# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_rkp_ap_171_0807_0m
_database_code_depnum_ccdc_archive 'CCDC 2333198'
loop_
_audit_author_name
_audit_author_address
'Anoop Yadav'
;IIT Roorkee
India
;
_audit_update_record             
;
2024-02-16 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_GOODF01_rkp_ap_171_0807_0m  
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: The crystal is of good quality
;
# Added during the CSD deposition process: Friday 16 February 2024 01:58 AM
# end Validation Reply Form

_audit_creation_date             2024-02-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.302
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.0955(6)
_cell_length_b                   6.0166(3)
_cell_length_c                   15.1711(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.195(1)
_cell_angle_gamma                90
_cell_volume                     1252.65(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      2.76
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1323 before and 0.0795 after correction.
The Ratio of minimum to maximum transmission is 0.8643.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             528.319
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.037
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.9977
_diffrn_reflns_Laue_measured_fraction_max 0.9977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32543
_diffrn_reflns_point_group_measured_fraction_full 0.9977
_diffrn_reflns_point_group_measured_fraction_max 0.9977
_diffrn_reflns_theta_full        25.0182
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.76
_diffrn_ambient_temperature      101.00
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1900
_reflns_number_total             2191
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3829
_refine_diff_density_min         -0.3120
_refine_diff_density_rms         0.0531
_refine_ls_d_res_high            0.8403
_refine_ls_d_res_low             7.3853
_refine_ls_goodness_of_fit_ref   0.5520
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      0.5520
_refine_ls_shift/su_max          0.0299
_refine_ls_shift/su_mean         0.0068
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1577P)²+2.4630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1373
_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:
 C00C(H00C), C00D(H00D), C00H(H00H), C00G(H00G), C00E(H00E), C00F(H00F),
 C00I(H00I), C00A(H00A), C004(H004), N002(H002), N003(H003)
2.b Idealised Me refined as rotating group:
 C00J(H00b,H00j,H00k)
;
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_refinement_flags_posn
O001 O 0.38566(8) 0.16614(18) 0.45066(7) 0.0257(3) Uani 1.000000 .
N002 N 0.54269(9) 0.1825(2) 0.42708(9) 0.0230(3) Uani 1.000000 .
N003 N 0.28432(9) 0.5537(2) 0.39351(8) 0.0236(3) Uani 1.000000 .
C004 C 0.36572(11) 0.6163(3) 0.36834(10) 0.0222(4) Uani 1.000000 .
C005 C 0.45153(11) 0.2647(3) 0.42284(10) 0.0215(4) Uani 1.000000 .
C006 C 0.59851(11) 0.3360(3) 0.39163(10) 0.0220(4) Uani 1.000000 .
C007 C 0.44629(11) 0.4839(3) 0.38074(10) 0.0214(4) Uani 1.000000 .
C008 C 0.19740(11) 0.6760(3) 0.38561(10) 0.0220(4) Uani 1.000000 .
C009 C 0.54119(11) 0.5243(3) 0.36092(10) 0.0217(4) Uani 1.000000 .
C00A C 0.18553(11) 0.8893(3) 0.34972(10) 0.0254(4) Uani 1.000000 .
C00B C 0.01878(11) 0.8996(3) 0.36818(10) 0.0265(4) Uani 1.000000 .
C00C C 0.69457(11) 0.3188(3) 0.38573(10) 0.0256(4) Uani 1.000000 .
C00D C 0.73427(12) 0.4964(3) 0.34767(11) 0.0277(4) Uani 1.000000 .
C00E C 0.12072(11) 0.5766(3) 0.41439(11) 0.0255(4) Uani 1.000000 .
C00F C 0.03292(12) 0.6877(3) 0.40559(11) 0.0281(4) Uani 1.000000 .
C00G C 0.58137(11) 0.6981(3) 0.32153(10) 0.0247(4) Uani 1.000000 .
C00H C 0.67808(12) 0.6830(3) 0.31537(11) 0.0284(4) Uani 1.000000 .
C00I C 0.09656(12) 0.9967(3) 0.34023(11) 0.0272(4) Uani 1.000000 .
C00J C -0.07680(12) 1.0202(3) 0.35893(13) 0.0367(5) Uani 1.000000 .
