# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1470277'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Methyl (E)-5-(5-acetyl-4-methyl-3-phenylthiazol-2(3H)-ylidene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O4 S2'
_chemical_formula_weight         464.54

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                   9.0844(8)
_cell_length_b                   11.8316(10)
_cell_length_c                   11.9311(10)
_cell_angle_alpha                117.753(2)
_cell_angle_beta                 97.176(2)
_cell_angle_gamma                101.322(2)
_cell_volume                     1077.64(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2227
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      23.58

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8930
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker SMART APEX CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12248
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4020
_reflns_number_gt                3001
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009)
;

_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)+(0.0506P)²+0.2882P] 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         4020
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.15639(7) 0.19632(6) 0.39255(6) 0.0438(2) Uani 1 1 d . . .
S2 S 0.24040(8) -0.08746(6) 0.51833(6) 0.04239(19) Uani 1 1 d . . .
O1 O -0.2417(2) -0.10625(19) 0.03355(19) 0.0679(6) Uani 1 1 d . . .
O2 O -0.2097(2) -0.25175(16) 0.09654(17) 0.0555(5) Uani 1 1 d . . .
O3 O 0.0305(2) -0.16982(15) 0.30788(17) 0.0531(5) Uani 1 1 d . . .
O4 O 0.3512(3) -0.1951(2) 0.6673(2) 0.0682(6) Uani 1 1 d . . .
N1 N -0.0582(3) 0.1456(2) 0.1835(2) 0.0453(6) Uani 1 1 d . . .
H1A H -0.123(3) 0.088(3) 0.123(3) 0.051(9) Uiso 1 1 d . . .
N6 N 0.3731(2) 0.16104(18) 0.61237(19) 0.0394(5) Uani 1 1 d . . .
C1 C 0.0037(3) 0.0971(2) 0.2537(2) 0.0383(6) Uani 1 1 d . . .
C2 C -0.0448(3) -0.0355(2) 0.2215(2) 0.0380(6) Uani 1 1 d . . .
C3 C 0.0446(3) -0.0616(2) 0.3116(2) 0.0385(6) Uani 1 1 d . . .
C4 C 0.1607(3) 0.0590(2) 0.4124(2) 0.0384(6) Uani 1 1 d . . .
C5 C 0.2559(3) 0.0573(2) 0.5102(2) 0.0361(5) Uani 1 1 d . . .
C7 C 0.4539(3) 0.1277(2) 0.6941(2) 0.0419(6) Uani 1 1 d . . .
C8 C 0.3960(3) -0.0015(2) 0.6584(2) 0.0421(6) Uani 1 1 d . . .
C9 C 0.4330(3) -0.0807(3) 0.7163(3) 0.0496(7) Uani 1 1 d . . .
C10 C 0.5682(4) -0.0236(3) 0.8321(3) 0.0753(10) Uani 1 1 d . . .
H10A H 0.5748 -0.0898 0.8561 0.113 Uiso 1 1 calc R . .
H10B H 0.5541 0.0527 0.9043 0.113 Uiso 1 1 calc R . .
H10C H 0.6620 0.0029 0.8101 0.113 Uiso 1 1 calc R . .
C11 C 0.5903(3) 0.2332(3) 0.8016(3) 0.0610(8) Uani 1 1 d . . .
H11A H 0.6353 0.1968 0.8496 0.092 Uiso 1 1 calc R . .
H11B H 0.5569 0.3068 0.8593 0.092 Uiso 1 1 calc R . .
H11C H 0.6660 0.2635 0.7647 0.092 Uiso 1 1 calc R . .
C12 C -0.1718(3) -0.1307(2) 0.1099(2) 0.0442(6) Uani 1 1 d . . .
C13 C -0.3273(4) -0.3538(3) -0.0187(3) 0.0749(10) Uani 1 1 d . . .
H13A H -0.3457 -0.4365 -0.0187 0.112 Uiso 1 1 calc R . .
H13B H -0.2933 -0.3645 -0.0951 0.112 Uiso 1 1 calc R . .
H13C H -0.4214 -0.3285 -0.0191 0.112 Uiso 1 1 calc R . .
