -0.7885 0.047 Uiso 1 1 calc R . .
C30 C 0.4903(2) -0.2715(2) -0.49587(19) 0.0270(8) Uani 1 1 d . . .
C31 C 0.3854(2) -0.2331(3) -0.4267(2) 0.0406(10) Uani 1 1 d . . .
C33 C 0.6415(2) -0.2381(3) -0.1519(2) 0.0386(10) Uani 1 1 d . . .
C36 C 0.4038(2) -0.3562(2) -0.61952(19) 0.0262(8) Uani 1 1 d . . .
C39 C 0.4559(3) -0.1258(3) -0.5718(2) 0.0457(11) Uani 1 1 d . . .
C40 C 0.3479(2) -0.3288(3) -0.6956(2) 0.0375(10) Uani 1 1 d . . .
H40 H 0.3102 -0.2824 -0.7046 0.045 Uiso 1 1 calc R . .
C42 C 0.4577(2) -0.4680(3) -0.6712(2) 0.0366(9) Uani 1 1 d . . .
H42 H 0.4940 -0.5158 -0.6630 0.044 Uiso 1 1 calc R . .
C43 C 0.3485(2) -0.3708(3) -0.7584(2) 0.0459(11) Uani 1 1 d . . .
H43 H 0.3109 -0.3522 -0.8092 0.055 Uiso 1 1 calc R . .
C45 C 0.5942(2) -0.2080(3) -0.2872(2) 0.0397(10) Uani 1 1 d . . .
H45 H 0.5638 -0.1720 -0.3317 0.048 Uiso 1 1 calc R . .
C47 C 0.5969(2) -0.1852(3) -0.2187(2) 0.0469(11) Uani 1 1 d . . .
H47 H 0.5685 -0.1336 -0.2173 0.056 Uiso 1 1 calc R . .
C51 C 0.3339(2) -0.3791(3) -0.4067(2) 0.0453(11) Uani 1 1 d . . .
H51 H 0.3266 -0.3469 -0.3703 0.054 Uiso 1 1 calc R . .
C52 C 0.6835(2) -0.3135(3) -0.1553(2) 0.0420(10) Uani 1 1 d . . .
H52 H 0.7143 -0.3491 -0.1107 0.050 Uiso 1 1 calc R . .
C53 C 0.4072(3) -0.0668(3) -0.5592(3) 0.0607(13) Uani 1 1 d . . .
H53 H 0.4102 -0.0665 -0.5110 0.073 Uiso 1 1 calc R . .
C56 C 0.6809(2) -0.3377(2) -0.2240(2) 0.0374(9) Uani 1 1 d . . .
H56 H 0.7089 -0.3896 -0.2257 0.045 Uiso 1 1 calc R . .
C59 C 0.3516(4) -0.0056(4) -0.6867(4) 0.105(3) Uani 1 1 d . . .
H59 H 0.3160 0.0348 -0.7257 0.126 Uiso 1 1 calc R . .
C60 C 0.3536(3) -0.0076(3) -0.6180(4) 0.091(2) Uani 1 1 d . . .
H60 H 0.3192 0.0307 -0.6100 0.109 Uiso 1 1 calc R . .
C61 C 0.4543(4) -0.1234(3) -0.6413(3) 0.0797(17) Uani 1 1 d . . .
H61 H 0.4882 -0.1620 -0.6496 0.096 Uiso 1 1 calc R . .
C65 C 0.6434(3) -0.2112(3) -0.0775(2) 0.0641(14) Uani 1 1 d . . .
H65A H 0.6703 -0.2588 -0.0390 0.096 Uiso 1 1 calc R . .
H65B H 0.5884 -0.2037 -0.0882 0.096 Uiso 1 1 calc R . .
H65C H 0.6726 -0.1540 -0.0581 0.096 Uiso 1 1 calc R . .
C66 C 0.4007(5) -0.0618(4) -0.7002(3) 0.104(3) Uani 1 1 d . . .
H66 H 0.3989 -0.0595 -0.7478 0.124 Uiso 1 1 calc R . .
O11 O 0.13804(18) -0.0627(2) -0.53038(17) 0.0677(9) Uani 1 1 d . . .
H11 H 0.1183 -0.0131 -0.5518 0.101 Uiso 1 1 d R . .
C57 C 0.2239(3) -0.0525(4) -0.4804(3) 0.0803(16) Uani 1 1 d . . .
H57A H 0.2482 -0.1121 -0.4609 0.120 Uiso 1 1 calc R . .
H57B H 0.2348 -0.0130 -0.4373 0.120 Uiso 1 1 calc R . .
H57C H 0.2468 -0.0256 -0.5091 0.120 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
S4 O5 1.429(2) . ?
S4 O6 1.446(2) . ?
S4 N1 1.625(3) . ?
S4 C19 1.762(3) . ?
O10 C48 1.242(4) . ?
N1 C9 1.306(4) . ?
N2 C9 1.341(4) . ?
N2 C6 1.439(4) . ?
N2 H2N 0.8690 . ?
N6 C10 1.146(4) . ?
N8 C34 1.319(4) . ?
N8 H8A 0.7507 . ?
C6 C63 1.360(5) . ?
C6 C41 1.382(5) . ?
C9 C21 1.531(4) . ?
C10 C18 1.410(5) . ?
C13 C49 1.382(4) . ?
C13 C37 1.400(4) . ?
C13 C21 1.530(4) . ?
C18 C34 1.402(5) . ?
C18 C48 1.431(5) . ?
C19 C50 1.377(5) . ?
C19 C54 1.387(4) . ?
C21 C34 1.517(4) . ?
C21 H21 0.9800 . ?
C32 C35 1.378(5) . ?
C32 C55 1.386(5) . ?
C32 C64 1.522(5) . ?
C35 C54 1.393(5) . ?
C35 H35 0.9300 . ?
C37 C46 1.384(5) . ?
C37 H37 0.9300 . ?
C38 C46 1.381(5) . ?
C38 C44 1.387(5) . ?
C38 H38 0.9300 . ?
C41 C58 1.392(6) . ?
C41 H41 0.9300 . ?
C44 C49 1.389(4) . ?
C44 H44 0.9300 . ?
C46 H46 0.9300 . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
C50 C55 1.393(5) . ?
C50 H50 0.9300 . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
C58 C62 1.386(8) . ?
C58 H58 0.9300 . ?
C62 C67 1.360(7) . ?
C62 H62 0.9300 . ?
C63 C67 1.387(6) . ?
C63 H63 0.9300 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
C67 H67 0.9300 . ?
S5 O8 1.427(2) . ?
