# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_1
_database_code_depnum_ccdc_archive 'CCDC 1964673'
loop_
_audit_author_name
_audit_author_address
'Prof.Dr.Ng Seik weng'
;Faculty of Science University of Malaya
Malaysia
;
_audit_update_record             
;
2019-11-09 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C1.9 H1.9 Cl0.1 F0.3 N0.1 O0.2 S0.1'
_chemical_formula_sum            'C1.90 H1.90 Cl0.10 F0.30 N0.10 O0.20 S0.10'
_chemical_formula_weight         41.79
_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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.6920(10)
_cell_length_b                   10.4626(12)
_cell_length_c                   12.9164(15)
_cell_angle_alpha                106.067(2)
_cell_angle_beta                 98.907(2)
_cell_angle_gamma                110.261(2)
_cell_volume                     1017.1(2)
_cell_formula_units_Z            20
_cell_measurement_reflns_used    2075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.886
_cell_measurement_theta_min      2.268
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5748
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.71
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2927
_reflns_number_total             4007
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'XS n/a (Sheldrick, 2008)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0870P)²+0.2458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1635
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 N1(H1), C8(H8), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44732(10) 0.29876(8) 0.73703(6) 0.0777(3) Uani 1 1 d . . .
Cl2 Cl -0.07676(11) 0.02263(9) 0.26126(7) 0.0931(3) Uani 1 1 d . . .
N1 N 0.6030(2) 0.50045(18) 0.64480(15) 0.0446(4) Uani 1 1 d . . .
H1 H 0.6234 0.4762 0.5808 0.054 Uiso 1 1 calc R . .
O2 O 0.4849(2) 0.64165(18) 0.59318(13) 0.0615(5) Uani 1 1 d . . .
O3 O 0.5328(2) 0.64734(18) 0.77106(13) 0.0576(4) Uani 1 1 d . . .
F4 F 0.6518(2) 0.24586(17) 0.56430(13) 0.0752(5) Uani 1 1 d . . .
C5 C 0.5354(3) 0.6010(2) 0.66510(18) 0.0462(5) Uani 1 1 d . . .
C6 C 0.6438(3) 0.4306(2) 0.71992(19) 0.0522(5) Uani 1 1 d . . .
F7 F 0.8843(2) 0.4328(2) 0.65272(18) 0.0989(6) Uani 1 1 d . . .
C8 C 0.1638(4) 0.0288(3) 0.4222(2) 0.0678(7) Uani 1 1 d . . .
H8 H 0.1491 -0.0606 0.3724 0.081 Uiso 1 1 calc R . .
C9 C 0.7607(3) 0.5368(3) 0.8359(2) 0.0577(6) Uani 1 1 d . . .
C10 C 0.3025(3) 0.2226(3) 0.6010(2) 0.0636(7) Uani 1 1 d . . .
F11 F 0.7853(3) 0.2755(2) 0.72858(17) 0.1178(8) Uani 1 1 d . . .
C12 C 0.2795(4) 0.0899(3) 0.5264(3) 0.0689(7) Uani 1 1 d . . .
H12 H 0.3433 0.0410 0.5470 0.083 Uiso 1 1 calc R . .
C13 C 0.7406(4) 0.3454(3) 0.6663(2) 0.0695(7) Uani 1 1 d . . .
C14 C 0.8855(3) 0.6689(3) 0.8465(2) 0.0608(6) Uani 1 1 d . . .
H14 H 0.8962 0.6931 0.7831 0.073 Uiso 1 1 calc R . .
C15 C 0.0704(3) 0.1018(3) 0.3930(2) 0.0654(7) Uani 1 1 d . . .
C16 C 0.4830(4) 0.7679(3) 0.8153(2) 0.0660(7) Uani 1 1 d . . .
C17 C 0.2045(3) 0.2922(3) 0.5703(3) 0.0700(7) Uani 1 1 d . . .
H17 H 0.2162 0.3803 0.6205 0.084 Uiso 1 1 calc R . .
C18 C 0.0887(4) 0.2318(3) 0.4651(3) 0.0752(8) Uani 1 1 d . . .
H18 H 0.0241 0.2798 0.4440 0.090 Uiso 1 1 calc R . .
C19 C 0.9943(4) 0.7650(3) 0.9501(3) 0.0775(8) Uani 1 1 d . . .
H19 H 1.0768 0.8537 0.9559 0.093 Uiso 1 1 calc R . .
C20 C 0.7509(5) 0.5041(4) 0.9317(2) 0.0968(12) Uani 1 1 d . . .
