# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_198
_audit_block_doi                 10.5517/ccdc.csd.cc24dps1
_database_code_depnum_ccdc_archive 'CCDC 1978413'
loop_
_audit_author_name
_audit_author_address
'Yibiao Li '
;Wuyi University
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
_audit_creation_date             2018-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 S2'
_chemical_formula_sum            'C12 H8 N2 S2'
_chemical_formula_weight         244.32
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.0865(10)
_cell_length_b                   17.576(4)
_cell_length_c                   20.351(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2177.1(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1450
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.1200
_cell_measurement_theta_min      2.5040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8203
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  80.00   1.00    8.00    --   11.74  57.00 -30.00   92
  2  ω    -15.00  79.00   1.00    8.00    --   11.74  77.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0196707000
_diffrn_orient_matrix_UB_12      -0.0325613000
_diffrn_orient_matrix_UB_13      0.0195796000
_diffrn_orient_matrix_UB_21      -0.0094844000
_diffrn_orient_matrix_UB_22      0.0234285000
_diffrn_orient_matrix_UB_23      0.0282462000
_diffrn_orient_matrix_UB_31      -0.1147412000
_diffrn_orient_matrix_UB_32      0.0036093000
_diffrn_orient_matrix_UB_33      -0.0057308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1403
_reflns_number_total             1914
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0974P)²+1.8875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1832
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C5(H5), C11(H11), C12(H12), C3(H3), C7(H7), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.37081(19) 0.42140(7) 0.49937(5) 0.0243(4) Uani 1 1 d . . . . .
S2 S 0.9042(2) 0.15156(7) 0.68305(6) 0.0301(4) Uani 1 1 d . . . . .
N1 N -0.2868(6) 0.3330(2) 0.49216(17) 0.0257(9) Uani 1 1 d . . . . .
N2 N 0.6773(7) 0.1172(2) 0.64873(18) 0.0300(10) Uani 1 1 d . . . . .
C1 C -0.0361(7) 0.3871(2) 0.56553(19) 0.0200(10) Uani 1 1 d . . . . .
C10 C 0.6073(7) 0.2483(2) 0.6611(2) 0.0213(10) Uani 1 1 d . . . . .
C4 C 0.1594(7) 0.3859(2) 0.60958(19) 0.0187(10) Uani 1 1 d . . . . .
C9 C 0.2874(7) 0.3211(2) 0.61530(19) 0.0207(10) Uani 1 1 d . . . . .
H9 H 0.248509 0.278004 0.591483 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4729(7) 0.3183(2) 0.65561(19) 0.0195(10) Uani 1 1 d . . . . .
C6 C 0.4024(7) 0.4494(3) 0.6858(2) 0.0229(10) Uani 1 1 d . . . . .
H6 H 0.441137 0.492523 0.709549 0.027 Uiso 1 1 calc R . . . .
C5 C 0.2176(7) 0.4511(2) 0.6458(2) 0.0225(10) Uani 1 1 d . . . . .
H5 H 0.132847 0.494963 0.642928 0.027 Uiso 1 1 calc R . . . .
C11 C 0.8151(8) 0.2421(3) 0.6870(2) 0.0250(11) Uani 1 1 d . . . . .
H11 H 0.895388 0.282384 0.704341 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5383(8) 0.1739(3) 0.6405(2) 0.0265(11) Uani 1 1 d . . . . .
H12 H 0.400496 0.166021 0.621969 0.032 Uiso 1 1 calc R . . . .
C3 C -0.1099(7) 0.3226(3) 0.5287(2) 0.0249(11) Uani 1 1 d . . . . .
H3 H -0.037562 0.276005 0.530495 0.030 Uiso 1 1 calc R . . . .
C7 C 0.5299(8) 0.3843(2) 0.6907(2) 0.0230(11) Uani 1 1 d . . . . .
H7 H 0.653828 0.384333 0.717450 0.028 Uiso 1 1 calc R . . . .
C2 C -0.1714(7) 0.4479(2) 0.5535(2) 0.0229(10) Uani 1 1 d . . . . .
H2 H -0.156672 0.495987 0.571937 0.028 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 0.0284(7) 0.0262(7) 0.0182(6) -0.0002(5) -0.0019(5) 0.0025(5)
S2 0.0323(7) 0.0320(8) 0.0259(7) 0.0001(5) -0.0053(5) 0.0037(5)
N1 0.029(2) 0.030(2) 0.019(2) -0.0020(16) -0.0010(17) 0.0026(18)
N2 0.037(2) 0.032(2) 0.021(2) -0.0037(17) -0.0035(19) 0.0069(19)
C1 0.029(2) 0.021(2) 0.010(2) -0.0010(17) 0.0071(18) -0.0035(19)
C10 0.030(3) 0.028(3) 0.006(2) 0.0019(17) 0.005(2) -0.005(2)
C4 0.024(2) 0.023(2) 0.009(2) 0.0024(17) 0.0044(18) -0.0024(19)
C9 0.030(2) 0.022(3) 0.010(2) -0.0009(17) 0.0054(19) -0.003(2)
C8 0.025(2) 0.024(3) 0.009(2) 0.0007(18) 0.0015(18) -0.0006(19)
C6 0.032(3) 0.024(3) 0.013(2) -0.0017(18) 0.003(2) -0.008(2)
C5 0.033(3) 0.023(2) 0.011(2) -0.0007(18) 0.001(2) -0.001(2)
C11 0.034(3) 0.028(3) 0.013(2) -0.0007(18) 0.000(2) -0.003(2)
C12 0.028(3) 0.034(3) 0.017(2) -0.002(2) -0.002(2) 0.000(2)
C3 0.030(3) 0.027(3) 0.018(2) 0.000(2) 0.000(2) 0.006(2)
C7 0.030(3) 0.028(3) 0.011(2) 0.0010(18) -0.0005(19) -0.004(2)
C2 0.029(3) 0.025(3) 0.015(2) -0.0050(18) 0.001(2) 0.002(2)