S5 O7 1.444(3) . ?
S5 N3 1.627(3) . ?
S5 C25 1.759(3) . ?
O9 C51 1.220(5) . ?
N3 C30 1.316(4) . ?
N4 C30 1.337(4) . ?
N4 C39 1.437(4) . ?
N4 H4N 0.8617 . ?
N5 C31 1.154(5) . ?
N7 C23 1.315(4) . ?
N7 H7A 0.7500 . ?
C23 C27 1.403(5) . ?
C23 C28 1.511(5) . ?
C24 C36 1.383(4) . ?
C24 C42 1.389(4) . ?
C24 H24 0.9300 . ?
C25 C45 1.371(5) . ?
C25 C56 1.385(4) . ?
C27 C31 1.425(5) . ?
C27 C51 1.431(5) . ?
C28 C30 1.524(4) . ?
C28 C36 1.536(4) . ?
C28 H28 0.9800 . ?
C29 C43 1.355(5) . ?
C29 C42 1.380(5) . ?
C29 H29 0.9300 . ?
C33 C52 1.373(5) . ?
C33 C47 1.386(5) . ?
C33 C65 1.512(5) . ?
C36 C40 1.390(4) . ?
C39 C61 1.368(6) . ?
C39 C53 1.372(6) . ?
C40 C43 1.392(5) . ?
C40 H40 0.9300 . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C45 C47 1.376(5) . ?
C45 H45 0.9300 . ?
C47 H47 0.9300 . ?
C51 H51 0.9300 . ?
C52 C56 1.387(5) . ?
C52 H52 0.9300 . ?
C53 C60 1.385(6) . ?
C53 H53 0.9300 . ?
C56 H56 0.9300 . ?
C59 C60 1.348(7) . ?
C59 C66 1.362(9) . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
C61 C66 1.408(7) . ?
C61 H61 0.9300 . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C66 H66 0.9300 . ?
O11 C57 1.419(5) . ?
O11 H11 0.8207 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S4 O6 116.43(16) . . ?
O5 S4 N1 107.48(14) . . ?
O6 S4 N1 112.71(14) . . ?
O5 S4 C19 107.81(15) . . ?
O6 S4 C19 107.77(15) . . ?
N1 S4 C19 103.80(16) . . ?
C9 N1 S4 124.6(2) . . ?
C9 N2 C6 125.8(3) . . ?
C9 N2 H2N 118.9 . . ?
C6 N2 H2N 114.9 . . ?
C34 N8 H8A 109.3 . . ?
C63 C6 C41 120.7(4) . . ?
C63 C6 N2 120.6(4) . . ?
C41 C6 N2 118.6(4) . . ?
N1 C9 N2 128.1(3) . . ?
N1 C9 C21 114.8(3) . . ?
N2 C9 C21 116.9(3) . . ?
N6 C10 C18 178.7(4) . . ?
C49 C13 C37 119.2(3) . . ?
C49 C13 C21 121.5(3) . . ?
C37 C13 C21 119.3(3) . . ?
C34 C18 C10 121.1(3) . . ?
C34 C18 C48 122.2(3) . . ?
C10 C18 C48 116.5(3) . . ?
C50 C19 C54 120.9(3) . . ?
C50 C19 S4 119.5(3) . . ?
C54 C19 S4 119.4(3) . . ?
C34 C21 C13 114.6(3) . . ?
C34 C21 C9 111.1(3) . . ?
C13 C21 C9 108.5(3) . . ?
C34 C21 H21 107.4 . . ?
C13 C21 H21 107.4 . . ?
C9 C21 H21 107.4 . . ?
C35 C32 C55 118.5(3) . . ?
C35 C32 C64 121.7(3) . . ?
C55 C32 C64 119.8(3) . . ?
N8 C34 C18 121.8(3) . . ?
N8 C34 C21 117.6(3) . . ?
C18 C34 C21 120.5(3) . . ?
C32 C35 C54 121.8(3) . . ?
C32 C35 H35 119.1 . . ?
C54 C35 H35 119.1 . . ?
C46 C37 C13 120.2(4) . . ?
C46 C37 H37 119.9 . . ?
C13 C37 H37 119.9 . . ?
C46 C38 C44 119.9(4) . . ?
C46 C38 H38 120.0 . . ?
C44 C38 H38 120.0 . . ?
C6 C41 C58 117.9(5) . . ?
C6 C41 H41 121.0 . . ?
C58 C41 H41 121.0 . . ?
C38 C44 C49 119.9(4) . . ?
C38 C44 H44 120.0 . . ?
C49 C44 H44 120.0 . . ?
C38 C46 C37 120.2(3) . . ?
C38 C46 H46 119.9 . . ?
C37 C46 H46 119.9 . . ?
O10 C48 C18 125.7(3) . . ?
O10 C48 H48 117.1 . . ?
C18 C48 H48 117.1 . . ?
C13 C49 C44 120.5(3) . . ?
C13 C49 H49 119.7 . . ?
C44 C49 H49 119.7 . . ?
C19 C50 C55 119.4(3) . . ?
C19 C50 H50 120.3 . . ?
C55 C50 H50 120.3 . . ?
C19 C54 C35 118.5(3) . . ?
C19 C54 H54 120.8 . . ?
C35 C54 H54 120.8 . . ?
C32 C55 C50 120.9(3) . . ?
C32 C55 H55 119.6 . . ?
C50 C55 H55 119.6 . . ?
C62 C58 C41 121.5(6) . . ?
C62 C58 H58 119.2 . . ?
C41 C58 H58 119.2 . . ?
C67 C62 C58 118.9(5) . . ?
C67 C62 H62 120.5 . . ?
C58 C62 H62 120.5 . . ?
C6 C63 C67 120.6(5) . . ?
C6 C63 H63 119.7 . . ?
C67 C63 H63 119.7 . . ?
C32 C64 H64A 109.5 . . ?
C32 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C32 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C62 C67 C63 120.3(5) . . ?
C62 C67 H67 119.8 . . ?
C63 C67 H67 119.8 . . ?
O8 S5 O7 116.44(16) . . ?
O8 S5 N3 107.25(14) . . ?
O7 S5 N3 112.71(14) . . ?
O8 S5 C25 108.45(15) . . ?
O7 S5 C25 107.56(15) . . ?
N3 S5 C25 103.60(15) . . ?
C30 N3 S5 124.5(2) . . ?
C30 N4 C39 126.5(3) . . ?
C30 N4 H4N 114.9 . . ?
C39 N4 H4N 118.5 . . ?
C23 N7 H7A 109.5 . . ?
N7 C23 C27 121.5(3) . . ?