H20 H 0.6695 0.4155 0.9270 0.116 Uiso 1 1 calc R . .
C21 C 0.9822(5) 0.7318(4) 1.0439(3) 0.0920(10) Uani 1 1 d . . .
H21 H 1.0562 0.7971 1.1134 0.110 Uiso 1 1 calc R . .
C22 C 0.8619(6) 0.6028(5) 1.0354(3) 0.1172(15) Uani 1 1 d . . .
H22 H 0.8532 0.5800 1.0995 0.141 Uiso 1 1 calc R . .
C1 C 0.5975(6) 0.9023(3) 0.7996(3) 0.1032(12) Uani 1 1 d . . .
H1A H 0.7146 0.9194 0.8272 0.155 Uiso 1 1 calc R . .
H1B H 0.5783 0.9847 0.8402 0.155 Uiso 1 1 calc R . .
H1C H 0.5728 0.8888 0.7213 0.155 Uiso 1 1 calc R . .
C2 C 0.5161(7) 0.7879(5) 0.9384(3) 0.1189(15) Uani 1 1 d . . .
H2A H 0.4503 0.6981 0.9465 0.178 Uiso 1 1 calc R . .
H2B H 0.4837 0.8630 0.9767 0.178 Uiso 1 1 calc R . .
H2C H 0.6353 0.8153 0.9702 0.178 Uiso 1 1 calc R . .
C3 C 0.2971(5) 0.7197(5) 0.7604(4) 0.1218(15) Uani 1 1 d . . .
H3A H 0.2813 0.7115 0.6832 0.183 Uiso 1 1 calc R . .
H3B H 0.2581 0.7901 0.7982 0.183 Uiso 1 1 calc R . .
H3C H 0.2330 0.6268 0.7645 0.183 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 C6 1.877(2) . ?
S1 C10 1.775(3) . ?
Cl2 C15 1.741(3) . ?
N1 H1 0.8600 . ?
N1 C5 1.358(3) . ?
N1 C6 1.438(3) . ?
O2 C5 1.208(3) . ?
O3 C5 1.326(3) . ?
O3 C16 1.470(3) . ?
F4 C13 1.336(3) . ?
C6 C9 1.528(3) . ?
C6 C13 1.530(4) . ?
F7 C13 1.339(4) . ?
C8 H8 0.9300 . ?
C8 C12 1.375(4) . ?
C8 C15 1.370(4) . ?
C9 C14 1.385(4) . ?
C9 C20 1.379(4) . ?
C10 C12 1.380(4) . ?
C10 C17 1.378(4) . ?
F11 C13 1.326(3) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C19 1.379(4) . ?
C15 C18 1.359(4) . ?
C16 C1 1.504(4) . ?
C16 C2 1.512(4) . ?
C16 C3 1.501(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C21 1.358(4) . ?
C20 H20 0.9300 . ?
C20 C22 1.391(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.353(5) . ?
C22 H22 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
C10 S1 C6 102.91(11) . . ?
C5 N1 H1 116.8 . . ?
C5 N1 C6 126.33(18) . . ?
C6 N1 H1 116.8 . . ?
C5 O3 C16 121.74(19) . . ?
O2 C5 N1 122.5(2) . . ?
O2 C5 O3 125.3(2) . . ?
O3 C5 N1 112.21(19) . . ?
N1 C6 S1 112.07(16) . . ?
N1 C6 C9 113.95(19) . . ?
N1 C6 C13 106.1(2) . . ?
C9 C6 S1 108.89(16) . . ?
C9 C6 C13 107.1(2) . . ?
C13 C6 S1 108.43(18) . . ?
C12 C8 H8 120.5 . . ?
C15 C8 H8 120.5 . . ?
C15 C8 C12 119.0(3) . . ?
C14 C9 C6 119.8(2) . . ?
C20 C9 C6 122.3(2) . . ?
C20 C9 C14 117.8(2) . . ?
C12 C10 S1 121.0(2) . . ?
C17 C10 S1 120.2(2) . . ?
C17 C10 C12 118.8(3) . . ?
C8 C12 C10 121.0(3) . . ?
C8 C12 H12 119.5 . . ?
C10 C12 H12 119.5 . . ?
F4 C13 C6 113.7(2) . . ?
F4 C13 F7 105.3(2) . . ?
F7 C13 C6 111.9(2) . . ?
F11 C13 F4 106.8(2) . . ?
F11 C13 C6 111.7(2) . . ?
F11 C13 F7 106.9(2) . . ?