H00C H 0.73216(11) 0.1905(3) 0.40689(10) 0.0307(5) Uiso 1.000000 R
H00D H 0.80049(12) 0.4907(3) 0.34359(11) 0.0332(5) Uiso 1.000000 R
H00H H 0.70637(12) 0.8014(3) 0.28879(11) 0.0341(5) Uiso 1.000000 R
H00G H 0.54346(11) 0.8252(3) 0.29916(10) 0.0296(5) Uiso 1.000000 R
H00E H 0.12852(11) 0.4320(3) 0.44018(11) 0.0306(5) Uiso 1.000000 R
H00F H -0.01880(12) 0.6176(3) 0.42557(11) 0.0337(5) Uiso 1.000000 R
H00I H 0.08858(12) 1.1407(3) 0.31388(11) 0.0327(5) Uiso 1.000000 R
H00A H 0.23805(11) 0.9614(3) 0.33174(10) 0.0305(5) Uiso 1.000000 R
H004 H 0.36725(11) 0.7579(3) 0.34093(10) 0.0266(4) Uiso 1.000000 R
H00b H -0.1291(2) 0.9334(12) 0.3204(8) 0.0551(7) Uiso 1.000000 GR
H00j H -0.0907(5) 1.039(2) 0.41889(17) 0.0551(7) Uiso 1.000000 GR
H00k H -0.0727(4) 1.1663(10) 0.3315(9) 0.0551(7) Uiso 1.000000 GR
H002 H 0.56341(9) 0.0513(2) 0.44902(9) 0.0276(4) Uiso 1.000000 R
H003 H 0.28533(9) 0.4206(2) 0.41778(8) 0.0283(4) Uiso 1.000000 R


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
O001 C005 1.2535(19) . ?
N002 C005 1.365(2) . ?
N002 C006 1.398(2) . ?
N002 H002 0.8800 . ?
N003 C004 1.343(2) . ?
N003 C008 1.411(2) . ?
N003 H003 0.8800 . ?
C004 C007 1.365(2) . ?
C004 H004 0.9500 . ?
C005 C007 1.460(2) . ?
C006 C009 1.408(2) . ?
C006 C00C 1.381(2) . ?
C007 C009 1.457(2) . ?
C008 C00A 1.389(2) . ?
C008 C00E 1.390(2) . ?
C009 C00G 1.388(2) . ?
C00A C00I 1.389(2) . ?
C00A H00A 0.9500 . ?
C00B C00F 1.391(2) . ?
C00B C00I 1.391(2) . ?
C00B C00J 1.508(2) . ?
C00C C00D 1.391(2) . ?
C00C H00C 0.9500 . ?
C00D C00H 1.397(2) . ?
C00D H00D 0.9500 . ?
C00E C00F 1.386(2) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00G C00H 1.390(2) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J H00b 0.9800 . ?
C00J H00j 0.9800 . ?
C00J H00k 0.9800 . ?

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
C006 N002 C005 110.42(13) . . ?
H002 N002 C005 124.79(9) . . ?
H002 N002 C006 124.79(8) . . ?
C008 N003 C004 127.66(14) . . ?
H003 N003 C004 116.17(9) . . ?
H003 N003 C008 116.17(9) . . ?
C007 C004 N003 122.33(15) . . ?
H004 C004 N003 118.83(9) . . ?
H004 C004 C007 118.83(9) . . ?
N002 C005 O001 125.06(15) . . ?
C007 C005 O001 127.41(14) . . ?
C007 C005 N002 107.53(13) . . ?
C009 C006 N002 109.15(13) . . ?
C00C C006 N002 128.44(14) . . ?
C00C C006 C009 122.40(15) . . ?
C005 C007 C004 123.03(14) . . ?
C009 C007 C004 130.44(15) . . ?
C009 C007 C005 106.49(13) . . ?
C00A C008 N003 122.67(15) . . ?
C00E C008 N003 118.13(14) . . ?
C00E C008 C00A 119.20(15) . . ?
C007 C009 C006 106.39(14) . . ?
C00G C009 C006 119.28(14) . . ?
C00G C009 C007 134.33(14) . . ?
C00I C00A C008 119.71(15) . . ?
H00A C00A C008 120.15(9) . . ?
H00A C00A C00I 120.15(10) . . ?
C00I C00B C00F 117.36(15) . . ?
C00J C00B C00F 121.36(16) . . ?
C00J C00B C00I 121.28(16) . . ?
C00D C00C C006 117.56(15) . . ?
H00C C00C C006 121.22(10) . . ?
H00C C00C C00D 121.22(9) . . ?
C00H C00D C00C 120.88(15) . . ?
H00D C00D C00C 119.56(9) . . ?
H00D C00D C00H 119.56(10) . . ?
C00F C00E C008 120.24(15) . . ?
H00E C00E C008 119.88(9) . . ?
H00E C00E C00F 119.88(10) . . ?
C00E C00F C00B 121.53(16) . . ?
H00F C00F C00B 119.23(9) . . ?
H00F C00F C00E 119.23(10) . . ?