N7 C23 C28 118.0(3) . . ?
C27 C23 C28 120.4(3) . . ?
C36 C24 C42 120.5(3) . . ?
C36 C24 H24 119.8 . . ?
C42 C24 H24 119.8 . . ?
C45 C25 C56 120.0(3) . . ?
C45 C25 S5 119.5(3) . . ?
C56 C25 S5 120.5(3) . . ?
C23 C27 C31 119.7(3) . . ?
C23 C27 C51 122.6(4) . . ?
C31 C27 C51 117.6(3) . . ?
C23 C28 C30 111.9(3) . . ?
C23 C28 C36 114.9(3) . . ?
C30 C28 C36 107.9(3) . . ?
C23 C28 H28 107.3 . . ?
C30 C28 H28 107.3 . . ?
C36 C28 H28 107.3 . . ?
C43 C29 C42 120.0(4) . . ?
C43 C29 H29 120.0 . . ?
C42 C29 H29 120.0 . . ?
N3 C30 N4 127.0(3) . . ?
N3 C30 C28 115.0(3) . . ?
N4 C30 C28 117.9(3) . . ?
N5 C31 C27 178.7(4) . . ?
C52 C33 C47 118.5(4) . . ?
C52 C33 C65 121.9(4) . . ?
C47 C33 C65 119.6(4) . . ?
C24 C36 C40 118.8(3) . . ?
C24 C36 C28 121.7(3) . . ?
C40 C36 C28 119.6(3) . . ?
C61 C39 C53 120.0(4) . . ?
C61 C39 N4 119.8(4) . . ?
C53 C39 N4 120.2(4) . . ?
C36 C40 C43 120.0(4) . . ?
C36 C40 H40 120.0 . . ?
C43 C40 H40 120.0 . . ?
C29 C42 C24 119.9(4) . . ?
C29 C42 H42 120.0 . . ?
C24 C42 H42 120.0 . . ?
C29 C43 C40 120.7(3) . . ?
C29 C43 H43 119.7 . . ?
C40 C43 H43 119.7 . . ?
C25 C45 C47 120.2(3) . . ?
C25 C45 H45 119.9 . . ?
C47 C45 H45 119.9 . . ?
C45 C47 C33 120.8(4) . . ?
C45 C47 H47 119.6 . . ?
C33 C47 H47 119.6 . . ?
O9 C51 C27 126.3(4) . . ?
O9 C51 H51 116.9 . . ?
C27 C51 H51 116.9 . . ?
C33 C52 C56 121.4(3) . . ?
C33 C52 H52 119.3 . . ?
C56 C52 H52 119.3 . . ?
C39 C53 C60 120.2(5) . . ?
C39 C53 H53 119.9 . . ?
C60 C53 H53 119.9 . . ?
C25 C56 C52 119.1(3) . . ?
C25 C56 H56 120.4 . . ?
C52 C56 H56 120.4 . . ?
C60 C59 C66 121.2(6) . . ?
C60 C59 H59 119.4 . . ?
C66 C59 H59 119.4 . . ?
C59 C60 C53 119.8(6) . . ?
C59 C60 H60 120.1 . . ?
C53 C60 H60 120.1 . . ?
C39 C61 C66 119.3(6) . . ?
C39 C61 H61 120.3 . . ?
C66 C61 H61 120.3 . . ?
C33 C65 H65A 109.5 . . ?
C33 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
C33 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C59 C66 C61 119.4(6) . . ?
C59 C66 H66 120.3 . . ?
C61 C66 H66 120.3 . . ?
C57 O11 H11 109.3 . . ?
O11 C57 H57A 109.5 . . ?
O11 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
O11 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.858
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.858
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 983980'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-amino-1,5-diphenyl-6-(tosylimino)-1,6-dihydropyridine-3-carboxamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C25 H22 N4 O3 S), C2 H3 O'
_chemical_formula_sum            'C25.50 H22.75 N4 O3.25 S'
_chemical_formula_weight         469.30

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                   11.546(3)
_cell_length_b                   13.445(3)
_cell_length_c                   17.259(4)
_cell_angle_alpha                96.731(4)
_cell_angle_beta                 99.473(4)
_cell_angle_gamma                113.714(4)
_cell_volume                     2369.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             983
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_process_details   ?
_exptl_special_details           
; 
 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11950
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8195
_reflns_number_gt                6059
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0984P)²+0.6130P] 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         8195
_refine_ls_number_parameters     624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1630
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.009
_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 0.33291(7) 0.92660(5) 0.14052(4) 0.03977(19) Uani 1 1 d . . .
O1 O 0.43817(19) 0.90032(17) 0.12684(12) 0.0536(5) Uani 1 1 d . . .
O2 O 0.3324(2) 1.02437(18) 0.11460(14) 0.0655(6) Uani 1 1 d . . .
O3 O 0.6801(2) 0.93307(19) 0.55183(14) 0.0722(7) Uani 1 1 d . . .
N35 N 0.3329(2) 0.82840(18) 0.32588(13) 0.0398(5) Uani 1 1 d . . .
N55 N 0.5558(3) 0.7506(2) 0.50280(15) 0.0585(7) Uani 1 1 d . . .
H55A H 0.5922 0.7321 0.5427 0.070 Uiso 1 1 calc R . .
H55B H 0.4950 0.7001 0.4651 0.070 Uiso 1 1 calc R . .
N57 N 0.7071(3) 1.0539(2) 0.43501(17) 0.0650(8) Uani 1 1 d . . .
H57A H 0.7451 1.1122 0.4163 0.078 Uiso 1 1 calc R . .
H57B H 0.7465 1.0436 0.4780 0.078 Uiso 1 1 calc R . .
N60 N 0.3144(2) 0.9275(2) 0.22715(13) 0.0476(6) Uani 1 1 d . . .
C1 C 0.5934(3) 0.8568(3) 0.49952(17) 0.0500(7) Uani 1 1 d . . .
C2 C 0.5241(3) 0.8814(2) 0.42819(16) 0.0406(6) Uani 1 1 d . . .
C3 C 0.4000(3) 0.8116(2) 0.39171(16) 0.0408(6) Uani 1 1 d . . .
H3 H 0.3582 0.7493 0.4124 0.049 Uiso 1 1 calc R . .
C4 C 0.3920(3) 0.9182(2) 0.29032(15) 0.0378(6) Uani 1 1 d . . .
C5 C 0.5198(3) 0.9937(2) 0.32714(15) 0.0381(6) Uani 1 1 d . . .
C6 C 0.5862(3) 0.9791(2) 0.39715(17) 0.0428(6) Uani 1 1 d . . .
