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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-acetyl-6-amino-1-(4-methoxyphenyl)-5-(methylthio)pyridin-2(1H)-one
_chemical_name_common            
3-acetyl-6-amino-1-(4-methoxyphenyl)-5-(methylthio)pyridin-2(1H)-one
_chemical_melting_point          238-240
_chemical_formula_moiety         'C15 H16 N2 O3 S'
_chemical_formula_sum            'C15 H16 N2 O3 S'
_chemical_formula_weight         304.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           ?
_symmetry_space_group_name_H-M   'P c c n'

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

_cell_length_a                   18.8609(15)
_cell_length_b                   9.2843(8)
_cell_length_c                   16.5808(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2903.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            15831
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2579
_reflns_number_gt                2001
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0550P)²+1.4948P] 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         2579
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.028
_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
S1 S 0.67545(3) 0.07042(7) 0.27447(4) 0.0333(2) Uani 1 1 d . . .
O3 O 1.12045(8) 0.05437(18) 0.46269(10) 0.0355(4) Uani 1 1 d . . .
N1 N 0.88808(9) 0.05922(19) 0.25405(10) 0.0235(4) Uani 1 1 d . . .
O2 O 0.96505(8) 0.06297(18) 0.14858(9) 0.0323(4) Uani 1 1 d . . .
C1 C 1.06392(11) 0.0642(3) 0.41120(13) 0.0259(5) Uani 1 1 d . . .
C8 C 0.84054(12) 0.0620(2) 0.11809(13) 0.0263(5) Uani 1 1 d . . .
C2 C 1.03358(12) -0.0657(3) 0.38818(14) 0.0310(6) Uani 1 1 d . . .
H2 H 1.0521 -0.1518 0.4076 0.037 Uiso 1 1 calc R . .
C4 C 0.94925(11) 0.0608(2) 0.30733(12) 0.0235(5) Uani 1 1 d . . .
O1 O 0.78902(9) 0.0429(2) -0.00913(10) 0.0536(6) Uani 1 1 d . . .
N2 N 0.81506(11) 0.0603(2) 0.36706(12) 0.0315(5) Uani 1 1 d . . .
C10 C 0.76216(11) 0.0591(2) 0.23538(13) 0.0251(5) Uani 1 1 d . . .
C7 C 0.90258(11) 0.0625(2) 0.16906(13) 0.0236(5) Uani 1 1 d . . .
C13 C 0.84354(13) 0.0630(3) 0.02973(14) 0.0310(6) Uani 1 1 d . . .
C3 C 0.97610(12) -0.0677(3) 0.33656(14) 0.0290(5) Uani 1 1 d . . .
H3 H 0.9556 -0.1548 0.3216 0.035 Uiso 1 1 calc R . .
C11 C 0.82147(11) 0.0600(2) 0.28733(12) 0.0250(5) Uani 1 1 d . . .
C9 C 0.77413(12) 0.0597(2) 0.15344(13) 0.0265(5) Uani 1 1 d . . .
H9 H 0.7349 0.0585 0.1195 0.032 Uiso 1 1 calc R . .
C6 C 1.03705(11) 0.1924(3) 0.38133(13) 0.0259(5) Uani 1 1 d . . .
H6 H 1.0574 0.2797 0.3962 0.031 Uiso 1 1 calc R . .
C5 C 0.97937(11) 0.1898(3) 0.32882(13) 0.0259(5) Uani 1 1 d . . .
H5 H 0.9613 0.2755 0.3083 0.031 Uiso 1 1 calc R . .
C12 C 0.91118(13) 0.0861(3) -0.01483(14) 0.0426(7) Uani 1 1 d . . .
H12A H 0.9384 -0.0012 -0.0145 0.064 Uiso 1 1 calc R . .
H12B H 0.9378 0.1615 0.0107 0.064 Uiso 1 1 calc R . .
H12C H 0.9009 0.1130 -0.0695 0.064 Uiso 1 1 calc R . .
C14 C 0.65463(15) -0.1141(3) 0.29671(17) 0.0504(8) Uani 1 1 d . . .
H14A H 0.6626 -0.1720 0.2496 0.076 Uiso 1 1 calc R . .
H14B H 0.6058 -0.1213 0.3126 0.076 Uiso 1 1 calc R . .
H14C H 0.6844 -0.1475 0.3398 0.076 Uiso 1 1 calc R . .
C15 C 1.15514(13) 0.1857(3) 0.48315(17) 0.0447(7) Uani 1 1 d . . .
H15A H 1.1701 0.2336 0.4348 0.067 Uiso 1 1 calc R . .
H15B H 1.1957 0.1653 0.5162 0.067 Uiso 1 1 calc R . .
H15C H 1.1229 0.2466 0.5123 0.067 Uiso 1 1 calc R . .
H1A H 0.7737(14) 0.071(3) 0.3901(16) 0.036(7) Uiso 1 1 d . . .
H1B H 0.8527(16) 0.070(3) 0.3981(19) 0.054(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0212(3) 0.0486(4) 0.0301(3) 0.0013(3) 0.0031(2) 0.0012(3)
O3 0.0295(9) 0.0352(11) 0.0419(10) 0.0019(8) -0.0136(8) -0.0011(8)
N1 0.0205(9) 0.0324(11) 0.0177(9) -0.0025(8) -0.0006(7) -0.0022(8)
O2 0.0219(9) 0.0496(11) 0.0253(8) -0.0010(8) 0.0044(6) -0.0036(8)
C1 0.0204(11) 0.0314(14) 0.0259(11) -0.0006(10) -0.0011(9) -0.0001(10)
C8 0.0269(12) 0.0308(13) 0.0211(11) 0.0012(10) 0.0014(9) -0.0024(10)
C2 0.0322(13) 0.0252(13) 0.0355(13) 0.0034(11) -0.0039(10) 0.0030(11)
C4 0.0189(11) 0.0314(13) 0.0203(11) -0.0014(10) 0.0015(8) -0.0012(10)
O1 0.0334(11) 0.1044(19) 0.0230(9) 0.0029(10) -0.0041(8) -0.0132(10)
N2 0.0222(11) 0.0519(15) 0.0204(10) -0.0002(9) 0.0017(9) -0.0024(10)
C10 0.0199(11) 0.0298(14) 0.0257(11) -0.0007(10) 0.0008(9) -0.0018(10)
C7 0.0245(12) 0.0245(12) 0.0218(11) -0.0021(9) 0.0021(9) -0.0026(10)
C13 0.0327(13) 0.0371(15) 0.0232(12) -0.0005(11) -0.0004(10) -0.0055(11)
C3 0.0287(13) 0.0272(13) 0.0311(12) -0.0018(10) -0.0008(10) -0.0052(10)
C11 0.0252(12) 0.0271(13) 0.0227(12) -0.0007(9) 0.0024(9) -0.0025(10)
C9 0.0219(11) 0.0323(14) 0.0252(12) 0.0016(10) -0.0030(9) -0.0020(10)
C6 0.0228(11) 0.0249(13) 0.0299(12) -0.0052(10) -0.0020(9) -0.0014(10)
C5 0.0248(11) 0.0266(13) 0.0262(11) 0.0021(10) 0.0001(9) 0.0025(10)
C12 0.0367(14) 0.069(2) 0.0220(12) -0.0029(13) 0.0029(10) -0.0130(14)
C14 0.0405(16) 0.059(2) 0.0520(18) -0.0021(15) 0.0097(13) -0.0180(14)
C15 0.0381(14) 0.0446(17) 0.0514(16) 0.0035(14) -0.0225(12) -0.0090(13)