_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 N1 1.642(4) . ?
S1 C2 1.703(4) . ?
S2 N2 1.661(4) . ?
S2 C11 1.683(5) . ?
N1 C3 1.322(5) . ?
N2 C12 1.318(6) . ?
C1 C4 1.490(6) . ?
C1 C3 1.431(6) . ?
C1 C2 1.370(6) . ?
C10 C8 1.481(6) . ?
C10 C11 1.375(6) . ?
C10 C12 1.436(6) . ?
C4 C9 1.385(6) . ?
C4 C5 1.406(6) . ?
C9 C8 1.396(6) . ?
C8 C7 1.407(6) . ?
C6 C5 1.389(6) . ?
C6 C7 1.385(6) . ?

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
N1 S1 C2 95.4(2) . . ?
N2 S2 C11 95.5(2) . . ?
C3 N1 S1 109.6(3) . . ?
C12 N2 S2 108.2(3) . . ?
C3 C1 C4 123.6(4) . . ?
C2 C1 C4 126.8(4) . . ?
C2 C1 C3 109.6(4) . . ?
C11 C10 C8 127.1(4) . . ?
C11 C10 C12 108.0(4) . . ?
C12 C10 C8 124.9(4) . . ?
C9 C4 C1 120.8(4) . . ?
C9 C4 C5 118.9(4) . . ?
C5 C4 C1 120.3(4) . . ?
C4 C9 C8 122.2(4) . . ?
C9 C8 C10 121.3(4) . . ?
C9 C8 C7 117.9(4) . . ?
C7 C8 C10 120.7(4) . . ?
C5 C6 C7 120.9(4) . . ?
C6 C5 C4 119.6(4) . . ?
C10 C11 S2 110.7(3) . . ?
N2 C12 C10 117.6(4) . . ?
N1 C3 C1 116.1(4) . . ?
C6 C7 C8 120.4(4) . . ?
C1 C2 S1 109.3(3) . . ?

_iucr_refine_instructions_details 
;
TITL 198_a.res in Pbca
    198.res
    created by SHELXL-2018/3 at 16:35:42 on 06-Jun-2018
REM Old TITL 198 in Pbca
REM SHELXT solution in Pbca: R1 0.158, Rweak 0.278, Alpha 0.038
REM <I/s> 0.722 for 367 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 N Cl2
CELL 0.71073 6.0865 17.5763 20.3512 90 90 90
ZERR 8 0.001 0.0036 0.0033 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N S
UNIT 96 64 16 16

L.S. 20
PLAN  20
BOND
list 4
fmap 2 53
acta
OMIT -3 50
REM <olex2.extras>
REM <HklSrc "%.\\198.hkl">
REM </olex2.extras>