C7 C 0.7159(4) 1.2002(4) 0.2133(2) 0.0839(12) Uani 1 1 d . . .
H7 H 0.7724 1.2055 0.1797 0.101 Uiso 1 1 calc R . .
C8 C 0.5811(3) 1.0964(2) 0.29442(17) 0.0445(7) Uani 1 1 d . . .
C9 C 0.6022(5) 1.2781(3) 0.2821(3) 0.0955(15) Uani 1 1 d . . .
H9 H 0.5813 1.3369 0.2952 0.115 Uiso 1 1 calc R . .
C10 C 0.6652(3) 1.1051(3) 0.2449(2) 0.0610(8) Uani 1 1 d . . .
H10 H 0.6882 1.0473 0.2324 0.073 Uiso 1 1 calc R . .
C11 C 0.5513(4) 1.1845(3) 0.3136(2) 0.0666(9) Uani 1 1 d . . .
H11 H 0.4963 1.1806 0.3481 0.080 Uiso 1 1 calc R . .
C12 C 0.6837(5) 1.2849(4) 0.2313(3) 0.0964(16) Uani 1 1 d . . .
H12 H 0.7167 1.3477 0.2092 0.116 Uiso 1 1 calc R . .
C13 C 0.1855(4) 0.7340(3) 0.0287(2) 0.0696(10) Uani 1 1 d . . .
H13 H 0.2636 0.7350 0.0205 0.084 Uiso 1 1 calc R . .
C14 C -0.0470(4) 0.7266(4) 0.0507(2) 0.0827(12) Uani 1 1 d . . .
H14 H -0.1251 0.7255 0.0588 0.099 Uiso 1 1 calc R . .
C15 C 0.1858(3) 0.8162(2) 0.08330(16) 0.0474(7) Uani 1 1 d . . .
C16 C -0.0489(4) 0.6438(3) -0.0039(3) 0.0785(11) Uani 1 1 d . . .
C17 C 0.0687(3) 0.8121(3) 0.0941(2) 0.0732(10) Uani 1 1 d . . .
H17 H 0.0676 0.8676 0.1312 0.088 Uiso 1 1 calc R . .
C18 C -0.1765(4) 0.5489(4) -0.0523(3) 0.121(2) Uani 1 1 d . . .
H18A H -0.1945 0.4851 -0.0280 0.182 Uiso 1 1 calc R . .
H18B H -0.1692 0.5306 -0.1062 0.182 Uiso 1 1 calc R . .
H18C H -0.2458 0.5711 -0.0531 0.182 Uiso 1 1 calc R . .
C19 C 0.0676(4) 0.6485(3) -0.0147(3) 0.0861(12) Uani 1 1 d . . .
H19 H 0.0682 0.5930 -0.0520 0.103 Uiso 1 1 calc R . .
C20 C 0.1980(3) 0.7504(2) 0.29250(16) 0.0438(7) Uani 1 1 d . . .
C21 C -0.0253(4) 0.7120(4) 0.2693(3) 0.0896(14) Uani 1 1 d . . .
H21 H -0.0905 0.7353 0.2720 0.108 Uiso 1 1 calc R . .
C22 C 0.1026(3) 0.7862(3) 0.2976(2) 0.0637(9) Uani 1 1 d . . .
H22 H 0.1247 0.8596 0.3200 0.076 Uiso 1 1 calc R . .
C23 C 0.0381(5) 0.5685(3) 0.2334(3) 0.0921(13) Uani 1 1 d . . .
H23 H 0.0152 0.4944 0.2122 0.111 Uiso 1 1 calc R . .
C24 C 0.1686(3) 0.6426(3) 0.2610(2) 0.0634(9) Uani 1 1 d . . .
H24 H 0.2339 0.6195 0.2581 0.076 Uiso 1 1 calc R . .
C25 C -0.0575(4) 0.6044(5) 0.2372(3) 0.1013(16) Uani 1 1 d . . .
H25 H -0.1445 0.5548 0.2177 0.122 Uiso 1 1 calc R . .
S2 S 0.33282(7) 0.44732(6) 0.35769(4) 0.03958(19) Uani 1 1 d . . .
O4 O 0.4266(2) 0.4112(2) 0.39402(13) 0.0635(6) Uani 1 1 d . . .
O5 O 0.3782(2) 0.56613(16) 0.37132(13) 0.0591(6) Uani 1 1 d . . .
O6 O 0.5338(3) 0.32812(19) -0.02066(15) 0.0826(8) Uani 1 1 d . . .
N3 N 0.2654(2) 0.26251(18) 0.16481(13) 0.0411(5) Uani 1 1 d . . .
N5 N 0.2684(2) 0.3871(2) 0.26847(13) 0.0487(6) Uani 1 1 d . . .
N9 N 0.4390(3) 0.1544(2) -0.00158(15) 0.0600(7) Uani 1 1 d . . .
H9A H 0.4663 0.1294 -0.0394 0.072 Uiso 1 1 calc R . .
H9B H 0.3929 0.1099 0.0249 0.072 Uiso 1 1 calc R . .
N15 N 0.5892(3) 0.4859(2) 0.10694(16) 0.0613(7) Uani 1 1 d . . .
H15A H 0.6291 0.5528 0.1342 0.074 Uiso 1 1 calc R . .
H15B H 0.6156 0.4662 0.0666 0.074 Uiso 1 1 calc R . .
C26 C 0.3302(3) 0.3686(2) 0.21301(15) 0.0381(6) Uani 1 1 d . . .
C27 C 0.4419(3) 0.4439(2) 0.19361(15) 0.0395(6) Uani 1 1 d . . .
C28 C 0.4853(3) 0.4118(2) 0.12751(16) 0.0413(6) Uani 1 1 d . . .
C29 C 0.4197(3) 0.3007(2) 0.08298(15) 0.0421(6) Uani 1 1 d . . .
C30 C 0.3106(3) 0.2313(2) 0.10302(16) 0.0435(7) Uani 1 1 d . . .
H30 H 0.2649 0.1593 0.0730 0.052 Uiso 1 1 calc R . .
C31 C 0.1492(3) 0.1786(2) 0.18023(18) 0.0487(7) Uani 1 1 d . . .
C32 C -0.0685(6) 0.0093(4) 0.2008(5) 0.127(2) Uani 1 1 d . . .
H32 H -0.1422 -0.0479 0.2081 0.152 Uiso 1 1 calc R . .
C33 C 0.0485(7) 0.0415(4) 0.2529(4) 0.117(2) Uani 1 1 d . . .
H33 H 0.0536 0.0056 0.2953 0.141 Uiso 1 1 calc R . .
