# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1484442'
_audit_update_record             
;
2016-06-10 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Methyl 3,5-diamino-6-(2-methoxyphenyl)-4-oxo-4,5-dihydrothieno[3,2-c]pyridine-2-carboxylate'
_chemical_name_common            thieno[3,2-c]pyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O4 S'
_chemical_formula_sum            'C16 H15 N3 O4 S'
_chemical_formula_weight         345.37

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                   11.6062(6)
_cell_length_b                   18.6702(6)
_cell_length_c                   7.5550(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.089(5)
_cell_angle_gamma                90.00
_cell_volume                     1564.81(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.234
_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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7105
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2753
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Xcalibur, Sapphire3'
_computing_cell_refinement       'X-calibur S SAINT'
_computing_data_reduction        'X-calibur S SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Oxford SHELXTL'
_computing_publication_material  'Oxford SHELXTL'

_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)+(0.0645P)²+1.0000P] 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         2749
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003

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 0.31755(5) 0.04036(3) 0.40645(8) 0.0386(2) Uani 1 1 d . . .
O2 O 0.20643(15) -0.20887(8) 0.8230(2) 0.0389(4) Uani 1 1 d . . .
O3 O 0.06396(17) 0.17804(9) 0.1556(2) 0.0463(5) Uani 1 1 d . . .
O1 O 0.03976(16) 0.03491(9) 0.7949(2) 0.0447(4) Uani 1 1 d . . .
O4 O 0.23984(16) 0.14677(10) 0.1079(2) 0.0483(5) Uani 1 1 d . . .
N1 N 0.19635(17) -0.04421(9) 0.8731(2) 0.0319(4) Uani 1 1 d . . .
N2 N 0.15394(19) -0.07144(11) 1.0168(3) 0.0400(5) Uani 1 1 d . . .
H2A H 0.1928 -0.1051 1.0871 0.048 Uiso 1 1 calc R . .
H2B H 0.0893 -0.0544 1.0340 0.048 Uiso 1 1 calc R . .
N3 N 0.01979(19) 0.11934(11) 0.4739(3) 0.0441(5) Uani 1 1 d . . .
H3A H -0.0108 0.1504 0.3889 0.053 Uiso 1 1 calc R . .
H3B H -0.0157 0.1098 0.5563 0.053 Uiso 1 1 calc R . .
C1 C 0.3150(2) -0.20089(12) 0.9566(3) 0.0316(5) Uani 1 1 d . . .
C9 C 0.2815(2) 0.00444(11) 0.5936(3) 0.0328(5) Uani 1 1 d . . .
C6 C 0.3612(2) -0.13139(12) 0.9774(3) 0.0323(5) Uani 1 1 d . . .
C7 C 0.3008(2) -0.07335(11) 0.8507(3) 0.0320(5) Uani 1 1 d . . .
C12 C 0.1228(2) 0.08586(11) 0.4779(3) 0.0337(5) Uani 1 1 d . . .
C10 C 0.1777(2) 0.03361(11) 0.6170(3) 0.0320(5) Uani 1 1 d . . .
C13 C 0.1899(2) 0.09542(12) 0.3557(3) 0.0354(5) Uani 1 1 d . . .
C8 C 0.3447(2) -0.04974(12) 0.7133(3) 0.0349(5) Uani 1 1 d . . .
H8 H 0.4152 -0.0690 0.6984 0.042 Uiso 1 1 calc R . .
C14 C 0.1568(2) 0.14334(12) 0.1994(3) 0.0361(5) Uani 1 1 d . . .
C5 C 0.4704(2) -0.11875(14) 1.1103(4) 0.0465(6) Uani 1 1 d . . .
H5 H 0.5025 -0.0727 1.1247 0.056 Uiso 1 1 calc R . .
C11 C 0.1304(2) 0.01044(12) 0.7627(3) 0.0335(5) Uani 1 1 d . . .
C16 C 0.1571(3) -0.27962(14) 0.7938(4) 0.0514(7) Uani 1 1 d . . .
H16A H 0.0817 -0.2786 0.6974 0.077 Uiso 1 1 calc R . .
H16B H 0.1442 -0.2969 0.9062 0.077 Uiso 1 1 calc R . .
H16C H 0.2123 -0.3108 0.7583 0.077 Uiso 1 1 calc R . .
C2 C 0.3781(2) -0.25568(13) 1.0648(3) 0.0401(6) Uani 1 1 d . . .
H2 H 0.3477 -0.3021 1.0492 0.048 Uiso 1 1 calc R . .
C3 C 0.4868(2) -0.24153(15) 1.1968(3) 0.0476(7) Uani 1 1 d . . .
H3 H 0.5291 -0.2787 1.2695 0.057 Uiso 1 1 calc R . .
C4 C 0.5325(3) -0.17341(15) 1.2216(4) 0.0507(7) Uani 1 1 d . . .
H4 H 0.6046 -0.1640 1.3125 0.061 Uiso 1 1 calc R . .
C15 C 0.2108(3) 0.19531(17) -0.0478(4) 0.0599(8) Uani 1 1 d . . .
H15A H 0.2743 0.1946 -0.1054 0.090 Uiso 1 1 calc R . .
H15B H 0.2021 0.2430 -0.0056 0.090 Uiso 1 1 calc R . .
H15C H 0.1366 0.1807 -0.1358 0.090 Uiso 1 1 calc R . .

