# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TAM027
_database_code_depnum_ccdc_archive 'CCDC 1410751'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'2-(6-hydroxy-2,6-diphenylthiazolo[3,2-b][1,2,4]triazol-5(6H)-ylidene)-1-phenylethanone (20)'
_chemical_name_common            ?
_chemical_melting_point          444-445
_chemical_formula_moiety         'C24 H17 N3 O2 S'
_chemical_formula_sum            'C24 H17 N3 O2 S'
_chemical_formula_weight         411.47

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.409(2)
_cell_length_b                   22.777(3)
_cell_length_c                   13.401(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.13
_cell_angle_gamma                90.00
_cell_volume                     4041.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            24458
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0923
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6851
_reflns_number_gt                3332
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0938P)²+41.4775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6851
_refine_ls_number_parameters     541
_refine_ls_number_restraints     167
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.2355
_refine_ls_wR_factor_gt          0.1990
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_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
C1 C 0.2130(10) 0.5729(6) -0.0964(11) 0.074(3) Uani 1 1 d U . .
C1A C 0.4330(10) 0.0454(5) 0.1969(9) 0.067(3) Uani 1 1 d DU . .
C2 C 0.1414(12) 0.6132(6) -0.0807(12) 0.089(4) Uani 1 1 d U . .
H2 H 0.0836 0.6009 -0.0563 0.106 Uiso 1 1 calc R . .
C2A C 0.4124(12) 0.0206(6) 0.2876(11) 0.083(4) Uani 1 1 d U . .
H2A H 0.4021 0.0446 0.3412 0.100 Uiso 1 1 calc R . .
C3 C 0.1543(14) 0.6720(7) -0.1010(15) 0.111(5) Uani 1 1 d U . .
H3 H 0.1052 0.6993 -0.0911 0.133 Uiso 1 1 calc R . .
C3A C 0.4077(13) -0.0383(6) 0.2957(14) 0.099(5) Uani 1 1 d U . .
H3A H 0.3948 -0.0542 0.3563 0.118 Uiso 1 1 calc R . .
C4 C 0.2413(15) 0.6899(7) -0.1363(14) 0.108(5) Uani 1 1 d U . .
H4 H 0.2518 0.7293 -0.1493 0.129 Uiso 1 1 calc R . .
C4A C 0.4207(15) -0.0748(7) 0.2208(16) 0.113(6) Uani 1 1 d U . .
H4A H 0.4160 -0.1152 0.2293 0.136 Uiso 1 1 calc R . .
C5 C 0.3110(15) 0.6488(7) -0.1514(15) 0.116(6) Uani 1 1 d U . .
H5 H 0.3693 0.6603 -0.1754 0.139 Uiso 1 1 calc R . .
C5A C 0.4409(15) -0.0523(7) 0.1318(14) 0.112(6) Uani 1 1 d U . .
H5A H 0.4522 -0.0771 0.0796 0.134 Uiso 1 1 calc R . .
C6 C 0.2971(12) 0.5931(6) -0.1325(13) 0.093(4) Uani 1 1 d U . .
H6 H 0.3462 0.5661 -0.1441 0.111 Uiso 1 1 calc R . .
C6A C 0.4441(15) 0.0066(6) 0.1208(11) 0.109(6) Uani 1 1 d DU . .
H6A H 0.4544 0.0217 0.0587 0.131 Uiso 1 1 calc R . .
C7 C 0.1907(10) 0.5096(6) -0.0797(12) 0.075(3) Uani 1 1 d U . .
C7A C 0.4362(8) 0.1089(5) 0.1804(10) 0.057(3) Uani 1 1 d U . .
C8 C 0.2563(10) 0.4635(5) -0.1076(10) 0.068(3) Uani 1 1 d U . .
H8 H 0.3155 0.4743 -0.1308 0.081 Uiso 1 1 calc R . .
C8A C 0.4043(8) 0.1520(5) 0.2508(9) 0.055(3) Uani 1 1 d U . .
H8A H 0.3841 0.1391 0.3103 0.066 Uiso 1 1 calc R . .
C9 C 0.2361(9) 0.4081(5) -0.1016(9) 0.056(3) Uani 1 1 d U . .
C9A C 0.4039(8) 0.2070(5) 0.2314(8) 0.054(3) Uani 1 1 d U . .
C10 C 0.1655(9) 0.3094(5) -0.0772(9) 0.058(3) Uani 1 1 d U . .
C10A C 0.4107(9) 0.3108(5) 0.1681(9) 0.056(3) Uani 1 1 d U . .
C11 C 0.3026(7) 0.3598(4) -0.1315(8) 0.046(2) Uani 1 1 d U . .
C11A C 0.3640(9) 0.2531(5) 0.3043(8) 0.057(2) Uani 1 1 d U . .
C12 C 0.3044(8) 0.3615(4) -0.2470(8) 0.048(2) Uani 1 1 d U . .
C12A C 0.2487(9) 0.2494(4) 0.2982(9) 0.053(2) Uani 1 1 d U . .
C13 C 0.2147(10) 0.3550(6) -0.3103(10) 0.074(4) Uani 1 1 d U . .
H13 H 0.1557 0.3497 -0.2832 0.089 Uiso 1 1 calc R . .
C13A C 0.2068(10) 0.2496(6) 0.3849(10) 0.074(3) Uani 1 1 d U . .
H13A H 0.2480 0.2506 0.4476 0.088 Uiso 1 1 calc R . .
C14 C 0.2103(11) 0.3563(7) -0.4144(10) 0.085(4) Uani 1 1 d U . .
H14 H 0.1495 0.3508 -0.4576 0.102 Uiso 1 1 calc R . .
C14A C 0.1025(11) 0.2482(7) 0.3787(12) 0.085(4) Uani 1 1 d U . .
H14A H 0.0736 0.2476 0.4373 0.102 Uiso 1 1 calc R . .
C15 C 0.3018(13) 0.3663(6) -0.4527(11) 0.084(4) Uani 1 1 d U . .
H15 H 0.3018 0.3677 -0.5220 0.101 Uiso 1 1 calc R . .
C15A C 0.0438(11) 0.2478(6) 0.2888(14) 0.087(4) Uani 1 1 d U . .
H15A H -0.0261 0.2468 0.2845 0.104 Uiso 1 1 calc R . .
C16 C 0.3873(12) 0.3735(7) -0.3890(11) 0.085(4) Uani 1 1 d U . .
H16 H 0.4467 0.3812 -0.4144 0.101 Uiso 1 1 calc R . .
C16A C 0.0860(11) 0.2488(7) 0.2038(13) 0.095(4) Uani 1 1 d U . .
H16A H 0.0443 0.2499 0.1414 0.114 Uiso 1 1 calc R . .
C17 C 0.3900(9) 0.3700(5) -0.2857(10) 0.067(3) Uani 1 1 d U . .
H17 H 0.4513 0.3735 -0.2426 0.080 Uiso 1 1 calc R . .
C17A C 0.1860(10) 0.2483(6) 0.2070(10) 0.074(3) Uani 1 1 d U . .
H17A H 0.2130 0.2472 0.1473 0.089 Uiso 1 1 calc R . .
C18 C 0.2017(10) 0.2198(5) -0.0920(10) 0.066(3) Uani 1 1 d U . .
C18A C 0.3831(9) 0.3964(5) 0.2104(9) 0.056(3) Uani 1 1 d U . .
C19 C 0.1952(10) 0.1564(5) -0.0905(10) 0.070(3) Uani 1 1 d U . .
C19A C 0.3781(9) 0.4599(5) 0.2087(10) 0.067(3) Uani 1 1 d U . .
C20 C 0.2791(12) 0.1223(6) -0.1035(13) 0.097(5) Uani 1 1 d U . .
H20 H 0.3401 0.1405 -0.1088 0.116 Uiso 1 1 calc R . .
C20A C 0.3459(11) 0.4883(6) 0.2900(14) 0.088(4) Uani 1 1 d U . .
H20A H 0.3335 0.4668 0.3457 0.106 Uiso 1 1 calc R . .
C21 C 0.2724(16) 0.0645(8) -0.1082(19) 0.139(8) Uani 1 1 d U . .
H21 H 0.3282 0.0423 -0.1182 0.166 Uiso 1 1 calc R . .
C21A C 0.3322(12) 0.5496(6) 0.2878(15) 0.102(5) Uani 1 1 d U . .
H21A H 0.3065 0.5682 0.3400 0.122 Uiso 1 1 calc R . .
C22 C 0.1802(17) 0.0360(7) -0.0980(16) 0.126(7) Uani 1 1 d U . .
H22 H 0.1747 -0.0046 -0.1027 0.151 Uiso 1 1 calc R . .
C22A C 0.3566(12) 0.5821(6) 0.2091(16) 0.100(5) Uani 1 1 d U . .
H22A H 0.3507 0.6228 0.2097 0.120 Uiso 1 1 calc R . .
C23 C 0.1005(16) 0.0689(7) -0.0812(16) 0.120(6) Uani 1 1 d U . .
H23 H 0.0401 0.0510 -0.0726 0.144 Uiso 1 1 calc R . .
C23A C 0.3900(13) 0.5543(6) 0.1284(14) 0.101(5) Uani 1 1 d U . .
H23A H 0.4039 0.5762 0.0738 0.122 Uiso 1 1 calc R . .
C24 C 0.1091(10) 0.1295(5) -0.0770(10) 0.072(3) Uani 1 1 d U . .
H24 H 0.0544 0.1519 -0.0645 0.086 Uiso 1 1 calc R . .
C24A C 0.4029(12) 0.4931(6) 0.1289(12) 0.084(4) Uani 1 1 d U . .
H24A H 0.4279 0.4748 0.0761 0.101 Uiso 1 1 calc R . .
N1 N 0.2534(7) 0.3060(4) -0.1063(8) 0.060(2) Uani 1 1 d U . .
N1A N 0.3864(7) 0.3088(4) 0.2587(7) 0.057(2) Uani 1 1 d U . .
N2 N 0.2795(8) 0.2484(4) -0.1201(8) 0.066(3) Uani 1 1 d U . .
N2A N 0.3660(8) 0.3651(4) 0.2863(7) 0.063(3) Uani 1 1 d U . .
N3 N 0.1244(8) 0.2549(5) -0.0671(8) 0.067(2) Uani 1 1 d U . .
N3A N 0.4145(7) 0.3656(4) 0.1317(7) 0.059(2) Uani 1 1 d U . .
S1 S 0.1262(2) 0.37976(15) -0.0556(3) 0.0708(10) Uani 1 1 d U . .
S1A S 0.4391(3) 0.24101(14) 0.1219(3) 0.0667(10) Uani 1 1 d U . .
O1 O 0.1196(8) 0.4939(4) -0.0400(9) 0.094(3) Uani 1 1 d U . .
O1A O 0.4655(7) 0.1301(4) 0.1027(7) 0.076(3) Uani 1 1 d U . .
O2 O 0.4023(5) 0.3629(3) -0.0819(6) 0.0566(19) Uani 1 1 d U . .
H2O H 0.4032 0.3601 -0.0208 0.085 Uiso 1 1 calc R . .
O2A O 0.4112(6) 0.2481(3) 0.4026(6) 0.061(2) Uani 1 1 d U . .
H2O1 H 0.4726 0.2501 0.4045 0.092 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(17) . ?
C1 C6 1.375(19) . ?
C1 C7 1.495(19) . ?
C1A C6A 1.376(14) . ?
C1A C2A 1.407(18) . ?
C1A C7A 1.464(16) . ?
C2 C3 1.38(2) . ?
C2 H2 0.9300 . ?
C2A C3A 1.348(18) . ?
C2A H2A 0.9300 . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C3A C4A 1.34(2) . ?
C3A H3A 0.9300 . ?
C4 C5 1.36(2) . ?
C4 H4 0.9300 . ?
C4A C5A 1.37(2) . ?
C4A H4A 0.9300 . ?
C5 C6 1.31(2) . ?
C5 H5 0.9300 . ?
C5A C6A 1.35(2) . ?
C5A H5A 0.9300 . ?
C6 H6 0.9300 . ?
C6A H6A 0.9300 . ?
C7 O1 1.217(16) . ?
C7 C8 1.457(17) . ?
C7A O1A 1.266(14) . ?
C7A C8A 1.473(15) . ?
C8 C9 1.294(16) . ?
C8 H8 0.9300 . ?
C8A C9A 1.279(15) . ?
C8A H8A 0.9300 . ?
C9 C11 1.511(14) . ?
C9 S1 1.805(11) . ?
C9A C11A 1.584(15) . ?
C9A S1A 1.788(11) . ?
C10 N1 1.301(13) . ?
C10 N3 1.374(14) . ?
C10 S1 1.726(12) . ?
C10A N1A 1.308(14) . ?
C10A N3A 1.343(14) . ?
C10A S1A 1.770(12) . ?
C11 O2 1.397(12) . ?
C11 N1 1.458(13) . ?
C11 C12 1.552(15) . ?
C11A O2A 1.373(13) . ?
C11A N1A 1.459(14) . ?
C11A C12A 1.537(15) . ?
C12 C17 1.346(15) . ?
C12 C13 1.365(16) . ?
C12A C13A 1.370(15) . ?
C12A C17A 1.370(17) . ?
C13 C14 1.388(18) . ?
C13 H13 0.9300 . ?
C13A C14A 1.388(18) . ?
C13A H13A 0.9300 . ?
C14 C15 1.42(2) . ?
C14 H14 0.9300 . ?
C14A C15A 1.33(2) . ?
C14A H14A 0.9300 . ?
C15 C16 1.33(2) . ?
C15 H15 0.9300 . ?
C15A C16A 1.35(2) . ?
C15A H15A 0.9300 . ?
C16 C17 1.383(18) . ?
C16 H16 0.9300 . ?
C16A C17A 1.335(18) . ?
C16A H16A 0.9300 . ?
C17 H17 0.9300 . ?
C17A H17A 0.9300 . ?
C18 N2 1.333(15) . ?
C18 N3 1.390(16) . ?
C18 C19 1.447(17) . ?
C18A N2A 1.294(14) . ?
C18A N3A 1.386(14) . ?
C18A C19A 1.447(16) . ?
C19 C24 1.345(17) . ?
C19 C20 1.401(19) . ?
C19A C24A 1.393(18) . ?
C19A C20A 1.395(19) . ?
C20 C21 1.32(2) . ?
C20 H20 0.9300 . ?
C20A C21A 1.407(19) . ?
C20A H20A 0.9300 . ?
C21 C22 1.42(3) . ?
C21 H21 0.9300 . ?
C21A C22A 1.37(2) . ?
C21A H21A 0.9300 . ?
C22 C23 1.35(3) . ?
C22 H22 0.9300 . ?
C22A C23A 1.39(2) . ?
C22A H22A 0.9300 . ?
C23 C24 1.39(2) . ?
C23 H23 0.9300 . ?
C23A C24A 1.403(19) . ?
C23A H23A 0.9300 . ?
C24 H24 0.9300 . ?
C24A H24A 0.9300 . ?
N1 N2 1.377(13) . ?
N1A N2A 1.374(12) . ?
O2 H2O 0.8200 . ?
O2A H2O1 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.7(14) . . ?
C2 C1 C7 117.5(13) . . ?
C6 C1 C7 124.7(12) . . ?
C6A C1A C2A 116.2(13) . . ?
C6A C1A C7A 120.9(12) . . ?
C2A C1A C7A 122.8(11) . . ?
C1 C2 C3 120.4(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3A C2A C1A 119.2(14) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