C34 C 0.1602(4) 0.1271(3) 0.2437(2) 0.0778(11) Uani 1 1 d . . .
H34 H 0.2399 0.1490 0.2793 0.093 Uiso 1 1 calc R . .
C35 C -0.0776(5) 0.0602(4) 0.1386(4) 0.1179(18) Uani 1 1 d . . .
H35 H -0.1573 0.0376 0.1028 0.141 Uiso 1 1 calc R . .
C36 C 0.0317(4) 0.1458(3) 0.1285(3) 0.0798(11) Uani 1 1 d . . .
H36 H 0.0253 0.1814 0.0860 0.096 Uiso 1 1 calc R . .
C37 C 0.1984(3) 0.4016(2) 0.40314(15) 0.0406(6) Uani 1 1 d . . .
C38 C 0.0713(3) 0.3505(2) 0.36037(17) 0.0513(7) Uani 1 1 d . . .
H38 H 0.0518 0.3285 0.3049 0.062 Uiso 1 1 calc R . .
C39 C -0.0279(3) 0.3317(3) 0.40054(18) 0.0538(8) Uani 1 1 d . . .
H39 H -0.1138 0.2983 0.3712 0.065 Uiso 1 1 calc R . .
C40 C 0.2274(3) 0.4314(3) 0.48617(17) 0.0524(8) Uani 1 1 d . . .
H40 H 0.3134 0.4653 0.5155 0.063 Uiso 1 1 calc R . .
C41 C -0.0021(3) 0.3615(2) 0.48296(17) 0.0476(7) Uani 1 1 d . . .
C42 C 0.1267(3) 0.4099(3) 0.52456(17) 0.0552(8) Uani 1 1 d . . .
H42 H 0.1460 0.4286 0.5803 0.066 Uiso 1 1 calc R . .
C43 C -0.1104(3) 0.3418(3) 0.5258(2) 0.0637(9) Uani 1 1 d . . .
H43A H -0.1256 0.2776 0.5490 0.096 Uiso 1 1 calc R . .
H43B H -0.1882 0.3301 0.4882 0.096 Uiso 1 1 calc R . .
H43C H -0.0866 0.4053 0.5673 0.096 Uiso 1 1 calc R . .
C44 C 0.5156(3) 0.5621(2) 0.23626(15) 0.0392(6) Uani 1 1 d . . .
C45 C 0.6174(3) 0.5934(2) 0.30273(17) 0.0486(7) Uani 1 1 d . . .
H45 H 0.6348 0.5393 0.3244 0.058 Uiso 1 1 calc R . .
C46 C 0.4913(3) 0.6442(2) 0.20507(17) 0.0461(7) Uani 1 1 d . . .
H46 H 0.4227 0.6246 0.1608 0.055 Uiso 1 1 calc R . .
C47 C 0.5685(3) 0.7552(2) 0.23942(19) 0.0546(8) Uani 1 1 d . . .
H47 H 0.5518 0.8097 0.2180 0.066 Uiso 1 1 calc R . .
C48 C 0.6933(3) 0.7042(3) 0.33707(19) 0.0545(8) Uani 1 1 d . . .
H48 H 0.7608 0.7241 0.3820 0.065 Uiso 1 1 calc R . .
C49 C 0.6698(3) 0.7850(3) 0.3052(2) 0.0569(8) Uani 1 1 d . . .
H49 H 0.7221 0.8595 0.3280 0.068 Uiso 1 1 calc R . .
C99 C 0.4681(3) 0.2617(2) 0.01586(17) 0.0507(7) Uani 1 1 d . . .
O101 O 1.0087(8) 1.0852(6) 0.5789(5) 0.136(3) Uani 0.50 1 d P . .
C101 C 0.9644(8) 0.9125(7) 0.5396(6) 0.075(2) Uani 0.50 1 d P . .
H10A H 1.0378 0.9022 0.5655 0.090 Uiso 0.50 1 calc PR . .
H10B H 0.8915 0.8415 0.5188 0.090 Uiso 0.50 1 calc PR . .
H10C H 0.9425 0.9559 0.5777 0.090 Uiso 0.50 1 calc PR . .
C102 C 1.0079(8) 1.0382(12) 0.5168(6) 0.122(5) Uani 0.50 1 d P . .


_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 O2 1.439(2) . ?
S1 O1 1.442(2) . ?
S1 N60 1.544(2) . ?
S1 C15 1.772(3) . ?
O3 C1 1.236(4) . ?
N35 C3 1.361(3) . ?
N35 C4 1.396(3) . ?
N35 C20 1.451(4) . ?
N55 C1 1.327(4) . ?
N55 H55A 0.8600 . ?
N55 H55B 0.8600 . ?
N57 C6 1.343(4) . ?
N57 H57A 0.8600 . ?
N57 H57B 0.8600 . ?
N60 C4 1.345(3) . ?
C1 C2 1.499(4) . ?
C2 C3 1.347(4) . ?
C2 C6 1.436(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(4) . ?
C5 C6 1.399(4) . ?
C5 C8 1.501(4) . ?
C7 C12 1.352(6) . ?
C7 C10 1.393(5) . ?
C7 H7 0.9300 . ?
C8 C10 1.376(4) . ?
C8 C11 1.380(4) . ?
C9 C12 1.372(7) . ?
C9 C11 1.377(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C15 1.364(4) . ?
C13 C19 1.392(5) . ?
C13 H13 0.9300 . ?
C14 C16 1.362(6) . ?
C14 C17 1.379(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.375(4) . ?
C16 C19 1.366(6) . ?
C16 C18 1.526(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C20 C24 1.367(4) . ?
C20 C22 1.380(4) . ?
C21 C25 1.359(7) . ?
C21 C22 1.370(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C25 1.378(6) . ?
C23 C24 1.391(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
S2 O4 1.439(2) . ?
S2 O5 1.442(2) . ?
S2 N5 1.558(2) . ?
S2 C37 1.775(3) . ?
O6 C99 1.230(3) . ?
N3 C30 1.356(3) . ?
N3 C26 1.394(3) . ?
N3 C31 1.454(4) . ?
N5 C26 1.341(3) . ?
N9 C99 1.327(4) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N15 C28 1.349(4) . ?
N15 H15A 0.8600 . ?
N15 H15B 0.8600 . ?
C26 C27 1.405(4) . ?
C27 C28 1.409(3) . ?
C27 C44 1.491(4) . ?
C28 C29 1.423(4) . ?
C29 C30 1.361(4) . ?
C29 C99 1.495(4) . ?
C30 H30 0.9300 . ?
