# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 2014118'
loop_
_audit_author_name
_audit_author_address
'Guanjie A'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;
_audit_creation_date             2020-07-05
_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 H16 Cl N3 S'
_chemical_formula_sum            'C21 H16 Cl N3 S'
_chemical_formula_weight         377.88
_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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4738(5)
_cell_length_b                   9.6099(6)
_cell_length_c                   12.1060(9)
_cell_angle_alpha                88.370(2)
_cell_angle_beta                 69.823(2)
_cell_angle_gamma                84.352(2)
_cell_volume                     920.81(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4329
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.450
_cell_measurement_theta_min      2.266
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_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    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8701
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.130
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3422
_reflns_number_total             4160
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.024
_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)+(0.0393P)²+0.3707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0991
_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 Me refined with riding coordinates:
 C14(H14A,H14B,H14C)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12),
 C13(H13), C17(H17), C18(H18), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S S 0.09634(5) 0.95101(5) 0.26750(4) 0.03435(13) Uani 1 1 d . . . . .
Cl Cl 0.78661(6) 0.95135(6) 0.05809(5) 0.05295(16) Uani 1 1 d . . . . .
N1 N -0.08228(16) 0.67755(14) 0.58941(12) 0.0288(3) Uani 1 1 d . . . . .
H1 H 0.0234 0.6672 0.5479 0.035 Uiso 1 1 calc R . . . .
C1 C -0.18216(19) 0.75186(16) 0.53922(15) 0.0268(3) Uani 1 1 d . . . . .
N2 N -0.12663(16) 0.82982(14) 0.44474(13) 0.0302(3) Uani 1 1 d . . . . .
C2 C -0.36799(19) 0.74440(16) 0.58689(14) 0.0260(3) Uani 1 1 d . . . . .
N3 N 0.16974(16) 0.77394(14) 0.41397(12) 0.0286(3) Uani 1 1 d . . . . .
C3 C -0.47366(19) 0.86649(17) 0.59737(15) 0.0291(3) Uani 1 1 d . . . . .
H3 H -0.4277 0.9513 0.5758 0.035 Uiso 1 1 calc R . . . .
C4 C -0.6469(2) 0.86302(18) 0.63961(16) 0.0321(4) Uani 1 1 d . . . . .
H4 H -0.7173 0.9454 0.6469 0.039 Uiso 1 1 calc R . . . .
C5 C -0.7157(2) 0.73653(18) 0.67113(16) 0.0330(4) Uani 1 1 d . . . . .
H5 H -0.8323 0.7341 0.7013 0.040 Uiso 1 1 calc R . . . .
C6 C -0.6102(2) 0.61392(18) 0.65753(16) 0.0330(4) Uani 1 1 d . . . . .
H6 H -0.6565 0.5288 0.6760 0.040 Uiso 1 1 calc R . . . .
C7 C -0.4365(2) 0.61676(17) 0.61667(15) 0.0299(4) Uani 1 1 d . . . . .
H7 H -0.3662 0.5343 0.6092 0.036 Uiso 1 1 calc R . . . .
C8 C -0.12868(19) 0.61378(16) 0.70219(14) 0.0266(3) Uani 1 1 d . . . . .
C9 C -0.2509(2) 0.67774(19) 0.80005(16) 0.0368(4) Uani 1 1 d . . . . .
H9 H -0.3081 0.7632 0.7927 0.044 Uiso 1 1 calc R . . . .
C10 C -0.2873(2) 0.6137(2) 0.90877(17) 0.0455(5) Uani 1 1 d . . . . .
H10 H -0.3703 0.6567 0.9738 0.055 Uiso 1 1 calc R . . . .
C11 C -0.2031(2) 0.4871(2) 0.92295(18) 0.0439(5) Uani 1 1 d . . . . .
C12 C -0.0804(2) 0.4262(2) 0.82454(18) 0.0413(4) Uani 1 1 d . . . . .
H12 H -0.0220 0.3414 0.8319 0.050 Uiso 1 1 calc R . . . .
C13 C -0.0426(2) 0.48882(18) 0.71503(16) 0.0324(4) Uani 1 1 d . . . . .
H13 H 0.0412 0.4463 0.6501 0.039 Uiso 1 1 calc R . . . .
C14 C -0.2421(3) 0.4192(3) 1.0423(2) 0.0721(8) Uani 1 1 d . . . . .
H14A H -0.3301 0.4761 1.0997 0.108 Uiso 1 1 calc R . . . .
H14B H -0.2784 0.3283 1.0393 0.108 Uiso 1 1 calc R . . . .
H14C H -0.1425 0.4102 1.0637 0.108 Uiso 1 1 calc R . . . .
C15 C 0.04211(19) 0.83965(17) 0.39078(15) 0.0284(3) Uani 1 1 d . . . . .
C16 C 0.32157(19) 0.80951(16) 0.33352(14) 0.0273(3) Uani 1 1 d . . . . .
C17 C 0.4809(2) 0.76075(17) 0.33566(16) 0.0307(4) Uani 1 1 d . . . . .
H17 H 0.4917 0.6993 0.3939 0.037 Uiso 1 1 calc R . . . .