C2 C3 C4 119.3(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4A C3A C2A 123.0(17) . . ?
C4A C3A H3A 118.5 . . ?
C2A C3A H3A 118.5 . . ?
C5 C4 C3 118.9(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C3A C4A C5A 119.4(15) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C6 C5 C4 121.0(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6A C5A C4A 118.8(15) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C5 C6 C1 122.7(16) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
C5A C6A C1A 123.2(15) . . ?
C5A C6A H6A 118.4 . . ?
C1A C6A H6A 118.4 . . ?
O1 C7 C8 116.5(13) . . ?
O1 C7 C1 122.5(12) . . ?
C8 C7 C1 120.9(12) . . ?
O1A C7A C1A 121.4(10) . . ?
O1A C7A C8A 115.6(10) . . ?
C1A C7A C8A 122.9(11) . . ?
C9 C8 C7 123.0(12) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C9A C8A C7A 121.0(11) . . ?
C9A C8A H8A 119.5 . . ?
C7A C8A H8A 119.5 . . ?
C8 C9 C11 123.6(11) . . ?
C8 C9 S1 124.1(9) . . ?
C11 C9 S1 112.2(8) . . ?
C8A C9A C11A 120.9(10) . . ?
C8A C9A S1A 126.7(9) . . ?
C11A C9A S1A 112.2(8) . . ?
N1 C10 N3 111.8(11) . . ?
N1 C10 S1 115.0(8) . . ?
N3 C10 S1 133.2(9) . . ?
N1A C10A N3A 113.6(10) . . ?
N1A C10A S1A 113.1(9) . . ?
N3A C10A S1A 133.2(9) . . ?
O2 C11 N1 111.4(9) . . ?
O2 C11 C9 113.5(9) . . ?
N1 C11 C9 104.1(8) . . ?
O2 C11 C12 108.0(8) . . ?
N1 C11 C12 109.3(8) . . ?
C9 C11 C12 110.5(9) . . ?
O2A C11A N1A 112.3(10) . . ?
O2A C11A C12A 110.7(9) . . ?
N1A C11A C12A 107.3(9) . . ?
O2A C11A C9A 112.8(9) . . ?
N1A C11A C9A 101.8(8) . . ?
C12A C11A C9A 111.5(9) . . ?
C17 C12 C13 119.7(12) . . ?
C17 C12 C11 122.5(11) . . ?
C13 C12 C11 117.8(10) . . ?
C13A C12A C17A 118.7(12) . . ?
C13A C12A C11A 119.9(11) . . ?
C17A C12A C11A 121.3(10) . . ?
C12 C13 C14 121.1(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C12A C13A C14A 119.6(13) . . ?
C12A C13A H13A 120.2 . . ?
C14A C13A H13A 120.2 . . ?
C13 C14 C15 117.7(14) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C15A C14A C13A 120.0(13) . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C16 C15 C14 119.7(13) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C14A C15A C16A 119.8(14) . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A H15A 120.1 . . ?
C15 C16 C17 121.3(13) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C17A C16A C15A 121.7(15) . . ?
C17A C16A H16A 119.2 . . ?
C15A C16A H16A 119.1 . . ?
C12 C17 C16 120.5(13) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16A C17A C12A 120.1(13) . . ?
C16A C17A H17A 120.0 . . ?
C12A C17A H17A 120.0 . . ?
N2 C18 N3 115.7(10) . . ?
N2 C18 C19 122.9(12) . . ?
N3 C18 C19 121.4(11) . . ?
N2A C18A N3A 115.6(10) . . ?
N2A C18A C19A 123.4(11) . . ?
N3A C18A C19A 120.9(11) . . ?
C24 C19 C20 119.1(13) . . ?
C24 C19 C18 120.8(13) . . ?
C20 C19 C18 120.0(13) . . ?
C24A C19A C20A 119.3(13) . . ?
C24A C19A C18A 122.6(13) . . ?
C20A C19A C18A 118.1(12) . . ?
C21 C20 C19 120.7(17) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C19A C20A C21A 120.0(16) . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C20 C21 C22 120.2(18) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C22A C21A C20A 120.4(17) . . ?
C22A C21A H21A 119.8 . . ?
C20A C21A H21A 119.8 . . ?
C23 C22 C21 119.0(16) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C21A C22A C23A 119.9(15) . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C22 C23 C24 119.7(17) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C22A C23A C24A 120.3(17) . . ?
C22A C23A H23A 119.9 . . ?
C24A C23A H23A 119.9 . . ?
C19 C24 C23 121.1(15) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C19A C24A C23A 120.0(16) . . ?
C19A C24A H24A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C10 N1 N2 111.1(9) . . ?
C10 N1 C11 118.9(10) . . ?
N2 N1 C11 129.5(9) . . ?
C10A N1A N2A 107.8(9) . . ?
C10A N1A C11A 121.2(9) . . ?
N2A N1A C11A 129.4(8) . . ?
C18 N2 N1 101.5(10) . . ?
C18A N2A N1A 103.6(9) . . ?
C10 N3 C18 99.8(9) . . ?
C10A N3A C18A 99.2(9) . . ?
C10 S1 C9 89.3(5) . . ?
C10A S1A C9A 90.1(5) . . ?
C11 O2 H2O 109.5 . . ?
C11A O2A H2O1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0(2) . . . . ?
C7 C1 C2 C3 -175.9(15) . . . . ?
C6A C1A C2A C3A 2(2) . . . . ?
C7A C1A C2A C3A 178.0(13) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C1A C2A C3A C4A -1(3) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C2A C3A C4A C5A 1(3) . . . . ?
C3 C4 C5 C6 0(3) . . . . ?
C3A C4A C5A C6A -2(3) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C2 C1 C6 C5 1(3) . . . . ?
C7 C1 C6 C5 176.1(17) . . . . ?
C4A C5A C6A C1A 3(3) . . . . ?
C2A C1A C6A C5A -3(3) . . . . ?
C7A C1A C6A C5A -179.4(16) . . . . ?
C2 C1 C7 O1 -10(2) . . . . ?
C6 C1 C7 O1 173.9(16) . . . . ?
C2 C1 C7 C8 171.7(14) . . . . ?
C6 C1 C7 C8 -4(2) . . . . ?
C6A C1A C7A O1A -12(2) . . . . ?
C2A C1A C7A O1A 172.3(13) . . . . ?
C6A C1A C7A C8A 167.1(14) . . . . ?
C2A C1A C7A C8A -8.9(19) . . . . ?
O1 C7 C8 C9 7(2) . . . . ?
C1 C7 C8 C9 -174.7(13) . . . . ?
O1A C7A C8A C9A 2.1(17) . . . . ?
C1A C7A C8A C9A -176.8(12) . . . . ?
C7 C8 C9 C11 179.2(12) . . . . ?
C7 C8 C9 S1 -1(2) . . . . ?
C7A C8A C9A C11A 176.7(10) . . . . ?
C7A C8A C9A S1A 0.2(17) . . . . ?
C8 C9 C11 O2 55.4(16) . . . . ?
S1 C9 C11 O2 -124.1(9) . . . . ?
C8 C9 C11 N1 176.7(12) . . . . ?
S1 C9 C11 N1 -2.7(11) . . . . ?
C8 C9 C11 C12 -66.0(15) . . . . ?
S1 C9 C11 C12 114.5(8) . . . . ?
C8A C9A C11A O2A 54.2(15) . . . . ?
S1A C9A C11A O2A -128.9(9) . . . . ?
C8A C9A C11A N1A 174.8(11) . . . . ?
S1A C9A C11A N1A -8.3(11) . . . . ?
C8A C9A C11A C12A -71.1(14) . . . . ?
S1A C9A C11A C12A 105.8(9) . . . . ?
O2 C11 C12 C17 -5.4(13) . . . . ?
N1 C11 C12 C17 -126.8(11) . . . . ?
C9 C11 C12 C17 119.2(11) . . . . ?
O2 C11 C12 C13 175.7(10) . . . . ?
N1 C11 C12 C13 54.3(13) . . . . ?
C9 C11 C12 C13 -59.7(13) . . . . ?
O2A C11A C12A C13A 8.2(15) . . . . ?
N1A C11A C12A C13A -114.6(11) . . . . ?
C9A C11A C12A C13A 134.7(11) . . . . ?
O2A C11A C12A C17A -174.4(10) . . . . ?
N1A C11A C12A C17A 62.8(14) . . . . ?
C9A C11A C12A C17A -47.9(14) . . . . ?
C17 C12 C13 C14 1(2) . . . . ?
C11 C12 C13 C14 179.7(12) . . . . ?
C17A C12A C13A C14A 0.4(18) . . . . ?
C11A C12A C13A C14A 177.9(12) . . . . ?
C12 C13 C14 C15 -2(2) . . . . ?
C12A C13A C14A C15A -1(2) . . . . ?
C13 C14 C15 C16 0(2) . . . . ?
C13A C14A C15A C16A 0(2) . . . . ?
C14 C15 C16 C17 2(2) . . . . ?
C14A C15A C16A C17A 2(3) . . . . ?
C13 C12 C17 C16 1.5(19) . . . . ?
C11 C12 C17 C16 -177.4(11) . . . . ?
C15 C16 C17 C12 -3(2) . . . . ?
C15A C16A C17A C12A -3(2) . . . . ?
C13A C12A C17A C16A 2(2) . . . . ?
C11A C12A C17A C16A -175.8(12) . . . . ?
N2 C18 C19 C24 -169.6(13) . . . . ?
N3 C18 C19 C24 8(2) . . . . ?
N2 C18 C19 C20 10(2) . . . . ?
N3 C18 C19 C20 -172.0(13) . . . . ?
N2A C18A C19A C24A 175.8(13) . . . . ?
N3A C18A C19A C24A 0.8(19) . . . . ?
N2A C18A C19A C20A -5.0(19) . . . . ?
N3A C18A C19A C20A 180.0(12) . . . . ?
C24 C19 C20 C21 4(3) . . . . ?
C18 C19 C20 C21 -176.0(18) . . . . ?
C24A C19A C20A C21A 4(2) . . . . ?
C18A C19A C20A C21A -174.9(13) . . . . ?
C19 C20 C21 C22 -1(3) . . . . ?
C19A C20A C21A C22A -4(2) . . . . ?
C20 C21 C22 C23 -1(4) . . . . ?
C20A C21A C22A C23A 3(3) . . . . ?
C21 C22 C23 C24 2(3) . . . . ?
C21A C22A C23A C24A -3(3) . . . . ?
C20 C19 C24 C23 -4(2) . . . . ?
C18 C19 C24 C23 176.3(15) . . . . ?
C22 C23 C24 C19 1(3) . . . . ?
C20A C19A C24A C23A -4(2) . . . . ?
C18A C19A C24A C23A 175.7(13) . . . . ?
C22A C23A C24A C19A 3(2) . . . . ?
N3 C10 N1 N2 0.9(15) . . . . ?
S1 C10 N1 N2 178.9(8) . . . . ?
N3 C10 N1 C11 173.3(10) . . . . ?
S1 C10 N1 C11 -8.6(15) . . . . ?
O2 C11 N1 C10 129.8(11) . . . . ?
C9 C11 N1 C10 7.1(14) . . . . ?
C12 C11 N1 C10 -111.0(11) . . . . ?
O2 C11 N1 N2 -59.4(14) . . . . ?
C9 C11 N1 N2 178.0(11) . . . . ?
C12 C11 N1 N2 59.9(14) . . . . ?
N3A C10A N1A N2A 3.6(14) . . . . ?
S1A C10A N1A N2A -179.9(8) . . . . ?
N3A C10A N1A C11A 170.8(10) . . . . ?
S1A C10A N1A C11A -12.6(14) . . . . ?
O2A C11A N1A C10A 134.3(11) . . . . ?
C12A C11A N1A C10A -103.8(12) . . . . ?
C9A C11A N1A C10A 13.3(13) . . . . ?
O2A C11A N1A N2A -61.5(15) . . . . ?
C12A C11A N1A N2A 60.4(14) . . . . ?
C9A C11A N1A N2A 177.5(11) . . . . ?
N3 C18 N2 N1 3.8(14) . . . . ?
C19 C18 N2 N1 -178.3(12) . . . . ?
C10 N1 N2 C18 -2.7(13) . . . . ?
C11 N1 N2 C18 -174.2(11) . . . . ?
N3A C18A N2A N1A -0.3(14) . . . . ?
C19A C18A N2A N1A -175.5(11) . . . . ?
C10A N1A N2A C18A -1.9(13) . . . . ?
C11A N1A N2A C18A -167.7(11) . . . . ?
N1 C10 N3 C18 1.3(13) . . . . ?
S1 C10 N3 C18 -176.3(11) . . . . ?
N2 C18 N3 C10 -3.3(14) . . . . ?
C19 C18 N3 C10 178.8(12) . . . . ?
N1A C10A N3A C18A -3.4(13) . . . . ?
S1A C10A N3A C18A -179.1(10) . . . . ?
N2A C18A N3A C10A 2.2(14) . . . . ?
C19A C18A N3A C10A 177.6(11) . . . . ?
N1 C10 S1 C9 5.3(10) . . . . ?
N3 C10 S1 C9 -177.2(13) . . . . ?
C8 C9 S1 C10 179.5(13) . . . . ?
C11 C9 S1 C10 -1.0(9) . . . . ?
N1A C10A S1A C9A 5.0(9) . . . . ?
N3A C10A S1A C9A -179.3(12) . . . . ?
C8A C9A S1A C10A 179.2(12) . . . . ?
C11A C9A S1A C10A 2.5(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.089
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20janbm
_database_code_depnum_ccdc_archive 'CCDC 1410752'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'2-(methylthio)-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl(phenyl)methanone (23)'
_chemical_name_common            ?
_chemical_melting_point          455-456
_chemical_formula_moiety         'C19 H14 N4 O S'
_chemical_formula_sum            'C19 H14 N4 O S'
_chemical_formula_weight         346.40