C14 C -0.0240(3) 0.2748(2) 0.2009(3) 0.0420(6) Uani 1 1 d . . .
C15 C 0.0322(3) 0.3902(3) 0.3209(3) 0.0530(7) Uani 1 1 d . . .
H15A H 0.0498 0.3858 0.3970 0.064 Uiso 1 1 calc R . .
C16 C 0.0622(3) 0.5129(3) 0.3275(3) 0.0617(8) Uani 1 1 d . . .
H16A H 0.1022 0.5908 0.4083 0.074 Uiso 1 1 calc R . .
C17 C 0.0333(4) 0.5204(3) 0.2162(4) 0.0676(9) Uani 1 1 d . . .
H17A H 0.0542 0.6031 0.2215 0.081 Uiso 1 1 calc R . .
C18 C -0.0264(4) 0.4058(3) 0.0971(4) 0.0701(9) Uani 1 1 d . . .
H18A H -0.0479 0.4108 0.0215 0.084 Uiso 1 1 calc R . .
C19 C -0.0547(3) 0.2832(3) 0.0891(3) 0.0560(7) Uani 1 1 d . . .
H19A H -0.0948 0.2056 0.0079 0.067 Uiso 1 1 calc R . .
C20 C 0.4012(3) 0.2972(2) 0.6387(2) 0.0365(5) Uani 1 1 d . . .
C21 C 0.5217(3) 0.3493(2) 0.6012(2) 0.0442(6) Uani 1 1 d . . .
H21A H 0.5856 0.2987 0.5609 0.053 Uiso 1 1 calc R . .
C22 C 0.5459(3) 0.4776(3) 0.6243(3) 0.0531(7) Uani 1 1 d . . .
H22A H 0.6273 0.5147 0.6002 0.064 Uiso 1 1 calc R . .
C23 C 0.4503(3) 0.5506(3) 0.6827(3) 0.0543(7) Uani 1 1 d . . .
H23A H 0.4660 0.6367 0.6968 0.065 Uiso 1 1 calc R . .
C24 C 0.3314(3) 0.4979(2) 0.7208(3) 0.0503(7) Uani 1 1 d . . .
H24A H 0.2680 0.5489 0.7613 0.060 Uiso 1 1 calc R . .
C25 C 0.3053(3) 0.3698(2) 0.6992(2) 0.0424(6) Uani 1 1 d . . .
H25A H 0.2251 0.3335 0.7249 0.051 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.738(2) . ?
S1 C4 1.754(2) . ?
S2 C5 1.739(2) . ?
S2 C8 1.757(2) . ?
O1 C12 1.221(3) . ?
O2 C12 1.333(3) . ?
O2 C13 1.439(3) . ?
O3 C3 1.241(3) . ?
O4 C9 1.219(3) . ?
N1 C1 1.343(3) . ?
N1 C14 1.406(3) . ?
N1 H1A 0.78(3) . ?
N6 C5 1.377(3) . ?
N6 C7 1.392(3) . ?
N6 C20 1.451(3) . ?
C1 C2 1.389(3) . ?
C2 C12 1.443(3) . ?
C2 C3 1.449(3) . ?
C3 C4 1.445(3) . ?
C4 C5 1.374(3) . ?
C7 C8 1.348(3) . ?
C7 C11 1.497(3) . ?
C8 C9 1.461(3) . ?
C9 C10 1.502(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.378(3) . ?
C14 C19 1.382(3) . ?
C15 C16 1.386(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.368(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(3) . ?
C20 C25 1.376(3) . ?
C21 C22 1.376(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.368(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.372(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.378(3) . ?
C24 H24A 0.9300 . ?
C25 H25A 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
C1 S1 C4 90.88(11) . . ?
C5 S2 C8 90.45(11) . . ?
C12 O2 C13 116.2(2) . . ?
C1 N1 C14 131.4(2) . . ?
C1 N1 H1A 110.0(19) . . ?
C14 N1 H1A 118.6(19) . . ?
C5 N6 C7 115.21(19) . . ?
C5 N6 C20 122.02(18) . . ?
