# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_vjs-54-d-
_database_code_depnum_ccdc_archive 'CCDC 1038008'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Dimethyl 3-amino-5-(2-oxo-2-phenylethyl)thiophene-2,4-dicarboxylate '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N O5 S'
_chemical_formula_weight         333.35

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 1 21/c 1'

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                   14.073(5)
_cell_length_b                   13.465(5)
_cell_length_c                   8.576(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.433(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1622.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3117
_cell_measurement_theta_min      3.0988
_cell_measurement_theta_max      29.0134

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_T_max  0.9608
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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       ?
_diffrn_detector_area_resol_mean 15.9853
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9249
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         29.08
_reflns_number_total             3729
_reflns_number_gt                2932
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_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)+(0.0535P)²+0.3164P] 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         3729
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.73465(3) 0.37481(3) 0.13362(5) 0.04345(15) Uani 1 1 d . . .
O5 O 0.79006(10) 0.57872(10) 0.20567(17) 0.0595(4) Uani 1 1 d . . .
O1 O 0.60947(9) 0.16338(10) 0.30779(15) 0.0520(3) Uani 1 1 d . . .
O2 O 0.83476(9) 0.06708(9) 0.26706(16) 0.0541(3) Uani 1 1 d . . .
N1 N 0.95444(12) 0.34192(16) 0.4277(2) 0.0571(5) Uani 1 1 d . . .
C7 C 0.63845(11) 0.12107(12) 0.19563(19) 0.0369(4) Uani 1 1 d . . .
O3 O 0.95177(10) 0.13951(11) 0.41331(19) 0.0679(4) Uani 1 1 d . . .
O4 O 0.91106(11) 0.54677(10) 0.38091(18) 0.0692(4) Uani 1 1 d . . .
C1 C 0.61160(11) 0.01540(12) 0.1616(2) 0.0386(4) Uani 1 1 d . . .
C9 C 0.76154(12) 0.25307(12) 0.16694(19) 0.0385(4) Uani 1 1 d . . .
C10 C 0.83971(11) 0.24072(12) 0.27063(19) 0.0387(4) Uani 1 1 d . . .
C8 C 0.70082(13) 0.17477(12) 0.0853(2) 0.0423(4) Uani 1 1 d . . .
H8A H 0.7400(5) 0.1288(6) 0.0392(7) 0.051 Uiso 1 1 calc R . .
H8B H 0.6624(5) 0.2044(4) 0.0060(11) 0.051 Uiso 1 1 calc R . .
C4 C 0.55702(16) -0.18063(16) 0.1089(3) 0.0674(6) Uani 1 1 d . . .
H4 H 0.5374(5) -0.2539(18) 0.0898(6) 0.081 Uiso 1 1 calc R . .
C5 C 0.60351(16) -0.12966(15) -0.0007(3) 0.0650(6) Uani 1 1 d . . .
H5 H 0.6158(4) -0.1579(8) -0.085(2) 0.078 Uiso 1 1 calc R . .
C6 C 0.63081(13) -0.03160(14) 0.0247(2) 0.0506(5) Uani 1 1 d . . .
H6 H 0.6618(7) 0.0019(8) -0.0500(17) 0.061 Uiso 1 1 calc R . .
C11 C 0.88189(13) 0.14612(14) 0.3242(2) 0.0457(4) Uani 1 1 d . . .
C13 C 0.87861(11) 0.33431(13) 0.3248(2) 0.0405(4) Uani 1 1 d . . .
C14 C 0.82783(12) 0.41396(13) 0.2597(2) 0.0417(4) Uani 1 1 d . . .
C3 C 0.53664(18) -0.13414(16) 0.2440(3) 0.0719(7) Uani 1 1 d . . .
H3 H 0.5048(9) -0.1677(10) 0.317(2) 0.086 Uiso 1 1 calc R . .
C2 C 0.56361(15) -0.03659(16) 0.2721(3) 0.0585(5) Uani 1 1 d . . .
H2 H 0.5490(4) -0.0047(8) 0.369(2) 0.070 Uiso 1 1 calc R . .
C15 C 0.84853(13) 0.51697(14) 0.2896(2) 0.0472(4) Uani 1 1 d . . .
C16 C 0.81051(19) 0.68337(15) 0.2245(4) 0.0837(9) Uani 1 1 d . . .
H16A H 0.7673(11) 0.7193(6) 0.165(2) 0.126 Uiso 1 1 calc R . .
H16B H 0.8702(11) 0.6962(4) 0.194(2) 0.126 Uiso 1 1 calc R . .
H16C H 0.8069(14) 0.7006(5) 0.3267(18) 0.126 Uiso 1 1 calc R . .
C12 C 0.87058(18) -0.02923(15) 0.3161(3) 0.0729(7) Uani 1 1 d . . .
H12A H 0.8305(9) -0.0780(7) 0.2751(18) 0.109 Uiso 1 1 calc R . .
H12B H 0.8735(12) -0.0329(5) 0.4235(16) 0.109 Uiso 1 1 calc R . .
H12C H 0.9305(10) -0.0382(6) 0.2809(18) 0.109 Uiso 1 1 calc R . .
H1" H 0.9701(16) 0.4021(18) 0.461(3) 0.071(7) Uiso 1 1 d . . .
H1' H 0.9770(17) 0.2882(18) 0.472(3) 0.074(8) 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 C9 1.7026(18) . ?
S1 C14 1.7311(18) . ?
O5 C15 1.347(2) . ?
O5 C16 1.445(2) . ?
O1 C7 1.210(2) . ?
O2 C11 1.332(2) . ?
O2 C12 1.445(2) . ?
N1 C13 1.347(2) . ?
N1 H1" 0.88(2) . ?
N1 H1' 0.87(2) . ?
C7 C1 1.496(2) . ?
C7 C8 1.513(2) . ?
O3 C11 1.212(2) . ?
O4 C15 1.211(2) . ?
C1 C6 1.374(3) . ?
C1 C2 1.386(3) . ?
C9 C10 1.383(2) . ?
C9 C8 1.504(2) . ?
C10 C13 1.440(2) . ?
C10 C11 1.467(2) . ?
C8 H8A 0.9320 . ?
C8 H8B 0.9320 . ?
C4 C3 1.362(3) . ?
C4 C5 1.363(3) . ?
C4 H4 1.0347 . ?
C5 C6 1.389(3) . ?
C5 H5 0.8424 . ?
C6 H6 0.9155 . ?
C13 C14 1.387(3) . ?
C14 C15 1.437(2) . ?
C3 C2 1.384(3) . ?
C3 H3 0.9108 . ?
C2 H2 0.9668 . ?
C16 H16A 0.9113 . ?
C16 H16B 0.9113 . ?
C16 H16C 0.9113 . ?
C12 H12A 0.9210 . ?
C12 H12B 0.9210 . ?
C12 H12C 0.9210 . ?