WGHT    0.097400    1.887500
FVAR       0.24537
S1    4   -0.370805    0.421397    0.499375    11.00000    0.02838    0.02619 =
         0.01818   -0.00018   -0.00192    0.00246
S2    4    0.904171    0.151557    0.683050    11.00000    0.03227    0.03204 =
         0.02589    0.00007   -0.00532    0.00373
N1    3   -0.286766    0.333044    0.492155    11.00000    0.02885    0.02970 =
         0.01868   -0.00201   -0.00100    0.00264
N2    3    0.677316    0.117248    0.648730    11.00000    0.03668    0.03220 =
         0.02119   -0.00367   -0.00353    0.00691
C1    1   -0.036146    0.387136    0.565526    11.00000    0.02933    0.02054 =
         0.01002   -0.00097    0.00714   -0.00350
C10   1    0.607253    0.248336    0.661076    11.00000    0.02993    0.02825 =
         0.00570    0.00190    0.00548   -0.00545
C4    1    0.159418    0.385934    0.609577    11.00000    0.02415    0.02305 =
         0.00876    0.00238    0.00438   -0.00238
C9    1    0.287419    0.321106    0.615298    11.00000    0.02982    0.02175 =
         0.01043   -0.00087    0.00538   -0.00274
AFIX  43
H9    2    0.248509    0.278004    0.591483    11.00000   -1.20000
AFIX   0
C8    1    0.472890    0.318277    0.655611    11.00000    0.02497    0.02416 =
         0.00942    0.00070    0.00145   -0.00059
C6    1    0.402406    0.449378    0.685767    11.00000    0.03169    0.02413 =
         0.01291   -0.00167    0.00272   -0.00752
AFIX  43
H6    2    0.441137    0.492523    0.709549    11.00000   -1.20000
AFIX   0
C5    1    0.217589    0.451057    0.645765    11.00000    0.03309    0.02297 =
         0.01145   -0.00072    0.00100   -0.00061
AFIX  43
H5    2    0.132847    0.494963    0.642928    11.00000   -1.20000
AFIX   0
C11   1    0.815063    0.242100    0.687000    11.00000    0.03448    0.02765 =
         0.01279   -0.00065    0.00040   -0.00295
AFIX  43
H11   2    0.895388    0.282384    0.704341    11.00000   -1.20000
AFIX   0
C12   1    0.538325    0.173926    0.640476    11.00000    0.02821    0.03413 =
         0.01715   -0.00223   -0.00206   -0.00018
AFIX  43
H12   2    0.400496    0.166021    0.621969    11.00000   -1.20000
AFIX   0
C3    1   -0.109862    0.322575    0.528749    11.00000    0.03004    0.02664 =
         0.01795   -0.00049    0.00017    0.00551
AFIX  43
H3    2   -0.037562    0.276005    0.530495    11.00000   -1.20000
AFIX   0
C7    1    0.529860    0.384333    0.690735    11.00000    0.02981    0.02838 =
         0.01079    0.00097   -0.00054   -0.00366
AFIX  43
H7    2    0.653828    0.384333    0.717450    11.00000   -1.20000
AFIX   0
C2    1   -0.171413    0.447857    0.553472    11.00000    0.02944    0.02478 =
         0.01460   -0.00498    0.00144    0.00179
AFIX  43
H2    2   -0.156672    0.495987    0.571937    11.00000   -1.20000
AFIX   0
HKLF 4




REM  198_a.res in Pbca
REM wR2 = 0.1832, GooF = S = 1.022, Restrained GooF = 1.022 for all data
REM R1 = 0.0701 for 1403 Fo > 4sig(Fo) and 0.0960 for all 1914 data
REM 145 parameters refined using 0 restraints

END  
     
WGHT      0.0805      1.5479 

REM Highest difference peak  0.614,  deepest hole -0.458,  1-sigma level  0.113
Q1    1  -0.5267  0.4218  0.5012  11.00000  0.05    0.61
Q2    1  -0.4113  0.3603  0.4980  11.00000  0.05    0.54
Q3    1  -0.2171  0.4361  0.5037  11.00000  0.05    0.54
Q4    1   1.0548  0.1466  0.6799  11.00000  0.05    0.51
Q5    1   0.8021  0.1977  0.6820  11.00000  0.05    0.49
Q6    1   0.9219  0.2036  0.6819  11.00000  0.05    0.48
Q7    1   0.7517  0.1252  0.6790  11.00000  0.05    0.47
Q8    1  -0.3697  0.2972  0.4972  11.00000  0.05    0.43
Q9    1   0.9819  0.1000  0.6802  11.00000  0.05    0.40
Q10   1  -0.2532  0.3764  0.4987  11.00000  0.05    0.39
Q11   1  -0.3431  0.4803  0.4983  11.00000  0.05    0.36
Q12   1   0.5124  0.2445  0.6734  11.00000  0.05    0.35
Q13   1   0.5593  0.4395  0.6793  11.00000  0.05    0.34
Q14   1   0.2084  0.3540  0.5001  11.00000  0.05    0.33
Q15   1   0.6229  0.2218  0.6422  11.00000  0.05    0.33
Q16   1   0.1554  0.3241  0.6195  11.00000  0.05    0.32
Q17   1   0.8347  0.2637  0.6822  11.00000  0.05    0.32
Q18   1  -0.2810  0.5413  0.5011  11.00000  0.05    0.31
Q19   1   0.5573  0.2648  0.6631  11.00000  0.05    0.30
Q20   1   0.6983  0.1648  0.6483  11.00000  0.05    0.30