C7 N6 C20 122.58(19) . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 S1 122.18(18) . . ?
C2 C1 S1 114.02(17) . . ?
C1 C2 C12 120.9(2) . . ?
C1 C2 C3 112.3(2) . . ?
C12 C2 C3 126.7(2) . . ?
O3 C3 C4 121.7(2) . . ?
O3 C3 C2 127.5(2) . . ?
C4 C3 C2 110.72(19) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 S1 127.68(18) . . ?
C3 C4 S1 112.03(17) . . ?
C4 C5 N6 128.3(2) . . ?
C4 C5 S2 121.76(17) . . ?
N6 C5 S2 109.96(16) . . ?
C8 C7 N6 111.9(2) . . ?
C8 C7 C11 129.9(2) . . ?
N6 C7 C11 118.2(2) . . ?
C7 C8 C9 132.7(2) . . ?
C7 C8 S2 112.43(17) . . ?
C9 C8 S2 114.85(19) . . ?
O4 C9 C8 118.0(2) . . ?
O4 C9 C10 120.8(2) . . ?
C8 C9 C10 121.2(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 O2 121.4(2) . . ?
O1 C12 C2 125.0(2) . . ?
O2 C12 C2 113.6(2) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.4(2) . . ?
C15 C14 N1 124.2(2) . . ?
C19 C14 N1 116.4(2) . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19A 119.8 . . ?
C14 C19 H19A 119.8 . . ?
C21 C20 C25 122.0(2) . . ?
C21 C20 N6 119.2(2) . . ?
C25 C20 N6 118.9(2) . . ?
C20 C21 C22 118.8(2) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C23 C24 C25 120.5(2) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C20 C25 C24 118.1(2) . . ?
C20 C25 H25A 120.9 . . ?
C24 C25 H25A 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C1 C2 -179.8(3) . . . . ?
C14 N1 C1 S1 -1.2(4) . . . . ?
C4 S1 C1 N1 -178.6(2) . . . . ?
C4 S1 C1 C2 0.2(2) . . . . ?
N1 C1 C2 C12 -2.1(4) . . . . ?
S1 C1 C2 C12 179.16(19) . . . . ?
N1 C1 C2 C3 178.3(2) . . . . ?
S1 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 O3 -179.0(2) . . . . ?
C12 C2 C3 O3 1.5(4) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C12 C2 C3 C4 -179.1(2) . . . . ?
O3 C3 C4 C5 -2.2(4) . . . . ?
C2 C3 C4 C5 178.3(2) . . . . ?
O3 C3 C4 S1 179.1(2) . . . . ?
C2 C3 C4 S1 -0.4(3) . . . . ?
C1 S1 C4 C5 -178.4(2) . . . . ?
C1 S1 C4 C3 0.1(2) . . . . ?
C3 C4 C5 N6 179.1(2) . . . . ?
S1 C4 C5 N6 -2.5(4) . . . . ?
C3 C4 C5 S2 -0.7(3) . . . . ?
S1 C4 C5 S2 177.79(15) . . . . ?
C7 N6 C5 C4 -177.7(2) . . . . ?
C20 N6 C5 C4 7.1(4) . . . . ?
C7 N6 C5 S2 2.0(3) . . . . ?
C20 N6 C5 S2 -173.08(17) . . . . ?
C8 S2 C5 C4 178.8(2) . . . . ?
C8 S2 C5 N6 -0.98(18) . . . . ?
C5 N6 C7 C8 -2.3(3) . . . . ?
C20 N6 C7 C8 172.8(2) . . . . ?
C5 N6 C7 C11 175.7(2) . . . . ?
C20 N6 C7 C11 -9.2(4) . . . . ?
N6 C7 C8 C9 -175.5(3) . . . . ?
C11 C7 C8 C9 6.8(5) . . . . ?
N6 C7 C8 S2 1.4(3) . . . . ?
C11 C7 C8 S2 -176.2(2) . . . . ?
C5 S2 C8 C7 -0.2(2) . . . . ?
C5 S2 C8 C9 177.3(2) . . . . ?
C7 C8 C9 O4 174.0(3) . . . . ?