C00H C00G C009 118.86(15) . . ?
H00G C00G C009 120.57(9) . . ?
H00G C00G C00H 120.57(10) . . ?
C00G C00H C00D 121.00(16) . . ?
H00H C00H C00D 119.50(10) . . ?
H00H C00H C00G 119.50(10) . . ?
C00B C00I C00A 121.93(16) . . ?
H00I C00I C00A 119.03(10) . . ?
H00I C00I C00B 119.03(10) . . ?
H00b C00J C00B 109.5 . . ?
H00j C00J C00B 109.5 . . ?
H00j C00J H00b 109.5 . . ?
H00k C00J C00B 109.5 . . ?
H00k C00J H00b 109.5 . . ?
H00k C00J H00j 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
O001 C005 N002 C006 -178.99(16) . . . . ?
O001 C005 C007 C004 1.90(19) . . . . ?
O001 C005 C007 C009 179.78(17) . . . . ?
N002 C005 C007 C004 -178.07(12) . . . . ?
N002 C005 C007 C009 -0.19(13) . . . . ?
N002 C006 C009 C007 1.25(13) . . . . ?
N002 C006 C009 C00G -179.02(12) . . . . ?
N002 C006 C00C C00D -179.67(16) . . . . ?
N003 C004 C007 C005 -0.52(17) . . . . ?
N003 C004 C007 C009 -177.85(13) . . . . ?
N003 C008 C00A C00I 177.19(15) . . . . ?
N003 C008 C00E C00F -178.15(14) . . . . ?
C004 C007 C009 C006 177.02(18) . . . . ?
C004 C007 C009 C00G -2.7(2) . . . . ?
C005 C007 C009 C006 -0.65(13) . . . . ?
C005 C007 C009 C00G 179.68(12) . . . . ?
C006 C009 C00G C00H -1.41(16) . . . . ?
C006 C00C C00D C00H -1.05(17) . . . . ?
C007 C009 C00G C00H 178.23(18) . . . . ?
C008 C00A C00I C00B 1.94(18) . . . . ?
C008 C00E C00F C00B -0.01(18) . . . . ?
C009 C00G C00H C00D 0.32(18) . . . . ?
C00A C00I C00B C00F -0.65(19) . . . . ?
C00A C00I C00B C00J 178.90(17) . . . . ?
C00C C00D C00H C00G 0.95(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        (Z)-3-((p-tolylamino)methylene)indolin-2-one
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_rkp_pd_131_0041_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333319'
loop_
_audit_author_name
_audit_author_address
'POOJA DAHIYA'
;IIT Roorkee
India
;
_audit_update_record             
;
2024-02-16 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_rkp_pd_131_0041_0m_a 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: This was the best crystal grown.
;
_vrf_PLAT088_rkp_pd_131_0041_0m_a 
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.12 Note
RESPONSE: We got  only this best crystal
;
# Added during the CSD deposition process: Friday 16 February 2024 02:13 PM
# end Validation Reply Form

_audit_creation_date             2024-02-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_chemical_formula_moiety         'C20 H14 Cl N O2'
_chemical_formula_sum            'C20 H14 Cl N O2'
_chemical_formula_weight         335.792
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.6971(12)
_cell_length_b                   3.9784(3)
_cell_length_c                   25.694(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.365(2)
_cell_angle_gamma                90
_cell_volume                     1498.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5404
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.812
_cell_measurement_theta_min      2.780
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.5081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1498 before and 0.0845 after correction.
The Ratio of minimum to maximum transmission is 0.6824.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             696.993
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19469
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 1.0000
_diffrn_reflns_theta_full        20.8731
_diffrn_reflns_theta_max         20.87
_diffrn_reflns_theta_min         1.39
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              3
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                1367
_reflns_number_total             1552
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2193
_refine_diff_density_min         -0.2146
_refine_diff_density_rms         0.0488
_refine_ls_d_res_high            0.9974
_refine_ls_d_res_low             14.6545
_refine_ls_goodness_of_fit_ref   1.0572
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.0572
_refine_ls_shift/su_max          -0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+1.0284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0823
_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:
 N004(H004), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00c,H00e,H00h)
;
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_refinement_flags_posn
Cl01 Cl 0.23198(4) 1.26039(17) 0.30706(2) 0.0208(3) Uani 1.000000 .
O002 O 0.04007(11) 1.3974(4) 0.30919(6) 0.0184(5) Uani 1.000000 .
O003 O 0.15868(12) 0.3337(5) 0.57254(7) 0.0215(5) Uani 1.000000 .
N004 N 0.18865(14) 0.7099(5) 0.48468(8) 0.0165(6) Uani 1.000000 .
