# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1880535'
_audit_update_record             
;
2018-11-21 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Compound 3'
_chemical_name_common            
2-phenylthieno[3,2-c]pyridine-4,6,7(5H)-trione
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 N O3 S'
_chemical_formula_weight         257.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   5.4276(4)
_cell_length_b                   9.6873(7)
_cell_length_c                   10.8442(8)
_cell_angle_alpha                69.319(6)
_cell_angle_beta                 82.283(6)
_cell_angle_gamma                83.399(5)
_cell_volume                     527.20(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    1048
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      67.72

_exptl_crystal_description       plate
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .03
_exptl_crystal_size_mid          .02
_exptl_crystal_size_min          .005
_exptl_absorpt_coefficient_mu    2.742
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98
_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            6359
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.380
_diffrn_reflns_theta_max         68.418
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1890
_reflns_number_gt                1464
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1890
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_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 0.77479(12) 0.58185(8) 0.17914(7) 0.0319(2) Uani 1 1 d . . . . .
O1 O 0.9861(4) 0.8570(2) 0.2133(2) 0.0391(5) Uani 1 1 d . . . . .
N1 N 0.4448(4) 0.8322(3) 0.4489(2) 0.0324(6) Uani 1 1 d . . . . .
H1N H 0.378(6) 0.879(3) 0.503(3) 0.042(9) Uiso 1 1 d . . . . .
C1 C 0.6708(5) 0.6889(3) 0.2751(3) 0.0297(6) Uani 1 1 d . . . . .
O2 O 0.7609(4) 0.9836(2) 0.3939(2) 0.0393(5) Uani 1 1 d . . . . .
C2 C 0.7950(5) 0.8100(3) 0.2796(3) 0.0305(6) Uani 1 1 d . . . . .
O3 O 0.1269(3) 0.6828(2) 0.5067(2) 0.0368(5) Uani 1 1 d . . . . .
C3 C 0.6676(5) 0.8845(3) 0.3787(3) 0.0307(6) Uani 1 1 d . . . . .
C4 C 0.3234(5) 0.7183(3) 0.4403(3) 0.0280(6) Uani 1 1 d . . . . .
C5 C 0.4475(5) 0.6440(3) 0.3488(3) 0.0292(6) Uani 1 1 d . . . . .
C6 C 0.3610(5) 0.5246(3) 0.3274(3) 0.0289(6) Uani 1 1 d . . . . .
H6A H 0.211420 0.481781 0.369429 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5190(5) 0.4766(3) 0.2381(3) 0.0289(6) Uani 1 1 d . . . . .
C8 C 0.4910(5) 0.3534(3) 0.1925(3) 0.0292(6) Uani 1 1 d . . . . .
C9 C 0.2854(5) 0.2694(3) 0.2433(3) 0.0334(7) Uani 1 1 d . . . . .
H9A H 0.166661 0.291622 0.306404 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2542(5) 0.1525(3) 0.2016(3) 0.0366(7) Uani 1 1 d . . . . .
H10A H 0.113475 0.097266 0.235077 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4313(6) 0.1182(3) 0.1108(3) 0.0383(7) Uani 1 1 d . . . . .
H11A H 0.412714 0.038290 0.083637 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6360(6) 0.2013(3) 0.0596(3) 0.0393(7) Uani 1 1 d . . . . .
H12A H 0.754610 0.178340 -0.003207 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6670(5) 0.3173(3) 0.1001(3) 0.0361(7) Uani 1 1 d . . . . .
H13A H 0.807440 0.372550 0.065310 0.043 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 1.717(3) . ?
S1 C7 1.733(3) . ?
O1 C2 1.215(3) . ?
N1 C4 1.384(3) . ?
N1 C3 1.385(3) . ?
N1 H1N 0.88(3) . ?
C1 C5 1.383(4) . ?
C1 C2 1.437(4) . ?
O2 C3 1.204(3) . ?
C2 C3 1.546(4) . ?
O3 C4 1.216(3) . ?
C4 C5 1.474(4) . ?
C5 C6 1.398(3) . ?
C6 C7 1.375(4) . ?
C6 H6A 0.9400 . ?
C7 C8 1.473(3) . ?
C8 C9 1.392(4) . ?
C8 C13 1.398(4) . ?
C9 C10 1.394(4) . ?
C9 H9A 0.9400 . ?
C10 C11 1.381(4) . ?
C10 H10A 0.9400 . ?
C11 C12 1.383(4) . ?
C11 H11A 0.9400 . ?
C12 C13 1.377(4) . ?
C12 H12A 0.9400 . ?
C13 H13A 0.9400 . ?

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 91.75(13) . . ?
C4 N1 C3 126.7(2) . . ?
C4 N1 H1N 119(2) . . ?
C3 N1 H1N 114(2) . . ?
C5 C1 C2 123.6(2) . . ?
C5 C1 S1 110.98(19) . . ?
C2 C1 S1 125.4(2) . . ?
O1 C2 C1 126.0(2) . . ?
O1 C2 C3 118.8(2) . . ?
C1 C2 C3 115.2(2) . . ?
O2 C3 N1 122.0(3) . . ?
O2 C3 C2 120.6(2) . . ?
N1 C3 C2 117.4(2) . . ?
O3 C4 N1 120.6(2) . . ?
O3 C4 C5 123.1(2) . . ?
N1 C4 C5 116.2(2) . . ?
C1 C5 C6 113.4(2) . . ?
C1 C5 C4 120.9(2) . . ?
C6 C5 C4 125.7(2) . . ?
C7 C6 C5 112.6(2) . . ?
C7 C6 H6A 123.7 . . ?
C5 C6 H6A 123.7 . . ?
C6 C7 C8 127.9(2) . . ?
C6 C7 S1 111.26(19) . . ?
C8 C7 S1 120.8(2) . . ?
C9 C8 C13 118.8(2) . . ?
C9 C8 C7 119.5(2) . . ?
C13 C8 C7 121.8(2) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13A 119.8 . . ?
C8 C13 H13A 119.8 . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058