C9 C14 H14 119.7 . . ?
C19 C14 C9 120.7(3) . . ?
C19 C14 H14 119.7 . . ?
C8 C15 Cl2 118.5(2) . . ?
C18 C15 Cl2 120.1(2) . . ?
C18 C15 C8 121.4(3) . . ?
O3 C16 C1 109.8(2) . . ?
O3 C16 C2 101.6(2) . . ?
O3 C16 C3 108.8(2) . . ?
C1 C16 C2 110.6(3) . . ?
C3 C16 C1 113.6(3) . . ?
C3 C16 C2 111.7(3) . . ?
C10 C17 H17 119.8 . . ?
C10 C17 C18 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C15 C18 C17 119.4(3) . . ?
C15 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C14 C19 H19 119.6 . . ?
C21 C19 C14 120.8(3) . . ?
C21 C19 H19 119.6 . . ?
C9 C20 H20 119.8 . . ?
C9 C20 C22 120.5(3) . . ?
C22 C20 H20 119.8 . . ?
C19 C21 H21 120.2 . . ?
C22 C21 C19 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C22 H22 119.7 . . ?
C21 C22 C20 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C16 C1 H1A 109.5 . . ?
C16 C1 H1B 109.5 . . ?
C16 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 C2 H2A 109.5 . . ?
C16 C2 H2B 109.5 . . ?
C16 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 C3 H3A 109.5 . . ?
C16 C3 H3B 109.5 . . ?
C16 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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
S1 C6 C9 C14 -160.3(2) . . . . ?
S1 C6 C9 C20 22.0(3) . . . . ?
S1 C6 C13 F4 61.6(3) . . . . ?
S1 C6 C13 F7 -179.16(18) . . . . ?
S1 C6 C13 F11 -59.3(3) . . . . ?
S1 C10 C12 C8 178.1(2) . . . . ?
S1 C10 C17 C18 -178.6(2) . . . . ?
Cl2 C15 C18 C17 179.0(2) . . . . ?
N1 C6 C9 C14 -34.4(3) . . . . ?
N1 C6 C9 C20 147.9(3) . . . . ?
N1 C6 C13 F4 -59.0(3) . . . . ?
N1 C6 C13 F7 60.3(3) . . . . ?
N1 C6 C13 F11 -179.9(2) . . . . ?
C5 N1 C6 S1 70.2(2) . . . . ?
C5 N1 C6 C9 -54.0(3) . . . . ?
C5 N1 C6 C13 -171.6(2) . . . . ?
C5 O3 C16 C1 -57.9(3) . . . . ?
C5 O3 C16 C2 -174.9(3) . . . . ?
C5 O3 C16 C3 67.1(3) . . . . ?
C6 S1 C10 C12 97.9(2) . . . . ?
C6 S1 C10 C17 -85.4(2) . . . . ?
C6 N1 C5 O2 -170.6(2) . . . . ?
C6 N1 C5 O3 9.6(3) . . . . ?
C6 C9 C14 C19 -178.8(2) . . . . ?
C6 C9 C20 C22 178.8(3) . . . . ?
C8 C15 C18 C17 0.2(4) . . . . ?
C9 C6 C13 F4 179.0(2) . . . . ?
C9 C6 C13 F7 -61.8(3) . . . . ?
C9 C6 C13 F11 58.0(3) . . . . ?
C9 C14 C19 C21 0.5(4) . . . . ?
C9 C20 C22 C21 -0.6(7) . . . . ?
C10 S1 C6 N1 36.2(2) . . . . ?
C10 S1 C6 C9 163.24(17) . . . . ?
C10 S1 C6 C13 -80.58(18) . . . . ?
C10 C17 C18 C15 1.1(4) . . . . ?
C12 C8 C15 Cl2 -179.5(2) . . . . ?
C12 C8 C15 C18 -0.7(4) . . . . ?
C12 C10 C17 C18 -1.9(4) . . . . ?
C13 C6 C9 C14 82.7(3) . . . . ?
C13 C6 C9 C20 -95.1(3) . . . . ?
C14 C9 C20 C22 1.0(5) . . . . ?
C14 C19 C21 C22 -0.1(6) . . . . ?
C15 C8 C12 C10 -0.1(4) . . . . ?
C16 O3 C5 N1 173.09(19) . . . . ?
C16 O3 C5 O2 -6.8(4) . . . . ?
C17 C10 C12 C8 1.4(4) . . . . ?
C19 C21 C22 C20 0.2(7) . . . . ?
C20 C9 C14 C19 -1.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
