# 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_vsk5
_database_code_depnum_ccdc_archive 'CCDC 1965348'
loop_
_audit_author_name
_audit_author_address
vishal
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      301(2)
_chemical_formula_weight         312.36

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.5419(6)
_cell_length_b                   15.7313(6)
_cell_length_c                   7.0669(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.8219(17)
_cell_angle_gamma                90
_cell_volume                     1615.83(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9543
_cell_measurement_theta_min      2.945
_cell_measurement_theta_max      27.065
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8374
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            29530
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.945
_diffrn_reflns_theta_max         27.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3531
_reflns_number_gt                2660
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1363P)²+1.0193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3531
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2456
_refine_ls_wR_factor_gt          0.2011
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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
O O 0.50629(12) 0.76232(11) 0.3417(3) 0.0577(5) Uani 1 1 d . . . . .
N1 N 0.41541(13) 0.52227(12) 0.2196(3) 0.0416(5) Uani 1 1 d . . . . .
N2 N 0.53365(12) 0.62115(12) 0.2920(3) 0.0400(5) Uani 1 1 d . . . . .
C1 C 0.35285(15) 0.58876(14) 0.2220(3) 0.0387(5) Uani 1 1 d . . . . .
C2 C 0.25975(16) 0.57158(15) 0.1795(3) 0.0452(5) Uani 1 1 d . . . . .
H2A H 0.2414 0.5166 0.1482 0.054 Uiso 1 1 calc R U . . .
C3 C 0.19558(16) 0.63554(15) 0.1841(3) 0.0437(5) Uani 1 1 d . . . . .
H3A H 0.1343 0.6229 0.1549 0.052 Uiso 1 1 calc R U . . .
C4 C 0.22000(15) 0.71983(14) 0.2318(3) 0.0380(5) Uani 1 1 d . . . . .
C5 C 0.31232(15) 0.73709(14) 0.2717(3) 0.0376(5) Uani 1 1 d . . . . .
H5A H 0.3304 0.7922 0.3027 0.045 Uiso 1 1 calc R U . . .
C6 C 0.37847(14) 0.67238(13) 0.2658(3) 0.0356(5) Uani 1 1 d . . . . .
C7 C 0.47514(15) 0.69193(14) 0.3034(3) 0.0393(5) Uani 1 1 d . . . . .
C8 C 0.50126(15) 0.53941(14) 0.2537(3) 0.0388(5) Uani 1 1 d . . . . .
C9 C 0.14917(15) 0.78714(15) 0.2370(3) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.06144(16) 0.76922(18) 0.3017(4) 0.0495(6) Uani 1 1 d . . . . .
H10A H 0.0472 0.7145 0.3410 0.059 Uiso 1 1 calc R U . . .
C11 C -0.00450(19) 0.8328(2) 0.3076(5) 0.0655(8) Uani 1 1 d . . . . .
H11A H -0.0624 0.8205 0.3528 0.079 Uiso 1 1 calc R U . . .
C12 C 0.0149(2) 0.9138(2) 0.2471(6) 0.0762(10) Uani 1 1 d . . . . .
H12A H -0.0299 0.9559 0.2498 0.091 Uiso 1 1 calc R U . . .
C13 C 0.1011(2) 0.9320(2) 0.1826(5) 0.0699(9) Uani 1 1 d . . . . .
H13A H 0.1146 0.9868 0.1425 0.084 Uiso 1 1 calc R U . . .
C14 C 0.16782(18) 0.86938(17) 0.1773(4) 0.0520(6) Uani 1 1 d . . . . .
H14A H 0.2257 0.8824 0.1332 0.062 Uiso 1 1 calc R U . . .
C15 C 0.63121(16) 0.63537(15) 0.3188(4) 0.0473(6) Uani 1 1 d . . . . .
C16 C 0.6698(2) 0.6356(2) 0.4990(5) 0.0689(8) Uani 1 1 d . . . . .
H16A H 0.6329 0.6301 0.6033 0.083 Uiso 1 1 calc R U . . .
C17 C 0.7637(2) 0.6438(2) 0.5235(7) 0.0927(13) Uani 1 1 d . . . . .
H17A H 0.7901 0.6435 0.6451 0.111 Uiso 1 1 calc R U . . .
C18 C 0.8178(2) 0.6525(2) 0.3730(9) 0.0970(16) Uani 1 1 d . . . . .
H18A H 0.8811 0.6577 0.3910 0.116 Uiso 1 1 calc R U . . .
C19 C 0.7793(3) 0.6535(3) 0.1940(9) 0.1071(17) Uani 1 1 d . . . . .
H19A H 0.8169 0.6598 0.0909 0.128 Uiso 1 1 calc R U . . .
C20 C 0.6840(2) 0.6453(2) 0.1637(6) 0.0790(10) Uani 1 1 d . . . . .
H20A H 0.6575 0.6465 0.0422 0.095 Uiso 1 1 calc R U . . .
C21 C 0.56920(17) 0.46844(15) 0.2586(4) 0.0467(6) Uani 1 1 d . . . . .
H21A H 0.6297 0.4907 0.2852 0.070 Uiso 1 1 calc R U . . .
H21B H 0.5536 0.4287 0.3556 0.070 Uiso 1 1 calc R U . . .
H21C H 0.5680 0.4402 0.1382 0.070 Uiso 1 1 calc R U . . .


