# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_iminopyridinedione_13
_database_code_depnum_ccdc_archive 'CCDC 1476250'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
7-imino-2-phenylthieno[3,2-c]pyridine-4,6(5H,7H)-dione
_chemical_name_common            'compound 13; JMS-631-053 '
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 N2 O2 S'
_chemical_formula_weight         256.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.4286(3)
_cell_length_b                   7.4520(3)
_cell_length_c                   11.7070(5)
_cell_angle_alpha                89.263(2)
_cell_angle_beta                 78.416(2)
_cell_angle_gamma                84.742(2)
_cell_volume                     547.09(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    2.595
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8782
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.854
_diffrn_reflns_theta_max         68.295
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1955
_reflns_number_gt                1761
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1955
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.479
_refine_ls_restrained_S_all      1.479
_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 0.68246(8) 0.20728(7) 0.57834(4) 0.0287(2) Uani 1 1 d . . . . .
C1 C 0.4811(3) 0.3040(3) 0.68347(18) 0.0257(5) Uani 1 1 d . . . . .
N1 N 0.1143(3) 0.4623(2) 0.82919(15) 0.0299(4) Uani 1 1 d . . . . .
H1N H -0.017(5) 0.503(3) 0.874(3) 0.042(7) Uiso 1 1 d . . . . .
O1 O 0.2640(3) 0.4168(2) 0.98717(14) 0.0385(4) Uani 1 1 d . . . . .
C2 C 0.4866(3) 0.3262(3) 0.80546(19) 0.0272(5) Uani 1 1 d . . . . .
N2 N 0.6501(3) 0.2810(3) 0.84828(17) 0.0348(5) Uani 1 1 d . . . . .
H2N H 0.622(5) 0.311(4) 0.918(3) 0.062(10) Uiso 1 1 d . . . . .
O2 O -0.0401(2) 0.5162(2) 0.67332(14) 0.0368(4) Uani 1 1 d . . . . .
C3 C 0.2793(3) 0.4055(3) 0.88206(18) 0.0276(5) Uani 1 1 d . . . . .
C4 C 0.1132(3) 0.4522(3) 0.71031(19) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.3047(3) 0.3598(3) 0.63786(18) 0.0249(5) Uani 1 1 d . . . . .
C6 C 0.3305(3) 0.3230(3) 0.51801(18) 0.0254(5) Uani 1 1 d . . . . .
H6 H 0.237(4) 0.348(3) 0.473(2) 0.035(7) Uiso 1 1 d . . . . .
C7 C 0.5295(3) 0.2380(3) 0.47253(18) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.6133(3) 0.1783(3) 0.35150(17) 0.0262(5) Uani 1 1 d . . . . .
C9 C 0.4862(4) 0.2040(3) 0.26786(19) 0.0320(5) Uani 1 1 d . . . . .
H9 H 0.338(5) 0.255(4) 0.288(2) 0.045(8) Uiso 1 1 d . . . . .
C10 C 0.5611(4) 0.1460(3) 0.1547(2) 0.0372(5) Uani 1 1 d . . . . .
H10 H 0.473(5) 0.164(4) 0.099(3) 0.067(10) Uiso 1 1 d . . . . .
C11 C 0.7650(4) 0.0618(3) 0.1213(2) 0.0403(6) Uani 1 1 d . . . . .
H11 H 0.812(5) 0.025(4) 0.040(3) 0.056(8) Uiso 1 1 d . . . . .
C12 C 0.8937(4) 0.0362(3) 0.2031(2) 0.0404(6) Uani 1 1 d . . . . .
H12 H 1.046(5) -0.016(4) 0.180(3) 0.051(8) Uiso 1 1 d . . . . .
C13 C 0.8189(4) 0.0937(3) 0.3166(2) 0.0328(5) Uani 1 1 d . . . . .
H13 H 0.903(5) 0.076(4) 0.372(3) 0.061(9) 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 C1 1.709(2) . ?
S1 C7 1.730(2) . ?
C1 C5 1.377(3) . ?
C1 C2 1.448(3) . ?
N1 C3 1.365(3) . ?
N1 C4 1.396(3) . ?
N1 H1N 0.93(3) . ?
O1 C3 1.218(3) . ?
C2 N2 1.270(3) . ?
C2 C3 1.522(3) . ?
N2 H2N 0.83(4) . ?
O2 C4 1.211(3) . ?
C4 C5 1.466(3) . ?
C5 C6 1.407(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.88(3) . ?
C7 C8 1.470(3) . ?
C8 C13 1.396(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.98(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.95(3) . ?
C11 C12 1.386(4) . ?
C11 H11 0.98(3) . ?
C12 C13 1.379(3) . ?
C12 H12 1.01(3) . ?
C13 H13 0.93(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
C1 S1 C7 92.09(10) . . ?
C5 C1 C2 122.5(2) . . ?
C5 C1 S1 111.09(16) . . ?
C2 C1 S1 126.37(17) . . ?
C3 N1 C4 126.54(19) . . ?
C3 N1 H1N 119.9(16) . . ?
C4 N1 H1N 113.4(17) . . ?
N2 C2 C1 123.4(2) . . ?
N2 C2 C3 121.0(2) . . ?
C1 C2 C3 115.54(18) . . ?
C2 N2 H2N 108(2) . . ?
O1 C3 N1 121.9(2) . . ?
O1 C3 C2 120.18(19) . . ?
N1 C3 C2 117.96(18) . . ?
O2 C4 N1 120.11(19) . . ?
O2 C4 C5 124.23(19) . . ?
N1 C4 C5 115.65(18) . . ?
C1 C5 C6 113.66(19) . . ?
C1 C5 C4 121.34(19) . . ?
C6 C5 C4 124.98(18) . . ?
C7 C6 C5 111.96(19) . . ?
C7 C6 H6 120.6(18) . . ?
C5 C6 H6 127.5(18) . . ?
C6 C7 C8 127.46(19) . . ?
C6 C7 S1 111.19(16) . . ?
C8 C7 S1 121.35(16) . . ?
C13 C8 C9 118.0(2) . . ?
C13 C8 C7 121.7(2) . . ?
C9 C8 C7 120.20(19) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 117.3(17) . . ?
C8 C9 H9 121.6(17) . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 120(2) . . ?
C11 C10 H10 119(2) . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 117.5(18) . . ?
C12 C11 H11 123.1(18) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 118.7(18) . . ?
C11 C12 H12 120.9(18) . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 121(2) . . ?
C8 C13 H13 118(2) . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6