S2 C8 C9 O4 -2.9(3) . . . . ?
C7 C8 C9 C10 -6.4(5) . . . . ?
S2 C8 C9 C10 176.7(2) . . . . ?
C13 O2 C12 O1 5.4(4) . . . . ?
C13 O2 C12 C2 -175.3(2) . . . . ?
C1 C2 C12 O1 2.8(4) . . . . ?
C3 C2 C12 O1 -177.6(3) . . . . ?
C1 C2 C12 O2 -176.5(2) . . . . ?
C3 C2 C12 O2 3.0(4) . . . . ?
C1 N1 C14 C15 -30.3(4) . . . . ?
C1 N1 C14 C19 152.0(3) . . . . ?
C19 C14 C15 C16 -2.3(4) . . . . ?
N1 C14 C15 C16 -179.9(2) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C18 C19 C14 0.3(5) . . . . ?
C15 C14 C19 C18 1.4(4) . . . . ?
N1 C14 C19 C18 179.3(3) . . . . ?
C5 N6 C20 C21 -102.1(3) . . . . ?
C7 N6 C20 C21 83.2(3) . . . . ?
C5 N6 C20 C25 77.2(3) . . . . ?
C7 N6 C20 C25 -97.5(3) . . . . ?
C25 C20 C21 C22 -0.5(4) . . . . ?
N6 C20 C21 C22 178.8(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C21 C20 C25 C24 0.8(4) . . . . ?
N6 C20 C25 C24 -178.5(2) . . . . ?
C23 C24 C25 C20 -0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_bak11a
_database_code_depnum_ccdc_archive 'CCDC 1470358'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-5-(5-acetyl-4-methyl-3-phenylthiazol-2(3H)-ylidene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O4 S2'
_chemical_formula_sum            'C25 H22 N2 O4 S2'
_chemical_formula_weight         478.57

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'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   7.1651(6)
_cell_length_b                   16.4460(11)
_cell_length_c                   19.7840(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.202(4)
_cell_angle_gamma                90.00
_cell_volume                     2294.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4981
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Blessing, 1995'

_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  Triumph
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            42161
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.37
_reflns_number_total             5724
_reflns_number_gt                4981
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_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)+(0.0434P)²+18.6861P] 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         5724
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.2145
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25040(16) 1.08241(6) 0.48066(5) 0.0177(2) Uani 1 1 d . . .
C1 C 0.2869(6) 0.9955(3) 0.5311(2) 0.0153(8) Uani 1 1 d . . .
O1 O 0.4332(6) 1.2762(2) 0.58822(18) 0.0321(9) Uani 1 1 d . . .
N1 N 0.3654(5) 1.0157(2) 0.59723(17) 0.0164(7) Uani 1 1 d . . .
S2 S 0.26646(16) 0.82554(6) 0.54634(5) 0.0176(2) Uani 1 1 d . . .
N2 N 0.1572(6) 0.6937(2) 0.4657(2) 0.0249(8) Uani 1 1 d . C .
H2 H 0.105(8) 0.682(4) 0.423(3) 0.027(15) Uiso 1 1 d . . .
O2 O 0.1317(5) 0.9716(2) 0.39381(16) 0.0264(7) Uani 1 1 d . . .
C2 C 0.4010(6) 1.0985(3) 0.6082(2) 0.0174(8) Uani 1 1 d . . .
O3 O 0.0091(5) 0.7240(2) 0.33425(18) 0.0285(8) Uani 1 1 d . . .
C3 C 0.3475(6) 1.1437(3) 0.5510(2) 0.0180(8) Uani 1 1 d . . .
C4 C 0.3576(7) 1.2318(3) 0.5423(2) 0.0208(9) Uani 1 1 d . . .
O4 O -0.0052(5) 0.8542(2) 0.29992(16) 0.0250(7) Uani 1 1 d . . .
C5 C 0.2715(7) 1.2666(3) 0.4731(2) 0.0257(10) Uani 1 1 d . . .
H5A H 0.1385 1.2498 0.4612 0.039 Uiso 1 1 calc R . .
H5B H 0.3415 1.2465 0.4382 0.039 Uiso 1 1 calc R . .
