# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_3Facetonad_a
_database_code_depnum_ccdc_archive 'CCDC 2110241'
loop_
_audit_author_name
_audit_author_address
'Jose Antonio Paixao'
;University of Coimbra
Portugal
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
5-acetyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile
;
_chemical_name_common            ?
_chemical_melting_point          454.2
_chemical_formula_moiety         'C13 H9 N3 O3 S'
_chemical_formula_sum            'C13 H9 N3 O3 S'
_chemical_formula_weight         287.29

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.451(3)
_cell_length_b                   14.4966(14)
_cell_length_c                   7.1113(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.795(6)
_cell_angle_gamma                90
_cell_volume                     2610.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      5.620
_cell_measurement_theta_max      43.397

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  
;
Bruker APEXII CCD area-detector diffractometer  
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            207226
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4598
_reflns_number_gt                3090
_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       'APEXIII (Bruker AXS, 2016)'
_computing_cell_refinement       'APEXIII (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0545P)²+2.8905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4598
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 0.28073(4) 0.23419(6) 0.46997(14) 0.0504(3) Uani 1 1 d . . . . .
N1 N 0.33962(16) -0.0984(3) 0.4818(7) 0.0869(12) Uani 1 1 d . . . . .
N2 N 0.37014(12) 0.1403(2) 0.3918(5) 0.0488(8) Uani 1 1 d . . . . .
H2 H 0.3844(15) 0.090(3) 0.378(5) 0.059 Uiso 1 1 d . U . . .
N3 N 0.47593(13) 0.0970(2) 0.3038(5) 0.0609(9) Uani 1 1 d . . . . .
O1 O 0.17683(12) 0.2918(2) 0.5654(5) 0.0850(10) Uani 1 1 d . . . . .
O2 O 0.44633(11) 0.03151(19) 0.3209(5) 0.0836(10) Uani 1 1 d . . . . .
O3 O 0.52147(12) 0.0849(2) 0.2718(6) 0.1015(12) Uani 1 1 d . . . . .
C1 C 0.32058(13) 0.1404(2) 0.4470(5) 0.0423(8) Uani 1 1 d . . . . .
C2 C 0.29533(14) 0.0595(2) 0.4902(5) 0.0506(9) Uani 1 1 d . . . . .
C3 C 0.24369(15) 0.0749(3) 0.5386(5) 0.0570(10) Uani 1 1 d . . . . .
H3 H 0.221247 0.028048 0.570259 0.068 Uiso 1 1 calc R U . . .
C4 C 0.23038(14) 0.1647(3) 0.5339(5) 0.0511(9) Uani 1 1 d . . . . .
C5 C 0.18106(15) 0.2083(3) 0.5716(6) 0.0601(10) Uani 1 1 d . . . . .
C6 C 0.13698(16) 0.1467(4) 0.6238(7) 0.0859(15) Uani 1 1 d . . . . .
H6A H 0.103720 0.170876 0.569656 0.129 Uiso 1 1 calc R U . . .
H6B H 0.137372 0.144482 0.758860 0.129 Uiso 1 1 calc R U . . .
H6C H 0.141813 0.085704 0.576100 0.129 Uiso 1 1 calc R U . . .
C7 C 0.31987(16) -0.0286(3) 0.4854(6) 0.0589(10) Uani 1 1 d . . . . .
C8 C 0.40535(13) 0.2104(2) 0.3636(5) 0.0422(8) Uani 1 1 d . . . . .
C9 C 0.39223(14) 0.3036(2) 0.3754(5) 0.0481(9) Uani 1 1 d . . . . .
H9 H 0.358748 0.320140 0.405186 0.058 Uiso 1 1 calc R U . . .
C10 C 0.42808(16) 0.3712(3) 0.3435(5) 0.0570(10) Uani 1 1 d . . . . .
H10 H 0.418276 0.432790 0.350677 0.068 Uiso 1 1 calc R U . . .
C11 C 0.47814(16) 0.3497(3) 0.3013(6) 0.0615(11) Uani 1 1 d . . . . .
H11 H 0.501902 0.396369 0.279928 0.074 Uiso 1 1 calc R U . . .
C12 C 0.49263(15) 0.2600(3) 0.2910(6) 0.0572(10) Uani 1 1 d . . . . .
H12 H 0.526590 0.245097 0.263787 0.069 Uiso 1 1 calc R U . . .
C13 C 0.45695(13) 0.1904(2) 0.3209(5) 0.0461(8) Uani 1 1 d . . . . .
