# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_621
_database_code_depnum_ccdc_archive 'CCDC 936463'
_audit_update_record             
;
2013-04-29 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 thiophene.... 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N4 O2 S2'
_chemical_formula_sum            'C10 H12 N4 O2 S2'
_chemical_formula_weight         284.36

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'
_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                   6.069(4)
_cell_length_b                   8.501(2)
_cell_length_c                   12.518(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.00(4)
_cell_angle_gamma                90.00
_cell_volume                     639.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    682
_cell_measurement_theta_min      3.2858
_cell_measurement_theta_max      29.1306

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.7141
_exptl_crystal_size_mid          0.1180
_exptl_crystal_size_min          0.0820
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.416

_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00  -11.00   1.0000    9.2800
omega____ theta____ kappa____ phi______ frames
    -      -17.9289  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -55.00   1.0000    9.2800
omega____ theta____ kappa____ phi______ frames
    -      -17.9289  -77.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega   67.00   93.00   1.0000    9.2800
omega____ theta____ kappa____ phi______ frames
    -       18.7101 -162.0000  -16.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   48.00   1.0000    9.2800
omega____ theta____ kappa____ phi______ frames
    -       18.7101  -77.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   47.00   1.0000    9.2800
omega____ theta____ kappa____ phi______ frames
    -       18.7101   25.0000  -30.0000 56

;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            2455
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1131
_reflns_number_gt                911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  SHELXL97

_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)+(0.0340P)²+0.2299P] 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         1131
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.55067(11) 0.14083(9) 0.31221(5) 0.0551(3) Uani 1 1 d . . .
C5 C 0.2043(4) 0.3364(3) 0.33878(17) 0.0360(5) Uani 1 1 d . . .
O1 O 0.1257(3) 0.3118(2) 0.24394(12) 0.0515(5) Uani 1 1 d . . .
N1 N 0.1118(3) 0.4358(3) 0.40113(16) 0.0448(5) Uani 1 1 d . . .
C4 C 0.4087(4) 0.2585(3) 0.39040(17) 0.0380(6) Uani 1 1 d . . .
C3 C 0.5107(4) 0.2619(3) 0.49563(19) 0.0465(6) Uani 1 1 d . . .
H3 H 0.4578 0.3186 0.5503 0.056 Uiso 1 1 calc R . .
N2 N -0.0996(4) 0.5029(3) 0.36864(17) 0.0478(6) Uani 1 1 d . . .
C2 C 0.7048(4) 0.1691(3) 0.5107(2) 0.0550(7) Uani 1 1 d . . .
H2 H 0.7954 0.1583 0.5766 0.066 Uiso 1 1 calc R . .
C1 C 0.7452(4) 0.0977(3) 0.4193(2) 0.0572(7) Uani 1 1 d . . .
H1 H 0.8662 0.0319 0.4153 0.069 Uiso 1 1 calc R . .
H2A H -0.079(4) 0.584(3) 0.328(2) 0.057(9) Uiso 1 1 d . . .
H2B H -0.176(4) 0.435(3) 0.324(2) 0.052(8) Uiso 1 1 d . . .
H1A H 0.153(4) 0.442(3) 0.4682(19) 0.045(7) Uiso 1 1 d . . .

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 0.0502(4) 0.0662(5) 0.0472(4) -0.0134(3) 0.0010(3) 0.0112(3)
C5 0.0359(12) 0.0348(13) 0.0363(12) 0.0023(10) 0.0016(10) -0.0064(10)
O1 0.0551(11) 0.0579(12) 0.0374(9) -0.0068(8) -0.0075(8) 0.0081(9)
N1 0.0423(12) 0.0527(13) 0.0367(11) -0.0035(10) -0.0043(10) 0.0111(10)
C4 0.0357(12) 0.0369(13) 0.0405(12) -0.0021(10) 0.0018(10) -0.0027(10)
C3 0.0461(14) 0.0503(15) 0.0406(12) -0.0018(11) -0.0025(11) 0.0063(12)
N2 0.0456(13) 0.0497(14) 0.0457(12) 0.0046(12) -0.0029(11) 0.0094(11)
C2 0.0494(16) 0.0604(18) 0.0498(14) -0.0011(13) -0.0122(13) 0.0081(14)
C1 0.0422(15) 0.0611(18) 0.0649(17) -0.0073(14) -0.0041(13) 0.0117(13)

_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 1.698(3) . ?
S1 C4 1.714(2) . ?
C5 O1 1.234(3) . ?
C5 N1 1.327(3) . ?
C5 C4 1.473(3) . ?
N1 N2 1.411(3) . ?
N1 H1A 0.84(2) . ?
C4 C3 1.376(3) . ?
C3 C2 1.409(4) . ?
C3 H3 0.9300 . ?
N2 H2A 0.87(3) . ?
N2 H2B 0.89(3) . ?
C2 C1 1.348(4) . ?
C2 H2 0.9300 . ?
C1 H1 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 91.43(12) . . ?
O1 C5 N1 122.3(2) . . ?
O1 C5 C4 122.4(2) . . ?
N1 C5 C4 115.32(19) . . ?
C5 N1 N2 122.0(2) . . ?
C5 N1 H1A 122.1(17) . . ?
N2 N1 H1A 113.2(17) . . ?
C3 C4 C5 130.5(2) . . ?
C3 C4 S1 111.35(19) . . ?
C5 C4 S1 118.13(16) . . ?
C4 C3 C2 111.9(2) . . ?
C4 C3 H3 124.0 . . ?
C2 C3 H3 124.0 . . ?
N1 N2 H2A 106.8(18) . . ?
N1 N2 H2B 107.0(17) . . ?
H2A N2 H2B 105(2) . . ?
C1 C2 C3 112.7(2) . . ?
C1 C2 H2 123.7 . . ?
C3 C2 H2 123.7 . . ?
C2 C1 S1 112.6(2) . . ?
C2 C1 H1 123.7 . . ?
S1 C1 H1 123.7 . . ?