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0701 for 1403 Fo > 4sig(Fo) and 0.0960 for all 10709 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.61, deepest hole -0.46
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0960
  REM R1_gt = 0.0701
  REM wR_ref = 0.1832
  REM GOOF = 1.022
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 10709
  REM Reflections_gt = 1403
  REM Parameters = n/a
  REM Hole = -0.46
  REM Peak = 0.61
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.905
_oxdiff_exptl_absorpt_empirical_full_min 0.644
####################################################################### 
# 
# 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_hgl217
_database_code_depnum_ccdc_archive 'CCDC 1978414'
loop_
_audit_author_name
_audit_author_address
'Yibiao Li '
;Wuyi University
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
_audit_creation_date             2018-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 N2 S2'
_chemical_formula_sum            'C18 H12 N2 S2'
_chemical_formula_weight         320.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   7.8212(6)
_cell_length_b                   5.9264(4)
_cell_length_c                   16.1736(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.155(7)
_cell_angle_gamma                90
_cell_volume                     749.52(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7140
_cell_measurement_theta_min      2.8900
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3560
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.113
_diffrn_reflns_theta_min         2.519
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  40.00   1.00    1.00    --   11.74 -57.00   0.00   99
  2  ω    -16.00  75.00   1.00    1.00    --   11.74  77.00 -90.00   91
  3  ω     -8.00  79.00   1.00    1.00    --   11.74  57.00 150.00   87
  4  ω     35.00  90.00   1.00    1.00    --   11.74-178.00-150.00   55
  5  ω     34.00  55.00   1.00    1.00    --   11.74-121.00-137.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0868504000
_diffrn_orient_matrix_UB_12      -0.0308004000
_diffrn_orient_matrix_UB_13      0.0048836000
_diffrn_orient_matrix_UB_21      0.0139008000
_diffrn_orient_matrix_UB_22      -0.0086471000
_diffrn_orient_matrix_UB_23      0.0433506000
_diffrn_orient_matrix_UB_31      -0.0222213000
_diffrn_orient_matrix_UB_32      0.1153158000
_diffrn_orient_matrix_UB_33      0.0045614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                1667
_reflns_number_total             1748
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.1754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C4(H4), C5(H5), C8(H8), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.71386(8) 0.07763(12) 0.55775(4) 0.02094(19) Uani 1 1 d . . . . .
N1 N 0.7570(3) 0.1689(4) 0.65267(14) 0.0234(5) Uani 1 1 d . . . . .
C1 C 0.3920(3) 0.5662(5) 0.62215(13) 0.0147(5) Uani 1 1 d . . . . .
C7 C 0.5236(3) 0.3913(5) 0.60881(16) 0.0155(5) Uani 1 1 d . . . . .
C6 C 0.2252(3) 0.5448(5) 0.59107(16) 0.0206(6) Uani 1 1 d . . . . .
H6 H 0.195096 0.418756 0.559787 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5469(3) 0.2599(4) 0.54000(15) 0.0152(5) Uani 1 1 d . . . . .
C2 C 0.4326(4) 0.7563(4) 0.67003(15) 0.0170(5) Uani 1 1 d . . . . .
H2 H 0.542693 0.772582 0.692072 0.020 Uiso 1 1 calc R . . . .
C4 C 0.1467(4) 0.8992(5) 0.65248(17) 0.0226(6) Uani 1 1 d . . . . .
H4 H 0.065828 1.011043 0.661487 0.027 Uiso 1 1 calc R . . . .
C5 C 0.1040(4) 0.7089(5) 0.60624(17) 0.0236(6) Uani 1 1 d . . . . .
H5 H -0.006913 0.691856 0.585340 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6489(4) 0.3310(5) 0.67056(16) 0.0191(6) Uani 1 1 d . . . . .
H8 H 0.653806 0.403707 0.721505 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3111(4) 0.9203(5) 0.68499(17) 0.0213(6) Uani 1 1 d . . . . .
H3 H 0.340001 1.045396 0.717049 0.026 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 0.0236(4) 0.0231(3) 0.0162(3) 0.0019(3) 0.0007(2) 0.0081(3)
N1 0.0209(13) 0.0322(13) 0.0169(11) 0.0036(10) -0.0034(9) 0.0053(10)
C1 0.0154(12) 0.0169(12) 0.0118(10) 0.0023(13) -0.0005(8) 0.0013(12)
C7 0.0133(13) 0.0183(12) 0.0148(12) 0.0021(10) -0.0022(10) -0.0020(10)
C6 0.0202(14) 0.0258(17) 0.0155(11) -0.0038(12) -0.0048(10) 0.0023(12)
C9 0.0165(13) 0.0156(12) 0.0135(12) 0.0020(10) 0.0011(10) -0.0006(10)
C2 0.0176(13) 0.0195(13) 0.0137(12) 0.0017(10) 0.0011(10) -0.0024(11)
C4 0.0246(15) 0.0249(15) 0.0184(13) 0.0034(12) 0.0043(11) 0.0089(12)
C5 0.0168(14) 0.0353(17) 0.0187(14) -0.0007(13) -0.0026(11) 0.0061(12)
C8 0.0190(14) 0.0255(15) 0.0127(12) 0.0008(11) -0.0031(11) 0.0011(11)
C3 0.0284(16) 0.0175(13) 0.0181(13) -0.0009(11) 0.0056(11) -0.0018(12)

_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 N1 1.656(2) . ?
S1 C9 1.714(3) . ?
N1 C8 1.316(4) . ?
C1 C7 1.479(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.400(4) . ?
C7 C9 1.374(4) . ?
C7 C8 1.431(4) . ?
C6 C5 1.384(4) . ?
C9 C9 1.475(5) 2_656 ?
C2 C3 1.384(4) . ?
C4 C5 1.390(4) . ?
C4 C3 1.385(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
N1 S1 C9 95.15(12) . . ?
C8 N1 S1 108.8(2) . . ?
C6 C1 C7 122.1(3) . . ?
C6 C1 C2 118.2(3) . . ?
C2 C1 C7 119.6(2) . . ?
C9 C7 C1 128.3(2) . . ?
C9 C7 C8 108.9(2) . . ?
C8 C7 C1 122.8(2) . . ?
C5 C6 C1 120.8(3) . . ?
C7 C9 S1 109.6(2) . . ?
C7 C9 C9 129.7(2) . 2_656 ?
C9 C9 S1 120.73(18) 2_656 . ?
C3 C2 C1 120.9(3) . . ?
C3 C4 C5 119.3(3) . . ?
C6 C5 C4 120.5(3) . . ?
N1 C8 C7 117.6(2) . . ?
C4 C3 C2 120.4(3) . . ?

