# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_170
_audit_block_doi                 10.5517/ccdc.csd.cc1yzm8t
_database_code_depnum_ccdc_archive 'CCDC 1816887'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N S2'
_chemical_formula_sum            'C14 H11 N S2'
_chemical_formula_weight         257.36
_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 0.0181 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                   7.26150(10)
_cell_length_b                   11.8328(2)
_cell_length_c                   14.2292(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.546(2)
_cell_angle_gamma                90
_cell_volume                     1218.78(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7264
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8950
_cell_measurement_theta_min      6.2570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10496
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.867
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  21.00   1.00    2.00    --    0.00  77.00  90.00   51
  2  ω     13.00  58.00   1.00    2.00    --    0.00  38.00  60.00   45
  3  ω    -14.00  12.00   1.00    2.00    --    0.00  38.00 -60.00   26
  4  ω     31.00  89.00   1.00    2.00    --    0.00  77.00  90.00   58
  5  ω    -18.00  10.00   1.00    2.00    --    0.00  38.00  60.00   28
  6  ω     55.00  87.00   1.00    2.00    --    0.00  38.00 -30.00   32
  7  ω     50.00  78.00   1.00    2.00    --    0.00  38.00 -60.00   28
  8  ω     -1.00  26.00   1.00    2.00    --    0.00  38.00 -30.00   27
  9  ω     13.00 126.00   1.00    4.00    --   95.80 -82.00   0.00  113
 10  ω     39.00  85.00   1.00    4.00    --   95.80 -77.00-150.00   46
 11  ω     61.00 113.00   1.00    4.00    --   95.80 -30.00-180.00   52
 12  ω     89.00 115.00   1.00    4.00    --   95.80 -77.00-150.00   26
 13  ω     32.00 127.00   1.00    4.00    --   95.80 -82.00 150.00   95
 14  ω     22.00  47.00   1.00    4.00    --   95.80 -82.00 -90.00   25
 15  ω      6.00  53.00   1.00    4.00    --   95.80 -30.00-180.00   47
 16  ω     80.00 110.00   1.00    4.00    --   95.80 -77.00  60.00   30
 17  ω      6.00  36.00   1.00    4.00    --   95.80 -77.00  60.00   30
 18  ω      6.00 116.00   1.00    4.00    --   95.80 -61.00   0.00  110
 19  ω     23.00 119.00   1.00    4.00    --   95.80 -15.00  60.00   96
 20  ω     80.00 106.00   1.00    4.00    --   95.80 -82.00 -90.00   26
 21  ω     20.00  73.00   1.00    4.00    --   95.80 -77.00 -30.00   53
 22  ω     68.00 182.00   1.00    4.00    --   95.80   0.00 150.00  114
 23  ω     34.00  60.00   1.00    4.00    --   95.80 -82.00-180.00   26
 24  ω     81.00 106.00   1.00    4.00    --   95.80 -82.00-180.00   25
 25  ω    153.00 178.00   1.00    4.00    --   95.80  30.00-150.00   25
 26  ω      6.00  46.00   1.00    4.00    --   95.80   0.00 150.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0342936000
_diffrn_orient_matrix_UB_12      0.1278995000
_diffrn_orient_matrix_UB_13      -0.0086031000
_diffrn_orient_matrix_UB_21      0.1538707000
_diffrn_orient_matrix_UB_22      -0.0072866000
_diffrn_orient_matrix_UB_23      0.0806978000
_diffrn_orient_matrix_UB_31      0.1429623000
_diffrn_orient_matrix_UB_32      -0.0231936000
_diffrn_orient_matrix_UB_33      -0.0721766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2008
_reflns_number_total             2151
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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         0.178
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.071
_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)+(0.0540P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0954
_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:
 C13(H13), C5(H5), C12(H12), C10(H10), C1(H1), C11(H11), C4(H4), C3(H3), 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 0.70694(6) 0.44562(4) 0.32091(3) 0.05067(17) Uani 1 1 d . . . . .
S2 S 0.70021(7) 0.63334(5) 0.18190(4) 0.06380(19) Uani 1 1 d . . . . .
N1 N 0.41991(18) 0.56650(11) 0.28468(9) 0.0386(3) Uani 1 1 d . . . . .
C14 C 0.3698(2) 0.48764(14) 0.35154(11) 0.0371(3) Uani 1 1 d . . . . .