H5C H 0.2787 1.3261 0.4750 0.039 Uiso 1 1 calc R . .
C6 C 0.4880(7) 1.1260(3) 0.6781(2) 0.0246(10) Uani 1 1 d . . .
H6A H 0.6236 1.1131 0.6866 0.037 Uiso 1 1 calc R . .
H6B H 0.4266 1.0983 0.7121 0.037 Uiso 1 1 calc R . .
H6C H 0.4711 1.1849 0.6817 0.037 Uiso 1 1 calc R . .
C7 C 0.3876(7) 0.9576(3) 0.6533(2) 0.0185(8) Uani 1 1 d . . .
C8 C 0.5667(7) 0.9293(3) 0.6809(2) 0.0254(10) Uani 1 1 d . . .
H8 H 0.6754 0.9460 0.6631 0.031 Uiso 1 1 calc R . .
C9 C 0.5810(9) 0.8752(3) 0.7359(3) 0.0346(13) Uani 1 1 d . . .
H9 H 0.7016 0.8539 0.7558 0.041 Uiso 1 1 calc R . .
C10 C 0.4211(10) 0.8520(3) 0.7622(3) 0.0380(14) Uani 1 1 d . . .
H10 H 0.4334 0.8156 0.8001 0.046 Uiso 1 1 calc R . .
C11 C 0.2462(9) 0.8814(3) 0.7336(3) 0.0339(12) Uani 1 1 d . . .
H11 H 0.1372 0.8648 0.7513 0.041 Uiso 1 1 calc R . .
C12 C 0.2277(7) 0.9358(3) 0.6784(2) 0.0252(10) Uani 1 1 d . . .
H12 H 0.1071 0.9573 0.6587 0.030 Uiso 1 1 calc R . .
C13 C 0.2382(6) 0.9193(3) 0.5051(2) 0.0169(8) Uani 1 1 d . . .
C14 C 0.1583(6) 0.9115(3) 0.4328(2) 0.0198(8) Uani 1 1 d . . .
C15 C 0.1191(6) 0.8269(3) 0.4150(2) 0.0184(8) Uani 1 1 d . . .
C16 C 0.1735(6) 0.7752(3) 0.4702(2) 0.0174(8) Uani 1 1 d . . .
C17 C 0.0373(6) 0.7956(3) 0.3477(2) 0.0204(9) Uani 1 1 d . . .
C18 C -0.0788(8) 0.8293(3) 0.2304(2) 0.0320(11) Uani 1 1 d . . .
H18A H -0.1979 0.7982 0.2287 0.038 Uiso 1 1 calc R . .
H18B H 0.0142 0.7943 0.2127 0.038 Uiso 1 1 calc R . .
C19 C -0.1150(9) 0.9047(3) 0.1882(3) 0.0350(12) Uani 1 1 d . . .
H19A H -0.2126 0.9373 0.2046 0.052 Uiso 1 1 calc R . .
H19B H -0.1585 0.8900 0.1400 0.052 Uiso 1 1 calc R . .
H19C H 0.0024 0.9364 0.1924 0.052 Uiso 1 1 calc R . .
C20 C 0.2202(12) 0.6320(3) 0.5134(3) 0.0507(19) Uani 1 1 d . . .
C21 C 0.2780(9) 0.6376(3) 0.5803(3) 0.0383(13) Uani 1 1 d . B .
H21 H 0.2772 0.6897 0.6010 0.046 Uiso 1 1 calc R . .
C22 C 0.3395(8) 0.5724(3) 0.6220(3) 0.0344(12) Uani 1 1 d . . .
