# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_6-w-c-129
_database_code_depnum_ccdc_archive 'CCDC 1986361'
loop_
_audit_author_name
_audit_author_address
'Bao-Yi Yu'
;Beijing University of Agriculture
China
;
_audit_update_record             
;
2020-02-26 deposited with the CCDC.	2020-05-28 downloaded from the CCDC.
;
_audit_creation_date             2019-05-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 S'
_chemical_formula_sum            'C14 H12 N2 S'
_chemical_formula_weight         240.32
_chemical_melting_point          159.5-160.3?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.6151(13)
_cell_length_b                   3.9563(4)
_cell_length_c                   18.379(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.928(7)
_cell_angle_gamma                90
_cell_volume                     1133.92(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1861
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.0490
_cell_measurement_theta_min      4.7610
_shelx_estimated_absorpt_T_max   0.784
_shelx_estimated_absorpt_T_min   0.617
_exptl_absorpt_coefficient_mu    2.322
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4798
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.429
_diffrn_reflns_theta_min         3.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  68.00   0.50    0.50    --    0.00  82.00-120.00   66
  2  ω     -6.00  54.00   0.50    0.50    --    0.00  57.00-150.00  120
  3  ω    -29.00  43.00   0.50    0.50    --    0.00  57.00 -30.00  144
  4  ω     22.00 117.00   0.50    1.20    --   95.80 -61.00  60.00  190
  5  ω     66.00 158.00   0.50    1.20    --   95.80  45.00  60.00  184
  6  ω     12.00  38.00   0.50    1.20    --   95.80 -45.00 150.00   52
  7  ω     63.00 133.00   0.50    1.20    --   95.80 -82.00  60.00  140
  8  ω     57.00 120.00   0.50    1.20    --   95.80 -45.00 150.00  126
  9  ω    149.00 184.00   0.50    1.20    --   95.80   0.00  60.00   70
 10  ω      6.00 121.00   0.50    1.20    --   95.80   0.00  60.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0816604000
_diffrn_orient_matrix_UB_12      0.0575209000
_diffrn_orient_matrix_UB_13      -0.0418755000
_diffrn_orient_matrix_UB_21      0.0551590000
_diffrn_orient_matrix_UB_22      -0.0365707000
_diffrn_orient_matrix_UB_23      0.0715267000
_diffrn_orient_matrix_UB_31      0.0067010000
_diffrn_orient_matrix_UB_32      -0.3834237000
_diffrn_orient_matrix_UB_33      -0.0133157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1871
_reflns_number_total             2163
_reflns_odcompleteness_completeness 98.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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         0.608
_refine_diff_density_min         -1.366
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      1.092
_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)+(0.1563P)²+0.5628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2141
_refine_ls_wR_factor_ref         0.2233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.28198(5) 0.3998(2) 0.43678(4) 0.0271(3) Uani 1 1 d . . . . .
N1 N 0.38810(16) 0.0920(6) 0.53000(14) 0.0250(6) Uani 1 1 d . . . . .
N2 N 0.44329(16) 0.1765(7) 0.41561(14) 0.0276(6) Uani 1 1 d . . . . .
H2 H 0.4909 0.0895 0.4320 0.033 Uiso 1 1 calc R . . . .
C1 C 0.38019(19) 0.2030(8) 0.46263(16) 0.0244(7) Uani 1 1 d . . . . .
C2 C 0.2487(2) 0.3301(8) 0.52416(17) 0.0251(7) Uani 1 1 d . . . . .
C3 C 0.1706(2) 0.4134(8) 0.55276(19) 0.0283(7) Uani 1 1 d . . . . .
H3 H 0.1280 0.5231 0.5245 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1582(2) 0.3274(8) 0.62511(19) 0.0296(7) Uani 1 1 d . . . . .
H4 H 0.1067 0.3818 0.6457 0.036 Uiso 1 1 calc R . . . .
C5 C 0.2221(2) 0.1607(8) 0.66684(18) 0.0299(7) Uani 1 1 d . . . . .
H5 H 0.2123 0.1026 0.7147 0.036 Uiso 1 1 calc R . . . .
C6 C 0.3002(2) 0.0795(8) 0.63844(17) 0.0279(7) Uani 1 1 d . . . . .
H6 H 0.3429 -0.0273 0.6671 0.034 Uiso 1 1 calc R . . . .
C7 C 0.31355(19) 0.1618(8) 0.56558(17) 0.0253(7) Uani 1 1 d . . . . .