C6 C 0.2719(2) 0.75186(14) 0.30884(11) 0.0395(4) Uani 1 1 d . . . . .
C9 C 0.5126(2) 0.41425(15) 0.38029(11) 0.0420(4) Uani 1 1 d . . . . .
C13 C 0.1979(2) 0.47708(15) 0.38706(12) 0.0445(4) Uani 1 1 d . . . . .
H13 H 0.101294 0.525530 0.367839 0.053 Uiso 1 1 calc R . . . .
C7 C 0.2904(2) 0.65241(15) 0.24381(11) 0.0432(4) Uani 1 1 d . . . . .
H7A H 0.169947 0.618049 0.230082 0.052 Uiso 1 1 calc R . . . .
H7B H 0.333059 0.679004 0.184823 0.052 Uiso 1 1 calc R . . . .
C8 C 0.5957(2) 0.55667(14) 0.25983(12) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.4194(2) 0.82440(15) 0.32931(12) 0.0463(4) Uani 1 1 d . . . . .
H5 H 0.530916 0.811173 0.303269 0.056 Uiso 1 1 calc R . . . .
C12 C 0.1749(3) 0.39219(17) 0.45192(13) 0.0523(4) Uani 1 1 d . . . . .
H12 H 0.060822 0.383377 0.476419 0.063 Uiso 1 1 calc R . . . .
C10 C 0.4893(3) 0.33000(16) 0.44593(13) 0.0519(4) Uani 1 1 d . . . . .
H10 H 0.585772 0.281704 0.465628 0.062 Uiso 1 1 calc R . . . .
C1 C 0.1067(3) 0.77399(16) 0.34738(14) 0.0522(4) Uani 1 1 d . . . . .
H1 H 0.005465 0.727050 0.333411 0.063 Uiso 1 1 calc R . . . .
C11 C 0.3183(3) 0.32006(17) 0.48114(14) 0.0555(5) Uani 1 1 d . . . . .
H11 H 0.299130 0.264060 0.525169 0.067 Uiso 1 1 calc R . . . .
C4 C 0.4025(3) 0.91648(16) 0.38822(14) 0.0572(5) Uani 1 1 d . . . . .
H4 H 0.502111 0.964843 0.401455 0.069 Uiso 1 1 calc R . . . .
C3 C 0.2384(4) 0.93610(17) 0.42694(14) 0.0629(5) Uani 1 1 d . . . . .
H3 H 0.227276 0.997358 0.467037 0.075 Uiso 1 1 calc R . . . .
C2 C 0.0913(3) 0.86574(18) 0.40669(16) 0.0658(6) Uani 1 1 d . . . . .
H2 H -0.019881 0.879576 0.432900 0.079 Uiso 1 1 calc R . . . .


_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 C9 1.7415(17) . ?
S1 C8 1.7388(18) . ?
S2 C8 1.6618(18) . ?
N1 C14 1.401(2) . ?
N1 C7 1.473(2) . ?
N1 C8 1.356(2) . ?
C14 C9 1.389(2) . ?
C14 C13 1.389(2) . ?
C6 C7 1.510(2) . ?
C6 C5 1.386(2) . ?
C6 C1 1.383(2) . ?
C9 C10 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.383(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(3) . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.367(3) . ?
C2 H2 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
C8 S1 C9 92.37(8) . . ?
C14 N1 C7 122.37(13) . . ?
C8 N1 C14 114.87(14) . . ?
C8 N1 C7 122.75(14) . . ?
C9 C14 N1 112.84(14) . . ?
C13 C14 N1 126.62(15) . . ?
C13 C14 C9 120.53(15) . . ?
C5 C6 C7 120.45(15) . . ?
C1 C6 C7 120.85(16) . . ?
C1 C6 C5 118.68(16) . . ?
C14 C9 S1 109.80(13) . . ?
C10 C9 S1 128.85(14) . . ?
C10 C9 C14 121.35(16) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 C14 117.87(16) . . ?
C12 C13 H13 121.1 . . ?
N1 C7 C6 112.40(13) . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
S2 C8 S1 121.83(10) . . ?
N1 C8 S1 110.12(13) . . ?
N1 C8 S2 128.04(14) . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.65(18) . . ?
C4 C5 H5 119.7 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.38(17) . . ?
C11 C12 H12 119.3 . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.86(17) . . ?
C11 C10 H10 121.1 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.30(19) . . ?