_iucr_refine_instructions_details 
;
TITL hgl217_a.res in I2
    hgl217.res
    created by SHELXL-2018/3 at 10:29:46 on 11-Aug-2018
REM Old TITL HGL217 in I2
REM SHELXT solution in I2: R1 0.083, Rweak 0.038, Alpha 0.003
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.158 ( 0.043 ) from 625 Parsons' quotients
REM Formula found by SHELXT: C9 N Cl
CELL 0.71073 7.8212 5.9264 16.1736 90 91.155 90
ZERR 2 0.0006 0.0004 0.0011 0 0.007 0
LATT -2
SYMM -X,+Y,-Z
SFAC C H N S
UNIT 36 24 4 4

L.S. 20
PLAN  20
SIZE 0.11 0.12 0.13
BOND
list 4
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\HGL217.hkl">
REM </olex2.extras>

WGHT    0.041200    0.175400
FVAR       0.78051
S1    4    0.713857    0.077629    0.557753    11.00000    0.02357    0.02310 =
         0.01616    0.00192    0.00071    0.00813
N1    3    0.757010    0.168867    0.652672    11.00000    0.02093    0.03215 =
         0.01687    0.00362   -0.00335    0.00530
C1    1    0.392048    0.566204    0.622154    11.00000    0.01544    0.01692 =
         0.01179    0.00232   -0.00051    0.00131
C7    1    0.523568    0.391335    0.608811    11.00000    0.01332    0.01831 =
         0.01476    0.00214   -0.00215   -0.00196
C6    1    0.225223    0.544816    0.591075    11.00000    0.02017    0.02583 =
         0.01548   -0.00379   -0.00482    0.00234
AFIX  43
H6    2    0.195096    0.418756    0.559787    11.00000   -1.20000
AFIX   0
C9    1    0.546932    0.259909    0.539997    11.00000    0.01649    0.01556 =
         0.01352    0.00201    0.00107   -0.00065
C2    1    0.432644    0.756278    0.670028    11.00000    0.01764    0.01951 =
         0.01373    0.00168    0.00106   -0.00238
AFIX  43
H2    2    0.542693    0.772582    0.692072    11.00000   -1.20000
AFIX   0
C4    1    0.146733    0.899172    0.652479    11.00000    0.02459    0.02494 =
         0.01840    0.00340    0.00425    0.00894
AFIX  43
H4    2    0.065828    1.011043    0.661487    11.00000   -1.20000
AFIX   0
C5    1    0.103978    0.708950    0.606239    11.00000    0.01684    0.03527 =
         0.01868   -0.00070   -0.00260    0.00607
AFIX  43
H5    2   -0.006913    0.691856    0.585340    11.00000   -1.20000
AFIX   0
C8    1    0.648909    0.330981    0.670559    11.00000    0.01899    0.02552 =
         0.01269    0.00085   -0.00306    0.00110
AFIX  43
H8    2    0.653806    0.403707    0.721505    11.00000   -1.20000
AFIX   0
C3    1    0.311100    0.920302    0.684986    11.00000    0.02843    0.01750 =
         0.01808   -0.00092    0.00564   -0.00177
AFIX  43
H3    2    0.340001    1.045396    0.717049    11.00000   -1.20000
AFIX   0
HKLF 4




REM  hgl217_a.res in I2
REM wR2 = 0.0822, GooF = S = 1.047, Restrained GooF = 1.047 for all data
REM R1 = 0.0352 for 1667 Fo > 4sig(Fo) and 0.0374 for all 1748 data
REM 100 parameters refined using 1 restraints