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.337(4)
_cell_length_b                   9.368(4)
_cell_length_c                   10.286(5)
_cell_angle_alpha                113.699(7)
_cell_angle_beta                 97.243(8)
_cell_angle_gamma                97.258(8)
_cell_volume                     801.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   Multi-Scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            4302
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2902
_reflns_number_gt                2508
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0867P)²+0.8117P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         2902
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0354(3) -0.3587(4) 0.4115(3) 0.0314(7) Uani 1 1 d . . .
H1A H -0.1097 -0.4334 0.4200 0.047 Uiso 1 1 calc R . .
H1B H 0.0462 -0.4083 0.3821 0.047 Uiso 1 1 calc R . .
H1C H -0.0756 -0.3248 0.3405 0.047 Uiso 1 1 calc R . .
C2 C 0.1564(3) -0.0760(3) 0.5394(3) 0.0221(6) Uani 1 1 d . . .
C3 C 0.3201(3) 0.1167(3) 0.5706(3) 0.0205(6) Uani 1 1 d . . .
C4 C 0.5030(3) 0.2646(3) 0.5297(3) 0.0194(6) Uani 1 1 d . . .
C5 C 0.4844(3) 0.1520(3) 0.3857(3) 0.0201(6) Uani 1 1 d . . .
H5 H 0.5453 0.1693 0.3264 0.024 Uiso 1 1 calc R . .
C6 C 0.3773(3) 0.0165(3) 0.3310(3) 0.0191(6) Uani 1 1 d . . .
C7 C 0.3431(3) -0.0991(3) 0.1769(3) 0.0194(6) Uani 1 1 d . . .
C8 C 0.1996(3) -0.1803(3) 0.1055(3) 0.0233(6) Uani 1 1 d . . .
H8 H 0.1236 -0.1702 0.1570 0.028 Uiso 1 1 calc R . .
C9 C 0.1711(3) -0.2753(3) -0.0414(3) 0.0247(6) Uani 1 1 d . . .
H9 H 0.0754 -0.3279 -0.0887 0.030 Uiso 1 1 calc R . .
C10 C 0.2842(3) -0.2931(3) -0.1197(3) 0.0259(6) Uani 1 1 d . . .
H10 H 0.2641 -0.3564 -0.2189 0.031 Uiso 1 1 calc R . .
C11 C 0.4264(3) -0.2161(3) -0.0487(3) 0.0222(6) Uani 1 1 d . . .
H11 H 0.5027 -0.2293 -0.1000 0.027 Uiso 1 1 calc R . .
C12 C 0.4563(3) -0.1192(3) 0.0984(3) 0.0208(6) Uani 1 1 d . . .
H12 H 0.5523 -0.0673 0.1452 0.025 Uiso 1 1 calc R . .
C13 C 0.6193(3) 0.4137(3) 0.5775(3) 0.0214(6) Uani 1 1 d . . .
C14 C 0.6753(3) 0.5284(3) 0.7318(3) 0.0190(6) Uani 1 1 d . . .
C15 C 0.6575(3) 0.4973(3) 0.8511(3) 0.0236(6) Uani 1 1 d . . .
H15 H 0.6045 0.3999 0.8377 0.028 Uiso 1 1 calc R . .
C16 C 0.7191(3) 0.6123(3) 0.9899(3) 0.0260(6) Uani 1 1 d . . .
H16 H 0.7087 0.5906 1.0692 0.031 Uiso 1 1 calc R . .
C17 C 0.7960(3) 0.7589(3) 1.0110(3) 0.0255(6) Uani 1 1 d . . .
H17 H 0.8353 0.8360 1.1044 0.031 Uiso 1 1 calc R . .
C18 C 0.8141(3) 0.7905(3) 0.8938(3) 0.0231(6) Uani 1 1 d . . .
H18 H 0.8667 0.8885 0.9080 0.028 Uiso 1 1 calc R . .
C19 C 0.7535(3) 0.6757(3) 0.7537(3) 0.0215(6) Uani 1 1 d . . .
H19 H 0.7653 0.6976 0.6747 0.026 Uiso 1 1 calc R . .
N1 N 0.2291(2) 0.0680(3) 0.6413(2) 0.0230(5) Uani 1 1 d . . .
N2 N 0.2982(2) 0.0006(3) 0.4287(2) 0.0180(5) Uani 1 1 d . . .
N3 N 0.1923(2) -0.1253(3) 0.4089(2) 0.0212(5) Uani 1 1 d . . .
N4 N 0.4209(2) 0.2502(3) 0.6227(2) 0.0215(5) Uani 1 1 d . . .
O1 O 0.6663(2) 0.4371(2) 0.4805(2) 0.0289(5) Uani 1 1 d . . .
S1 S 0.02648(7) -0.18938(9) 0.58349(8) 0.0264(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 S1 1.799(3) . ?
C2 N3 1.335(4) . ?
C2 N1 1.353(4) . ?
C2 S1 1.734(3) . ?
C3 N4 1.331(3) . ?
C3 N1 1.335(4) . ?
C3 N2 1.396(3) . ?
C4 N4 1.335(4) . ?
C4 C5 1.404(4) . ?
C4 C13 1.518(4) . ?
C5 C6 1.375(4) . ?
C6 N2 1.363(3) . ?
C6 C7 1.480(4) . ?
C7 C12 1.395(4) . ?
C7 C8 1.400(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.385(4) . ?
C13 O1 1.224(3) . ?
C13 C14 1.492(4) . ?
C14 C19 1.394(4) . ?
C14 C15 1.395(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.386(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.396(4) . ?
N2 N3 1.368(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C2 N1 117.2(2) . . ?
N3 C2 S1 123.1(2) . . ?
N1 C2 S1 119.7(2) . . ?
N4 C3 N1 127.7(3) . . ?
N4 C3 N2 123.2(2) . . ?
N1 C3 N2 109.0(2) . . ?
N4 C4 C5 123.9(2) . . ?
N4 C4 C13 119.3(2) . . ?
C5 C4 C13 116.8(2) . . ?
C6 C5 C4 120.9(3) . . ?
N2 C6 C5 114.5(2) . . ?
N2 C6 C7 121.9(2) . . ?
C5 C6 C7 123.5(2) . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 C6 118.7(2) . . ?
C8 C7 C6 122.0(2) . . ?
C9 C8 C7 119.9(3) . . ?
C8 C9 C10 120.7(3) . . ?
C11 C10 C9 119.4(3) . . ?
C10 C11 C12 120.4(3) . . ?
C11 C12 C7 120.4(2) . . ?
O1 C13 C14 120.4(2) . . ?
O1 C13 C4 115.9(2) . . ?
C14 C13 C4 123.7(2) . . ?
C19 C14 C15 119.4(2) . . ?
C19 C14 C13 115.4(2) . . ?
C15 C14 C13 125.2(2) . . ?
C16 C15 C14 119.8(3) . . ?
C17 C16 C15 120.6(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.1(3) . . ?
C14 C19 C18 120.2(3) . . ?
C3 N1 C2 102.8(2) . . ?
C6 N2 N3 127.8(2) . . ?
C6 N2 C3 122.3(2) . . ?
N3 N2 C3 109.8(2) . . ?
C2 N3 N2 101.2(2) . . ?
C3 N4 C4 115.1(2) . . ?
C2 S1 C1 100.34(14) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.162
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_datam
_database_code_depnum_ccdc_archive 'CCDC 1410753'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'2-(3,6-diphenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene)-1-phenylethanone (24)'
_chemical_name_common            ?
_chemical_melting_point          514-515
_chemical_formula_moiety         'C24 H16 N4 O S'
_chemical_formula_sum            'C24 H16 N4 O S'
_chemical_formula_weight         408.47