C18 C 0.6225(2) 0.80467(18) 0.25034(17) 0.0348(4) Uani 1 1 d . . . . .
H18 H 0.7294 0.7727 0.2509 0.042 Uiso 1 1 calc R . . . .
C19 C 0.6054(2) 0.89665(19) 0.16349(16) 0.0349(4) Uani 1 1 d . . . . .
C20 C 0.4498(2) 0.94872(18) 0.15954(15) 0.0324(4) Uani 1 1 d . . . . .
H20 H 0.4405 1.0112 0.1015 0.039 Uiso 1 1 calc R . . . .
C21 C 0.30770(19) 0.90412(17) 0.24564(15) 0.0290(3) 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
S C15 1.7653(17) . ?
S C21 1.7325(16) . ?
Cl C19 1.7412(17) . ?
N1 H1 0.8600 . ?
N1 C1 1.344(2) . ?
N1 C8 1.423(2) . ?
C1 N2 1.319(2) . ?
C1 C2 1.487(2) . ?
N2 C15 1.363(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.394(2) . ?
N3 C15 1.308(2) . ?
N3 C16 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(2) . ?
C8 C13 1.376(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 C12 1.381(3) . ?
C11 C14 1.510(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.393(2) . ?
C16 C21 1.408(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(3) . ?
C19 C20 1.379(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(2) . ?

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
C21 S C15 89.09(8) . . ?
C1 N1 H1 115.8 . . ?
C1 N1 C8 128.44(13) . . ?
C8 N1 H1 115.8 . . ?
N1 C1 C2 120.05(14) . . ?
N2 C1 N1 124.39(14) . . ?
N2 C1 C2 115.51(14) . . ?
C1 N2 C15 120.52(14) . . ?
C3 C2 C1 118.91(14) . . ?
C3 C2 C7 119.89(14) . . ?
C7 C2 C1 121.16(14) . . ?
C15 N3 C16 110.66(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.41(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.89(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.76(15) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.65(16) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.36(15) . . ?
C6 C7 H7 120.3 . . ?
C9 C8 N1 121.86(15) . . ?
C13 C8 N1 118.59(14) . . ?
C13 C8 C9 119.44(16) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.66(17) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.60(17) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C14 121.1(2) . . ?
C12 C11 C10 117.70(18) . . ?
C12 C11 C14 121.2(2) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.44(18) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 120.14(16) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
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 . . ?
N2 C15 S 115.19(12) . . ?
N3 C15 S 115.36(12) . . ?
N3 C15 N2 129.38(15) . . ?
N3 C16 C17 125.01(15) . . ?
N3 C16 C21 115.43(14) . . ?
C17 C16 C21 119.55(14) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.26(16) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.06(15) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 Cl 118.86(13) . . ?
C20 C19 Cl 118.80(14) . . ?
C20 C19 C18 122.32(15) . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.37(16) . . ?
C21 C20 H20 121.3 . . ?
C16 C21 S 109.46(12) . . ?
C20 C21 S 129.11(14) . . ?
C20 C21 C16 121.42(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl C19 C20 C21 -179.34(13) . . . . ?
N1 C1 N2 C15 -0.1(3) . . . . ?
N1 C1 C2 C3 137.53(17) . . . . ?
N1 C1 C2 C7 -44.9(2) . . . . ?
N1 C8 C9 C10 -177.70(16) . . . . ?
N1 C8 C13 C12 177.73(15) . . . . ?
C1 N1 C8 C9 -38.7(2) . . . . ?
C1 N1 C8 C13 145.02(17) . . . . ?
C1 N2 C15 S -178.61(12) . . . . ?
C1 N2 C15 N3 4.7(3) . . . . ?
C1 C2 C3 C4 178.99(16) . . . . ?
C1 C2 C7 C6 -178.11(16) . . . . ?
N2 C1 C2 C3 -45.1(2) . . . . ?
N2 C1 C2 C7 132.50(17) . . . . ?
C2 C1 N2 C15 -177.35(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
N3 C16 C17 C18 -179.81(16) . . . . ?
N3 C16 C21 S 1.00(18) . . . . ?
N3 C16 C21 C20 179.92(15) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C7 2.3(3) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
C7 C2 C3 C4 1.4(3) . . . . ?
C8 N1 C1 N2 166.28(15) . . . . ?
C8 N1 C1 C2 -16.5(2) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C8 C13 C12 1.3(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C14 179.1(2) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
C14 C11 C12 C13 -179.2(2) . . . . ?
C15 S C21 C16 -0.69(13) . . . . ?
C15 S C21 C20 -179.50(17) . . . . ?
C15 N3 C16 C17 178.11(16) . . . . ?
C15 N3 C16 C21 -0.8(2) . . . . ?
C16 N3 C15 S 0.24(18) . . . . ?
C16 N3 C15 N2 176.90(17) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C16 C21 S -177.98(12) . . . . ?
C17 C16 C21 C20 0.9(2) . . . . ?
C17 C18 C19 Cl 179.35(13) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C19 C20 C21 S 178.68(14) . . . . ?
C19 C20 C21 C16 0.0(2) . . . . ?
C21 S C15 N2 -176.87(14) . . . . ?
C21 S C15 N3 0.28(14) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
