# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_120112h_0m
_database_code_depnum_ccdc_archive 'CCDC 869512'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'ethyl (S)-3-nitro-2-phenyl-2,5-dihydrothiophene-2-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         279.31
_chemical_formula_sum            'C13 H13 N O4 S'
_chemical_formula_weight         279.30

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   7.9060(10)
_cell_length_b                   10.5987(14)
_cell_length_c                   16.010(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1341.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6776
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      31.24

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10715
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3240
_reflns_number_gt                3073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0407P)²+0.1405P] 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     SHELXL
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0771
_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
C1 C 0.21806(17) 0.13966(12) 0.21919(8) 0.0391(3) Uani 1 1 d . . .
C2 C 0.35019(17) 0.22402(13) 0.20557(10) 0.0444(3) Uani 1 1 d . . .
H2 H 0.3578 0.2669 0.1550 0.053 Uiso 1 1 calc R . .
C3 C 0.47101(19) 0.24433(17) 0.26740(12) 0.0571(4) Uani 1 1 d . . .
H3 H 0.5569 0.3027 0.2584 0.069 Uiso 1 1 calc R . .
C4 C 0.4651(2) 0.1795(2) 0.34141(13) 0.0673(5) Uani 1 1 d . . .
H4 H 0.5452 0.1947 0.3828 0.081 Uiso 1 1 calc R . .
C5 C 0.3406(3) 0.09228(19) 0.35380(12) 0.0720(5) Uani 1 1 d . . .
H5 H 0.3390 0.0453 0.4029 0.086 Uiso 1 1 calc R . .
C6 C 0.2161(2) 0.07295(16) 0.29390(10) 0.0560(4) Uani 1 1 d . . .
H6 H 0.1305 0.0147 0.3039 0.067 Uiso 1 1 calc R . .
C7 C 0.07354(16) 0.11825(11) 0.15762(8) 0.0357(2) Uani 1 1 d . . .
C8 C 0.03843(19) -0.01903(11) 0.14074(8) 0.0410(3) Uani 1 1 d . . .
C9 C -0.1058(2) -0.07044(13) 0.16489(9) 0.0498(3) Uani 1 1 d . . .
H9 H -0.1306 -0.1550 0.1554 0.060 Uiso 1 1 calc R . .
C10 C -0.2253(2) 0.01490(15) 0.20799(12) 0.0566(4) Uani 1 1 d . . .
H10A H -0.2414 -0.0115 0.2655 0.068 Uiso 1 1 calc R . .
H10B H -0.3341 0.0147 0.1800 0.068 Uiso 1 1 calc R . .
C11 C 0.08486(18) 0.18898(12) 0.07455(8) 0.0413(3) Uani 1 1 d . . .
C12 C 0.0946(3) 0.38927(14) 0.00987(11) 0.0620(5) Uani 1 1 d . . .
H12A H -0.0194 0.3936 -0.0123 0.074 Uiso 1 1 calc R . .
H12B H 0.1675 0.3523 -0.0323 0.074 Uiso 1 1 calc R . .
C13 C 0.1547(3) 0.51644(15) 0.03173(12) 0.0699(5) Uani 1 1 d . . .
H13A H 0.0845 0.5509 0.0750 0.105 Uiso 1 1 calc R . .
H13B H 0.1495 0.5698 -0.0167 0.105 Uiso 1 1 calc R . .
H13C H 0.2695 0.5116 0.0511 0.105 Uiso 1 1 calc R . .
N1 N 0.1684(2) -0.09350(11) 0.09894(8) 0.0539(3) Uani 1 1 d . . .
O1 O 0.31044(18) -0.04928(12) 0.09481(10) 0.0736(4) Uani 1 1 d . . .
O2 O 0.1294(3) -0.19600(12) 0.07124(11) 0.0931(5) Uani 1 1 d . . .
O3 O 0.0744(2) 0.13843(11) 0.00790(7) 0.0716(4) Uani 1 1 d . . .
O4 O 0.09727(14) 0.31224(8) 0.08574(6) 0.0472(2) Uani 1 1 d . . .
S1 S -0.13082(4) 0.17077(3) 0.20392(3) 0.04968(11) Uani 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
C1 C6 1.390(2) . ?
C1 C2 1.3922(19) . ?
C1 C7 1.5259(19) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.5057(16) . ?
C7 C11 1.5294(17) . ?
C7 S1 1.8627(13) . ?
C8 C9 1.322(2) . ?
C8 N1 1.4583(19) . ?
C9 C10 1.479(2) . ?
C9 H9 0.9300 . ?
C10 S1 1.8141(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.1970(17) . ?
C11 O4 1.3222(15) . ?
C12 O4 1.4638(17) . ?
C12 C13 1.471(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 O2 1.2132(18) . ?
N1 O1 1.219(2) . ?