H22 H 0.3307 0.5749 0.6693 0.041 Uiso 1 1 calc R A 1
C23 C 0.4095(17) 0.5074(6) 0.5981(7) 0.037(3) Uani 0.50 1 d P B 1
H23 H 0.4598 0.4644 0.6280 0.044 Uiso 0.50 1 calc PR B 1
C24 C 0.4086(15) 0.5027(6) 0.5277(7) 0.035(2) Uani 0.50 1 d P . 1
H24 H 0.4605 0.4564 0.5090 0.041 Uiso 0.50 1 calc PR . 1
C25 C 0.3325(14) 0.5651(6) 0.4851(6) 0.028(2) Uani 0.50 1 d P C 1
H25 H 0.3497 0.5665 0.4386 0.034 Uiso 0.50 1 calc PR C 1
C23A C 0.2724(16) 0.4922(7) 0.5982(6) 0.032(2) Uani 0.50 1 d P B 2
H23A H 0.3057 0.4454 0.6260 0.039 Uiso 0.50 1 calc PR B 2
C24A C 0.1578(15) 0.4857(6) 0.5336(6) 0.032(2) Uani 0.50 1 d P . 2
H24A H 0.1088 0.4342 0.5176 0.038 Uiso 0.50 1 calc PR . 2
C25A C 0.1148(14) 0.5541(6) 0.4925(5) 0.0260(19) Uani 0.50 1 d P . 2
H25A H 0.0209 0.5517 0.4521 0.031 Uiso 0.50 1 calc PR . 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.737(4) . ?
S1 C3 1.759(4) . ?
C1 N1 1.370(5) . ?
C1 C13 1.375(6) . ?
O1 C4 1.215(6) . ?
N1 C2 1.394(5) . ?
N1 C7 1.451(5) . ?
S2 C13 1.740(4) . ?
S2 C16 1.744(4) . ?
N2 C16 1.347(6) . ?
N2 C20 1.404(7) . ?
N2 H2 0.88(6) . ?
O2 C14 1.248(5) . ?
C2 C3 1.352(6) . ?
C2 C6 1.484(6) . ?
O3 C17 1.216(6) . ?
C3 C4 1.462(6) . ?
C4 C5 1.512(6) . ?
O4 C17 1.347(6) . ?
O4 C18 1.442(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.375(7) . ?
C7 C8 1.383(7) . ?
C8 C9 1.396(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(7) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.448(6) . ?
C14 C15 1.451(6) . ?
C15 C16 1.384(6) . ?
C15 C17 1.451(6) . ?
C18 C19 1.492(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.319(8) . ?
C20 C25A 1.508(11) . ?
C20 C25 1.527(12) . ?
C21 C22 1.376(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.305(13) . ?
C22 C23A 1.453(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(18) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(15) . ?
C24 C24 1.85(2) 3_666 ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C23A C24A 1.396(16) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.390(15) . ?
C24A C25A 2.037(14) 3_566 ?
C24A H24A 0.9500 . ?
C25A C24A 2.037(14) 3_566 ?
C25A H25A 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 C3 91.1(2) . . ?
N1 C1 C13 127.8(4) . . ?
N1 C1 S1 110.0(3) . . ?
C13 C1 S1 122.1(3) . . ?
C1 N1 C2 114.7(3) . . ?
C1 N1 C7 122.7(4) . . ?
C2 N1 C7 122.2(3) . . ?
C13 S2 C16 91.2(2) . . ?
C16 N2 C20 131.3(4) . . ?
C16 N2 H2 107(4) . . ?
C20 N2 H2 121(4) . . ?
C3 C2 N1 113.0(4) . . ?
C3 C2 C6 128.5(4) . . ?
N1 C2 C6 118.5(4) . . ?
C2 C3 C4 129.1(4) . . ?
C2 C3 S1 111.1(3) . . ?
C4 C3 S1 119.8(3) . . ?
O1 C4 C3 122.2(4) . . ?
O1 C4 C5 120.4(4) . . ?
C3 C4 C5 117.4(4) . . ?
C17 O4 C18 117.8(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 123.0(4) . . ?
C12 C7 N1 117.5(4) . . ?
C8 C7 N1 119.5(4) . . ?
C7 C8 C9 117.2(5) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.1(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.1(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 118.6(5) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C1 C13 C14 118.7(4) . . ?
C1 C13 S2 129.1(3) . . ?
C14 C13 S2 112.2(3) . . ?
O2 C14 C13 122.1(4) . . ?
O2 C14 C15 127.4(4) . . ?
C13 C14 C15 110.5(4) . . ?
C16 C15 C17 121.2(4) . . ?