END  
     
WGHT      0.0401      0.1987 

REM Highest difference peak  0.268,  deepest hole -0.265,  1-sigma level  0.055
Q1    1   0.8267  0.0785  0.5366  11.00000  0.05    0.27
Q2    1   0.4632  0.5174  0.6055  11.00000  0.05    0.25
Q3    1   0.5945  0.1046  0.5648  11.00000  0.05    0.24
Q4    1   0.3322  0.5705  0.5849  11.00000  0.05    0.23
Q5    1   0.4082  0.9026  0.6575  11.00000  0.05    0.22
Q6    1   0.6585  0.2465  0.5413  11.00000  0.05    0.20
Q7    1   0.7414  0.3318  0.6340  11.00000  0.05    0.19
Q8    1   0.4551  0.0814  0.5381  11.00000  0.05    0.18
Q9    1   0.4902  0.2869  0.5845  11.00000  0.05    0.18
Q10   1   0.1402  0.8921  0.6069  11.00000  0.05    0.18
Q11   1   0.5002 -0.0751  0.5164  11.00000  0.05    0.18
Q12   1   0.4250  0.6699  0.6352  11.00000  0.05    0.18
Q13   1   0.0066  1.0851  0.6639  11.00000  0.05    0.17
Q14   1   0.2947  0.5665  0.6352  11.00000  0.05    0.17
Q15   1   0.4782  0.1253  0.5967  11.00000  0.05    0.16
Q16   1   0.3449  1.1719  0.6821  11.00000  0.05    0.16
Q17   1   0.8801  0.1084  0.6474  11.00000  0.05    0.16
Q18   1   0.4255  0.3721  0.6511  11.00000  0.05    0.16
Q19   1   0.6680  0.2012  0.6595  11.00000  0.05    0.15
Q20   1   0.7644 -0.0442  0.6609  11.00000  0.05    0.15

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0352 for 1667 Fo > 4sig(Fo) and 0.0374 for all 3560 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.27, deepest hole -0.26
  REM Mean Shift 0, Max Shift -0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0374
  REM R1_gt = 0.0352
  REM wR_ref = 0.0822
  REM GOOF = 1.047
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 3560
  REM Reflections_gt = 1667
  REM Parameters = n/a
  REM Hole = -0.26
  REM Peak = 0.27
  REM Flack = 0.03(6)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_hgl_203
_database_code_depnum_ccdc_archive 'CCDC 1902238'
loop_
_audit_author_name
_audit_author_address
hgl
;wiyi university
China
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
_audit_creation_date             2018-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 N O2 S'
_chemical_formula_sum            'C10 H7 N O2 S'
_chemical_formula_weight         205.23
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.9853(19)
_cell_length_b                   8.3741(16)
_cell_length_c                   14.638(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.28(2)
_cell_angle_gamma                90
_cell_volume                     845.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1418
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.2090
_cell_measurement_theta_min      2.9480
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3223
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  53.00   1.00    1.50    --   11.74 -99.00 -30.00   73
  2  ω     39.00  70.00   1.00    1.50    --   11.74  37.00 -90.00   31
  3  ω    -14.00  61.00   1.00    1.50    --   11.74  57.00 150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661715000
_diffrn_orient_matrix_UB_12      0.0318068000
_diffrn_orient_matrix_UB_13      0.0373365000
_diffrn_orient_matrix_UB_21      -0.0363780000
_diffrn_orient_matrix_UB_22      0.0780026000
_diffrn_orient_matrix_UB_23      -0.0111542000
_diffrn_orient_matrix_UB_31      -0.0695728000
_diffrn_orient_matrix_UB_32      -0.0103371000
_diffrn_orient_matrix_UB_33      0.0298441000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1194
_reflns_number_total             1438