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
C6 C1 C2 118.03(14) . . ?
C6 C1 C7 118.17(12) . . ?
C2 C1 C7 123.79(12) . . ?
C1 C2 C3 120.18(15) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.91(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.33(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.69(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.76(16) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C1 113.44(10) . . ?
C8 C7 C11 109.17(10) . . ?
C1 C7 C11 116.43(11) . . ?
C8 C7 S1 101.55(9) . . ?
C1 C7 S1 110.36(8) . . ?
C11 C7 S1 104.50(9) . . ?
C9 C8 N1 121.27(12) . . ?
C9 C8 C7 120.33(13) . . ?
N1 C8 C7 118.39(12) . . ?
C8 C9 C10 115.81(12) . . ?
C8 C9 H9 122.1 . . ?
C10 C9 H9 122.1 . . ?
C9 C10 S1 106.11(11) . . ?
C9 C10 H10A 110.5 . . ?
S1 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
S1 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
O3 C11 O4 124.62(13) . . ?
O3 C11 C7 123.50(11) . . ?
O4 C11 C7 111.77(11) . . ?
O4 C12 C13 107.99(14) . . ?
O4 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O4 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 N1 O1 123.96(16) . . ?
O2 N1 C8 118.25(16) . . ?
O1 N1 C8 117.78(13) . . ?
C11 O4 C12 115.95(12) . . ?
C10 S1 C7 95.69(7) . . ?

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
C6 C1 C2 C3 -3.1(2) . . . . ?
C7 C1 C2 C3 175.61(12) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -2.9(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
C7 C1 C6 C5 -177.39(16) . . . . ?
C6 C1 C7 C8 -49.34(17) . . . . ?
C2 C1 C7 C8 131.94(13) . . . . ?
C6 C1 C7 C11 -177.30(13) . . . . ?
C2 C1 C7 C11 3.98(17) . . . . ?
C6 C1 C7 S1 63.85(14) . . . . ?
C2 C1 C7 S1 -114.87(12) . . . . ?
C1 C7 C8 C9 113.64(15) . . . . ?
C11 C7 C8 C9 -114.74(14) . . . . ?
S1 C7 C8 C9 -4.77(15) . . . . ?
C1 C7 C8 N1 -65.11(16) . . . . ?
C11 C7 C8 N1 66.51(15) . . . . ?
S1 C7 C8 N1 176.49(10) . . . . ?
N1 C8 C9 C10 178.86(14) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 S1 4.77(18) . . . . ?
C8 C7 C11 O3 -3.1(2) . . . . ?
C1 C7 C11 O3 126.93(17) . . . . ?
S1 C7 C11 O3 -111.08(16) . . . . ?
C8 C7 C11 O4 173.16(12) . . . . ?
C1 C7 C11 O4 -56.82(15) . . . . ?
S1 C7 C11 O4 65.17(13) . . . . ?
C9 C8 N1 O2 15.0(2) . . . . ?
C7 C8 N1 O2 -166.24(15) . . . . ?
C9 C8 N1 O1 -164.18(16) . . . . ?
C7 C8 N1 O1 14.6(2) . . . . ?
O3 C11 O4 C12 1.1(2) . . . . ?
C7 C11 O4 C12 -175.09(14) . . . . ?
C13 C12 O4 C11 -164.99(16) . . . . ?
C9 C10 S1 C7 -6.39(13) . . . . ?
C8 C7 S1 C10 6.15(10) . . . . ?
C1 C7 S1 C10 -114.44(10) . . . . ?
C11 C7 S1 C10 119.67(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.029
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