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   'P 21/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                   6.992
_cell_length_b                   14.617
_cell_length_c                   19.051
_cell_angle_alpha                90.00
_cell_angle_beta                 95.50
_cell_angle_gamma                90.00
_cell_volume                     1938.1
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.869
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.189
_exptl_crystal_density_meas      1.400
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848.0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury 375R/M CCD (XtaLAB mini)'
_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            20237
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.56
_reflns_number_total             4460
_reflns_number_gt                3891
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0821P)²+0.5738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4460
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_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 0.76280(7) 0.02855(3) 0.95824(3) 0.02808(17) Uani 1 1 d . . .
O1 O 0.8489(2) 0.00869(11) 0.82597(8) 0.0358(3) Uani 1 1 d . . .
N1 N 0.7283(2) -0.04072(10) 1.09040(9) 0.0249(3) Uani 1 1 d . . .
C1 C 0.7767(2) -0.09087(13) 0.94901(10) 0.0248(4) Uani 1 1 d . . .
C10 C 0.7489(2) -0.15287(13) 1.00831(10) 0.0241(4) Uani 1 1 d . . .
C17 C 0.7257(3) 0.03327(12) 1.04677(11) 0.0275(4) Uani 1 1 d . . .
C3 C 0.8373(3) -0.07511(14) 0.82277(10) 0.0283(4) Uani 1 1 d . . .
N4 N 0.6734(3) 0.08100(12) 1.15175(10) 0.0340(4) Uani 1 1 d . . .
N2 N 0.7290(2) -0.13175(10) 1.07311(8) 0.0255(3) Uani 1 1 d . . .
C11 C 0.7464(3) -0.25396(13) 0.99702(9) 0.0242(4) Uani 1 1 d . . .
C16 C 0.8796(3) -0.30684(14) 1.03717(11) 0.0321(4) Uani 1 1 d . . .
H16 H 0.9732 -0.2792 1.0681 0.039 Uiso 1 1 calc R . .
C4 C 0.8485(3) -0.12595(14) 0.75581(10) 0.0284(4) Uani 1 1 d . . .
N3 N 0.6934(3) 0.10809(12) 1.08219(10) 0.0340(4) Uani 1 1 d . . .
C12 C 0.6059(3) -0.29521(14) 0.95101(10) 0.0292(4) Uani 1 1 d . . .
H12 H 0.5162 -0.2596 0.9241 0.035 Uiso 1 1 calc R . .
C5 C 0.7773(3) -0.21449(14) 0.74616(11) 0.0325(4) Uani 1 1 d . . .
H5 H 0.7193 -0.2429 0.7823 0.039 Uiso 1 1 calc R . .
C13 C 0.6000(3) -0.38979(14) 0.94543(11) 0.0348(5) Uani 1 1 d . . .
H13 H 0.5063 -0.4179 0.9148 0.042 Uiso 1 1 calc R . .
C18 C 0.6934(3) -0.00802(15) 1.15583(11) 0.0289(4) Uani 1 1 d . . .
C7 C 0.8801(3) -0.21907(17) 0.63020(11) 0.0387(5) Uani 1 1 d . . .
H7 H 0.8926 -0.2503 0.5883 0.046 Uiso 1 1 calc R . .
C14 C 0.7338(3) -0.44206(15) 0.98547(12) 0.0378(5) Uani 1 1 d . . .
H14 H 0.7299 -0.5055 0.9817 0.045 Uiso 1 1 calc R . .
C24 C 0.5698(3) -0.03294(15) 1.27130(12) 0.0355(5) Uani 1 1 d . . .
H24 H 0.5077 0.0233 1.2661 0.043 Uiso 1 1 calc R . .
C9 C 0.9337(3) -0.08384(16) 0.70102(11) 0.0359(5) Uani 1 1 d . . .
H9 H 0.9793 -0.0242 0.7061 0.043 Uiso 1 1 calc R . .
C6 C 0.7916(3) -0.26085(16) 0.68343(11) 0.0360(5) Uani 1 1 d . . .
H6 H 0.7420 -0.3196 0.6773 0.043 Uiso 1 1 calc R . .
C2 C 0.8122(3) -0.12822(14) 0.88655(10) 0.0290(4) Uani 1 1 d . . .
C20 C 0.7773(3) -0.14714(14) 1.22904(11) 0.0329(4) Uani 1 1 d . . .
H20 H 0.8545 -0.1679 1.1952 0.039 Uiso 1 1 calc R . .
C19 C 0.6809(3) -0.06439(14) 1.21918(10) 0.0281(4) Uani 1 1 d . . .
C21 C 0.7593(3) -0.19884(16) 1.28867(12) 0.0385(5) Uani 1 1 d . . .
H21 H 0.8233 -0.2545 1.2947 0.046 Uiso 1 1 calc R . .
C15 C 0.8728(3) -0.40122(15) 1.03094(12) 0.0391(5) Uani 1 1 d . . .
H15 H 0.9626 -0.4371 1.0576 0.047 Uiso 1 1 calc R . .
C22 C 0.6460(3) -0.16801(18) 1.33964(12) 0.0411(5) Uani 1 1 d . . .
H22 H 0.6334 -0.2029 1.3797 0.049 Uiso 1 1 calc R . .
C23 C 0.5523(3) -0.08535(19) 1.33059(12) 0.0421(5) Uani 1 1 d . . .
H23 H 0.4764 -0.0646 1.3648 0.050 Uiso 1 1 calc R . .
C8 C 0.9500(3) -0.13128(17) 0.63887(12) 0.0402(5) Uani 1 1 d . . .
H8 H 1.0089 -0.1035 0.6026 0.048 Uiso 1 1 calc R . .
H2 H 0.820(3) -0.1938(16) 0.8832(12) 0.028(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C17 1.732(2) . ?
S1 C1 1.758(2) . ?
O1 C3 1.229(3) . ?
N1 C17 1.363(2) . ?
N1 N2 1.371(2) . ?
N1 C18 1.378(3) . ?
C1 C2 1.354(3) . ?
C1 C10 1.475(3) . ?
C10 N2 1.293(2) . ?
C10 C11 1.493(3) . ?
C17 N3 1.316(3) . ?
C3 C2 1.467(3) . ?
C3 C4 1.485(3) . ?
N4 C18 1.310(3) . ?
N4 N3 1.403(3) . ?
C11 C16 1.383(3) . ?
C11 C12 1.390(3) . ?
C16 C15 1.385(3) . ?
C16 H16 0.9300 . ?
C4 C5 1.392(3) . ?
C4 C9 1.394(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C18 C19 1.471(3) . ?
C7 C8 1.377(3) . ?
C7 C6 1.380(3) . ?
C7 H7 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C24 C23 1.380(3) . ?
C24 C19 1.396(3) . ?
C24 H24 0.9300 . ?
C9 C8 1.386(3) . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.96(2) . ?
C20 C21 1.380(3) . ?
C20 C19 1.389(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9300 . ?
C15 H15 0.9300 . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C8 H8 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
C17 S1 C1 98.72(9) . . ?
C17 N1 N2 128.58(16) . . ?
C17 N1 C18 106.45(16) . . ?
N2 N1 C18 123.97(17) . . ?
C2 C1 C10 118.29(17) . . ?
C2 C1 S1 120.32(15) . . ?
C10 C1 S1 121.39(14) . . ?
N2 C10 C1 128.20(17) . . ?
N2 C10 C11 111.90(16) . . ?
C1 C10 C11 119.89(16) . . ?
N3 C17 N1 109.86(19) . . ?
N3 C17 S1 125.55(16) . . ?
N1 C17 S1 124.59(15) . . ?
O1 C3 C2 119.94(18) . . ?
O1 C3 C4 122.20(17) . . ?
C2 C3 C4 117.86(18) . . ?
C18 N4 N3 108.46(16) . . ?
C10 N2 N1 117.67(16) . . ?
C16 C11 C12 120.28(18) . . ?
C16 C11 C10 118.38(17) . . ?
C12 C11 C10 121.19(16) . . ?
C11 C16 C15 119.6(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C5 C4 C9 118.98(19) . . ?
C5 C4 C3 122.06(17) . . ?
C9 C4 C3 118.95(19) . . ?
C17 N3 N4 106.70(17) . . ?
C13 C12 C11 119.64(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C6 C5 C4 120.93(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C18 N1 108.53(17) . . ?
N4 C18 C19 126.20(18) . . ?
N1 C18 C19 125.27(18) . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C23 C24 C19 119.9(2) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C8 C9 C4 119.7(2) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C1 C2 C3 124.16(19) . . ?
C1 C2 H2 118.5(13) . . ?
C3 C2 H2 117.4(13) . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C19 C24 119.1(2) . . ?
C20 C19 C18 122.19(18) . . ?
C24 C19 C18 118.69(19) . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.7(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?