C16 C15 C14 112.5(4) . . ?
C17 C15 C14 126.3(4) . . ?
N2 C16 C15 123.3(4) . . ?
N2 C16 S2 123.0(3) . . ?
C15 C16 S2 113.6(3) . . ?
O3 C17 O4 122.0(4) . . ?
O3 C17 C15 124.7(4) . . ?
O4 C17 C15 113.3(4) . . ?
O4 C18 C19 107.2(4) . . ?
O4 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O4 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N2 129.1(5) . . ?
C21 C20 C25A 112.8(6) . . ?
N2 C20 C25A 110.1(6) . . ?
C21 C20 C25 109.0(7) . . ?
N2 C20 C25 113.7(6) . . ?
C25A C20 C25 63.8(6) . . ?
C20 C21 C22 123.9(5) . . ?
C20 C21 H21 118.1 . . ?
C22 C21 H21 118.1 . . ?
C23 C22 C21 121.7(7) . . ?
C23 C22 C23A 42.7(7) . . ?
C21 C22 C23A 117.5(6) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C23A C22 H22 106.3 . . ?
C22 C23 C24 118.1(9) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C25 C24 C23 120.1(10) . . ?
C25 C24 C24 85.4(9) . 3_666 ?
C23 C24 C24 135.6(12) . 3_666 ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C24 H24 50.6 3_666 . ?
C24 C25 C20 119.3(9) . . ?
C24 C25 H25 120.3 . . ?
C20 C25 H25 120.3 . . ?
C24A C23A C22 118.2(9) . . ?
C24A C23A H23A 120.9 . . ?
C22 C23A H23A 120.9 . . ?
C25A C24A C23A 120.5(9) . . ?
C25A C24A C25A 90.5(7) . 3_566 ?
C23A C24A C25A 129.7(9) . 3_566 ?
C25A C24A H24A 119.7 . . ?
C23A C24A H24A 119.7 . . ?
C25A C24A H24A 49.3 3_566 . ?
C24A C25A C20 118.6(8) . . ?
C24A C25A C24A 89.5(8) . 3_566 ?
C20 C25A C24A 138.9(7) . 3_566 ?
C24A C25A H25A 120.7 . . ?
C20 C25A H25A 120.7 . . ?
C24A C25A H25A 43.1 3_566 . ?

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
C3 S1 C1 N1 1.0(3) . . . . ?
C3 S1 C1 C13 -179.7(4) . . . . ?
C13 C1 N1 C2 179.4(4) . . . . ?
S1 C1 N1 C2 -1.4(5) . . . . ?
C13 C1 N1 C7 -8.1(7) . . . . ?
S1 C1 N1 C7 171.1(3) . . . . ?
C1 N1 C2 C3 1.1(6) . . . . ?
C7 N1 C2 C3 -171.5(4) . . . . ?
C1 N1 C2 C6 -179.3(4) . . . . ?
C7 N1 C2 C6 8.1(6) . . . . ?
N1 C2 C3 C4 178.5(4) . . . . ?
C6 C2 C3 C4 -1.1(8) . . . . ?
N1 C2 C3 S1 -0.2(5) . . . . ?
C6 C2 C3 S1 -179.8(4) . . . . ?
C1 S1 C3 C2 -0.5(4) . . . . ?
C1 S1 C3 C4 -179.3(4) . . . . ?
C2 C3 C4 O1 5.7(8) . . . . ?
S1 C3 C4 O1 -175.7(4) . . . . ?
C2 C3 C4 C5 -175.0(5) . . . . ?
S1 C3 C4 C5 3.6(6) . . . . ?
C1 N1 C7 C12 -74.8(5) . . . . ?
C2 N1 C7 C12 97.1(5) . . . . ?
C1 N1 C7 C8 107.9(5) . . . . ?
C2 N1 C7 C8 -80.2(5) . . . . ?
C12 C7 C8 C9 1.1(7) . . . . ?
N1 C7 C8 C9 178.3(4) . . . . ?
C7 C8 C9 C10 -0.9(7) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C8 C7 C12 C11 -1.2(7) . . . . ?
N1 C7 C12 C11 -178.4(4) . . . . ?