C8 C 0.43829(19) 0.2788(8) 0.34167(16) 0.0254(7) Uani 1 1 d . . . . .
C9 C 0.5074(2) 0.4567(8) 0.31549(17) 0.0262(7) Uani 1 1 d . . . . .
H9 H 0.5535 0.5152 0.3470 0.031 Uiso 1 1 calc R . . . .
C10 C 0.5076(2) 0.5468(8) 0.24245(18) 0.0273(7) Uani 1 1 d . . . . .
H10 H 0.5548 0.6598 0.2254 0.033 Uiso 1 1 calc R . . . .
C11 C 0.4388(2) 0.4718(8) 0.19425(18) 0.0280(7) Uani 1 1 d . . . . .
C12 C 0.3697(2) 0.2971(9) 0.22121(17) 0.0296(7) Uani 1 1 d . . . . .
H12 H 0.3226 0.2465 0.1900 0.035 Uiso 1 1 calc R . . . .
C13 C 0.36958(19) 0.1964(9) 0.29410(17) 0.0277(7) Uani 1 1 d . . . . .
H13 H 0.3236 0.0744 0.3107 0.033 Uiso 1 1 calc R . . . .
C14 C 0.4390(2) 0.5760(9) 0.11557(18) 0.0356(8) Uani 1 1 d . . . . .
H14A H 0.3930 0.4646 0.0885 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.4927 0.5136 0.0961 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.4316 0.8163 0.1119 0.053 Uiso 1 1 calc GR . . . .


_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 1.763(3) . ?
S1 C2 1.735(3) . ?
N1 C1 1.314(4) . ?
N1 C7 1.392(4) . ?
N2 H2 0.8600 . ?
N2 C1 1.347(4) . ?
N2 C8 1.416(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.404(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.404(4) . ?
C8 C9 1.395(4) . ?
C8 C13 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(4) . ?
C11 C12 1.393(5) . ?
C11 C14 1.504(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.398(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C2 S1 C1 88.75(14) . . ?
C1 N1 C7 109.6(3) . . ?
C1 N2 H2 117.0 . . ?
C1 N2 C8 125.9(3) . . ?
C8 N2 H2 117.0 . . ?
N1 C1 S1 116.1(2) . . ?
N1 C1 N2 122.8(3) . . ?
N2 C1 S1 121.1(2) . . ?
C3 C2 S1 128.5(3) . . ?
C3 C2 C7 122.0(3) . . ?
C7 C2 S1 109.6(2) . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.7(3) . . ?
C7 C6 H6 120.6 . . ?
N1 C7 C2 115.9(3) . . ?
N1 C7 C6 124.8(3) . . ?
C2 C7 C6 119.3(3) . . ?
C9 C8 N2 118.0(3) . . ?
C13 C8 N2 122.7(3) . . ?
C13 C8 C9 119.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 117.8(3) . . ?
C10 C11 C14 121.0(3) . . ?
C12 C11 C14 121.2(3) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 119.9(3) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.544
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_cw128
_database_code_depnum_ccdc_archive 'CCDC 1986400'
loop_
_audit_author_name
_audit_author_address
'Bao-Yi Yu'
;Beijing University of Agriculture
China
;
_audit_update_record             
;
2020-02-26 deposited with the CCDC.	2020-05-28 downloaded from the CCDC.