H004 H 0.14951(14) 0.6044(5) 0.50318(8) 0.0198(7) Uiso 1.000000 R
C005 C 0.15153(17) 0.8768(6) 0.43956(10) 0.0147(7) Uani 1.000000 .
C006 C 0.07210(17) 1.2200(6) 0.35249(10) 0.0144(7) Uani 1.000000 .
C007 C 0.39126(17) 0.3050(6) 0.61869(10) 0.0130(7) Uani 1.000000 .
C008 C 0.30054(17) 0.2161(6) 0.62604(10) 0.0149(7) Uani 1.000000 .
C009 C 0.46516(17) 0.2197(6) 0.65350(10) 0.0154(7) Uani 1.000000 .
C00A C 0.27689(17) 0.6928(6) 0.50283(10) 0.0142(7) Uani 1.000000 .
H00A H 0.32124(17) 0.8006(6) 0.48358(10) 0.0171(8) Uiso 1.000000 R
C00B C 0.44414(17) 0.0294(7) 0.69766(10) 0.0174(7) Uani 1.000000 .
H00B H 0.49177(17) -0.0393(7) 0.72245(10) 0.0209(8) Uiso 1.000000 R
C00C C 0.39828(16) 0.4961(6) 0.57242(9) 0.0128(6) Uani 1.000000 .
C00D C 0.48330(17) 0.6071(6) 0.56200(10) 0.0168(7) Uani 1.000000 .
H00D H 0.49106(17) 0.7391(6) 0.53185(10) 0.0202(8) Uiso 1.000000 R
C00E C 0.16442(17) 1.1446(6) 0.35702(10) 0.0143(7) Uani 1.000000 .
C00F C 0.05847(17) 0.9386(6) 0.43433(10) 0.0163(7) Uani 1.000000 .
H00F H 0.02113(17) 0.8627(6) 0.46055(10) 0.0195(8) Uiso 1.000000 R
C00G C 0.20489(17) 0.9752(6) 0.39979(10) 0.0152(7) Uani 1.000000 .
H00G H 0.26836(17) 0.9267(6) 0.40196(10) 0.0182(8) Uiso 1.000000 R
C00H C 0.24342(18) 0.3551(6) 0.58057(10) 0.0164(7) Uani 1.000000 .
C00I C 0.35509(18) -0.0567(7) 0.70493(10) 0.0193(7) Uani 1.000000 .
H00I H 0.34275(18) -0.1828(7) 0.73498(10) 0.0231(8) Uiso 1.000000 R
C00J C 0.01936(17) 1.1091(6) 0.39145(10) 0.0166(7) Uani 1.000000 .
H00J H -0.04448(17) 1.1507(6) 0.38867(10) 0.0199(8) Uiso 1.000000 R
C00K C 0.55196(17) 0.3347(7) 0.64085(10) 0.0172(7) Uani 1.000000 .
H00K H 0.60482(17) 0.2817(7) 0.66292(10) 0.0206(8) Uiso 1.000000 R
C00L C 0.28191(18) 0.0361(7) 0.66933(10) 0.0189(7) Uani 1.000000 .
H00L H 0.22104(18) -0.0248(7) 0.67522(10) 0.0226(8) Uiso 1.000000 R
C00M C 0.30534(16) 0.5280(7) 0.54751(10) 0.0141(6) Uani 1.000000 .
C00N C 0.55951(17) 0.5229(7) 0.59669(10) 0.0170(7) Uani 1.000000 .
H00N H 0.61820(17) 0.5999(7) 0.58903(10) 0.0204(8) Uiso 1.000000 R
C00O C -0.05666(16) 1.4429(7) 0.30142(10) 0.0214(7) Uani 1.000000 .
H00c H -0.07097(18) 1.579(3) 0.2701(4) 0.0321(11) Uiso 1.000000 GR
H00e H -0.08645(18) 1.2233(8) 0.2970(6) 0.0321(11) Uiso 1.000000 GR
H00h H -0.0788(2) 1.557(3) 0.3318(3) 0.0321(11) Uiso 1.000000 GR


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
Cl01 C00E 1.744(3) . ?
O002 C006 1.370(3) . ?
O002 C00O 1.432(3) . ?
O003 C00H 1.250(3) . ?
N004 H004 0.8800 . ?
N004 C005 1.409(3) . ?
N004 C00A 1.346(3) . ?
C005 C00F 1.386(4) . ?
C005 C00G 1.391(3) . ?
C006 C00E 1.386(4) . ?
C006 C00J 1.384(4) . ?
C007 C008 1.406(4) . ?