C2 C1 H1 119.8 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.01(17) . . ?
C10 C11 H11 119.5 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.11(19) . . ?
C2 C3 H3 119.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?

_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 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_203
_audit_block_doi                 10.5517/ccdc.csd.cc1yzmbw
_database_code_depnum_ccdc_archive 'CCDC 1816889'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N S2'
_chemical_formula_sum            'C15 H13 N S2'
_chemical_formula_weight         271.38
_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 0.0181 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/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                   8.3766(2)
_cell_length_b                   6.28950(10)
_cell_length_c                   25.7206(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.618(2)
_cell_angle_gamma                90
_cell_volume                     1348.57(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4510
_cell_measurement_theta_min      5.2880
_shelx_estimated_absorpt_T_max   0.483
_shelx_estimated_absorpt_T_min   0.374
_exptl_absorpt_coefficient_mu    3.402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11187
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         5.306
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  77.00   1.00    1.00    --    0.00  38.00 -30.00   27
  2  ω    -59.00  -5.00   1.00    1.00    --    0.00 -38.00-150.00   54
  3  ω    -86.00 -55.00   1.00    1.00    --    0.00 -38.00  60.00   31
  4  ω    -49.00  18.00   1.00    1.00    --    0.00 -38.00  60.00   67
  5  ω    -84.00  13.00   1.00    1.00    --    0.00 -38.00 -30.00   97
  6  ω      6.00 118.00   1.00    3.00    --   95.80 -82.00 150.00  112
  7  ω      6.00 100.00   1.00    3.00    --   95.80 -82.00   0.00   94
  8  ω    143.00 185.00   1.00    3.00    --   95.80  61.00  90.00   42
  9  ω      6.00  94.00   1.00    3.00    --   95.80 -30.00  30.00   88
 10  ω     91.00 126.00   1.00    3.00    --   95.80 -82.00-180.00   35
 11  ω     81.00 116.00   1.00    3.00    --   95.80 -82.00 -90.00   35
 12  ω     21.00  47.00   1.00    3.00    --   95.80 -82.00-150.00   26
 13  ω     93.00 124.00   1.00    3.00    --   95.80 -82.00-150.00   31
 14  ω     70.00  96.00   1.00    3.00    --   95.80 -30.00 -60.00   26
 15  ω     87.00 118.00   1.00    3.00    --   95.80 -82.00  30.00   31
 16  ω     76.00 180.00   1.00    3.00    --   95.80  15.00 -90.00  104
 17  ω      6.00  38.00   1.00    3.00    --   95.80 -30.00 -60.00   32
 18  ω     37.00  63.00   1.00    3.00    --   95.80 -82.00 -90.00   26
 19  ω     10.00 112.00   1.00    3.00    --   95.80 -30.00 150.00  102
 20  ω     16.00  80.00   1.00    3.00    --   95.80 -61.00 150.00   64
 21  ω     19.00 119.00   1.00    3.00    --   95.80 -61.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1748475000
_diffrn_orient_matrix_UB_12      -0.0554834000
_diffrn_orient_matrix_UB_13      0.0082691000
_diffrn_orient_matrix_UB_21      -0.0499387000
_diffrn_orient_matrix_UB_22      0.0393413000
_diffrn_orient_matrix_UB_23      -0.0584703000
_diffrn_orient_matrix_UB_31      0.0328750000
_diffrn_orient_matrix_UB_32      -0.2352328000
_diffrn_orient_matrix_UB_33      -0.0117359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2083
_reflns_number_total             2408
_reflns_odcompleteness_completeness 99.85
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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         0.224
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.043
_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)+(0.0500P)²+0.3970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1121
_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:
 C1(H1A,H1B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_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 0.03553(8) 0.78869(10) 0.67392(3) 0.0681(2) Uani 1 1 d . . . . .
S2 S 0.04612(8) 0.86675(11) 0.56325(3) 0.0725(2) Uani 1 1 d . . . . .
N1 N 0.1595(2) 0.5114(3) 0.61103(6) 0.0507(4) Uani 1 1 d . . . . .
C1 C 0.1581(3) 0.3568(4) 0.65393(8) 0.0599(6) Uani 1 1 d . . . . .
H1A H 0.223921 0.235647 0.646535 0.072 Uiso 1 1 calc R . . . .
H1B H 0.049322 0.306227 0.655571 0.072 Uiso 1 1 calc R . . . .
