# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_20170912-1
_database_code_depnum_ccdc_archive 'CCDC 1818722'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N3 S'
_chemical_formula_sum            'C21 H15 N3 S'
_chemical_formula_weight         341.42
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.3793(3)
_cell_length_b                   7.23290(10)
_cell_length_c                   19.5343(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.6530(10)
_cell_angle_gamma                90
_cell_volume                     3299.71(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6063
_cell_measurement_temperature    298.87(12)
_cell_measurement_theta_max      73.3960
_cell_measurement_theta_min      6.3480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
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    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8549
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.565
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_min         3.785
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.87(12)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku IP'
_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    -89.00  17.00   0.50    3.00    --    0.00 -37.00-150.00  212
  2  ω    -22.00  89.00   0.50    3.00    --    0.00  57.00  90.00  222
  3  ω    -89.00  18.00   0.50    3.00    --    0.00 -19.00 -60.00  214
  4  ω     24.00 114.00   0.50   14.00    --   94.60 -45.00 150.00  180
  5  ω     75.00 147.00   0.50   14.00    --   94.60  45.00 -90.00  144
  6  ω     19.00 120.00   0.50   14.00    --   94.60 -82.00   0.00  202
  7  ω     13.00 117.00   0.50   14.00    --   94.60 -15.00  90.00  208
  8  ω     36.00  67.50   0.50   14.00    --   94.60 -15.00-150.00   63
  9  ω    111.00 137.00   0.50   14.00    --   94.60  30.00 -60.00   52
 10  ω     12.00 118.00   0.50   14.00    --   94.60 -61.00   0.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0260631000
_diffrn_orient_matrix_UB_12      0.0681017000
_diffrn_orient_matrix_UB_13      0.0693749000
_diffrn_orient_matrix_UB_21      0.0597665000
_diffrn_orient_matrix_UB_22      0.0029506000
_diffrn_orient_matrix_UB_23      -0.0299907000
_diffrn_orient_matrix_UB_31      -0.0097406000
_diffrn_orient_matrix_UB_32      0.2018439000
_diffrn_orient_matrix_UB_33      -0.0229106000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2614
_reflns_number_total             2882
_reflns_odcompleteness_completeness 98.78
_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 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (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         0.199
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.094
_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)+(0.0820P)²+1.2330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1321
_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:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_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 0.43550(2) 0.33795(7) 0.41781(2) 0.04992(19) Uani 1 1 d . . . . .
N1 N 0.47570(6) 0.2154(2) 0.63687(7) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.50286(6) 0.2277(2) 0.52786(7) 0.0382(3) Uani 1 1 d . . . . .
N3 N 0.54471(6) 0.2336(2) 0.42341(7) 0.0448(4) Uani 1 1 d . . . . .
C1 C 0.53332(7) 0.1722(2) 0.63536(9) 0.0417(4) Uani 1 1 d . . . . .
C2 C 0.57149(8) 0.1297(3) 0.69009(10) 0.0517(5) Uani 1 1 d . . . . .
H2 H 0.5595 0.1249 0.7348 0.062 Uiso 1 1 calc R . . . .
C3 C 0.62733(8) 0.0953(3) 0.67543(10) 0.0578(5) Uani 1 1 d . . . . .
H3 H 0.6537 0.0659 0.7109 0.069 Uiso 1 1 calc R . . . .
C4 C 0.64543(8) 0.1036(3) 0.60843(11) 0.0579(5) Uani 1 1 d . . . . .
H4 H 0.6837 0.0800 0.6005 0.070 Uiso 1 1 calc R . . . .
C5 C 0.60842(8) 0.1458(3) 0.55341(10) 0.0494(5) Uani 1 1 d . . . . .
H5 H 0.6208 0.1516 0.5089 0.059 Uiso 1 1 calc R . . . .
C6 C 0.55193(7) 0.1788(2) 0.56817(9) 0.0396(4) Uani 1 1 d . . . . .
C7 C 0.45883(7) 0.2482(2) 0.57331(8) 0.0385(4) Uani 1 1 d . . . . .
C8 C 0.40143(7) 0.3045(2) 0.55161(9) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.35933(8) 0.3192(3) 0.59983(10) 0.0500(5) Uani 1 1 d . . . . .
H9 H 0.3680 0.2862 0.6451 0.060 Uiso 1 1 calc R . . . .
C10 C 0.30545(8) 0.3815(3) 0.58131(12) 0.0619(6) Uani 1 1 d . . . . .
H10 H 0.2778 0.3898 0.6139 0.074 Uiso 1 1 calc R . . . .