_reflns_odcompleteness_completeness 96.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0962P)²+0.5824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1685
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.16223(12) 0.91440(11) 0.44553(6) 0.0271(4) Uani 1 1 d . . . . .
O2 O 1.0464(3) 0.4518(3) 0.63441(16) 0.0262(6) Uani 1 1 d . . . . .
O1 O 0.9387(3) 0.3591(3) 0.76647(15) 0.0277(6) Uani 1 1 d . . . . .
N1 N 0.3460(4) 0.9015(3) 0.39146(19) 0.0244(7) Uani 1 1 d . . . . .
C5 C 0.7516(5) 0.6038(4) 0.5741(2) 0.0192(8) Uani 1 1 d . . . . .
H5 H 0.796784 0.638832 0.521185 0.023 Uiso 1 1 calc R . . . .
C4 C 0.5663(4) 0.6474(4) 0.5921(2) 0.0176(7) Uani 1 1 d . . . . .
C1 C 0.7993(5) 0.4539(4) 0.7158(2) 0.0201(8) Uani 1 1 d . . . . .
C6 C 0.8616(5) 0.5088(4) 0.6370(2) 0.0207(8) Uani 1 1 d . . . . .
C3 C 0.5070(5) 0.5924(4) 0.6732(2) 0.0210(8) Uani 1 1 d . . . . .
H3 H 0.385681 0.622947 0.685416 0.025 Uiso 1 1 calc R . . . .
C2 C 0.6211(5) 0.4943(4) 0.7363(2) 0.0230(8) Uani 1 1 d . . . . .
H2 H 0.578735 0.457969 0.789664 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2560(5) 0.7989(4) 0.5360(2) 0.0233(8) Uani 1 1 d . . . . .
H9 H 0.192876 0.773388 0.585363 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4381(5) 0.7478(4) 0.5268(2) 0.0187(7) Uani 1 1 d . . . . .
C10 C 0.4818(5) 0.8104(4) 0.4424(2) 0.0223(8) Uani 1 1 d . . . . .
H10 H 0.599659 0.789199 0.423017 0.027 Uiso 1 1 calc R . . . .
C7 C 1.0989(5) 0.3628(4) 0.7179(2) 0.0268(8) Uani 1 1 d . . . . .
H7A H 1.134587 0.254799 0.703462 0.032 Uiso 1 1 calc R . . . .
H7B H 1.209548 0.412166 0.756013 0.032 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 0.0228(6) 0.0329(6) 0.0251(6) 0.0015(4) 0.0029(4) 0.0028(4)
O2 0.0179(13) 0.0390(15) 0.0226(12) 0.0073(10) 0.0061(10) 0.0064(10)
O1 0.0221(13) 0.0374(15) 0.0242(13) 0.0105(11) 0.0052(11) 0.0067(11)
N1 0.0346(18) 0.0231(16) 0.0163(14) 0.0012(11) 0.0066(13) -0.0042(13)
C5 0.0192(18) 0.0244(18) 0.0146(16) -0.0004(13) 0.0045(14) -0.0032(13)
C4 0.0173(17) 0.0183(16) 0.0173(16) -0.0047(13) 0.0029(13) -0.0040(13)
C1 0.0205(18) 0.0213(17) 0.0178(16) 0.0006(13) 0.0005(14) -0.0034(13)
C6 0.0187(18) 0.0245(18) 0.0194(17) -0.0060(14) 0.0050(14) -0.0045(14)
C3 0.0205(18) 0.0231(18) 0.0204(17) -0.0011(13) 0.0061(14) -0.0003(13)
C2 0.027(2) 0.0257(18) 0.0180(17) -0.0012(14) 0.0086(15) -0.0046(15)
C9 0.0234(19) 0.0286(19) 0.0185(17) -0.0007(14) 0.0052(15) -0.0016(14)
C8 0.0164(17) 0.0202(17) 0.0192(16) -0.0058(13) 0.0020(13) -0.0054(13)
C10 0.0215(18) 0.0239(18) 0.0221(17) -0.0003(14) 0.0055(14) 0.0024(14)
C7 0.0223(19) 0.034(2) 0.0240(18) 0.0065(16) 0.0026(15) 0.0020(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 N1 1.617(3) . ?
S1 C9 1.685(3) . ?
O2 C6 1.382(4) . ?
O2 C7 1.428(4) . ?
O1 C1 1.377(4) . ?
O1 C7 1.420(4) . ?
N1 C10 1.345(4) . ?
C5 C4 1.410(4) . ?
C5 C6 1.358(5) . ?
C4 C3 1.397(4) . ?
C4 C8 1.465(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.370(5) . ?
C3 C2 1.388(5) . ?
C9 C8 1.369(4) . ?
C8 C10 1.420(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
N1 S1 C9 96.18(15) . . ?
C6 O2 C7 105.6(2) . . ?
C1 O1 C7 105.3(2) . . ?
C10 N1 S1 108.1(2) . . ?
C6 C5 C4 117.5(3) . . ?
C5 C4 C8 120.7(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C8 120.7(3) . . ?
C6 C1 O1 110.6(3) . . ?
C2 C1 O1 127.8(3) . . ?
C2 C1 C6 121.5(3) . . ?
C5 C6 O2 127.8(3) . . ?
C5 C6 C1 122.9(3) . . ?
C1 C6 O2 109.3(3) . . ?
C2 C3 C4 123.0(3) . . ?
C1 C2 C3 116.4(3) . . ?
C8 C9 S1 110.6(2) . . ?
C9 C8 C4 126.5(3) . . ?
C9 C8 C10 107.7(3) . . ?
C10 C8 C4 125.8(3) . . ?
N1 C10 C8 117.4(3) . . ?
O1 C7 O2 109.0(3) . . ?