C2 C 0.2188(3) 0.4477(4) 0.70579(8) 0.0563(5) Uani 1 1 d . . . . .
C3 C 0.3237(3) 0.3383(5) 0.74132(10) 0.0759(7) Uani 1 1 d . . . . .
H3 H 0.362287 0.205588 0.732698 0.091 Uiso 1 1 calc R . . . .
C4 C 0.3709(4) 0.4272(7) 0.78974(12) 0.0966(11) Uani 1 1 d . . . . .
H4 H 0.439379 0.352617 0.813864 0.116 Uiso 1 1 calc R . . . .
C5 C 0.3167(4) 0.6250(7) 0.80213(11) 0.0984(11) Uani 1 1 d . . . . .
H5 H 0.348741 0.683041 0.834742 0.118 Uiso 1 1 calc R . . . .
C6 C 0.2168(4) 0.7372(5) 0.76743(10) 0.0790(8) Uani 1 1 d . . . . .
H6 H 0.182520 0.872433 0.775868 0.095 Uiso 1 1 calc R . . . .
C7 C 0.1664(3) 0.6473(4) 0.71907(8) 0.0592(6) Uani 1 1 d . . . . .
C8 C 0.0914(2) 0.7018(3) 0.61317(8) 0.0536(5) Uani 1 1 d . . . . .
C9 C 0.2154(3) 0.4292(4) 0.56235(8) 0.0551(5) Uani 1 1 d . . . . .
H9A H 0.183874 0.527255 0.534074 0.066 Uiso 1 1 calc R . . . .
H9B H 0.163926 0.293777 0.553858 0.066 Uiso 1 1 calc R . . . .
C10 C 0.4949(3) 0.5678(4) 0.58043(10) 0.0667(6) Uani 1 1 d . . . . .
H10 H 0.451844 0.697625 0.589291 0.080 Uiso 1 1 calc R . . . .
C11 C 0.6589(3) 0.5459(5) 0.58123(12) 0.0828(8) Uani 1 1 d . . . . .
H11 H 0.725457 0.660965 0.590420 0.099 Uiso 1 1 calc R . . . .
C12 C 0.7240(3) 0.3562(6) 0.56862(9) 0.0778(8) Uani 1 1 d . . . . .
H12 H 0.834630 0.342033 0.569139 0.093 Uiso 1 1 calc R . . . .
C13 C 0.6262(3) 0.1870(5) 0.55522(9) 0.0774(8) Uani 1 1 d . . . . .
H13 H 0.670012 0.057160 0.546722 0.093 Uiso 1 1 calc R . . . .
C14 C 0.4617(3) 0.2095(4) 0.55434(9) 0.0645(6) Uani 1 1 d . . . . .
H14 H 0.395528 0.094011 0.545247 0.077 Uiso 1 1 calc R . . . .
C15 C 0.3946(2) 0.4004(3) 0.56671(7) 0.0472(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.758(3) . ?
S1 C8 1.761(2) . ?
S2 C8 1.665(2) . ?
N1 C1 1.472(3) . ?
N1 C8 1.330(3) . ?
N1 C9 1.473(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.494(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C15 1.506(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C10 C15 1.372(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(3) . ?

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
C7 S1 C8 103.09(10) . . ?
C1 N1 C9 115.59(17) . . ?
C8 N1 C1 121.95(17) . . ?
C8 N1 C9 121.63(18) . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
N1 C1 C2 112.91(18) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C3 C2 C1 122.5(2) . . ?
C7 C2 C1 118.6(2) . . ?
C7 C2 C3 118.9(2) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 S1 119.23(17) . . ?
C2 C7 C6 120.8(3) . . ?
C6 C7 S1 119.9(2) . . ?
S2 C8 S1 115.49(13) . . ?
N1 C8 S1 117.93(16) . . ?
N1 C8 S2 126.54(17) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
N1 C9 C15 112.12(16) . . ?
H9A C9 H9B 107.9 . . ?
C15 C9 H9A 109.2 . . ?
C15 C9 H9B 109.2 . . ?
C11 C10 H10 119.6 . . ?
C15 C10 H10 119.6 . . ?
C15 C10 C11 120.8(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C9 120.5(2) . . ?
C10 C15 C14 118.4(2) . . ?
C14 C15 C9 121.0(2) . . ?

_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 2.838
_oxdiff_exptl_absorpt_empirical_full_min 0.437