C31 C36 1.364(5) . ?
C31 C34 1.378(4) . ?
C32 C35 1.350(8) . ?
C32 C33 1.363(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.389(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.378(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.372(4) . ?
C37 C40 1.388(4) . ?
C38 C39 1.388(4) . ?
C38 H38 0.9300 . ?
C39 C41 1.380(4) . ?
C39 H39 0.9300 . ?
C40 C42 1.380(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.382(4) . ?
C41 C43 1.505(4) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.385(4) . ?
C44 C46 1.388(4) . ?
C45 C48 1.383(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.387(4) . ?
C46 H46 0.9300 . ?
C47 C49 1.378(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.372(4) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
O101 C102 1.175(9) . ?
C101 C102 1.254(17) 2_776 ?
C101 C102 1.675(19) . ?
C101 H10A 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10C 0.9600 . ?
C102 C102 1.05(2) 2_776 ?
C102 C101 1.254(16) 2_776 ?

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
O2 S1 O1 115.75(13) . . ?
O2 S1 N60 110.61(13) . . ?
O1 S1 N60 113.83(12) . . ?
O2 S1 C15 104.93(14) . . ?
O1 S1 C15 107.61(13) . . ?
N60 S1 C15 102.80(13) . . ?
C3 N35 C4 121.1(2) . . ?
C3 N35 C20 118.7(2) . . ?
C4 N35 C20 120.2(2) . . ?
C1 N55 H55A 120.0 . . ?
C1 N55 H55B 120.0 . . ?
H55A N55 H55B 120.0 . . ?
C6 N57 H57A 120.0 . . ?
C6 N57 H57B 120.0 . . ?
H57A N57 H57B 120.0 . . ?
C4 N60 S1 127.35(19) . . ?
O3 C1 N55 123.1(3) . . ?
O3 C1 C2 120.6(3) . . ?
N55 C1 C2 116.4(3) . . ?
C3 C2 C6 118.0(2) . . ?
C3 C2 C1 120.2(3) . . ?
C6 C2 C1 121.7(3) . . ?
C2 C3 N35 122.9(2) . . ?
C2 C3 H3 118.6 . . ?
N35 C3 H3 118.6 . . ?
N60 C4 N35 115.4(2) . . ?
N60 C4 C5 126.6(2) . . ?
N35 C4 C5 117.8(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 C8 120.2(2) . . ?
C4 C5 C8 118.7(2) . . ?
N57 C6 C5 121.2(3) . . ?
N57 C6 C2 119.6(3) . . ?
C5 C6 C2 119.1(2) . . ?
C12 C7 C10 120.5(4) . . ?
C12 C7 H7 119.7 . . ?
C10 C7 H7 119.7 . . ?
C10 C8 C11 118.7(3) . . ?
C10 C8 C5 122.0(3) . . ?
C11 C8 C5 119.2(3) . . ?
C12 C9 C11 120.3(4) . . ?
C12 C9 H9 119.9 . . ?
C11 C9 H9 119.9 . . ?
C8 C10 C7 120.2(3) . . ?
C8 C10 H10 119.9 . . ?
C7 C10 H10 119.9 . . ?
C9 C11 C8 120.5(4) . . ?
C9 C11 H11 119.7 . . ?
C8 C11 H11 119.7 . . ?
C7 C12 C9 119.8(4) . . ?
C7 C12 H12 120.1 . . ?
C9 C12 H12 120.1 . . ?
C15 C13 C19 119.6(4) . . ?
C15 C13 H13 120.2 . . ?
C19 C13 H13 120.2 . . ?
C16 C14 C17 121.2(4) . . ?
C16 C14 H14 119.4 . . ?
C17 C14 H14 119.4 . . ?
C13 C15 C17 118.8(3) . . ?
C13 C15 S1 121.5(3) . . ?
C17 C15 S1 119.7(3) . . ?
C14 C16 C19 117.8(4) . . ?
C14 C16 C18 121.6(4) . . ?
C19 C16 C18 120.5(5) . . ?
C15 C17 C14 120.8(4) . . ?
C15 C17 H17 119.6 . . ?
C14 C17 H17 119.6 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 C13 121.8(4) . . ?
C16 C19 H19 119.1 . . ?
C13 C19 H19 119.1 . . ?
C24 C20 C22 121.9(3) . . ?
C24 C20 N35 119.4(3) . . ?
C22 C20 N35 118.6(3) . . ?
C25 C21 C22 120.4(4) . . ?
C25 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C20 119.0(4) . . ?
C21 C22 H22 120.5 . . ?
C20 C22 H22 120.5 . . ?
C25 C23 C24 120.2(4) . . ?
C25 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C20 C24 C23 118.0(4) . . ?
C20 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C21 C25 C23 120.4(4) . . ?
C21 C25 H25 119.8 . . ?
C23 C25 H25 119.8 . . ?
O4 S2 O5 114.31(14) . . ?
O4 S2 N5 112.19(13) . . ?
O5 S2 N5 114.32(13) . . ?
O4 S2 C37 108.61(13) . . ?
O5 S2 C37 104.04(12) . . ?
N5 S2 C37 102.10(13) . . ?
C30 N3 C26 121.6(2) . . ?
C30 N3 C31 116.7(2) . . ?
C26 N3 C31 121.7(2) . . ?
C26 N5 S2 126.1(2) . . ?
C99 N9 H9A 120.0 . . ?
C99 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C28 N15 H15A 120.0 . . ?
C28 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
N5 C26 N3 113.6(2) . . ?
N5 C26 C27 128.6(2) . . ?
N3 C26 C27 117.6(2) . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 C44 123.5(2) . . ?
C28 C27 C44 116.1(2) . . ?
N15 C28 C27 120.1(3) . . ?
N15 C28 C29 120.1(2) . . ?
C27 C28 C29 119.8(2) . . ?
C30 C29 C28 117.7(2) . . ?
C30 C29 C99 121.1(3) . . ?
C28 C29 C99 121.2(2) . . ?
N3 C30 C29 122.9(3) . . ?
N3 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
C36 C31 C34 120.4(3) . . ?
C36 C31 N3 119.8(3) . . ?
C34 C31 N3 119.6(3) . . ?
C35 C32 C33 120.3(5) . . ?
C35 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 121.2(5) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C31 C34 C33 117.9(5) . . ?
C31 C34 H34 121.0 . . ?
C33 C34 H34 121.0 . . ?
C32 C35 C36 119.7(5) . . ?
C32 C35 H35 120.2 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 120.5(4) . . ?
C31 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C38 C37 C40 120.3(3) . . ?