C007 C009 1.395(4) . ?
C007 C00C 1.422(4) . ?
C008 C00H 1.492(4) . ?
C008 C00L 1.368(4) . ?
C009 C00B 1.418(4) . ?
C009 C00K 1.416(4) . ?
C00A H00A 0.9500 . ?
C00A C00M 1.360(3) . ?
C00B H00B 0.9500 . ?
C00B C00I 1.379(4) . ?
C00C C00D 1.371(3) . ?
C00C C00M 1.469(3) . ?
C00D H00D 0.9500 . ?
C00D C00N 1.418(3) . ?
C00E C00G 1.384(3) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.381(3) . ?
C00G H00G 0.9500 . ?
C00H C00M 1.463(4) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.407(4) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00K C00N 1.371(4) . ?
C00L H00L 0.9500 . ?
C00N H00N 0.9500 . ?
C00O H00c 0.9800 . ?
C00O H00e 0.9800 . ?
C00O H00h 0.9800 . ?

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
C00O O002 C006 117.03(19) . . ?
C005 N004 H004 116.16(13) . . ?
C00A N004 H004 116.16(14) . . ?
C00A N004 C005 127.7(2) . . ?
C00F C005 N004 118.7(2) . . ?
C00G C005 N004 122.2(2) . . ?
C00G C005 C00F 119.1(2) . . ?
C00E C006 O002 117.0(2) . . ?
C00J C006 O002 125.1(2) . . ?
C00J C006 C00E 118.0(2) . . ?
C009 C007 C008 123.5(2) . . ?
C00C C007 C008 112.1(2) . . ?
C00C C007 C009 124.3(2) . . ?
C00H C008 C007 106.5(2) . . ?
C00L C008 C007 119.4(2) . . ?
C00L C008 C00H 134.0(2) . . ?
C00B C009 C007 115.9(2) . . ?
C00K C009 C007 116.4(2) . . ?
C00K C009 C00B 127.7(2) . . ?
H00A C00A N004 118.55(14) . . ?
C00M C00A N004 122.9(2) . . ?
C00M C00A H00A 118.55(14) . . ?
H00B C00B C009 119.74(15) . . ?
C00I C00B C009 120.5(2) . . ?
C00I C00B H00B 119.74(16) . . ?
C00D C00C C007 117.5(2) . . ?
C00M C00C C007 106.6(2) . . ?
C00M C00C C00D 135.9(2) . . ?
H00D C00D C00C 120.35(15) . . ?
C00N C00D C00C 119.3(2) . . ?
C00N C00D H00D 120.35(15) . . ?
C006 C00E Cl01 119.3(2) . . ?
C00G C00E Cl01 118.61(19) . . ?
C00G C00E C006 122.1(2) . . ?
H00F C00F C005 119.60(15) . . ?
C00J C00F C005 120.8(2) . . ?
C00J C00F H00F 119.60(15) . . ?
C00E C00G C005 119.2(2) . . ?
H00G C00G C005 120.40(15) . . ?
H00G C00G C00E 120.40(14) . . ?
C008 C00H O003 126.7(2) . . ?
C00M C00H O003 126.3(2) . . ?
C00M C00H C008 106.9(2) . . ?
H00I C00I C00B 118.89(16) . . ?
C00L C00I C00B 122.2(2) . . ?
C00L C00I H00I 118.89(15) . . ?
C00F C00J C006 120.8(2) . . ?
H00J C00J C006 119.62(15) . . ?
H00J C00J C00F 119.62(15) . . ?
H00K C00K C009 120.08(15) . . ?
C00N C00K C009 119.8(2) . . ?
C00N C00K H00K 120.08(15) . . ?
C00I C00L C008 118.4(2) . . ?
H00L C00L C008 120.80(15) . . ?
H00L C00L C00I 120.80(15) . . ?
C00C C00M C00A 128.7(2) . . ?
C00H C00M C00A 123.5(2) . . ?
C00H C00M C00C 107.8(2) . . ?
C00K C00N C00D 122.7(2) . . ?
H00N C00N C00D 118.67(15) . . ?
H00N C00N C00K 118.67(15) . . ?
H00c C00O O002 109.5 . . ?
H00e C00O O002 109.5 . . ?
H00e C00O H00c 109.5 . . ?
H00h C00O O002 109.5 . . ?
H00h C00O H00c 109.5 . . ?
H00h C00O H00e 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
Cl01 C00E C006 O002 -2.8(2) . . . . ?
Cl01 C00E C006 C00J 176.61(19) . . . . ?
Cl01 C00E C00G C005 -179.03(19) . . . . ?
O002 C006 C00E C00G 178.1(2) . . . . ?