;
_audit_creation_date             2019-01-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N3 S2'
_chemical_formula_sum            'C21 H15 N3 S2'
_chemical_formula_weight         373.48
_chemical_melting_point          202.8-204.1?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.25580(10)
_cell_length_b                   10.26980(10)
_cell_length_c                   21.4706(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.1910(10)
_cell_angle_gamma                90
_cell_volume                     1809.78(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6105
_cell_measurement_temperature    299.17(10)
_cell_measurement_theta_max      73.9570
_cell_measurement_theta_min      4.7330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10385
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.144
_diffrn_reflns_theta_min         4.142
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.17(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9625
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  89.00   0.50    0.50    --    0.00  77.00-120.00  116
  2  ω    -37.00  29.00   0.50    0.50    --    0.00  82.00 120.00  132
  3  ω    -30.00  22.00   0.50    0.50    --    0.00  57.00-120.00  104
  4  ω     68.00 113.00   0.50    1.89    --   95.80 -30.00  30.00   90
  5  ω     60.00 110.00   0.50    1.89    --   95.80 -82.00 -60.00  100
  6  ω     59.00 128.00   0.50    1.89    --   95.80  30.00 -90.00  138
  7  ω    112.00 168.00   0.50    1.89    --   95.80  61.00   0.00  112
  8  ω     69.00 184.00   0.50    1.89    --   95.80  45.00 -60.00  230
  9  ω      9.00 133.00   0.50    1.89    --   95.80 -82.00   0.00  248
 10  ω     86.00 111.00   0.50    1.89    --   95.80 -82.00-120.00   50
 11  ω     11.00 125.00   0.50    1.89    --   95.80 -61.00   0.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0176876000
_diffrn_orient_matrix_UB_12      -0.0089968000
_diffrn_orient_matrix_UB_13      0.0705582000
_diffrn_orient_matrix_UB_21      -0.1868312000
_diffrn_orient_matrix_UB_22      -0.0012009000
_diffrn_orient_matrix_UB_23      -0.0145706000
_diffrn_orient_matrix_UB_31      0.0026270000
_diffrn_orient_matrix_UB_32      -0.1497648000
_diffrn_orient_matrix_UB_33      -0.0041252000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3159
_reflns_number_total             3540
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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         0.150
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.066
_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)+(0.0519P)²+0.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 0.31263(4) 0.38478(3) 0.42077(2) 0.04288(12) Uani 1 1 d . . . . .
S2 S 0.49656(5) 0.32206(4) 0.64156(2) 0.04814(12) Uani 1 1 d . . . . .
N1 N 0.53388(14) 0.20452(11) 0.41639(6) 0.0403(3) Uani 1 1 d . . . . .
N2 N 0.50470(14) 0.26844(11) 0.51891(5) 0.0397(3) Uani 1 1 d . . . . .
N3 N 0.30453(14) 0.41468(13) 0.54743(6) 0.0428(3) Uani 1 1 d . . . . .
C1 C 0.46200(16) 0.27687(13) 0.45457(6) 0.0360(3) Uani 1 1 d . . . . .
C2 C 0.35410(17) 0.32882(14) 0.34770(7) 0.0417(3) Uani 1 1 d . . . . .
C3 C 0.2871(2) 0.36883(17) 0.28829(8) 0.0512(4) Uani 1 1 d . . . . .
H3 H 0.2095 0.4348 0.2835 0.061 Uiso 1 1 calc R . . . .
C4 C 0.3394(2) 0.30760(19) 0.23687(8) 0.0558(4) Uani 1 1 d . . . . .
H4 H 0.2967 0.3329 0.1969 0.067 Uiso 1 1 calc R . . . .
C5 C 0.4552(2) 0.20848(19) 0.24389(8) 0.0576(4) Uani 1 1 d . . . . .
H5 H 0.4873 0.1677 0.2085 0.069 Uiso 1 1 calc R . . . .
C6 C 0.5229(2) 0.16999(17) 0.30251(8) 0.0521(4) Uani 1 1 d . . . . .
H6 H 0.6003 0.1039 0.3069 0.062 Uiso 1 1 calc R . . . .
C7 C 0.47346(17) 0.23162(14) 0.35502(7) 0.0403(3) Uani 1 1 d . . . . .
C8 C 0.42589(16) 0.33745(14) 0.56192(6) 0.0385(3) Uani 1 1 d . . . . .
C9 C 0.34930(17) 0.43490(15) 0.65739(7) 0.0445(3) Uani 1 1 d . . . . .
C10 C 0.3221(2) 0.48903(18) 0.71467(8) 0.0548(4) Uani 1 1 d . . . . .
H10 H 0.3835 0.4635 0.7515 0.066 Uiso 1 1 calc R . . . .
C11 C 0.2020(2) 0.58117(18) 0.71535(9) 0.0590(4) Uani 1 1 d . . . . .
H11 H 0.1830 0.6198 0.7531 0.071 Uiso 1 1 calc R . . . .
C12 C 0.1080(2) 0.61764(17) 0.66025(9) 0.0571(4) Uani 1 1 d . . . . .
H12 H 0.0259 0.6791 0.6619 0.068 Uiso 1 1 calc R . . . .
C13 C 0.13448(19) 0.56442(17) 0.60342(8) 0.0524(4) Uani 1 1 d . . . . .
H13 H 0.0711 0.5893 0.5669 0.063 Uiso 1 1 calc R . . . .