S1' S 0.22111(4) 0.54839(6) 0.55678(15) 0.0531(3) Uani 1 1 d . . . . .
N1' N 0.16577(15) 0.8814(2) 0.5760(6) 0.0757(11) Uani 1 1 d . . . . .
N2' N 0.13069(12) 0.6453(2) 0.6115(5) 0.0510(8) Uani 1 1 d . . . . .
H2' H 0.1207(15) 0.694(3) 0.636(6) 0.061 Uiso 1 1 d . U . . .
N3' N 0.03323(13) 0.6901(2) 0.7673(6) 0.0734(11) Uani 1 1 d . . . . .
O1' O 0.32773(12) 0.4873(2) 0.4995(5) 0.0900(11) Uani 1 1 d . . . . .
O2' O 0.06262(12) 0.7555(2) 0.7402(6) 0.0909(11) Uani 1 1 d . . . . .
O3' O -0.00855(14) 0.7023(3) 0.8329(7) 0.1258(17) Uani 1 1 d . . . . .
C1' C 0.18208(12) 0.6437(2) 0.5748(5) 0.0401(8) Uani 1 1 d . . . . .
C2' C 0.20986(13) 0.7238(2) 0.5519(5) 0.0453(8) Uani 1 1 d . . . . .
C3' C 0.26276(14) 0.7080(3) 0.5205(5) 0.0514(9) Uani 1 1 d . . . . .
H3' H 0.286727 0.754862 0.503036 0.062 Uiso 1 1 calc R U . . .
C4' C 0.27500(14) 0.6176(3) 0.5184(5) 0.0525(9) Uani 1 1 d . . . . .
C5' C 0.32506(16) 0.5709(3) 0.4996(6) 0.0665(11) Uani 1 1 d . . . . .
C6' C 0.37239(16) 0.6318(4) 0.4814(9) 0.0925(17) Uani 1 1 d . . . . .
H6A' H 0.384620 0.656828 0.602945 0.139 Uiso 1 1 calc R U . . .
H6B' H 0.362598 0.681171 0.395022 0.139 Uiso 1 1 calc R U . . .
H6C' H 0.400052 0.596025 0.434699 0.139 Uiso 1 1 calc R U . . .
C7' C 0.18644(15) 0.8124(3) 0.5642(5) 0.0527(9) Uani 1 1 d . . . . .
C8' C 0.09594(13) 0.5762(2) 0.6508(5) 0.0448(8) Uani 1 1 d . . . . .
C9' C 0.10573(15) 0.4835(2) 0.6168(6) 0.0555(10) Uani 1 1 d . . . . .
H9' H 0.136904 0.466647 0.568026 0.067 Uiso 1 1 calc R U . . .
C10' C 0.07015(16) 0.4167(3) 0.6540(6) 0.0654(11) Uani 1 1 d . . . . .
H10' H 0.077591 0.355354 0.629581 0.078 Uiso 1 1 calc R U . . .
C11' C 0.02364(16) 0.4385(3) 0.7268(6) 0.0655(11) Uani 1 1 d . . . . .
H11' H -0.000103 0.392376 0.751734 0.079 Uiso 1 1 calc R U . . .
C12' C 0.01296(14) 0.5279(3) 0.7617(6) 0.0592(10) Uani 1 1 d . . . . .
H12' H -0.018373 0.543259 0.810929 0.071 Uiso 1 1 calc R U . . .
C13' C 0.04813(14) 0.5967(2) 0.7248(5) 0.0509(9) 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
S1 C1 1.714(3) . ?
S1 C4 1.727(4) . ?
N1 C7 1.132(5) . ?
N2 C1 1.358(4) . ?
N2 C8 1.383(4) . ?
N2 H2 0.83(4) . ?
N3 O3 1.216(4) . ?
N3 O2 1.225(4) . ?
N3 C13 1.447(5) . ?
O1 C5 1.215(5) . ?
C1 C2 1.387(5) . ?
C2 C3 1.410(5) . ?
C2 C7 1.423(5) . ?
C3 C4 1.344(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.454(5) . ?
C5 C6 1.509(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.396(5) . ?
C8 C13 1.408(5) . ?
C9 C10 1.373(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
S1' C1' 1.715(3) . ?
S1' C4' 1.743(4) . ?
N1' C7' 1.138(5) . ?
N2' C1' 1.360(4) . ?
N2' C8' 1.383(4) . ?
N2' H2' 0.78(4) . ?
N3' O3' 1.216(4) . ?