_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 C10 1.762(2) . ?
S1 C14 1.795(3) . ?
O3 C1 1.369(3) . ?
O3 C15 1.425(3) . ?
N1 C11 1.372(3) . ?
N1 C7 1.436(3) . ?
N1 C4 1.453(3) . ?
O2 C7 1.226(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.389(3) . ?
C8 C9 1.383(3) . ?
C8 C7 1.443(3) . ?
C8 C13 1.466(3) . ?
C2 C3 1.381(3) . ?
C4 C5 1.372(3) . ?
C4 C3 1.384(3) . ?
O1 C13 1.228(3) . ?
N2 C11 1.328(3) . ?
C10 C9 1.377(3) . ?
C10 C11 1.412(3) . ?
C13 C12 1.490(3) . ?
C6 C5 1.394(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
C10 S1 C14 102.81(12) . . ?
C1 O3 C15 116.68(18) . . ?
C11 N1 C7 124.67(17) . . ?
C11 N1 C4 118.84(17) . . ?
C7 N1 C4 116.44(16) . . ?
O3 C1 C6 124.4(2) . . ?
O3 C1 C2 115.7(2) . . ?
C6 C1 C2 119.8(2) . . ?
C9 C8 C7 119.08(19) . . ?
C9 C8 C13 117.3(2) . . ?
C7 C8 C13 123.6(2) . . ?
C3 C2 C1 120.4(2) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 N1 119.69(19) . . ?
C3 C4 N1 119.65(19) . . ?
C9 C10 C11 118.2(2) . . ?
C9 C10 S1 120.98(17) . . ?
C11 C10 S1 120.70(16) . . ?
O2 C7 N1 117.05(19) . . ?
O2 C7 C8 128.1(2) . . ?
N1 C7 C8 114.85(18) . . ?
O1 C13 C8 119.4(2) . . ?
O1 C13 C12 118.6(2) . . ?
C8 C13 C12 122.0(2) . . ?
C2 C3 C4 119.5(2) . . ?
N2 C11 N1 118.93(19) . . ?
N2 C11 C10 122.4(2) . . ?
N1 C11 C10 118.69(19) . . ?
C10 C9 C8 124.5(2) . . ?
C1 C6 C5 119.6(2) . . ?
C4 C5 C6 120.0(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 1013387'