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
C17 S1 C1 C2 -177.84(15) . . . . ?
C17 S1 C1 C10 2.58(16) . . . . ?
C2 C1 C10 N2 174.00(19) . . . . ?
S1 C1 C10 N2 -6.4(3) . . . . ?
C2 C1 C10 C11 -4.4(3) . . . . ?
S1 C1 C10 C11 175.21(13) . . . . ?
N2 N1 C17 N3 169.45(17) . . . . ?
C18 N1 C17 N3 0.7(2) . . . . ?
N2 N1 C17 S1 -11.3(3) . . . . ?
C18 N1 C17 S1 179.88(14) . . . . ?
C1 S1 C17 N3 -175.88(18) . . . . ?
C1 S1 C17 N1 5.02(18) . . . . ?
C1 C10 N2 N1 1.7(3) . . . . ?
C11 C10 N2 N1 -179.81(15) . . . . ?
C17 N1 N2 C10 7.7(3) . . . . ?
C18 N1 N2 C10 174.69(17) . . . . ?
N2 C10 C11 C16 -57.1(2) . . . . ?
C1 C10 C11 C16 121.52(19) . . . . ?
N2 C10 C11 C12 118.45(19) . . . . ?
C1 C10 C11 C12 -62.9(2) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C10 C11 C16 C15 175.98(18) . . . . ?
O1 C3 C4 C5 -159.40(19) . . . . ?
C2 C3 C4 C5 20.8(3) . . . . ?
O1 C3 C4 C9 20.8(3) . . . . ?
C2 C3 C4 C9 -158.91(18) . . . . ?
N1 C17 N3 N4 -0.3(2) . . . . ?
S1 C17 N3 N4 -179.50(14) . . . . ?
C18 N4 N3 C17 -0.2(2) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 -175.60(17) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -179.24(18) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
N3 N4 C18 N1 0.6(2) . . . . ?
N3 N4 C18 C19 -179.37(18) . . . . ?
C17 N1 C18 N4 -0.8(2) . . . . ?
N2 N1 C18 N4 -170.22(17) . . . . ?
C17 N1 C18 C19 179.21(17) . . . . ?
N2 N1 C18 C19 9.8(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C5 C4 C9 C8 -1.5(3) . . . . ?
C3 C4 C9 C8 178.26(19) . . . . ?
C8 C7 C6 C5 -1.3(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C10 C1 C2 C3 178.23(17) . . . . ?
S1 C1 C2 C3 -1.4(3) . . . . ?
O1 C3 C2 C1 8.5(3) . . . . ?
C4 C3 C2 C1 -171.72(18) . . . . ?
C21 C20 C19 C24 1.8(3) . . . . ?
C21 C20 C19 C18 -178.87(19) . . . . ?
C23 C24 C19 C20 -2.0(3) . . . . ?
C23 C24 C19 C18 178.63(19) . . . . ?
N4 C18 C19 C20 -152.6(2) . . . . ?
N1 C18 C19 C20 27.5(3) . . . . ?
N4 C18 C19 C24 26.8(3) . . . . ?
N1 C18 C19 C24 -153.19(19) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C11 C16 C15 C14 -0.4(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C19 C24 C23 C22 1.1(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C4 C9 C8 C7 1.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.156
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r3213
_database_code_depnum_ccdc_archive 'CCDC 1410754'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'1, 4-diphenyl-2-((1-phenyl-1H-tetrazol-5-yl)thio)but-2-ene-1,4-dione (26'
_chemical_name_common            ?
_chemical_melting_point          429-430
_chemical_formula_moiety         'C23 H16 N4 O2 S'
_chemical_formula_sum            'C23 H16 N4 O2 S'
_chemical_formula_weight         412.46