_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
O C7 1.223(3) . ?
N1 C8 1.292(3) . ?
N1 C1 1.387(3) . ?
N2 C8 1.393(3) . ?
N2 C7 1.405(3) . ?
N2 C15 1.443(3) . ?
C1 C2 1.404(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.411(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.390(3) . ?
C4 C9 1.479(3) . ?
C5 C6 1.402(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.455(3) . ?
C8 C21 1.490(3) . ?
C9 C14 1.390(4) . ?
C9 C10 1.397(3) . ?
C10 C11 1.387(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.375(4) . ?
C15 C20 1.366(4) . ?
C16 C17 1.377(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.350(7) . ?
C17 H17A 0.9300 . ?
C18 C19 1.367(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.402(5) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C8 N1 C1 118.07(19) . . ?
C8 N2 C7 122.76(18) . . ?
C8 N2 C15 119.57(18) . . ?
C7 N2 C15 117.66(18) . . ?
N1 C1 C2 118.7(2) . . ?
N1 C1 C6 122.8(2) . . ?
C2 C1 C6 118.5(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 C9 121.6(2) . . ?
C3 C4 C9 120.59(19) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 120.74(19) . . ?
C5 C6 C7 120.05(19) . . ?
C1 C6 C7 119.21(19) . . ?
O C7 N2 120.6(2) . . ?
O C7 C6 125.5(2) . . ?
N2 C7 C6 113.91(19) . . ?
N1 C8 N2 123.2(2) . . ?
N1 C8 C21 118.9(2) . . ?
N2 C8 C21 117.85(19) . . ?
C14 C9 C10 118.4(2) . . ?
C14 C9 C4 121.1(2) . . ?
C10 C9 C4 120.5(2) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C9 C14 C13 120.7(3) . . ?
C9 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C16 C15 C20 121.3(3) . . ?
C16 C15 N2 119.5(2) . . ?
C20 C15 N2 119.2(3) . . ?
C15 C16 C17 119.4(4) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C18 C19 C20 120.9(4) . . ?
C18 C19 H19A 119.5 . . ?
C20 C19 H19A 119.5 . . ?
C15 C20 C19 117.7(4) . . ?
C15 C20 H20A 121.1 . . ?
C19 C20 H20A 121.1 . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.072

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_vsk6
_database_code_depnum_ccdc_archive 'CCDC 1965475'
loop_
_audit_author_name
_audit_author_address
vishal
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H11 Cl N2 O'
_chemical_formula_sum            'C15 H11 Cl N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         270.71