C38 C37 S2 123.4(2) . . ?
C40 C37 S2 116.0(2) . . ?
C37 C38 C39 119.5(3) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C41 C39 C38 121.5(3) . . ?
C41 C39 H39 119.2 . . ?
C38 C39 H39 119.2 . . ?
C42 C40 C37 118.9(3) . . ?
C42 C40 H40 120.6 . . ?
C37 C40 H40 120.6 . . ?
C39 C41 C42 117.6(3) . . ?
C39 C41 C43 121.0(3) . . ?
C42 C41 C43 121.4(3) . . ?
C40 C42 C41 122.2(3) . . ?
C40 C42 H42 118.9 . . ?
C41 C42 H42 118.9 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C46 118.7(3) . . ?
C45 C44 C27 121.0(2) . . ?
C46 C44 C27 120.0(2) . . ?
C44 C45 C48 120.6(3) . . ?
C44 C45 H45 119.7 . . ?
C48 C45 H45 119.7 . . ?
C47 C46 C44 120.4(3) . . ?
C47 C46 H46 119.8 . . ?
C44 C46 H46 119.8 . . ?
C49 C47 C46 120.2(3) . . ?
C49 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C49 C48 C45 120.4(3) . . ?
C49 C48 H48 119.8 . . ?
C45 C48 H48 119.8 . . ?
C48 C49 C47 119.6(3) . . ?
C48 C49 H49 120.2 . . ?
C47 C49 H49 120.2 . . ?
O6 C99 N9 122.0(3) . . ?
O6 C99 C29 120.4(3) . . ?
N9 C99 C29 117.6(2) . . ?
C102 C101 C102 38.8(6) 2_776 . ?
C102 C101 H10A 109.5 2_776 . ?
C102 C101 H10A 112.2 . . ?
C102 C101 H10B 109.5 2_776 . ?
C102 C101 H10B 134.6 . . ?
H10A C101 H10B 109.5 . . ?
C102 C101 H10C 109.5 2_776 . ?
C102 C101 H10C 72.6 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C102 C102 O101 146(3) 2_776 . ?
C102 C102 C101 92.8(15) 2_776 2_776 ?
O101 C102 C101 121.6(15) . 2_776 ?
C102 C102 C101 48.4(15) 2_776 . ?
O101 C102 C101 97.2(13) . . ?
C101 C102 C101 141.2(6) 2_776 . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 983981'
#######################################################################
#
#                 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_x166m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-(4-amino-5-cyano-3-phenylpyridin-2-yl)-4-methyl-N-phenylbenzenesulfonamide  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 N4 O2 S'
_chemical_formula_sum            'C25 H20 N4 O2 S'
_chemical_formula_weight         440.51

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.031(3)
_cell_length_b                   16.026(5)
_cell_length_c                   15.958(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.402(6)
_cell_angle_gamma                90.00
_cell_volume                     2284.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1300
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      18.86

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14392
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.10
_reflns_number_total             4500
_reflns_number_gt                2181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0531P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4500
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.006
_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 1.03200(9) 0.70820(5) 0.69858(5) 0.0687(3) Uani 1 1 d . . .
C7 C 0.6008(3) 0.63453(17) 0.67870(17) 0.0549(7) Uani 1 1 d . . .
N4 N 0.8826(3) 0.70930(16) 0.86221(15) 0.0704(7) Uani 1 1 d . . .
O2 O 1.0419(2) 0.73233(14) 0.61324(11) 0.0848(7) Uani 1 1 d . . .
C13 C 0.7839(3) 0.80652(18) 0.68035(17) 0.0566(7) Uani 1 1 d . . .
C3 C 0.7021(4) 0.62299(17) 0.91753(17) 0.0600(8) Uani 1 1 d . . .
N3 N 0.8620(2) 0.73377(14) 0.71565(13) 0.0580(6) Uani 1 1 d . . .
C26 C 0.8047(3) 0.69374(17) 0.78524(17) 0.0567(7) Uani 1 1 d . . .
C19 C 1.1617(3) 0.76863(19) 0.76554(16) 0.0585(8) Uani 1 1 d . . .
N1 N 0.5007(3) 0.55808(15) 0.82471(14) 0.0769(8) Uani 1 1 d . . .
H1A H 0.4704 0.5344 0.8674 0.092 Uiso 1 1 calc R . .
H1B H 0.4537 0.5499 0.7745 0.092 Uiso 1 1 calc R . .
C5 C 0.6769(3) 0.64590(16) 0.76719(16) 0.0515(7) Uani 1 1 d . . .
C4 C 0.6218(3) 0.60795(17) 0.83635(17) 0.0557(7) Uani 1 1 d . . .
C8 C 0.6737(4) 0.59654(17) 0.61818(18) 0.0649(8) Uani 1 1 d . . .
H8 H 0.7694 0.5749 0.6335 0.078 Uiso 1 1 calc R . .
C14 C 0.7377(4) 0.8655(2) 0.7334(2) 0.0745(9) Uani 1 1 d . . .
H14 H 0.7645 0.8605 0.7917 0.089 Uiso 1 1 calc R . .
O1 O 1.0517(2) 0.62253(13) 0.72406(14) 0.0899(7) Uani 1 1 d . . .
C20 C 1.2434(4) 0.7348(2) 0.83753(19) 0.0771(9) Uani 1 1 d . . .
H20 H 1.2266 0.6801 0.8532 0.092 Uiso 1 1 calc R . .
C6 C 0.6601(4) 0.5843(2) 0.9917(2) 0.0744(10) Uani 1 1 d . . .
C9 C 0.4575(4) 0.6645(2) 0.65448(19) 0.0733(9) Uani 1 1 d . . .
H9 H 0.4071 0.6900 0.6944 0.088 Uiso 1 1 calc R . .
C21 C 1.1870(4) 0.8498(2) 0.74328(19) 0.0761(9) Uani 1 1 d . . .
H21 H 1.1335 0.8729 0.6946 0.091 Uiso 1 1 calc R . .
C22 C 1.3501(4) 0.7831(3) 0.88603(19) 0.0853(11) Uani 1 1 d . . .
H22 H 1.4059 0.7597 0.9339 0.102 Uiso 1 1 calc R . .
C10 C 0.6044(5) 0.5907(2) 0.5351(2) 0.0813(10) Uani 1 1 d . . .
H10 H 0.6544 0.5659 0.4946 0.098 Uiso 1 1 calc R . .
C2 C 0.8279(4) 0.67331(19) 0.92615(19) 0.0707(9) Uani 1 1 d . . .
H2 H 0.8777 0.6826 0.9806 0.085 Uiso 1 1 calc R . .