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.1611(14)
_cell_length_b                   13.5100(15)
_cell_length_c                   10.7868(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.381(4)
_cell_angle_gamma                90
_cell_volume                     1897.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5236
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.139
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'sadabs v2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19879
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         27.358
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4283
_reflns_number_gt                3266
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+1.0328P] 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         4283
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66724(3) 0.53555(3) 0.83666(4) 0.01365(11) Uani 1 1 d . . . . .
O1 O 0.52954(9) 0.57140(9) 0.63981(10) 0.0156(3) Uani 1 1 d . . . . .
O2 O 0.87387(9) 0.65614(9) 0.86975(11) 0.0173(3) Uani 1 1 d . . . . .
N1 N 0.73915(11) 0.57809(11) 1.08435(13) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.80954(11) 0.53719(11) 1.17573(13) 0.0173(3) Uani 1 1 d . . . . .
N3 N 0.85623(11) 0.46348(11) 1.13230(13) 0.0168(3) Uani 1 1 d . . . . .
N4 N 0.81730(10) 0.45545(10) 1.00931(12) 0.0130(3) Uani 1 1 d . . . . .
C1 C 0.69739(12) 0.65655(13) 0.79315(15) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.64325(12) 0.70222(13) 0.69478(15) 0.0136(4) Uani 1 1 d . . . . .
H2 H 0.6645 0.7661 0.6721 0.016 Uiso 1 1 calc R U . . .
C3 C 0.55250(12) 0.65756(13) 0.62077(15) 0.0130(3) Uani 1 1 d . . . . .
C4 C 0.49024(12) 0.71779(13) 0.52212(15) 0.0127(3) Uani 1 1 d . . . . .
C5 C 0.43083(13) 0.66880(13) 0.42341(15) 0.0154(4) Uani 1 1 d . . . . .
H5 H 0.4297 0.5985 0.4212 0.018 Uiso 1 1 calc R U . . .
C6 C 0.37345(13) 0.72227(14) 0.32868(16) 0.0186(4) Uani 1 1 d . . . . .
H6 H 0.3331 0.6886 0.2615 0.022 Uiso 1 1 calc R U . . .
C7 C 0.37472(13) 0.82478(14) 0.33159(16) 0.0181(4) Uani 1 1 d . . . . .
H7 H 0.3354 0.8613 0.2662 0.022 Uiso 1 1 calc R U . . .
C8 C 0.43322(13) 0.87398(14) 0.42954(16) 0.0172(4) Uani 1 1 d . . . . .
H8 H 0.4338 0.9443 0.4316 0.021 Uiso 1 1 calc R U . . .
C9 C 0.49100(12) 0.82080(13) 0.52461(15) 0.0155(4) Uani 1 1 d . . . . .
H9 H 0.5312 0.8547 0.5917 0.019 Uiso 1 1 calc R U . . .
C10 C 0.79448(12) 0.70309(13) 0.86140(15) 0.0135(4) Uani 1 1 d . . . . .
C11 C 0.79005(12) 0.80340(13) 0.91669(14) 0.0126(3) Uani 1 1 d . . . . .
C12 C 0.70313(13) 0.86320(13) 0.90137(15) 0.0147(4) Uani 1 1 d . . . . .
H12 H 0.6414 0.8400 0.8534 0.018 Uiso 1 1 calc R U . . .
C13 C 0.70588(13) 0.95625(14) 0.95545(15) 0.0174(4) Uani 1 1 d . . . . .
H13 H 0.6469 0.9976 0.9422 0.021 Uiso 1 1 calc R U . . .
C14 C 0.79452(14) 0.98884(14) 1.02868(16) 0.0202(4) Uani 1 1 d . . . . .
H14 H 0.7962 1.0523 1.0669 0.024 Uiso 1 1 calc R U . . .
C15 C 0.88106(14) 0.92896(14) 1.04636(17) 0.0217(4) Uani 1 1 d . . . . .
H15 H 0.9416 0.9512 1.0976 0.026 Uiso 1 1 calc R U . . .
C16 C 0.87943(13) 0.83728(14) 0.98979(15) 0.0178(4) Uani 1 1 d . . . . .
H16 H 0.9393 0.7971 1.0007 0.021 Uiso 1 1 calc R U . . .
C17 C 0.74620(12) 0.52653(12) 0.98227(15) 0.0123(3) Uani 1 1 d . . . . .
C18 C 0.85547(12) 0.38336(13) 0.92955(14) 0.0128(3) Uani 1 1 d . . . . .
C19 C 0.91830(14) 0.41572(14) 0.84567(16) 0.0190(4) Uani 1 1 d . . . . .
H19 H 0.9355 0.4838 0.8410 0.023 Uiso 1 1 calc R U . . .
C20 C 0.95570(14) 0.34660(14) 0.76848(16) 0.0203(4) Uani 1 1 d . . . . .
H20 H 0.9995 0.3672 0.7107 0.024 Uiso 1 1 calc R U . . .
C21 C 0.92946(13) 0.24788(14) 0.77528(15) 0.0168(4) Uani 1 1 d . . . . .
H21 H 0.9546 0.2011 0.7214 0.020 Uiso 1 1 calc R U . . .
C22 C 0.86680(13) 0.21695(13) 0.86026(15) 0.0166(4) Uani 1 1 d . . . . .
H22 H 0.8494 0.1489 0.8648 0.020 Uiso 1 1 calc R U . . .
C23 C 0.82912(13) 0.28490(13) 0.93896(15) 0.0151(4) Uani 1 1 d . . . . .
H23 H 0.7863 0.2642 0.9978 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C17 1.7567(16) . ?
S1 C1 1.7620(18) . ?
O1 C3 1.227(2) . ?
O2 C10 1.214(2) . ?
N1 C17 1.318(2) . ?
N1 N2 1.3671(19) . ?
N2 N3 1.293(2) . ?
N3 N4 1.3550(18) . ?
N4 C17 1.343(2) . ?
N4 C18 1.438(2) . ?
C1 C2 1.339(2) . ?
C1 C10 1.515(2) . ?
C2 C3 1.466(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.487(2) . ?
C4 C9 1.392(2) . ?
C4 C5 1.393(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.485(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.395(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C23 1.382(2) . ?
C18 C19 1.383(2) . ?
C19 C20 1.388(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 H23 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
C17 S1 C1 100.12(8) . . ?
C17 N1 N2 105.42(13) . . ?
N3 N2 N1 110.97(13) . . ?
N2 N3 N4 106.53(13) . . ?
C17 N4 N3 107.91(13) . . ?
C17 N4 C18 130.36(13) . . ?
N3 N4 C18 121.66(13) . . ?
C2 C1 C10 120.49(15) . . ?
C2 C1 S1 121.60(13) . . ?
C10 C1 S1 117.53(12) . . ?
C1 C2 C3 122.61(16) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
O1 C3 C2 120.00(15) . . ?
O1 C3 C4 121.01(15) . . ?
C2 C3 C4 118.98(15) . . ?
C9 C4 C5 119.44(15) . . ?
C9 C4 C3 122.11(15) . . ?
C5 C4 C3 118.44(15) . . ?
C6 C5 C4 120.13(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.14(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.08(16) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.04(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 120.17(16) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
O2 C10 C11 122.05(15) . . ?
O2 C10 C1 118.35(16) . . ?
C11 C10 C1 119.60(14) . . ?
C12 C11 C16 119.22(16) . . ?
C12 C11 C10 124.21(15) . . ?
C16 C11 C10 116.56(15) . . ?
C13 C12 C11 120.47(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.89(17) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.03(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.21(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.15(16) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N1 C17 N4 109.16(14) . . ?
N1 C17 S1 127.29(13) . . ?
N4 C17 S1 123.13(12) . . ?
C23 C18 C19 122.19(16) . . ?
C23 C18 N4 119.65(15) . . ?
C19 C18 N4 118.15(15) . . ?
C18 C19 C20 118.55(17) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 120.27(17) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.27(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.34(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 118.37(16) . . ?
C18 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N1 N2 N3 -0.89(18) . . . . ?
N1 N2 N3 N4 0.67(18) . . . . ?
N2 N3 N4 C17 -0.19(17) . . . . ?
N2 N3 N4 C18 177.06(14) . . . . ?
C17 S1 C1 C2 -169.83(14) . . . . ?
C17 S1 C1 C10 17.18(14) . . . . ?
C10 C1 C2 C3 176.08(15) . . . . ?
S1 C1 C2 C3 3.3(2) . . . . ?
C1 C2 C3 O1 -7.5(3) . . . . ?
C1 C2 C3 C4 173.27(16) . . . . ?
O1 C3 C4 C9 157.83(16) . . . . ?
C2 C3 C4 C9 -22.9(2) . . . . ?
O1 C3 C4 C5 -23.2(2) . . . . ?
C2 C3 C4 C5 156.03(15) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 -178.77(15) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C3 C4 C9 C8 178.84(15) . . . . ?
C2 C1 C10 O2 -122.82(18) . . . . ?
S1 C1 C10 O2 50.24(19) . . . . ?
C2 C1 C10 C11 57.7(2) . . . . ?
S1 C1 C10 C11 -129.24(14) . . . . ?
O2 C10 C11 C12 174.72(16) . . . . ?
C1 C10 C11 C12 -5.8(2) . . . . ?
O2 C10 C11 C16 -6.3(2) . . . . ?
C1 C10 C11 C16 173.17(15) . . . . ?
C16 C11 C12 C13 1.6(2) . . . . ?
C10 C11 C12 C13 -179.48(15) . . . . ?
C11 C12 C13 C14 -2.2(2) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -1.4(3) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C10 C11 C16 C15 -178.82(15) . . . . ?
N2 N1 C17 N4 0.74(18) . . . . ?
N2 N1 C17 S1 173.50(12) . . . . ?
N3 N4 C17 N1 -0.36(18) . . . . ?
C18 N4 C17 N1 -177.29(15) . . . . ?
N3 N4 C17 S1 -173.49(12) . . . . ?
C18 N4 C17 S1 9.6(2) . . . . ?
C1 S1 C17 N1 65.22(17) . . . . ?
C1 S1 C17 N4 -122.95(14) . . . . ?
C17 N4 C18 C23 -108.4(2) . . . . ?
N3 N4 C18 C23 75.0(2) . . . . ?
C17 N4 C18 C19 71.8(2) . . . . ?
N3 N4 C18 C19 -104.74(18) . . . . ?
C23 C18 C19 C20 0.1(2) . . . . ?
N4 C18 C19 C20 179.86(15) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
N4 C18 C23 C22 179.72(14) . . . . ?
C21 C22 C23 C18 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 N1 0.95 2.56 3.501(2) 169.9 4_575
C19 H19 O2 0.95 2.50 3.317(2) 144.2 .