N3' O2' 1.235(4) . ?
N3' C13' 1.447(5) . ?
O1' C5' 1.214(5) . ?
C1' C2' 1.377(4) . ?
C2' C3' 1.406(5) . ?
C2' C7' 1.422(5) . ?
C3' C4' 1.348(5) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.461(5) . ?
C5' C6' 1.510(6) . ?
C6' H6A' 0.9600 . ?
C6' H6B' 0.9600 . ?
C6' H6C' 0.9600 . ?
C8' C9' 1.393(5) . ?
C8' C13' 1.405(5) . ?
C9' C10' 1.369(5) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.376(5) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.352(5) . ?
C11' H11' 0.9300 . ?
C12' C13' 1.383(5) . ?
C12' H12' 0.9300 . ?

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 C4 91.39(18) . . ?
C1 N2 C8 132.5(3) . . ?
C1 N2 H2 118(3) . . ?
C8 N2 H2 110(3) . . ?
O3 N3 O2 120.9(3) . . ?
O3 N3 C13 118.9(3) . . ?
O2 N3 C13 120.2(3) . . ?
N2 C1 C2 121.9(3) . . ?
N2 C1 S1 127.1(3) . . ?
C2 C1 S1 111.0(3) . . ?
C1 C2 C3 112.6(3) . . ?
C1 C2 C7 122.6(3) . . ?
C3 C2 C7 124.8(3) . . ?
C4 C3 C2 112.7(3) . . ?
C4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3 C4 C5 129.5(4) . . ?
C3 C4 S1 112.3(3) . . ?
C5 C4 S1 118.2(3) . . ?
O1 C5 C4 120.1(4) . . ?
O1 C5 C6 122.2(4) . . ?
C4 C5 C6 117.7(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C2 179.7(5) . . ?
N2 C8 C9 122.7(3) . . ?
N2 C8 C13 120.8(3) . . ?
C9 C8 C13 116.5(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 121.4(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 121.5(3) . . ?
C12 C13 N3 116.0(3) . . ?
C8 C13 N3 122.5(3) . . ?
C1' S1' C4' 91.09(17) . . ?
C1' N2' C8' 132.4(3) . . ?
C1' N2' H2' 114(3) . . ?
C8' N2' H2' 113(3) . . ?
O3' N3' O2' 121.0(4) . . ?
O3' N3' C13' 118.3(4) . . ?
O2' N3' C13' 120.7(3) . . ?
N2' C1' C2' 121.6(3) . . ?
N2' C1' S1' 127.1(3) . . ?
C2' C1' S1' 111.2(2) . . ?
C1' C2' C3' 113.1(3) . . ?
C1' C2' C7' 122.0(3) . . ?
C3' C2' C7' 124.8(3) . . ?
C4' C3' C2' 112.7(3) . . ?
C4' C3' H3' 123.6 . . ?
C2' C3' H3' 123.6 . . ?
C3' C4' C5' 131.0(4) . . ?
C3' C4' S1' 111.8(3) . . ?
C5' C4' S1' 117.1(3) . . ?
O1' C5' C4' 120.8(4) . . ?
O1' C5' C6' 122.6(4) . . ?
C4' C5' C6' 116.6(4) . . ?
C5' C6' H6A' 109.5 . . ?
C5' C6' H6B' 109.5 . . ?
H6A' C6' H6B' 109.5 . . ?
C5' C6' H6C' 109.5 . . ?
H6A' C6' H6C' 109.5 . . ?
H6B' C6' H6C' 109.5 . . ?
N1' C7' C2' 177.0(4) . . ?
N2' C8' C9' 122.3(3) . . ?
N2' C8' C13' 121.2(3) . . ?
C9' C8' C13' 116.5(3) . . ?
C10' C9' C8' 121.0(3) . . ?
C10' C9' H9' 119.5 . . ?
C8' C9' H9' 119.5 . . ?
C9' C10' C11' 121.5(4) . . ?
C9' C10' H10' 119.3 . . ?
C11' C10' H10' 119.3 . . ?
C12' C11' C10' 119.0(4) . . ?
C12' C11' H11' 120.5 . . ?
C10' C11' H11' 120.5 . . ?
C11' C12' C13' 120.7(4) . . ?
C11' C12' H12' 119.6 . . ?
C13' C12' H12' 119.6 . . ?
C12' C13' C8' 121.4(3) . . ?
C12' C13' N3' 116.6(3) . . ?
C8' C13' N3' 122.1(3) . . ?