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
O1 C5 N1 N2 9.4(4) . . . . ?
C4 C5 N1 N2 -171.1(2) . . . . ?
O1 C5 C4 C3 -174.6(2) . . . . ?
N1 C5 C4 C3 6.0(4) . . . . ?
O1 C5 C4 S1 4.7(3) . . . . ?
N1 C5 C4 S1 -174.75(17) . . . . ?
C1 S1 C4 C3 -0.3(2) . . . . ?
C1 S1 C4 C5 -179.70(19) . . . . ?
C5 C4 C3 C2 179.8(2) . . . . ?
S1 C4 C3 C2 0.5(3) . . . . ?
C4 C3 C2 C1 -0.5(3) . . . . ?
C3 C2 C1 S1 0.2(3) . . . . ?
C4 S1 C1 C2 0.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042

_iucr_refine_instructions_details 
;
TITL exp_621 in P21/c #14
CELL 0.71073 6.069289 8.500528 12.518344 90 98.0009 90
ZERR 2 0.003894 0.002429 0.002645 0 0.0352 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
 
SFAC C H N O S
UNIT 20 24 8 4 4
SHEL 9999.99 0.84
L.S. 12 0 0 511
PLAN  20
REM reset to P21/c #14
BOND
BOND $H
CONF
fmap 2
acta
REM <HKL>D:/AlDamen/exp_612/exp_621/struct/olex2_exp_621/exp_621.hkl</HKL>
 
WGHT    0.034000    0.229900
FVAR       9.35641
S1    5    0.550666    0.140826    0.312209    11.00000    0.05022    0.06624 =
         0.04721   -0.01343    0.00099    0.01123
C5    1    0.204319    0.336404    0.338784    11.00000    0.03589    0.03475 =
         0.03630    0.00225    0.00158   -0.00645
O1    4    0.125652    0.311841    0.243937    11.00000    0.05515    0.05792 =
         0.03741   -0.00683   -0.00748    0.00813
N1    3    0.111756    0.435844    0.401125    11.00000    0.04233    0.05271 =
         0.03671   -0.00353   -0.00427    0.01105
C4    1    0.408666    0.258511    0.390399    11.00000    0.03568    0.03691 =
         0.04046   -0.00212    0.00177   -0.00275
C3    1    0.510667    0.261887    0.495631    11.00000    0.04615    0.05031 =
         0.04059   -0.00183   -0.00254    0.00632
AFIX  43
H3    2    0.457765    0.318629    0.550279    11.00000   -1.20000
AFIX   0
N2    3   -0.099584    0.502943    0.368641    11.00000    0.04556    0.04966 =
         0.04570    0.00458   -0.00286    0.00941
C2    1    0.704848    0.169106    0.510712    11.00000    0.04944    0.06035 =
         0.04975   -0.00111   -0.01222    0.00808
AFIX  43
H2    2    0.795408    0.158327    0.576616    11.00000   -1.20000
AFIX   0
C1    1    0.745173    0.097655    0.419286    11.00000    0.04225    0.06108 =
         0.06487   -0.00732   -0.00407    0.01167
AFIX  43
H1    2    0.866234    0.031919    0.415275    11.00000   -1.20000
AFIX   0
H2A   2   -0.079157    0.583952    0.328102    11.00000    0.05739
H2B   2   -0.176260    0.434782    0.324394    11.00000    0.05180
H1A   2    0.152863    0.441653    0.468190    11.00000    0.04484
 
HKLF 4
 
REM  exp_621 in P21/c #14
REM R1 =  0.0384 for    911 Fo > 4sig(Fo)  and  0.0500 for all   1131 data
REM     94 parameters refined using      0 restraints
 
END  
     
WGHT      0.0331      0.2350 
REM Highest difference peak  0.214,  deepest hole -0.216,  1-sigma level  0.042
Q1    1   0.5038  0.3060  0.4289  11.00000  0.05    0.21
Q2    1   0.0754  0.2326  0.2820  11.00000  0.05    0.17
Q3    1   0.4736  0.2232  0.3535  11.00000  0.05    0.16
Q4    1   0.3478  0.3058  0.3628  11.00000  0.05    0.15
Q5    1   0.4028  0.2214  0.4458  11.00000  0.05    0.15
Q6    1   0.7472  0.1064  0.6009  11.00000  0.05    0.13
Q7    1   0.5647  0.1954  0.4762  11.00000  0.05    0.12
Q8    1   0.4263  0.2267  0.5966  11.00000  0.05    0.12
Q9    1  -0.0115  0.2342  0.2291  11.00000  0.05    0.12
Q10   1   0.4953  0.2782  0.5266  11.00000  0.05    0.12
Q11   1  -0.1055  0.5697  0.4390  11.00000  0.05    0.12
Q12   1   0.6200  0.2592  0.2532  11.00000  0.05    0.12
Q13   1   0.6170  0.2527  0.5074  11.00000  0.05    0.11
Q14   1   0.2920  0.1191  0.4565  11.00000  0.05    0.11
Q15   1  -0.3681  0.3844  0.2610  11.00000  0.05    0.11
Q16   1   0.5260 -0.0257  0.3226  11.00000  0.05    0.11
Q17   1   0.7781  0.1738  0.4458  11.00000  0.05    0.10
Q18   1   0.5028  0.3960  0.5347  11.00000  0.05    0.10
Q19   1   0.8039  0.2286  0.5734  11.00000  0.05    0.10
Q20   1   0.4016  0.2708  0.6250  11.00000  0.05    0.10
;