O002 C006 C00J C00F -178.4(2) . . . . ?
O003 C00H C008 C007 -179.3(3) . . . . ?
O003 C00H C008 C00L 0.5(4) . . . . ?
O003 C00H C00M C00A 0.4(3) . . . . ?
O003 C00H C00M C00C 178.7(3) . . . . ?
N004 C005 C00F C00J 178.3(2) . . . . ?
N004 C005 C00G C00E -178.6(2) . . . . ?
N004 C00A C00M C00C -178.3(2) . . . . ?
N004 C00A C00M C00H -0.5(3) . . . . ?
C005 C00F C00J C006 0.5(3) . . . . ?
C005 C00G C00E C006 0.1(3) . . . . ?
C007 C008 C00H C00M -0.4(2) . . . . ?
C007 C008 C00L C00I -0.6(3) . . . . ?
C007 C009 C00B C00I -1.0(3) . . . . ?
C007 C009 C00K C00N 0.8(3) . . . . ?
C007 C00C C00D C00N 1.1(3) . . . . ?
C007 C00C C00M C00A 178.9(2) . . . . ?
C007 C00C C00M C00H 0.7(2) . . . . ?
C008 C00H C00M C00A -178.47(19) . . . . ?
C008 C00H C00M C00C -0.2(2) . . . . ?
C008 C00L C00I C00B 0.4(3) . . . . ?
C009 C00B C00I C00L 0.5(3) . . . . ?
C009 C00K C00N C00D -0.7(3) . . . . ?
C00A C00M C00C C00D 0.2(4) . . . . ?
C00C C00D C00N C00K -0.4(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
(Z)-2-(((3-chloro-4-methoxyphenyl)amino)methylene)acenaphthylen-1(2H)-one
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_rkp_ap119_0917_0m
_database_code_depnum_ccdc_archive 'CCDC 2340128'
loop_
_audit_author_name
_audit_author_address
'Monojit Nandi'
;Research Scholar
India
;
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-03-13
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 Cl O S'
_chemical_formula_sum            'C19 H11 Cl O S'
_chemical_formula_weight         322.79
_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'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   3.8430(2)
_cell_length_b                   14.0193(7)
_cell_length_c                   26.2392(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.8200(10)
_cell_angle_gamma                90
_cell_volume                     1411.96(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1299 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.9554.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.023
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31649
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         1.554
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2237
_reflns_number_total             2499
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.036
_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)+(0.0470P)²+1.1040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M)
;
_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
Cl01 Cl 0.71119(13) 0.17687(3) 0.50121(2) 0.02199(16) Uani 1 1 d . . . . .
S002 S 0.35964(13) 0.30354(3) 0.58357(2) 0.01992(16) Uani 1 1 d . . . . .
O003 O 0.6948(4) 0.44567(10) 0.73773(5) 0.0240(3) Uani 1 1 d . . . . .
C004 C 0.2106(5) 0.52297(13) 0.62525(7) 0.0163(4) Uani 1 1 d . . . . .
C005 C 0.2424(5) 0.60625(13) 0.65599(7) 0.0151(4) Uani 1 1 d . . . . .
C006 C 0.4562(5) 0.18161(13) 0.59601(7) 0.0175(4) Uani 1 1 d . . . . .
C007 C 0.4282(5) 0.59017(13) 0.70262(7) 0.0155(4) Uani 1 1 d . . . . .
C008 C 0.3744(5) 0.13841(14) 0.64215(8) 0.0201(4) Uani 1 1 d . . . . .
H008 H 0.272211 0.175180 0.667898 0.024 Uiso 1 1 calc R . . . .
C009 C 0.1104(5) 0.69577(13) 0.64121(7) 0.0168(4) Uani 1 1 d . . . . .
C00A C 0.4918(5) 0.66443(14) 0.73566(7) 0.0179(4) Uani 1 1 d . . . . .
H00A H 0.621446 0.654920 0.767013 0.021 Uiso 1 1 calc R . . . .
C00B C 0.0360(5) 0.53017(14) 0.57837(7) 0.0191(4) Uani 1 1 d . . . . .
H00B H 0.008996 0.476060 0.556743 0.023 Uiso 1 1 calc R . . . .
C00C C 0.3606(5) 0.75524(14) 0.72212(8) 0.0197(4) Uani 1 1 d . . . . .
H00C H 0.401450 0.807067 0.744958 0.024 Uiso 1 1 calc R . . . .
C00D C 0.1748(5) 0.77098(14) 0.67671(8) 0.0195(4) Uani 1 1 d . . . . .
H00D H 0.088362 0.833067 0.668995 0.023 Uiso 1 1 calc R . . . .