C10 C11 C12 C7 1.0(7) . . . . ?
N1 C1 C13 C14 -179.4(4) . . . . ?
S1 C1 C13 C14 1.5(6) . . . . ?
N1 C1 C13 S2 -2.0(7) . . . . ?
S1 C1 C13 S2 178.8(3) . . . . ?
C16 S2 C13 C1 -177.7(4) . . . . ?
C16 S2 C13 C14 -0.3(3) . . . . ?
C1 C13 C14 O2 -0.3(7) . . . . ?
S2 C13 C14 O2 -178.1(4) . . . . ?
C1 C13 C14 C15 179.2(4) . . . . ?
S2 C13 C14 C15 1.4(5) . . . . ?
O2 C14 C15 C16 177.3(5) . . . . ?
C13 C14 C15 C16 -2.2(6) . . . . ?
O2 C14 C15 C17 -1.1(8) . . . . ?
C13 C14 C15 C17 179.4(4) . . . . ?
C20 N2 C16 C15 173.1(6) . . . . ?
C20 N2 C16 S2 -6.7(9) . . . . ?
C17 C15 C16 N2 0.8(7) . . . . ?
C14 C15 C16 N2 -177.7(4) . . . . ?
C17 C15 C16 S2 -179.5(3) . . . . ?
C14 C15 C16 S2 2.0(5) . . . . ?
C13 S2 C16 N2 178.7(4) . . . . ?
C13 S2 C16 C15 -1.0(4) . . . . ?
C18 O4 C17 O3 -2.6(7) . . . . ?
C18 O4 C17 C15 177.0(4) . . . . ?
C16 C15 C17 O3 0.5(7) . . . . ?
C14 C15 C17 O3 178.7(5) . . . . ?
C16 C15 C17 O4 -179.2(4) . . . . ?
C14 C15 C17 O4 -1.0(7) . . . . ?
C17 O4 C18 C19 179.6(4) . . . . ?
C16 N2 C20 C21 15.8(13) . . . . ?
C16 N2 C20 C25A 161.9(6) . . . . ?
C16 N2 C20 C25 -128.8(7) . . . . ?
N2 C20 C21 C22 -179.0(7) . . . . ?
C25A C20 C21 C22 35.6(11) . . . . ?
C25 C20 C21 C22 -33.1(10) . . . . ?
C20 C21 C22 C23 25.1(12) . . . . ?
C20 C21 C22 C23A -24.2(11) . . . . ?
C21 C22 C23 C24 -4.5(15) . . . . ?
C23A C22 C23 C24 93.0(14) . . . . ?
C22 C23 C24 C25 -1.0(17) . . . . ?
C22 C23 C24 C24 116.3(15) . . . 3_666 ?
C23 C24 C25 C20 -10.3(15) . . . . ?
C24 C24 C25 C20 -151.7(9) 3_666 . . . ?
C21 C20 C25 C24 25.8(12) . . . . ?
N2 C20 C25 C24 177.5(8) . . . . ?
C25A C20 C25 C24 -80.9(10) . . . . ?
C23 C22 C23A C24A -105.1(14) . . . . ?
C21 C22 C23A C24A 3.0(12) . . . . ?
C22 C23A C24A C25A 2.1(15) . . . . ?
C22 C23A C24A C25A -118.0(10) . . . 3_566 ?
C23A C24A C25A C20 10.4(15) . . . . ?
C25A C24A C25A C20 148.6(10) 3_566 . . . ?
C23A C24A C25A C24A -138.2(11) . . . 3_566 ?
C25A C24A C25A C24A 0.0 3_566 . . 3_566 ?
C21 C20 C25A C24A -28.0(12) . . . . ?
N2 C20 C25A C24A -180.0(8) . . . . ?
C25 C20 C25A C24A 72.8(10) . . . . ?
C21 C20 C25A C24A 99.6(12) . . . 3_566 ?
N2 C20 C25A C24A -52.4(13) . . . 3_566 ?
C25 C20 C25A C24A -159.6(13) . . . 3_566 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.88(6) 1.90(6) 2.676(5) 146(5) 1_555

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.109