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
C8 N2 C1 C2 -171.1(4) . . . . ?
C8 N2 C1 S1 10.0(6) . . . . ?
C4 S1 C1 N2 178.3(3) . . . . ?
C4 S1 C1 C2 -0.8(3) . . . . ?
N2 C1 C2 C3 -178.2(3) . . . . ?
S1 C1 C2 C3 0.9(4) . . . . ?
N2 C1 C2 C7 1.9(6) . . . . ?
S1 C1 C2 C7 -179.0(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C7 C2 C3 C4 179.4(4) . . . . ?
C2 C3 C4 C5 179.1(4) . . . . ?
C2 C3 C4 S1 0.0(4) . . . . ?
C1 S1 C4 C3 0.5(3) . . . . ?
C1 S1 C4 C5 -178.8(3) . . . . ?
C3 C4 C5 O1 177.9(4) . . . . ?
S1 C4 C5 O1 -3.0(6) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
S1 C4 C5 C6 178.9(3) . . . . ?
C1 N2 C8 C9 -5.6(6) . . . . ?
C1 N2 C8 C13 174.5(4) . . . . ?
N2 C8 C9 C10 -179.0(3) . . . . ?
C13 C8 C9 C10 1.0(5) . . . . ?
C8 C9 C10 C11 -0.8(6) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C11 C12 C13 0.7(6) . . . . ?
C11 C12 C13 C8 -0.4(6) . . . . ?
C11 C12 C13 N3 179.0(4) . . . . ?
N2 C8 C13 C12 179.6(3) . . . . ?
C9 C8 C13 C12 -0.4(5) . . . . ?
N2 C8 C13 N3 0.1(5) . . . . ?
C9 C8 C13 N3 -179.8(3) . . . . ?
O3 N3 C13 C12 2.6(5) . . . . ?
O2 N3 C13 C12 -177.2(4) . . . . ?
O3 N3 C13 C8 -177.9(4) . . . . ?
O2 N3 C13 C8 2.2(6) . . . . ?
C8' N2' C1' C2' -175.5(4) . . . . ?
C8' N2' C1' S1' 2.7(6) . . . . ?
C4' S1' C1' N2' -178.3(3) . . . . ?
C4' S1' C1' C2' 0.0(3) . . . . ?
N2' C1' C2' C3' 178.2(3) . . . . ?
S1' C1' C2' C3' -0.2(4) . . . . ?
N2' C1' C2' C7' -0.4(5) . . . . ?
S1' C1' C2' C7' -178.8(3) . . . . ?
C1' C2' C3' C4' 0.3(5) . . . . ?
C7' C2' C3' C4' 178.9(4) . . . . ?
C2' C3' C4' C5' -176.8(4) . . . . ?
C2' C3' C4' S1' -0.3(4) . . . . ?
C1' S1' C4' C3' 0.2(3) . . . . ?
C1' S1' C4' C5' 177.1(3) . . . . ?
C3' C4' C5' O1' -179.4(5) . . . . ?
S1' C4' C5' O1' 4.3(6) . . . . ?
C3' C4' C5' C6' 0.8(7) . . . . ?
S1' C4' C5' C6' -175.4(4) . . . . ?
C1' N2' C8' C9' -15.3(6) . . . . ?
C1' N2' C8' C13' 165.7(4) . . . . ?
N2' C8' C9' C10' -178.9(4) . . . . ?
C13' C8' C9' C10' 0.1(6) . . . . ?
C8' C9' C10' C11' -0.2(7) . . . . ?
C9' C10' C11' C12' 0.2(7) . . . . ?
C10' C11' C12' C13' 0.0(7) . . . . ?
C11' C12' C13' C8' -0.1(6) . . . . ?
C11' C12' C13' N3' -179.8(4) . . . . ?
N2' C8' C13' C12' 179.1(4) . . . . ?
C9' C8' C13' C12' 0.1(6) . . . . ?
N2' C8' C13' N3' -1.3(6) . . . . ?
C9' C8' C13' N3' 179.7(4) . . . . ?
O3' N3' C13' C12' 0.4(6) . . . . ?
O2' N3' C13' C12' 179.3(4) . . . . ?
O3' N3' C13' C8' -179.3(4) . . . . ?