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 0.0352(4) 0.0409(4) 0.0425(4) 0.0045(2) 0.0157(3) 0.0024(3)
O2 0.0329(9) 0.0319(8) 0.0478(9) -0.0012(7) 0.0056(7) -0.0049(7)
O3 0.0443(11) 0.0483(10) 0.0453(10) 0.0088(8) 0.0114(8) 0.0100(9)
O1 0.0458(11) 0.0455(10) 0.0488(10) 0.0074(8) 0.0235(8) 0.0137(8)
O4 0.0419(11) 0.0603(11) 0.0431(10) 0.0148(8) 0.0134(8) 0.0031(9)
N1 0.0306(10) 0.0313(9) 0.0342(10) -0.0001(7) 0.0104(8) -0.0002(8)
N2 0.0411(12) 0.0452(11) 0.0376(10) 0.0102(9) 0.0176(9) 0.0103(9)
N3 0.0466(13) 0.0443(12) 0.0448(12) 0.0102(9) 0.0188(10) 0.0153(10)
C1 0.0310(12) 0.0339(11) 0.0321(11) 0.0001(9) 0.0128(9) 0.0010(9)
C9 0.0308(12) 0.0287(11) 0.0386(12) -0.0024(9) 0.0095(9) -0.0040(9)
C6 0.0291(12) 0.0318(11) 0.0360(12) -0.0010(9) 0.0098(9) 0.0008(9)
C7 0.0298(12) 0.0267(11) 0.0373(12) -0.0044(9) 0.0065(9) -0.0034(9)
C12 0.0365(13) 0.0287(11) 0.0342(11) -0.0030(9) 0.0079(9) 0.0005(9)
C10 0.0309(13) 0.0273(11) 0.0370(12) -0.0033(9) 0.0085(9) -0.0003(9)
C13 0.0331(13) 0.0339(12) 0.0383(12) 0.0000(9) 0.0093(10) 0.0012(10)
C8 0.0278(12) 0.0315(11) 0.0460(13) -0.0009(10) 0.0117(10) 0.0007(9)
C14 0.0377(14) 0.0347(12) 0.0342(12) -0.0046(9) 0.0076(10) -0.0040(10)
C5 0.0401(15) 0.0425(14) 0.0498(15) -0.0032(11) 0.0021(11) -0.0023(11)
C11 0.0326(13) 0.0309(11) 0.0369(12) -0.0024(9) 0.0101(9) 0.0007(10)
C16 0.0546(18) 0.0392(14) 0.0617(17) -0.0085(12) 0.0189(13) -0.0167(12)
C2 0.0473(15) 0.0339(12) 0.0444(13) 0.0071(10) 0.0217(11) 0.0044(11)
C3 0.0467(16) 0.0554(16) 0.0411(13) 0.0152(12) 0.0135(12) 0.0175(13)
C4 0.0390(15) 0.0616(17) 0.0432(14) 0.0013(12) -0.0010(11) 0.0057(13)
C15 0.0567(19) 0.077(2) 0.0471(16) 0.0229(14) 0.0169(13) 0.0021(16)

_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 C9 1.723(2) . ?
S1 C13 1.750(2) . ?
O2 C1 1.371(3) . ?
O2 C16 1.431(3) . ?
O3 C14 1.217(3) . ?
O1 C11 1.234(3) . ?
O4 C14 1.343(3) . ?
O4 C15 1.444(3) . ?
N1 C7 1.384(3) . ?
N1 C11 1.396(3) . ?
N1 N2 1.412(3) . ?
N3 C12 1.342(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.395(3) . ?
C9 C10 1.380(3) . ?
C9 C8 1.411(3) . ?
C6 C5 1.386(3) . ?
C6 C7 1.479(3) . ?
C7 C8 1.357(3) . ?
C12 C13 1.383(3) . ?
C12 C10 1.438(3) . ?
C10 C11 1.434(3) . ?
C13 C14 1.441(3) . ?
C5 C4 1.383(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.370(4) . ?

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
C9 S1 C13 90.83(11) . . ?
C1 O2 C16 116.95(19) . . ?
C14 O4 C15 114.7(2) . . ?
C7 N1 C11 124.12(19) . . ?
C7 N1 N2 117.93(18) . . ?
C11 N1 N2 117.95(18) . . ?
O2 C1 C2 124.7(2) . . ?
O2 C1 C6 115.07(19) . . ?
C2 C1 C6 120.3(2) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 S1 112.51(17) . . ?
C8 C9 S1 126.84(18) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 120.2(2) . . ?
C1 C6 C7 121.0(2) . . ?
C8 C7 N1 120.3(2) . . ?
C8 C7 C6 121.3(2) . . ?
N1 C7 C6 118.31(19) . . ?
N3 C12 C13 126.7(2) . . ?
N3 C12 C10 122.2(2) . . ?
C13 C12 C10 111.1(2) . . ?
C9 C10 C11 121.7(2) . . ?
C9 C10 C12 112.9(2) . . ?
C11 C10 C12 125.3(2) . . ?
C12 C13 C14 124.0(2) . . ?
C12 C13 S1 112.61(17) . . ?
C14 C13 S1 123.32(18) . . ?
C7 C8 C9 118.8(2) . . ?
O3 C14 O4 123.1(2) . . ?
O3 C14 C13 123.8(2) . . ?
O4 C14 C13 113.1(2) . . ?
C4 C5 C6 121.1(2) . . ?
O1 C11 N1 120.2(2) . . ?
O1 C11 C10 125.5(2) . . ?
N1 C11 C10 114.36(19) . . ?
C1 C2 C3 119.9(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 119.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.064
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'chloroform and methanol'
_chemical_compound_source        NA