C00E C 0.3906(5) 0.44611(13) 0.65391(7) 0.0164(4) Uani 1 1 d . . . . .
C00F C 0.6002(5) 0.12572(14) 0.55864(7) 0.0180(4) Uani 1 1 d . . . . .
C00G C 0.4416(5) 0.04272(15) 0.65032(8) 0.0227(5) Uani 1 1 d . . . . .
H00G H 0.392009 0.014228 0.681998 0.027 Uiso 1 1 calc R . . . .
C00H C -0.0704(5) 0.69987(14) 0.59253(8) 0.0189(4) Uani 1 1 d . . . . .
H00H H -0.168585 0.758423 0.580604 0.023 Uiso 1 1 calc R . . . .
C00I C -0.1029(5) 0.61985(15) 0.56296(7) 0.0210(4) Uani 1 1 d . . . . .
H00I H -0.224099 0.624545 0.530617 0.025 Uiso 1 1 calc R . . . .
C00J C 0.6622(5) 0.02945(14) 0.56662(8) 0.0212(4) Uani 1 1 d . . . . .
H00J H 0.759897 -0.008071 0.540777 0.025 Uiso 1 1 calc R . . . .
C00K C 0.5297(5) 0.48792(14) 0.70396(7) 0.0175(4) Uani 1 1 d . . . . .
C00L C 0.4626(5) 0.35516(14) 0.64216(7) 0.0175(4) Uani 1 1 d . . . . .
H00L H 0.577409 0.316841 0.667676 0.021 Uiso 1 1 calc R . . . .
C00M C 0.5812(5) -0.01166(14) 0.61232(8) 0.0234(5) Uani 1 1 d . . . . .
H00M H 0.621497 -0.077825 0.617744 0.028 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
Cl01 C00F 1.741(2) . ?
S002 C006 1.776(2) . ?
S002 C00L 1.7274(19) . ?
O003 C00K 1.218(2) . ?
C004 C005 1.421(3) . ?
C004 C00B 1.376(3) . ?
C004 C00E 1.468(3) . ?
C005 C007 1.404(3) . ?
C005 C009 1.401(3) . ?
C006 C008 1.403(3) . ?
C006 C00F 1.391(3) . ?
C007 C00A 1.369(3) . ?
C007 C00K 1.486(3) . ?
C008 C00G 1.381(3) . ?
C009 C00D 1.421(3) . ?
C009 C00H 1.425(3) . ?
C00A C00C 1.408(3) . ?
C00B C00I 1.417(3) . ?
C00C C00D 1.376(3) . ?
C00E C00K 1.512(3) . ?
C00E C00L 1.344(3) . ?
C00F C00J 1.385(3) . ?
C00G C00M 1.384(3) . ?
C00H C00I 1.366(3) . ?
C00J C00M 1.380(3) . ?

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
C00L S002 C006 101.71(9) . . ?
C005 C004 C00E 106.69(16) . . ?
C00B C004 C005 118.16(17) . . ?
C00B C004 C00E 135.15(18) . . ?
C007 C005 C004 112.88(17) . . ?
C009 C005 C004 123.98(17) . . ?
C009 C005 C007 123.13(18) . . ?
C008 C006 S002 121.35(15) . . ?
C00F C006 S002 119.96(15) . . ?
C00F C006 C008 118.61(18) . . ?
C005 C007 C00K 107.28(16) . . ?
C00A C007 C005 119.80(18) . . ?
C00A C007 C00K 132.88(18) . . ?
C00G C008 C006 120.34(19) . . ?
C005 C009 C00D 115.73(17) . . ?
C005 C009 C00H 116.00(17) . . ?
C00D C009 C00H 128.27(18) . . ?
C007 C00A C00C 118.50(18) . . ?
C004 C00B C00I 118.73(18) . . ?
C00D C00C C00A 121.82(18) . . ?
C00C C00D C009 120.99(18) . . ?
C004 C00E C00K 107.34(16) . . ?
C00L C00E C004 132.55(18) . . ?
C00L C00E C00K 119.95(17) . . ?
C006 C00F Cl01 120.07(15) . . ?
C00J C00F Cl01 119.00(15) . . ?
C00J C00F C006 120.92(18) . . ?
C008 C00G C00M 119.96(19) . . ?
C00I C00H C009 120.19(18) . . ?
C00H C00I C00B 122.94(18) . . ?
C00M C00J C00F 119.61(19) . . ?
O003 C00K C007 127.82(18) . . ?
O003 C00K C00E 126.36(17) . . ?
C007 C00K C00E 105.81(15) . . ?