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'
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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.6237(6)
_cell_length_b                   5.6260(2)
_cell_length_c                   12.7950(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.1143(15)
_cell_angle_gamma                90
_cell_volume                     1255.94(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      3.216
_cell_measurement_theta_max      27.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8677
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            24365
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.263
_diffrn_reflns_theta_max         27.916
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2977
_reflns_number_gt                2710
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0928P)²+1.0278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1508
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl Cl 0.15036(3) 0.57824(8) 0.51488(3) 0.02924(17) Uani 1 1 d . . . . .
O O 0.20276(7) 0.5654(2) 0.20977(10) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.24872(7) 0.3761(2) 0.36346(10) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.37318(8) 0.4428(3) 0.45548(11) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.25510(9) 0.5375(3) 0.28177(12) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.32763(9) 0.6680(3) 0.29471(13) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.34076(10) 0.8429(3) 0.22171(14) 0.0268(4) Uani 1 1 d . . . . .
H3A H 0.3040 0.8701 0.1611 0.032 Uiso 1 1 calc R U . . .
C4 C 0.40711(11) 0.9760(4) 0.23791(16) 0.0319(4) Uani 1 1 d . . . . .
H4A H 0.4164 1.0942 0.1882 0.038 Uiso 1 1 calc R U . . .
C5 C 0.46073(11) 0.9361(3) 0.32789(17) 0.0305(4) Uani 1 1 d . . . . .
H5A H 0.5056 1.0316 0.3400 0.037 Uiso 1 1 calc R U . . .
C6 C 0.44951(9) 0.7607(3) 0.39906(14) 0.0263(4) Uani 1 1 d . . . . .
H6A H 0.4870 0.7334 0.4588 0.032 Uiso 1 1 calc R U . . .
C7 C 0.38241(9) 0.6218(3) 0.38324(13) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.30907(9) 0.3275(3) 0.44376(12) 0.0203(3) Uani 1 1 d . . . . .
C9 C 0.29787(10) 0.1274(3) 0.51716(14) 0.0274(4) Uani 1 1 d . . . . .
H9A H 0.2466 0.0592 0.4977 0.041 Uiso 1 1 calc R U . . .
H9B H 0.3366 0.0046 0.5121 0.041 Uiso 1 1 calc R U . . .
H9C H 0.3030 0.1873 0.5897 0.041 Uiso 1 1 calc R U . . .
C10 C 0.17554(9) 0.2624(3) 0.36291(12) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.12487(10) 0.3427(3) 0.42948(13) 0.0234(3) Uani 1 1 d . . . . .
C12 C 0.05418(10) 0.2326(4) 0.42825(16) 0.0320(4) Uani 1 1 d . . . . .
H12A H 0.0197 0.2856 0.4741 0.038 Uiso 1 1 calc R U . . .
C13 C 0.03438(11) 0.0453(4) 0.35985(18) 0.0365(5) Uani 1 1 d . . . . .
H13A H -0.0141 -0.0296 0.3586 0.044 Uiso 1 1 calc R U . . .
C14 C 0.08442(12) -0.0343(4) 0.29311(17) 0.0348(4) Uani 1 1 d . . . . .
H14A H 0.0704 -0.1637 0.2467 0.042 Uiso 1 1 calc R U . . .
C15 C 0.15492(11) 0.0752(3) 0.29428(14) 0.0264(4) Uani 1 1 d . . . . .
H15A H 0.1891 0.0220 0.2481 0.032 Uiso 1 1 calc R U . . .


_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
Cl C11 1.7360(19) . ?
O C1 1.218(2) . ?
N1 C8 1.398(2) . ?
N1 C1 1.401(2) . ?
N1 C10 1.439(2) . ?
N2 C8 1.293(2) . ?
N2 C7 1.392(2) . ?
C1 C2 1.463(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.379(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.401(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.376(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.408(2) . ?
C6 H6A 0.9500 . ?
C8 C9 1.497(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.387(2) . ?
C10 C11 1.393(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.383(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?

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 N1 C1 122.85(13) . . ?
C8 N1 C10 120.35(13) . . ?
C1 N1 C10 116.79(13) . . ?
C8 N2 C7 117.91(14) . . ?
O C1 N1 121.03(15) . . ?
O C1 C2 125.26(15) . . ?
N1 C1 C2 113.68(13) . . ?
C3 C2 C7 120.60(15) . . ?
C3 C2 C1 120.12(15) . . ?
C7 C2 C1 119.23(15) . . ?
C4 C3 C2 119.89(17) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 119.73(17) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C6 C5 C4 121.05(17) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 119.94(16) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
N2 C7 C2 122.53(15) . . ?
N2 C7 C6 118.73(15) . . ?
C2 C7 C6 118.73(16) . . ?
N2 C8 N1 123.29(15) . . ?
N2 C8 C9 119.66(14) . . ?
N1 C8 C9 117.03(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.00(16) . . ?
C15 C10 N1 119.68(15) . . ?
C11 C10 N1 120.30(15) . . ?
C12 C11 C10 119.98(17) . . ?
C12 C11 Cl 119.96(15) . . ?
C10 C11 Cl 120.06(13) . . ?
C13 C12 C11 119.52(18) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 120.70(18) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C15 C14 C13 119.84(19) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C10 119.95(18) . . ?
C14 C15 H15A 120.0 . . ?
C10 C15 H15A 120.0 . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.101

