# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_LHR086
_database_code_depnum_ccdc_archive 'CCDC 1951504'
loop_
_audit_author_name
_audit_author_address
'Yuan jingmei'
;School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University
China
;
_audit_update_record             
;
2019-09-04 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Cl N4 S'
_chemical_formula_weight         382.90

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   13.793(5)
_cell_length_b                   8.597(3)
_cell_length_c                   16.140(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.275(5)
_cell_angle_gamma                90
_cell_volume                     1854.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3458
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      23.49

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.330
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20869
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.743
_diffrn_reflns_theta_max         26.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3834
_reflns_number_gt                2593
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1588P)²+3.9202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     241
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2914
_refine_ls_wR_factor_gt          0.2577
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.74885(10) 0.38410(17) 0.66119(7) 0.0506(4) Uani 1 1 d . . . . .
Cl1 Cl 0.13461(11) -0.1070(2) 0.49228(11) 0.0717(5) Uani 1 1 d . . . . .
N4 N 0.6853(3) 0.4393(5) 0.4993(2) 0.0437(6) Uani 1 1 d . U . . .
N2 N 0.5166(3) 0.3180(5) 0.4020(3) 0.0469(6) Uani 1 1 d D U . . .
N3 N 0.4757(3) 0.1124(5) 0.6280(3) 0.0448(6) Uani 1 1 d . U . . .
N1 N 0.6140(4) 0.4137(6) 0.2773(3) 0.0599(7) Uani 1 1 d . U . . .
C5 C 0.4976(3) 0.2592(6) 0.4735(3) 0.0430(5) Uani 1 1 d . U . . .
C13 C 0.5684(3) 0.2777(6) 0.5523(3) 0.0425(5) Uani 1 1 d . U . . .
C6 C 0.4075(3) 0.1737(6) 0.4757(3) 0.0431(6) Uani 1 1 d . U . . .
C14 C 0.6600(3) 0.3671(6) 0.5616(3) 0.0421(6) Uani 1 1 d . U . . .
C20 C 0.8245(4) 0.4934(6) 0.6123(3) 0.0472(6) Uani 1 1 d . U . . .
C11 C 0.4023(4) 0.1019(6) 0.5536(3) 0.0439(6) Uani 1 1 d . U . . .
C15 C 0.7781(4) 0.5110(6) 0.5256(3) 0.0462(6) Uani 1 1 d . U . . .
C9 C 0.2391(3) 0.0003(6) 0.4870(3) 0.0459(6) Uani 1 1 d . U . . .
C12 C 0.5524(3) 0.2008(6) 0.6249(3) 0.0440(6) Uani 1 1 d . U . . .
H12 H 0.601026 0.213928 0.675760 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3228(3) 0.1623(6) 0.4066(3) 0.0453(6) Uani 1 1 d . U . . .
H7 H 0.323213 0.214016 0.356126 0.054 Uiso 1 1 calc R U . . .
C19 C 0.9183(4) 0.5596(6) 0.6476(3) 0.0495(7) Uani 1 1 d . U . . .
H19 H 0.948883 0.549383 0.705510 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3167(3) 0.0145(6) 0.5567(3) 0.0449(6) Uani 1 1 d . U . . .
H10 H 0.313500 -0.034106 0.607449 0.054 Uiso 1 1 calc R U . . .
C8 C 0.2399(4) 0.0783(6) 0.4105(3) 0.0469(6) Uani 1 1 d . U . . .
H8 H 0.185116 0.072932 0.363546 0.056 Uiso 1 1 calc R U . . .
C18 C 0.9640(4) 0.6401(6) 0.5940(3) 0.0513(7) Uani 1 1 d . U . . .
H18 H 1.026846 0.683458 0.615887 0.062 Uiso 1 1 calc R U . . .
C17 C 0.9175(4) 0.6580(6) 0.5071(3) 0.0515(7) Uani 1 1 d . U . . .
H17 H 0.949807 0.713015 0.472088 0.062 Uiso 1 1 calc R U . . .
C16 C 0.8246(4) 0.5950(6) 0.4730(3) 0.0497(7) Uani 1 1 d . U . . .
H16 H 0.793317 0.608639 0.415490 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4703(4) 0.2830(7) 0.3127(3) 0.0525(7) Uani 1 1 d . U . . .
H4A H 0.421739 0.362796 0.288793 0.063 Uiso 1 1 calc R U . . .
H4B H 0.435772 0.183969 0.308444 0.063 Uiso 1 1 calc R U . . .
C3 C 0.5523(4) 0.2762(7) 0.2620(3) 0.0569(7) Uani 1 1 d . U . . .