C11 C 0.29213(8) 0.4318(4) 0.51459(12) 0.0650(6) Uani 1 1 d . . . . .
H11 H 0.2557 0.4763 0.5024 0.078 Uiso 1 1 calc R . . . .
C12 C 0.33274(8) 0.4164(3) 0.46554(11) 0.0589(5) Uani 1 1 d . . . . .
H12 H 0.3234 0.4489 0.4203 0.071 Uiso 1 1 calc R . . . .
C13 C 0.38727(8) 0.3529(2) 0.48367(9) 0.0437(4) Uani 1 1 d . . . . .
C14 C 0.50040(7) 0.2598(2) 0.45657(8) 0.0386(4) Uani 1 1 d . . . . .
C15 C 0.54247(8) 0.2724(3) 0.35002(9) 0.0485(4) Uani 1 1 d . . . . .
H15A H 0.5247 0.3919 0.3417 0.058 Uiso 1 1 calc R . . . .
H15B H 0.5191 0.1796 0.3262 0.058 Uiso 1 1 calc R . . . .
C16 C 0.60153(8) 0.2723(3) 0.32224(9) 0.0455(4) Uani 1 1 d . . . . .
C17 C 0.64498(9) 0.1627(3) 0.34998(11) 0.0568(5) Uani 1 1 d . . . . .
H17 H 0.6378 0.0843 0.3863 0.068 Uiso 1 1 calc R . . . .
C18 C 0.69915(10) 0.1680(4) 0.32435(13) 0.0712(7) Uani 1 1 d . . . . .
H18 H 0.7280 0.0933 0.3435 0.085 Uiso 1 1 calc R . . . .
C19 C 0.71044(10) 0.2830(4) 0.27075(12) 0.0773(8) Uani 1 1 d . . . . .
H19 H 0.7470 0.2873 0.2539 0.093 Uiso 1 1 calc R . . . .
C20 C 0.66759(11) 0.3913(4) 0.24222(11) 0.0737(7) Uani 1 1 d . . . . .
H20 H 0.6751 0.4685 0.2056 0.088 Uiso 1 1 calc R . . . .
C21 C 0.61305(9) 0.3868(3) 0.26760(9) 0.0579(5) Uani 1 1 d . . . . .
H21 H 0.5842 0.4607 0.2479 0.070 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 C13 1.7529(18) . ?
S1 C14 1.7575(17) . ?
N1 C1 1.385(2) . ?
N1 C7 1.307(2) . ?
N2 C6 1.406(2) . ?
N2 C7 1.398(2) . ?
N2 C14 1.410(2) . ?
N3 C14 1.261(2) . ?
N3 C15 1.459(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C7 C8 1.447(2) . ?
C8 C9 1.397(2) . ?
C8 C13 1.397(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.507(2) . ?
C16 C17 1.380(3) . ?
C16 C21 1.387(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(3) . ?
C21 H21 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
C13 S1 C14 105.99(8) . . ?
C7 N1 C1 105.78(14) . . ?
C6 N2 C14 126.10(13) . . ?
C7 N2 C6 106.06(13) . . ?
C7 N2 C14 127.74(14) . . ?
C14 N3 C15 118.85(15) . . ?
N1 C1 C2 128.46(17) . . ?
N1 C1 C6 110.88(15) . . ?
C2 C1 C6 120.65(17) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.45(18) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.39(18) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.19(18) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 121.8 . . ?
C4 C5 C6 116.40(17) . . ?
C6 C5 H5 121.8 . . ?
C1 C6 N2 104.61(14) . . ?
C5 C6 N2 133.45(16) . . ?
C5 C6 C1 121.92(17) . . ?
N1 C7 N2 112.67(14) . . ?
N1 C7 C8 124.36(14) . . ?
N2 C7 C8 122.95(15) . . ?
C9 C8 C7 119.77(16) . . ?
C13 C8 C7 121.63(15) . . ?
C13 C8 C9 118.55(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.96(19) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.15(18) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.15(18) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 S1 123.33(14) . . ?
C12 C13 S1 116.64(15) . . ?
C12 C13 C8 120.03(17) . . ?
N2 C14 S1 118.25(12) . . ?
N3 C14 S1 122.70(13) . . ?
N3 C14 N2 119.04(15) . . ?
N3 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
N3 C15 C16 111.21(15) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C17 C16 C15 121.93(16) . . ?
C17 C16 C21 118.66(18) . . ?
C21 C16 C15 119.40(18) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.2(2) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?

_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 3.351
_oxdiff_exptl_absorpt_empirical_full_min 0.262