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 C14 92.06(8) . . ?
C15 O5 C16 115.53(17) . . ?
C11 O2 C12 116.93(16) . . ?
C13 N1 H1" 117.0(14) . . ?
C13 N1 H1' 118.4(16) . . ?
H1" N1 H1' 123(2) . . ?
O1 C7 C1 120.64(15) . . ?
O1 C7 C8 120.56(15) . . ?
C1 C7 C8 118.79(14) . . ?
C6 C1 C2 118.70(17) . . ?
C6 C1 C7 122.96(15) . . ?
C2 C1 C7 118.33(16) . . ?
C10 C9 C8 128.57(16) . . ?
C10 C9 S1 112.58(12) . . ?
C8 C9 S1 118.85(13) . . ?
C9 C10 C13 112.01(15) . . ?
C9 C10 C11 126.67(15) . . ?
C13 C10 C11 121.32(15) . . ?
C9 C8 C7 112.24(15) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.35(19) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O3 C11 O2 122.73(18) . . ?
O3 C11 C10 123.98(17) . . ?
O2 C11 C10 113.28(15) . . ?
N1 C13 C14 124.99(17) . . ?
N1 C13 C10 123.29(17) . . ?
C14 C13 C10 111.71(15) . . ?
C13 C14 C15 125.47(16) . . ?
C13 C14 S1 111.63(13) . . ?
C15 C14 S1 122.90(14) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O4 C15 O5 122.54(17) . . ?
O4 C15 C14 124.53(18) . . ?
O5 C15 C14 112.93(15) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
O1 C7 C1 C6 170.29(17) . . . . ?
C8 C7 C1 C6 -8.4(2) . . . . ?
O1 C7 C1 C2 -8.5(2) . . . . ?
C8 C7 C1 C2 172.84(16) . . . . ?
C14 S1 C9 C10 -0.32(13) . . . . ?
C14 S1 C9 C8 179.49(14) . . . . ?
C8 C9 C10 C13 -179.62(16) . . . . ?
S1 C9 C10 C13 0.17(18) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
S1 C9 C10 C11 -179.79(13) . . . . ?
C10 C9 C8 C7 71.7(2) . . . . ?
S1 C9 C8 C7 -108.05(15) . . . . ?
O1 C7 C8 C9 30.9(2) . . . . ?
C1 C7 C8 C9 -150.38(14) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C7 C1 C6 C5 -179.53(17) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C12 O2 C11 O3 0.0(3) . . . . ?
C12 O2 C11 C10 -178.97(16) . . . . ?
C9 C10 C11 O3 178.55(18) . . . . ?
C13 C10 C11 O3 -1.4(3) . . . . ?
C9 C10 C11 O2 -2.5(2) . . . . ?
C13 C10 C11 O2 177.57(14) . . . . ?
C9 C10 C13 N1 179.39(16) . . . . ?
C11 C10 C13 N1 -0.6(3) . . . . ?
C9 C10 C13 C14 0.1(2) . . . . ?
C11 C10 C13 C14 -179.91(15) . . . . ?
N1 C13 C14 C15 0.9(3) . . . . ?
C10 C13 C14 C15 -179.86(16) . . . . ?
N1 C13 C14 S1 -179.61(15) . . . . ?
C10 C13 C14 S1 -0.36(18) . . . . ?
C9 S1 C14 C13 0.39(14) . . . . ?
C9 S1 C14 C15 179.90(15) . . . . ?
C5 C4 C3 C2 -0.9(4) . . . . ?
C4 C3 C2 C1 0.4(4) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C7 C1 C2 C3 179.27(19) . . . . ?
C16 O5 C15 O4 3.7(3) . . . . ?
C16 O5 C15 C14 -176.87(17) . . . . ?
C13 C14 C15 O4 -3.2(3) . . . . ?
S1 C14 C15 O4 177.40(16) . . . . ?
C13 C14 C15 O5 177.38(16) . . . . ?
S1 C14 C15 O5 -2.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.857
_diffrn_reflns_theta_full        29.08
_diffrn_measured_fraction_theta_full 0.857
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