O2' N3' C13' C8' -0.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N3 0.83(4) 2.44(4) 2.895(4) 115(3) . yes
N2 H2 O2 0.83(4) 1.87(4) 2.589(4) 145(4) . yes
C3 H3 N1' 0.93 2.55 3.461(5) 165.0 1_545 yes
C6 H6A O3' 0.96 2.63 3.411(5) 139.2 2_546 yes
C6 H6B O1 0.96 2.48 3.323(6) 145.8 4_566 yes
C9 H9 S1 0.93 2.43 3.147(4) 134.2 . yes
C9 H9 O1' 0.93 2.66 3.295(5) 126.5 . yes
N2' H2' N3' 0.78(4) 2.50(4) 2.891(4) 113(3) . yes
N2' H2' O2' 0.78(4) 1.93(4) 2.591(4) 141(4) . yes
C3' H3' N1 0.93 2.53 3.448(5) 169.3 1_565 yes
C6' H6C' O3 0.96 2.60 3.462(6) 149.4 2_655 yes
C9' H9' S1' 0.93 2.46 3.154(4) 131.7 . yes

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_2Facetonab_a
_database_code_depnum_ccdc_archive 'CCDC 2110242'
loop_
_audit_author_name
_audit_author_address
'Jose Antonio Paixao'
;University of Coimbra
Portugal
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
5-acetyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile
;
_chemical_name_common            ?
_chemical_melting_point          458.1
_chemical_formula_moiety         'C13 H9 N3 O3 S'
_chemical_formula_sum            'C13 H9 N3 O3 S'
_chemical_formula_weight         287.29

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.3354(2)
_cell_length_b                   14.2344(4)
_cell_length_c                   17.1709(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.567(2)
_cell_angle_gamma                90
_cell_volume                     1295.51(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9804
_cell_measurement_theta_min      4.776
_cell_measurement_theta_max      50.853

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  
;
Bruker APEXII CCD area-detector diffractometer  
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            122630
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.729
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2963
_reflns_number_gt                2292
_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       'APEXIII (Bruker AXS, 2016)'
_computing_cell_refinement       'APEXIII (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0479P)²+0.5373P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2963
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.26654(9) 0.31751(4) 0.62894(3) 0.05456(17) Uani 1 1 d . . . . .
O1 O 0.2270(3) 0.13653(12) 0.54883(11) 0.0855(5) Uani 1 1 d . . . . .
O2 O 0.2298(5) 0.68077(12) 0.69017(13) 0.0956(6) Uani 1 1 d . . . . .
O3 O 0.5820(5) 0.74409(14) 0.72987(15) 0.1227(8) Uani 1 1 d . . . . .
N2 N 0.2116(3) 0.49757(12) 0.68237(11) 0.0582(4) Uani 1 1 d . . . . .
H2 H 0.144(5) 0.549(2) 0.6757(16) 0.087 Uiso 1 1 d . U . . .
N1 N -0.3475(4) 0.58318(16) 0.57544(12) 0.0775(6) Uani 1 1 d . . . . .
N3 N 0.4452(5) 0.67624(14) 0.72343(14) 0.0794(6) Uani 1 1 d . . . . .
C1 C 0.1233(3) 0.42463(13) 0.63616(11) 0.0489(4) Uani 1 1 d . . . . .
C2 C -0.0963(3) 0.42995(14) 0.58427(11) 0.0515(4) Uani 1 1 d . . . . .
C3 C -0.1478(3) 0.34707(15) 0.54116(11) 0.0541(5) Uani 1 1 d . . . . .
H3 H -0.288556 0.339319 0.504447 0.065 Uiso 1 1 calc R U . . .
C4 C 0.0278(3) 0.27980(15) 0.55846(11) 0.0513(4) Uani 1 1 d . . . . .
C5 C 0.0441(4) 0.18453(16) 0.52840(12) 0.0594(5) Uani 1 1 d . . . . .
C6 C -0.1718(4) 0.14869(19) 0.47313(14) 0.0747(7) Uani 1 1 d . . . . .
H6A H -0.139720 0.084816 0.459329 0.112 Uiso 1 1 calc R U . . .
H6B H -0.190316 0.186736 0.426661 0.112 Uiso 1 1 calc R U . . .
H6C H -0.324039 0.151535 0.497935 0.112 Uiso 1 1 calc R U . . .
C7 C -0.2411(4) 0.51390(17) 0.57805(11) 0.0589(5) Uani 1 1 d . . . . .
C8 C 0.4198(4) 0.50297(14) 0.73829(11) 0.0516(4) Uani 1 1 d . . . . .
C9 C 0.5224(4) 0.42408(15) 0.77671(13) 0.0655(6) Uani 1 1 d . . . . .