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_datam
_database_code_depnum_ccdc_archive 'CCDC 1410755'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 7-oxo-2-phenyl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazine-5-carboxylate '
_chemical_name_common            ?
_chemical_melting_point          451-452
_chemical_formula_moiety         'C13 H9 N3 O3 S'
_chemical_formula_sum            'C13 H9 N3 O3 S'
_chemical_formula_weight         287.29

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   'P 21/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                   7.1783(10)
_cell_length_b                   14.804(2)
_cell_length_c                   12.0251(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.835(6)
_cell_angle_gamma                90.00
_cell_volume                     1265.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.748
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.161
_exptl_crystal_density_meas      1.507
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592.0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury 375/M CCD (Xta LAB mini)'
_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            13172
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2894
_reflns_number_gt                2631
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0808P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2894
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
H4 H 0.295(4) 0.2705(19) 0.726(2) 0.062(8) Uiso 1 1 d . . .
S1 S 0.14078(6) 0.33638(3) 0.43758(3) 0.03020(17) Uani 1 1 d . . .
N1 N 0.29468(19) 0.46417(10) 0.58830(12) 0.0268(3) Uani 1 1 d . . .
N2 N 0.3391(2) 0.55457(10) 0.59273(12) 0.0285(3) Uani 1 1 d . . .
O1 O 0.18786(19) 0.13358(8) 0.64088(11) 0.0367(3) Uani 1 1 d . . .
O2 O 0.0796(2) 0.15145(9) 0.45737(12) 0.0428(4) Uani 1 1 d . . .
N3 N 0.19946(19) 0.51538(10) 0.41754(12) 0.0291(3) Uani 1 1 d . . .
O3 O 0.3993(2) 0.43688(9) 0.77318(12) 0.0455(4) Uani 1 1 d . . .
C6 C 0.2124(2) 0.44310(11) 0.48210(14) 0.0261(3) Uani 1 1 d . . .
C5 C 0.3266(2) 0.40680(12) 0.68337(14) 0.0304(4) Uani 1 1 d . . .
C8 C 0.2997(2) 0.67559(11) 0.45264(14) 0.0263(4) Uani 1 1 d . . .
C2 C 0.1463(2) 0.18034(12) 0.54763(16) 0.0316(4) Uani 1 1 d . . .
C4 C 0.2713(2) 0.31367(12) 0.66288(15) 0.0307(4) Uani 1 1 d . . .
C1 C 0.1942(2) 0.27873(11) 0.56396(14) 0.0276(4) Uani 1 1 d . . .
C7 C 0.2801(2) 0.58162(11) 0.48898(14) 0.0263(3) Uani 1 1 d . . .
C12 C 0.4033(3) 0.82873(12) 0.49352(16) 0.0345(4) Uani 1 1 d . . .
H12 H 0.4593 0.8715 0.5441 0.041 Uiso 1 1 calc R . .
C13 C 0.3837(2) 0.74019(12) 0.52795(14) 0.0292(4) Uani 1 1 d . . .
H13 H 0.4268 0.7238 0.6016 0.035 Uiso 1 1 calc R . .
C9 C 0.2342(2) 0.70099(13) 0.34216(14) 0.0306(4) Uani 1 1 d . . .
H9 H 0.1774 0.6586 0.2914 0.037 Uiso 1 1 calc R . .
C10 C 0.2542(2) 0.78978(14) 0.30883(16) 0.0355(4) Uani 1 1 d . . .
H10 H 0.2103 0.8067 0.2355 0.043 Uiso 1 1 calc R . .
C11 C 0.3391(3) 0.85353(13) 0.38359(18) 0.0370(4) Uani 1 1 d . . .
H11 H 0.3530 0.9127 0.3602 0.044 Uiso 1 1 calc R . .
C3 C 0.1556(4) 0.03657(13) 0.63107(19) 0.0484(5) Uani 1 1 d . . .
H3A H 0.1901 0.0086 0.7030 0.073 Uiso 1 1 calc R . .
H3B H 0.2304 0.0118 0.5781 0.073 Uiso 1 1 calc R . .
H3C H 0.0250 0.0254 0.6057 0.073 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7238(17) . ?
S1 C1 1.7396(18) . ?
N1 C6 1.368(2) . ?
N1 N2 1.375(2) . ?
N1 C5 1.418(2) . ?
N2 C7 1.324(2) . ?
O1 C2 1.317(2) . ?
O1 C3 1.457(2) . ?
O2 C2 1.203(2) . ?
N3 C6 1.318(2) . ?
N3 C7 1.378(2) . ?
O3 C5 1.218(2) . ?
C5 C4 1.446(2) . ?
C8 C13 1.396(2) . ?
C8 C9 1.399(2) . ?
C8 C7 1.471(2) . ?
C2 C1 1.504(2) . ?
C4 C1 1.345(2) . ?
C4 H4 0.99(3) . ?
C12 C13 1.388(2) . ?
C12 C11 1.389(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
C6 S1 C1 99.06(8) . . ?
C6 N1 N2 109.06(13) . . ?
C6 N1 C5 128.17(15) . . ?
N2 N1 C5 122.73(14) . . ?
C7 N2 N1 102.41(13) . . ?
C2 O1 C3 115.73(15) . . ?
C6 N3 C7 102.76(14) . . ?
N3 C6 N1 110.58(15) . . ?
N3 C6 S1 124.56(13) . . ?
N1 C6 S1 124.85(13) . . ?
O3 C5 N1 119.91(16) . . ?
O3 C5 C4 125.03(16) . . ?
N1 C5 C4 115.04(15) . . ?
C13 C8 C9 119.43(16) . . ?
C13 C8 C7 120.37(15) . . ?
C9 C8 C7 120.19(16) . . ?
O2 C2 O1 126.67(17) . . ?
O2 C2 C1 121.19(17) . . ?
O1 C2 C1 112.13(15) . . ?
C1 C4 C5 125.96(17) . . ?
C1 C4 H4 116.0(17) . . ?
C5 C4 H4 118.0(17) . . ?
C4 C1 C2 123.18(16) . . ?
C4 C1 S1 126.81(14) . . ?
C2 C1 S1 110.00(12) . . ?
N2 C7 N3 115.19(15) . . ?
N2 C7 C8 122.33(15) . . ?
N3 C7 C8 122.49(15) . . ?
C13 C12 C11 119.99(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.39(16) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C10 C9 C8 119.62(17) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.76(17) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.80(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C7 0.15(16) . . . . ?
C5 N1 N2 C7 -177.62(14) . . . . ?
C7 N3 C6 N1 0.73(17) . . . . ?
C7 N3 C6 S1 -177.74(12) . . . . ?
N2 N1 C6 N3 -0.59(18) . . . . ?
C5 N1 C6 N3 177.03(15) . . . . ?
N2 N1 C6 S1 177.88(11) . . . . ?
C5 N1 C6 S1 -4.5(2) . . . . ?
C1 S1 C6 N3 -178.77(14) . . . . ?
C1 S1 C6 N1 2.98(15) . . . . ?
C6 N1 C5 O3 -178.68(16) . . . . ?
N2 N1 C5 O3 -1.4(3) . . . . ?
C6 N1 C5 C4 2.8(2) . . . . ?
N2 N1 C5 C4 -179.92(14) . . . . ?
C3 O1 C2 O2 2.5(3) . . . . ?
C3 O1 C2 C1 -176.71(16) . . . . ?
O3 C5 C4 C1 -178.62(18) . . . . ?
N1 C5 C4 C1 -0.2(3) . . . . ?
C5 C4 C1 C2 177.77(16) . . . . ?
C5 C4 C1 S1 -0.5(3) . . . . ?
O2 C2 C1 C4 -179.05(18) . . . . ?
O1 C2 C1 C4 0.2(2) . . . . ?
O2 C2 C1 S1 -0.5(2) . . . . ?
O1 C2 C1 S1 178.78(12) . . . . ?
C6 S1 C1 C4 -0.71(17) . . . . ?
C6 S1 C1 C2 -179.19(11) . . . . ?
N1 N2 C7 N3 0.33(17) . . . . ?
N1 N2 C7 C8 -179.49(13) . . . . ?
C6 N3 C7 N2 -0.68(18) . . . . ?
C6 N3 C7 C8 179.14(14) . . . . ?
C13 C8 C7 N2 0.3(2) . . . . ?
C9 C8 C7 N2 -179.67(14) . . . . ?
C13 C8 C7 N3 -179.51(14) . . . . ?
C9 C8 C7 N3 0.5(2) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -0.4(2) . . . . ?
C7 C8 C13 C12 179.62(15) . . . . ?
C13 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 C10 -179.74(15) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C13 C12 C11 C10 0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.134
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile:methanol (2:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r515
_database_code_depnum_ccdc_archive 'CCDC 1410756'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'methyl 3-((1H-1,2,4-triazol-3-yl)amino)acrylate (44)'
_chemical_name_common            ?
_chemical_melting_point          473
_chemical_formula_moiety         'C6 H7 N3 O2 S'
_chemical_formula_sum            'C6 H7 N3 O2 S'
_chemical_formula_weight         185.21