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_vskp3oac
_database_code_depnum_ccdc_archive 'CCDC 1965350'
loop_
_audit_author_name
_audit_author_address
vishal
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H7 N O S'
_chemical_formula_sum            'C9 H7 N O S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      285(2)
_chemical_formula_weight         177.22

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'
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      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                   5.7146(8)
_cell_length_b                   10.4692(19)
_cell_length_c                   13.978(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.873(6)
_cell_angle_gamma                90
_cell_volume                     828.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    285(2)
_cell_measurement_reflns_used    6344
_cell_measurement_theta_min      2.942
_cell_measurement_theta_max      26.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.334
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_T_max  0.9268
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            11618
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.528
_diffrn_reflns_theta_max         26.721
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             1644
_reflns_number_gt                1242
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0546P)²+1.9361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1644
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
S S 1.12209(18) 0.60442(11) 0.32181(8) 0.0461(3) Uani 1 1 d . . . . .
O O 1.0591(7) 0.8825(3) 0.3571(3) 0.0724(10) Uani 1 1 d . . . . .
N N 0.7563(5) 0.6052(3) 0.4132(2) 0.0344(7) Uani 1 1 d . . . . .
C1 C 0.9936(6) 0.4605(4) 0.3420(2) 0.0346(8) Uani 1 1 d . . . . .
C2 C 1.0567(7) 0.3375(4) 0.3164(3) 0.0441(9) Uani 1 1 d . . . . .
H2A H 1.1853 0.3250 0.2832 0.053 Uiso 1 1 calc R U . . .
C3 C 0.9266(8) 0.2356(4) 0.3407(3) 0.0482(10) Uani 1 1 d . . . . .
H3A H 0.9662 0.1533 0.3235 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7341(7) 0.2547(4) 0.3912(3) 0.0466(10) Uani 1 1 d . . . . .
H4A H 0.6476 0.1845 0.4073 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6706(7) 0.3743(4) 0.4174(3) 0.0401(9) Uani 1 1 d . . . . .
H5A H 0.5431 0.3856 0.4514 0.048 Uiso 1 1 calc R U . . .
C6 C 0.8004(6) 0.4794(3) 0.3924(2) 0.0315(7) Uani 1 1 d . . . . .
C7 C 0.9080(6) 0.6786(4) 0.3799(3) 0.0378(8) Uani 1 1 d . . . . .
C8 C 0.9081(7) 0.8204(4) 0.3887(3) 0.0473(10) Uani 1 1 d . . . . .
C9 C 0.7165(9) 0.8799(4) 0.4366(4) 0.0604(12) Uani 1 1 d . . . . .
H9A H 0.6160 0.8141 0.4562 0.091 Uiso 1 1 calc R U . . .
H9B H 0.7854 0.9272 0.4922 0.091 Uiso 1 1 calc R U . . .
H9C H 0.6251 0.9364 0.3921 0.091 Uiso 1 1 calc R U . . .


_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 C1 1.716(4) . ?
S C7 1.741(4) . ?
O C8 1.211(5) . ?
N C7 1.292(5) . ?
N C6 1.379(5) . ?
C1 C6 1.403(5) . ?
C1 C2 1.397(5) . ?
C2 C3 1.369(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.401(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(5) . ?
C5 H5A 0.9300 . ?
C7 C8 1.490(6) . ?
C8 C9 1.495(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C1 S C7 88.36(18) . . ?
C7 N C6 109.9(3) . . ?
C6 C1 C2 120.4(3) . . ?
C6 C1 S 110.0(3) . . ?
C2 C1 S 129.5(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
N C6 C5 125.4(3) . . ?
N C6 C1 114.8(3) . . ?
C5 C6 C1 119.8(3) . . ?
N C7 C8 123.8(3) . . ?
N C7 S 116.8(3) . . ?
C8 C7 S 119.4(3) . . ?
O C8 C7 119.8(4) . . ?
O C8 C9 122.8(4) . . ?
C7 C8 C9 117.3(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.072

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