H9 H 0.448650 0.365710 0.765442 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7317(5) 0.43047(18) 0.83137(14) 0.0782(7) Uani 1 1 d . . . . .
H10 H 0.796519 0.376208 0.856250 0.094 Uiso 1 1 calc R U . . .
C11 C 0.8461(5) 0.5145(2) 0.84986(16) 0.0808(7) Uani 1 1 d . . . . .
H11 H 0.988177 0.517729 0.886596 0.097 Uiso 1 1 calc R U . . .
C12 C 0.7483(5) 0.59369(19) 0.81343(15) 0.0746(7) Uani 1 1 d . . . . .
H12 H 0.824333 0.651492 0.825411 0.090 Uiso 1 1 calc R U . . .
C13 C 0.5372(4) 0.58883(14) 0.75890(12) 0.0589(5) 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
S1 C1 1.716(2) . ?
S1 C4 1.7384(18) . ?
O1 C5 1.210(2) . ?
O2 N3 1.225(3) . ?
O3 N3 1.208(3) . ?
N2 C1 1.358(3) . ?
N2 C8 1.385(3) . ?
N2 H2 0.82(3) . ?
N1 C7 1.136(3) . ?
N3 C13 1.446(3) . ?
C1 C2 1.390(2) . ?
C2 C3 1.403(3) . ?
C2 C7 1.420(3) . ?
C3 C4 1.349(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.457(3) . ?
C5 C6 1.496(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.383(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?

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 C4 91.59(9) . . ?
C1 N2 C8 130.15(17) . . ?
C1 N2 H2 119(2) . . ?
C8 N2 H2 111(2) . . ?
O3 N3 O2 121.7(2) . . ?
O3 N3 C13 118.5(3) . . ?
O2 N3 C13 119.8(2) . . ?
N2 C1 C2 122.92(18) . . ?
N2 C1 S1 126.42(14) . . ?
C2 C1 S1 110.59(15) . . ?
C1 C2 C3 113.09(17) . . ?
C1 C2 C7 120.35(19) . . ?
C3 C2 C7 126.56(17) . . ?
C4 C3 C2 113.04(17) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 C5 130.59(18) . . ?
C3 C4 S1 111.68(16) . . ?
C5 C4 S1 117.73(14) . . ?
O1 C5 C4 120.10(19) . . ?
O1 C5 C6 121.9(2) . . ?
C4 C5 C6 117.99(18) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C2 176.6(2) . . ?
C9 C8 N2 121.85(18) . . ?
C9 C8 C13 116.57(19) . . ?
N2 C8 C13 121.58(18) . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 N3 117.0(2) . . ?
C8 C13 N3 121.6(2) . . ?

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
C8 N2 C1 C2 177.68(19) . . . . ?
C8 N2 C1 S1 -5.7(3) . . . . ?
C4 S1 C1 N2 -178.31(18) . . . . ?
C4 S1 C1 C2 -1.38(15) . . . . ?
N2 C1 C2 C3 178.47(18) . . . . ?
S1 C1 C2 C3 1.4(2) . . . . ?
N2 C1 C2 C7 -0.5(3) . . . . ?
S1 C1 C2 C7 -177.60(15) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C7 C2 C3 C4 178.30(19) . . . . ?
C2 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 S1 -0.4(2) . . . . ?
C1 S1 C4 C3 1.05(16) . . . . ?
C1 S1 C4 C5 -178.52(17) . . . . ?
C3 C4 C5 O1 176.0(2) . . . . ?
S1 C4 C5 O1 -4.6(3) . . . . ?
C3 C4 C5 C6 -4.8(3) . . . . ?
S1 C4 C5 C6 174.66(17) . . . . ?
C1 N2 C8 C9 -24.6(4) . . . . ?
C1 N2 C8 C13 155.5(2) . . . . ?
N2 C8 C9 C10 179.1(2) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C8 -1.1(4) . . . . ?
C11 C12 C13 N3 179.7(2) . . . . ?
C9 C8 C13 C12 1.6(3) . . . . ?
N2 C8 C13 C12 -178.5(2) . . . . ?
C9 C8 C13 N3 -179.2(2) . . . . ?
N2 C8 C13 N3 0.7(3) . . . . ?
O3 N3 C13 C12 15.4(3) . . . . ?
O2 N3 C13 C12 -162.2(2) . . . . ?
O3 N3 C13 C8 -163.9(2) . . . . ?
O2 N3 C13 C8 18.6(3) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