H3A H 0.593715 0.184938 0.279269 0.068 Uiso 1 1 calc R U . . .
H3B H 0.521019 0.267422 0.201432 0.068 Uiso 1 1 calc R U . . .
C1 C 0.5625(5) 0.5509(8) 0.2376(4) 0.0727(11) Uani 1 1 d . U . . .
H1A H 0.544113 0.537440 0.176707 0.109 Uiso 1 1 calc R U . . .
H1B H 0.605773 0.639484 0.251929 0.109 Uiso 1 1 calc R U . . .
H1C H 0.503410 0.566988 0.257854 0.109 Uiso 1 1 calc R U . . .
C2 C 0.7065(5) 0.3944(8) 0.2513(4) 0.0713(11) Uani 1 1 d . U . . .
H2A H 0.746664 0.316073 0.286079 0.107 Uiso 1 1 calc R U . . .
H2B H 0.742418 0.491129 0.258201 0.107 Uiso 1 1 calc R U . . .
H2C H 0.691863 0.363225 0.192410 0.107 Uiso 1 1 calc R U . . .
H2 H 0.567(3) 0.377(6) 0.410(4) 0.066(18) Uiso 1 1 d 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 C20 1.733(5) . ?
S1 C14 1.770(5) . ?
Cl1 C9 1.731(5) . ?
N4 C14 1.301(6) . ?
N4 C15 1.389(6) . ?
N2 C5 1.343(6) . ?
N2 C4 1.457(6) . ?
N2 H2 0.846(10) . ?
N3 C12 1.313(6) . ?
N3 C11 1.370(6) . ?
N1 C3 1.441(7) . ?
N1 C1 1.442(8) . ?
N1 C2 1.448(8) . ?
C5 C13 1.408(6) . ?
C5 C6 1.453(6) . ?
C13 C12 1.410(6) . ?
C13 C14 1.455(6) . ?
C6 C7 1.405(6) . ?
C6 C11 1.418(7) . ?
C20 C15 1.396(7) . ?
C20 C19 1.399(7) . ?
C11 C10 1.410(7) . ?
C15 C16 1.386(7) . ?
C9 C10 1.354(7) . ?
C9 C8 1.407(7) . ?
C12 H12 0.9300 . ?
C7 C8 1.366(7) . ?
C7 H7 0.9300 . ?
C19 C18 1.376(7) . ?
C19 H19 0.9300 . ?
C10 H10 0.9300 . ?
C8 H8 0.9300 . ?
C18 C17 1.399(7) . ?
C18 H18 0.9300 . ?
C17 C16 1.376(7) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C4 C3 1.551(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C20 S1 C14 89.5(2) . . ?
C14 N4 C15 112.2(4) . . ?
C5 N2 C4 130.0(4) . . ?
C5 N2 H2 115(4) . . ?
C4 N2 H2 115(4) . . ?
C12 N3 C11 115.7(4) . . ?
C3 N1 C1 112.9(5) . . ?
C3 N1 C2 112.4(5) . . ?
C1 N1 C2 109.7(5) . . ?
N2 C5 C13 119.7(4) . . ?
N2 C5 C6 124.1(4) . . ?
C13 C5 C6 116.2(4) . . ?
C5 C13 C12 118.8(4) . . ?
C5 C13 C14 123.0(4) . . ?
C12 C13 C14 118.2(4) . . ?
C7 C6 C11 117.3(4) . . ?
C7 C6 C5 124.4(4) . . ?
C11 C6 C5 118.2(4) . . ?
N4 C14 C13 124.3(4) . . ?
N4 C14 S1 113.9(3) . . ?
C13 C14 S1 121.8(3) . . ?
C15 C20 C19 120.9(5) . . ?
C15 C20 S1 109.6(4) . . ?
C19 C20 S1 129.4(4) . . ?
N3 C11 C10 116.6(4) . . ?
N3 C11 C6 124.1(4) . . ?
C10 C11 C6 119.3(4) . . ?
C16 C15 N4 125.1(4) . . ?
C16 C15 C20 120.1(4) . . ?
N4 C15 C20 114.8(4) . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 Cl1 120.3(4) . . ?
C8 C9 Cl1 118.9(4) . . ?
N3 C12 C13 126.6(4) . . ?
N3 C12 H12 116.7 . . ?
C13 C12 H12 116.7 . . ?
C8 C7 C6 122.8(5) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C18 C19 C20 117.9(5) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C9 C10 C11 121.0(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C7 C8 C9 118.6(5) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C19 C18 C17 121.2(5) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C16 C17 C18 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C16 C15 119.2(5) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N2 C4 C3 109.4(4) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C3 C4 110.8(5) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.100