_iucr_refine_instructions_details 
;
TITL hgl_203_a.res in P2(1)/c
    hgl_203.res
    created by SHELXL-2018/3 at 17:44:50 on 06-Jun-2018
REM Old TITL hgl_203 in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.130, Rweak 0.242, Alpha 0.026
REM <I/s> 0.918 for 115 systematic absences, Orientation as input
REM Formula found by SHELXT: C9 N2 O2 S
CELL 0.71073 6.9853 8.3741 14.6382 90 99.283 90
ZERR 4 0.0019 0.0016 0.0026 0 0.02 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 40 28 4 8 4

L.S. 10
PLAN  20
SIZE 0.11 0.12 0.13
BOND
list 4
fmap 2 53
acta
OMIT -3 50
REM <olex2.extras>
REM <HklSrc "%.\\hgl_203.hkl">
REM </olex2.extras>

WGHT    0.096247    0.582429
FVAR       0.63569
S1    5    0.162234    0.914403    0.445526    11.00000    0.02283    0.03291 =
         0.02512    0.00146    0.00288    0.00281
O2    4    1.046449    0.451845    0.634408    11.00000    0.01790    0.03905 =
         0.02264    0.00728    0.00607    0.00638
O1    4    0.938717    0.359129    0.766471    11.00000    0.02213    0.03735 =
         0.02424    0.01047    0.00521    0.00665
N1    3    0.346031    0.901475    0.391463    11.00000    0.03459    0.02311 =
         0.01628    0.00124    0.00664   -0.00425
C5    1    0.751610    0.603801    0.574118    11.00000    0.01924    0.02441 =
         0.01464   -0.00042    0.00453   -0.00319
AFIX  43
H5    2    0.796784    0.638832    0.521185    11.00000   -1.20000
AFIX   0
C4    1    0.566303    0.647404    0.592071    11.00000    0.01732    0.01829 =
         0.01732   -0.00472    0.00293   -0.00402
C1    1    0.799335    0.453912    0.715764    11.00000    0.02049    0.02128 =
         0.01779    0.00063    0.00049   -0.00341
C6    1    0.861634    0.508757    0.636997    11.00000    0.01872    0.02447 =
         0.01942   -0.00605    0.00503   -0.00447
C3    1    0.507025    0.592428    0.673174    11.00000    0.02052    0.02305 =
         0.02036   -0.00105    0.00611   -0.00027
AFIX  43
H3    2    0.385681    0.622947    0.685416    11.00000   -1.20000
AFIX   0
C2    1    0.621066    0.494321    0.736297    11.00000    0.02683    0.02568 =
         0.01804   -0.00121    0.00859   -0.00458
AFIX  43
H2    2    0.578735    0.457969    0.789664    11.00000   -1.20000
AFIX   0
C9    1    0.256007    0.798899    0.536006    11.00000    0.02337    0.02856 =
         0.01848   -0.00072    0.00524   -0.00161
AFIX  43
H9    2    0.192876    0.773388    0.585363    11.00000   -1.20000
AFIX   0
C8    1    0.438100    0.747826    0.526750    11.00000    0.01644    0.02019 =
         0.01918   -0.00583    0.00196   -0.00539
C10   1    0.481772    0.810388    0.442352    11.00000    0.02147    0.02390 =
         0.02205   -0.00035    0.00548    0.00238
AFIX  43
H10   2    0.599659    0.789199    0.423017    11.00000   -1.20000
AFIX   0
C7    1    1.098905    0.362751    0.717885    11.00000    0.02226    0.03383 =
         0.02397    0.00647    0.00265    0.00198
AFIX  23
H7A   2    1.134587    0.254799    0.703462    11.00000   -1.20000
H7B   2    1.209548    0.412166    0.756013    11.00000   -1.20000
AFIX   0
HKLF 4




REM  hgl_203_a.res in P2(1)/c
REM wR2 = 0.1685, GooF = S = 1.069, Restrained GooF = 1.069 for all data
REM R1 = 0.0532 for 1194 Fo > 4sig(Fo) and 0.0646 for all 1438 data
REM 127 parameters refined using 0 restraints

END  
     
WGHT      0.0667      0.5091 

REM Highest difference peak  0.439,  deepest hole -0.443,  1-sigma level  0.088
Q1    1   0.4074  0.9072  0.4173  11.00000  0.05    0.44
Q2    1   0.2051  0.8048  0.4794  11.00000  0.05    0.40
Q3    1   0.8272  0.4895  0.6750  11.00000  0.05    0.35
Q4    1   0.2431  0.8850  0.3925  11.00000  0.05    0.34
Q5    1   0.8538  0.3993  0.7455  11.00000  0.05    0.31
Q6    1   0.6876  0.7804  0.5598  11.00000  0.05    0.27
Q7    1   0.5156  0.7695  0.4956  11.00000  0.05    0.27
Q8    1   0.1054  1.0280  0.4185  11.00000  0.05    0.27
Q9    1   1.0923  0.4008  0.5743  11.00000  0.05    0.26
Q10   1   0.9725  0.2573  0.7879  11.00000  0.05    0.26
Q11   1   0.9449  0.6138  0.6661  11.00000  0.05    0.25
Q12   1   0.0985  0.7518  0.4075  11.00000  0.05    0.25
Q13   1   0.2830  0.8586  0.3306  11.00000  0.05    0.25
Q14   1   0.7554  0.5174  0.7380  11.00000  0.05    0.25
Q15   1   0.5394  0.6377  0.6368  11.00000  0.05    0.25
Q16   1   0.4602  0.6400  0.4400  11.00000  0.05    0.24
Q17   1   0.6173  0.7950  0.3992  11.00000  0.05    0.24
Q18   1   0.0321  0.8951  0.3740  11.00000  0.05    0.24
Q19   1   1.0655  0.2540  0.6874  11.00000  0.05    0.24
Q20   1   0.6664  0.4039  0.7093  11.00000  0.05    0.24

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0532 for 1194 Fo > 4sig(Fo) and 0.0646 for all 4023 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.44, deepest hole -0.44
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0646
  REM R1_gt = 0.0532
  REM wR_ref = 0.1685
  REM GOOF = 1.069
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4023
  REM Reflections_gt = 1194
  REM Parameters = n/a
  REM Hole = -0.44
  REM Peak = 0.44
  REM Flack = n/a

  
;
_olex2_date_sample_data_collection 2018-06-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.659
_oxdiff_exptl_absorpt_empirical_full_min 0.567