C14 C 0.25806(17) 0.47262(14) 0.60159(7) 0.0416(3) Uani 1 1 d . . . . .
C15 C 0.65513(16) 0.20109(13) 0.54023(6) 0.0375(3) Uani 1 1 d . . . . .
C16 C 0.80085(18) 0.26722(15) 0.54048(8) 0.0471(3) Uani 1 1 d . . . . .
H16 H 0.8017 0.3540 0.5282 0.057 Uiso 1 1 calc R . . . .
C17 C 0.94536(19) 0.20338(17) 0.55913(8) 0.0513(4) Uani 1 1 d . . . . .
H17 H 1.0434 0.2480 0.5591 0.062 Uiso 1 1 calc R . . . .
C18 C 0.94717(18) 0.07441(16) 0.57779(7) 0.0468(3) Uani 1 1 d . . . . .
C19 C 0.7993(2) 0.01106(15) 0.57798(7) 0.0498(4) Uani 1 1 d . . . . .
H19 H 0.7980 -0.0754 0.5908 0.060 Uiso 1 1 calc R . . . .
C20 C 0.65253(19) 0.07369(14) 0.55938(7) 0.0448(3) Uani 1 1 d . . . . .
H20 H 0.5541 0.0298 0.5599 0.054 Uiso 1 1 calc R . . . .
C21 C 1.1058(2) 0.0052(2) 0.59725(9) 0.0695(5) Uani 1 1 d . . . . .
H21A H 1.1413 -0.0391 0.5618 0.104 Uiso 1 1 calc GR . . . .
H21B H 1.0903 -0.0569 0.6295 0.104 Uiso 1 1 calc GR . . . .
H21C H 1.1868 0.0676 0.6129 0.104 Uiso 1 1 calc GR . . . .


_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 1.7558(13) . ?
S1 C2 1.7391(15) . ?
S2 C8 1.7532(14) . ?
S2 C9 1.7394(16) . ?
N1 C1 1.2966(18) . ?
N1 C7 1.3858(18) . ?
N2 C1 1.3910(18) . ?
N2 C8 1.3814(18) . ?
N2 C15 1.4518(17) . ?
N3 C8 1.2894(18) . ?
N3 C14 1.3963(19) . ?
C2 C3 1.396(2) . ?
C2 C7 1.400(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(2) . ?
C9 C10 1.390(2) . ?
C9 C14 1.399(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(2) . ?
C15 C16 1.381(2) . ?
C15 C20 1.372(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 C19 1.383(2) . ?
C18 C21 1.509(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C2 S1 C1 88.08(7) . . ?
C9 S2 C8 87.96(7) . . ?
C1 N1 C7 110.11(12) . . ?
C1 N2 C15 117.35(11) . . ?
C8 N2 C1 123.01(11) . . ?
C8 N2 C15 118.83(11) . . ?
C8 N3 C14 109.72(12) . . ?
N1 C1 S1 116.69(10) . . ?
N1 C1 N2 120.53(12) . . ?
N2 C1 S1 122.77(10) . . ?
C3 C2 S1 129.03(12) . . ?
C3 C2 C7 121.14(14) . . ?
C7 C2 S1 109.83(10) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.00(15) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.12(15) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.92(16) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 118.94(16) . . ?
C7 C6 H6 120.5 . . ?
N1 C7 C2 115.26(12) . . ?
N1 C7 C6 124.89(13) . . ?
C6 C7 C2 119.84(13) . . ?
N2 C8 S2 118.33(10) . . ?
N3 C8 S2 117.32(11) . . ?
N3 C8 N2 124.34(12) . . ?
C10 C9 S2 128.51(13) . . ?
C10 C9 C14 121.56(15) . . ?
C14 C9 S2 109.88(11) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.13(16) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.85(16) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.27(16) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.73(16) . . ?
C14 C13 H13 120.6 . . ?
N3 C14 C9 115.10(13) . . ?
C13 C14 N3 125.44(14) . . ?
C13 C14 C9 119.44(14) . . ?
C16 C15 N2 118.82(12) . . ?
C20 C15 N2 120.55(13) . . ?
C20 C15 C16 120.63(13) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.48(14) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.34(14) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 117.98(14) . . ?
C17 C18 C21 120.86(16) . . ?
C19 C18 C21 121.17(16) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.54(14) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 119.02(14) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.686
_oxdiff_exptl_absorpt_empirical_full_min 0.712
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