C15 C 0.7474(4) 0.8160(2) 0.59383(19) 0.0781(10) Uani 1 1 d . . .
H15 H 0.7777 0.7762 0.5575 0.094 Uiso 1 1 calc R . .
C11 C 0.4621(5) 0.6215(2) 0.5122(2) 0.0882(11) Uani 1 1 d . . .
H11 H 0.4165 0.6180 0.4561 0.106 Uiso 1 1 calc R . .
C23 C 1.3763(4) 0.8643(3) 0.8657(2) 0.0851(11) Uani 1 1 d . . .
N2 N 0.6312(4) 0.55194(19) 1.05044(17) 0.1031(11) Uani 1 1 d . . .
C24 C 1.2933(4) 0.8967(2) 0.7944(2) 0.0912(11) Uani 1 1 d . . .
H24 H 1.3086 0.9519 0.7799 0.109 Uiso 1 1 calc R . .
C16 C 0.6164(4) 0.9411(3) 0.6135(3) 0.0995(13) Uani 1 1 d . . .
H16 H 0.5587 0.9860 0.5907 0.119 Uiso 1 1 calc R . .
C17 C 0.6667(5) 0.8838(3) 0.5614(3) 0.0979(12) Uani 1 1 d . . .
H17 H 0.6459 0.8908 0.5031 0.117 Uiso 1 1 calc R . .
C12 C 0.3878(4) 0.6571(2) 0.5717(2) 0.0895(11) Uani 1 1 d . . .
H12 H 0.2904 0.6764 0.5566 0.107 Uiso 1 1 calc R . .
C25 C 1.4931(5) 0.9154(3) 0.9205(2) 0.1323(16) Uani 1 1 d . . .
H25A H 1.5905 0.9017 0.9072 0.199 Uiso 1 1 calc R . .
H25B H 1.4893 0.9033 0.9791 0.199 Uiso 1 1 calc R . .
H25C H 1.4738 0.9736 0.9101 0.199 Uiso 1 1 calc R . .
C18 C 0.6511(4) 0.9324(2) 0.6999(3) 0.0960(12) Uani 1 1 d . . .
H18 H 0.6166 0.9713 0.7357 0.115 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 O2 1.4310(19) . ?
S1 O1 1.436(2) . ?
S1 N3 1.650(2) . ?
S1 C19 1.756(3) . ?
C7 C9 1.381(4) . ?
C7 C8 1.386(4) . ?
C7 C5 1.489(3) . ?
N4 C2 1.329(3) . ?
N4 C26 1.347(3) . ?
C13 C14 1.374(4) . ?
C13 C15 1.380(4) . ?
C13 N3 1.434(3) . ?
C3 C2 1.384(4) . ?
C3 C4 1.410(4) . ?
C3 C6 1.435(4) . ?
N3 C26 1.442(3) . ?
C26 C5 1.381(4) . ?
C19 C21 1.376(4) . ?
C19 C20 1.382(4) . ?
N1 C4 1.345(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C5 C4 1.413(3) . ?
C8 C10 1.384(4) . ?
C8 H8 0.9300 . ?
C14 C18 1.388(4) . ?
C14 H14 0.9300 . ?
C20 C22 1.381(4) . ?
C20 H20 0.9300 . ?
C6 N2 1.135(3) . ?
C9 C12 1.382(4) . ?
C9 H9 0.9300 . ?
C21 C24 1.388(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C2 H2 0.9300 . ?
C15 C17 1.367(5) . ?
C15 H15 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C23 C24 1.370(4) . ?
C23 C25 1.508(5) . ?
C24 H24 0.9300 . ?
C16 C17 1.360(5) . ?
C16 C18 1.376(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.37(14) . . ?
O2 S1 N3 106.19(12) . . ?
O1 S1 N3 105.72(13) . . ?
O2 S1 C19 107.53(14) . . ?
O1 S1 C19 108.11(14) . . ?
N3 S1 C19 108.45(13) . . ?
C9 C7 C8 118.6(3) . . ?
C9 C7 C5 120.4(3) . . ?
C8 C7 C5 120.9(3) . . ?
C2 N4 C26 114.6(3) . . ?
C14 C13 C15 119.4(3) . . ?
C14 C13 N3 119.5(3) . . ?
C15 C13 N3 120.9(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C6 118.8(3) . . ?
C4 C3 C6 121.4(3) . . ?
C13 N3 C26 116.9(2) . . ?
C13 N3 S1 123.57(18) . . ?
C26 N3 S1 117.63(19) . . ?
N4 C26 C5 127.1(3) . . ?
N4 C26 N3 114.9(3) . . ?
C5 C26 N3 118.0(2) . . ?
C21 C19 C20 119.8(3) . . ?
C21 C19 S1 119.0(2) . . ?
C20 C19 S1 121.1(3) . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C26 C5 C4 117.1(2) . . ?
C26 C5 C7 121.5(2) . . ?
C4 C5 C7 121.5(3) . . ?
N1 C4 C3 121.8(3) . . ?
N1 C4 C5 121.3(3) . . ?
C3 C4 C5 116.9(3) . . ?
C10 C8 C7 120.2(3) . . ?
C10 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C13 C14 C18 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C18 C14 H14 120.1 . . ?
C22 C20 C19 119.4(3) . . ?
C22 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
N2 C6 C3 177.6(4) . . ?
C12 C9 C7 121.0(3) . . ?
C12 C9 H9 119.5 . . ?
C7 C9 H9 119.5 . . ?
C19 C21 C24 119.2(3) . . ?
C19 C21 H21 120.4 . . ?
C24 C21 H21 120.4 . . ?
C23 C22 C20 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C20 C22 H22 119.0 . . ?
C11 C10 C8 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
N4 C2 C3 124.7(3) . . ?
N4 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C17 C15 C13 120.1(3) . . ?
C17 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C24 C23 C22 117.6(3) . . ?
C24 C23 C25 121.8(4) . . ?
C22 C23 C25 120.5(4) . . ?
C23 C24 C21 122.1(3) . . ?
C23 C24 H24 119.0 . . ?
C21 C24 H24 119.0 . . ?
C17 C16 C18 119.7(4) . . ?
C17 C16 H16 120.1 . . ?
C18 C16 H16 120.1 . . ?
C16 C17 C15 120.9(4) . . ?
C16 C17 H17 119.6 . . ?
C15 C17 H17 119.6 . . ?
C11 C12 C9 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C9 C12 H12 120.0 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C18 C14 119.8(4) . . ?
C16 C18 H18 120.1 . . ?
C14 C18 H18 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.10
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 983982'