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

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

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

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

_cell_length_a                   5.4918(4)
_cell_length_b                   16.0080(11)
_cell_length_c                   9.4419(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.129(4)
_cell_angle_gamma                90
_cell_volume                     808.37(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8434
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      36.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.201
_exptl_absorpt_coefficient_mu    0.361
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_T_max  0.8625
_exptl_absorpt_process_details   'sadabs v2014/3'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21213
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         36.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3867
_reflns_number_gt                3109
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3867
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71097(5) 0.61986(2) 0.43641(3) 0.01498(10) Uani 1 1 d . . . . .
O1 O 0.86298(17) 0.51630(6) 0.23001(10) 0.0220(2) Uani 1 1 d . . . . .
O2 O 0.61384(16) 0.41663(6) 0.10305(9) 0.01797(18) Uani 1 1 d . . . . .
N1 N 0.71793(17) 0.70547(7) 0.67981(10) 0.01548(19) Uani 1 1 d . . . . .
N2 N 0.55502(18) 0.75230(7) 0.73578(10) 0.0155(2) Uani 1 1 d . . . . .
N3 N 0.33451(17) 0.70747(7) 0.52684(10) 0.0165(2) Uani 1 1 d . . . . .
C1 C 0.57613(19) 0.68011(7) 0.55429(11) 0.0133(2) Uani 1 1 d . . . . .
C2 C 0.3298(2) 0.75213(8) 0.64509(13) 0.0180(2) Uani 1 1 d . . . . .
H2A H 0.1866 0.7799 0.6625 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4492(2) 0.56094(7) 0.35525(12) 0.0150(2) Uani 1 1 d . . . . .
H3 H 0.2985 0.5714 0.3856 0.018 Uiso 1 1 calc R U . . .
C4 C 0.4433(2) 0.50213(8) 0.25352(12) 0.0159(2) Uani 1 1 d . . . . .
H4 H 0.2913 0.4730 0.2169 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6621(2) 0.48114(7) 0.19688(12) 0.0153(2) Uani 1 1 d . . . . .
C6 C 0.8247(2) 0.38676(8) 0.04884(13) 0.0205(2) Uani 1 1 d . . . . .
H6A H 0.7681 0.3435 -0.0248 0.031 Uiso 1 1 calc R U . . .
H6B H 0.9508 0.3632 0.1294 0.031 Uiso 1 1 calc R U . . .
H6C H 0.8977 0.4333 0.0053 0.031 Uiso 1 1 calc R U . . .
H2 H 0.609(3) 0.7718(11) 0.8212(18) 0.023(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.7445(11) . ?
S1 C1 1.7583(11) . ?
O1 C5 1.2142(14) . ?
O2 C5 1.3473(14) . ?
O2 C6 1.4491(15) . ?
N1 C1 1.3254(13) . ?
N1 N2 1.3625(14) . ?
N2 C2 1.3348(15) . ?
N2 H2 0.852(17) . ?
N3 C2 1.3310(15) . ?
N3 C1 1.3651(14) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3401(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4610(16) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C3 S1 C1 98.69(5) . . ?
C5 O2 C6 115.56(9) . . ?
C1 N1 N2 102.19(9) . . ?
C2 N2 N1 110.15(10) . . ?
C2 N2 H2 132.7(11) . . ?
N1 N2 H2 116.9(11) . . ?
C2 N3 C1 102.49(9) . . ?
N1 C1 N3 114.82(10) . . ?
N1 C1 S1 119.19(8) . . ?
N3 C1 S1 125.93(8) . . ?
N3 C2 N2 110.33(11) . . ?
N3 C2 H2A 124.8 . . ?
N2 C2 H2A 124.8 . . ?
C4 C3 S1 125.30(9) . . ?
C4 C3 H3 117.4 . . ?
S1 C3 H3 117.4 . . ?
C3 C4 C5 122.42(10) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
O1 C5 O2 123.80(11) . . ?
O1 C5 C4 125.00(11) . . ?
O2 C5 C4 111.20(10) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C1 N1 N2 C2 0.66(13) . . . . ?
N2 N1 C1 N3 -0.10(13) . . . . ?
N2 N1 C1 S1 177.25(8) . . . . ?
C2 N3 C1 N1 -0.48(14) . . . . ?
C2 N3 C1 S1 -177.63(9) . . . . ?
C3 S1 C1 N1 149.42(9) . . . . ?
C3 S1 C1 N3 -33.55(11) . . . . ?
C1 N3 C2 N2 0.89(14) . . . . ?
N1 N2 C2 N3 -1.03(15) . . . . ?
C1 S1 C3 C4 -179.53(11) . . . . ?
S1 C3 C4 C5 -0.71(18) . . . . ?
C6 O2 C5 O1 3.91(17) . . . . ?
C6 O2 C5 C4 -175.56(10) . . . . ?
C3 C4 C5 O1 -3.5(2) . . . . ?
C3 C4 C5 O2 175.96(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
# C2 H2A S1  0.95 3.02 3.6064(13) 121.3 4_576 
# C3 H3 O1  0.95 2.66 3.2471(14) 120.7 1_455 
# C6 H6A N1  0.98 2.66 3.5929(16) 158.8 2_645 
C4 H4 O1 0.95 2.48 3.1524(15) 127.5 1_455
C6 H6B N1 0.98 2.51 3.4829(16) 175.2 3_766
N2 H2 N3 0.852(17) 2.080(17) 2.8994(13) 161.2(16) 4_676

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.142

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r615
_database_code_depnum_ccdc_archive 'CCDC 1410757'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'5-phenyl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-one (49)'
_chemical_name_common            ?
_chemical_melting_point          543
_chemical_formula_moiety         'C11 H7 N3 O S'
_chemical_formula_sum            'C11 H7 N3 O S'
_chemical_formula_weight         229.26

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

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

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

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

_cell_length_a                   6.9892(6)
_cell_length_b                   10.5036(10)
_cell_length_c                   13.4268(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.277(4)
_cell_angle_gamma                90
_cell_volume                     955.24(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6498
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      31.94

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_process_details   'sadabs v2014/4'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19126
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         32.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3319
_reflns_number_gt                2570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0871P)²] 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         3319
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.86424(5) 0.52186(3) 0.59908(3) 0.01333(12) Uani 1 1 d . . . . .
O1 O 0.52515(15) 0.86517(10) 0.64580(9) 0.0186(2) Uani 1 1 d . . . . .
N1 N 0.79372(17) 0.77876(11) 0.60186(9) 0.0109(2) Uani 1 1 d . . . . .
N2 N 0.87795(16) 0.89236(12) 0.58430(9) 0.0134(3) Uani 1 1 d . . . . .
N3 N 1.06864(18) 0.72463(12) 0.55894(10) 0.0144(3) Uani 1 1 d . . . . .
C1 C 0.91122(19) 0.68093(14) 0.58565(10) 0.0114(3) Uani 1 1 d . . . . .
C2 C 1.0392(2) 0.85313(14) 0.55935(11) 0.0142(3) Uani 1 1 d . . . . .
H2 H 1.1304 0.9114 0.5425 0.017 Uiso 1 1 calc R U . . .
C3 C 0.6122(2) 0.76984(14) 0.63081(11) 0.0125(3) Uani 1 1 d . . . . .
C4 C 0.54351(19) 0.64043(14) 0.63950(11) 0.0134(3) Uani 1 1 d . . . . .
H4 H 0.4183 0.6330 0.6547 0.016 Uiso 1 1 calc R U . . .
C5 C 0.63463(19) 0.52929(13) 0.62873(10) 0.0098(3) Uani 1 1 d . . . . .
C6 C 0.54862(19) 0.40211(13) 0.63976(10) 0.0108(3) Uani 1 1 d . . . . .
C7 C 0.3731(2) 0.39129(15) 0.67198(11) 0.0141(3) Uani 1 1 d . . . . .
H7 H 0.3098 0.4659 0.6880 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2906(2) 0.27256(15) 0.68067(12) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.1708 0.2666 0.7018 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3829(2) 0.16221(15) 0.65850(11) 0.0155(3) Uani 1 1 d . . . . .
H9 H 0.3268 0.0812 0.6649 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5578(2) 0.17131(15) 0.62695(11) 0.0153(3) Uani 1 1 d . . . . .
H10 H 0.6218 0.0964 0.6122 0.018 Uiso 1 1 calc R U . . .
C11 C 0.6386(2) 0.29030(14) 0.61698(11) 0.0141(3) Uani 1 1 d . . . . .
H11 H 0.7568 0.2958 0.5943 0.017 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7208(15) . ?
S1 C5 1.7479(14) . ?
O1 C3 1.2140(17) . ?
N1 C1 1.3659(18) . ?
N1 N2 1.3764(17) . ?
N1 C3 1.4185(18) . ?
N2 C2 1.3186(18) . ?
N3 C1 1.3208(18) . ?
N3 C2 1.3655(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.456(2) . ?
C4 C5 1.3545(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4872(19) . ?
C6 C11 1.4010(19) . ?
C6 C7 1.4027(18) . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 H11 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 C5 100.96(7) . . ?
C1 N1 N2 109.00(11) . . ?
C1 N1 C3 127.40(12) . . ?
N2 N1 C3 123.60(11) . . ?
C2 N2 N1 101.60(12) . . ?
C1 N3 C2 101.88(12) . . ?
N3 C1 N1 110.84(13) . . ?
N3 C1 S1 123.99(11) . . ?
N1 C1 S1 125.17(11) . . ?
N2 C2 N3 116.68(13) . . ?
N2 C2 H2 121.7 . . ?
N3 C2 H2 121.7 . . ?
O1 C3 N1 120.64(13) . . ?
O1 C3 C4 124.61(13) . . ?
N1 C3 C4 114.75(12) . . ?
C5 C4 C3 128.54(13) . . ?
C5 C4 H4 115.7 . . ?
C3 C4 H4 115.7 . . ?
C4 C5 C6 123.46(13) . . ?
C4 C5 S1 123.03(11) . . ?
C6 C5 S1 113.51(10) . . ?
C11 C6 C7 118.25(13) . . ?
C11 C6 C5 121.13(12) . . ?
C7 C6 C5 120.62(13) . . ?
C8 C7 C6 120.71(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.28(14) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.70(14) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 119.91(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 121.15(14) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?

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
C1 N1 N2 C2 -0.19(14) . . . . ?
C3 N1 N2 C2 -179.48(13) . . . . ?
C2 N3 C1 N1 -0.34(15) . . . . ?
C2 N3 C1 S1 -179.74(11) . . . . ?
N2 N1 C1 N3 0.35(16) . . . . ?
C3 N1 C1 N3 179.61(13) . . . . ?
N2 N1 C1 S1 179.75(10) . . . . ?
C3 N1 C1 S1 -1.0(2) . . . . ?
C5 S1 C1 N3 -177.41(12) . . . . ?
C5 S1 C1 N1 3.27(13) . . . . ?
N1 N2 C2 N3 -0.02(16) . . . . ?
C1 N3 C2 N2 0.23(16) . . . . ?
C1 N1 C3 O1 177.73(13) . . . . ?
N2 N1 C3 O1 -3.1(2) . . . . ?
C1 N1 C3 C4 -2.7(2) . . . . ?
N2 N1 C3 C4 176.45(12) . . . . ?
O1 C3 C4 C5 -176.78(15) . . . . ?
N1 C3 C4 C5 3.7(2) . . . . ?
C3 C4 C5 C6 179.87(13) . . . . ?
C3 C4 C5 S1 -0.8(2) . . . . ?
C1 S1 C5 C4 -2.39(14) . . . . ?
C1 S1 C5 C6 176.98(10) . . . . ?
C4 C5 C6 C11 173.01(13) . . . . ?
S1 C5 C6 C11 -6.35(17) . . . . ?
C4 C5 C6 C7 -6.1(2) . . . . ?
S1 C5 C6 C7 174.56(10) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C8 178.90(13) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C6 1.0(2) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C5 C6 C11 C10 -179.77(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 N2 0.95 2.67 3.4282(19) 137.7 3_776
C4 H4 N3 0.95 2.65 3.3462(18) 130.9 1_455

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.118

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