C00E C00L S002 124.13(15) . . ?
C00J C00M C00G 120.53(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_EX_IITR_AP180_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333486'
loop_
_audit_author_name
_audit_author_address
'Anoop Yadav'
;IIT Roorkee
India
;
_audit_update_record             
;
2024-02-18 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT138_EX_IITR_AP180_1_0m_a 
;
PROBLEM: Monoclinic: More than one Angle Unequal 90.0 ...     Please Check
RESPONSE: The crystal is of good quality
;
_vrf_RINTA01_EX_IITR_AP180_1_0m_a 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: this crystal was best grown crystal
;
_vrf_SYMMS02_EX_IITR_AP180_1_0m_a 
;
PROBLEM: Two angles should be 90 for a monoclinic cell
RESPONSE: yes, it is and this is the  best crystal grown , may be machinery error
;
_vrf_PLAT911_EX_IITR_AP180_1_0m_a 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        266 Report
RESPONSE: The crystal is of good quality
;
_vrf_PLAT919_EX_IITR_AP180_1_0m_a 
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: The crystal is of good quality
;
# Added during the CSD deposition process: Sunday 18 February 2024 03:45 AM
# end Validation Reply Form

_audit_creation_date             2024-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C22 H16 Cl N O S'
_chemical_formula_sum            'C22 H16 Cl N O S'
_chemical_formula_weight         377.897
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   20.066(4)
_cell_length_b                   5.963(2)
_cell_length_c                   16.542(3)
_cell_angle_alpha                90.25(3)
_cell_angle_beta                 112.50(3)
_cell_angle_gamma                90.04(3)
_cell_volume                     1828.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3694
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.74
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4566
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1698 before and 0.1042 after correction.
The Ratio of minimum to maximum transmission is 0.6123.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             785.473
_diffrn_reflns_av_R_equivalents  0.1833
_diffrn_reflns_av_unetI/netI     0.1055
_diffrn_reflns_Laue_measured_fraction_full 0.9192
_diffrn_reflns_Laue_measured_fraction_max 0.9318
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            61685
_diffrn_reflns_point_group_measured_fraction_full 0.9192
_diffrn_reflns_point_group_measured_fraction_max 0.9318
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         1.10
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9192
_diffrn_measured_fraction_theta_max 0.9318
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              24
_reflns_limit_h_min              -26
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2339
_reflns_number_total             4332
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.8690
_refine_diff_density_min         -0.6899
_refine_diff_density_rms         0.1365
_refine_ls_d_res_high            0.7432
_refine_ls_d_res_low             18.5386
_refine_ls_goodness_of_fit_ref   0.9228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      0.9228
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1104P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2002
_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:
 C00B(H00b,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00d), C00D(H00e), C00E(H00f), C00F(H00g), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S01 S 0.65463(5) 0.62078(15) 0.75124(6) 0.0474(3) Uani 1.000000 .
Cl02 Cl 0.38903(6) 1.24962(17) 0.55838(8) 0.0659(3) Uani 1.000000 .
O003 O 0.71925(15) 0.2731(4) 0.53857(17) 0.0537(7) Uani 1.000000 .
N004 N 0.78115(14) 0.0228(4) 0.64997(18) 0.0381(6) Uani 1.000000 .
C005 C 0.73908(18) 0.2098(5) 0.6143(2) 0.0390(8) Uani 1.000000 .
C006 C 0.88046(17) -0.1481(5) 0.6136(2) 0.0358(7) Uani 1.000000 .
C007 C 0.76068(16) 0.1786(5) 0.7661(2) 0.0347(7) Uani 1.000000 .
C008 C 0.79483(15) 0.0017(5) 0.7397(2) 0.0341(7) Uani 1.000000 .
C009 C 0.72300(17) 0.3134(5) 0.6891(2) 0.0373(7) Uani 1.000000 .
C00A C 0.83406(19) -0.1634(6) 0.7971(2) 0.0437(8) Uani 1.000000 .
H00A H 0.85664(19) -0.2778(6) 0.7789(2) 0.0524(10) Uiso 1.000000 R
C00B C 0.80061(18) -0.1433(5) 0.5968(2) 0.0412(8) Uani 1.000000 .
H00b H 0.78618(18) -0.2909(5) 0.6087(2) 0.0495(9) Uiso 1.000000 R
H00c H 0.77367(18) -0.1109(5) 0.5354(2) 0.0495(9) Uiso 1.000000 R
C00C C 0.9216(2) -0.3350(6) 0.6490(3) 0.0473(9) Uani 1.000000 .
H00d H 0.9006(2) -0.4570(6) 0.6652(3) 0.0567(11) Uiso 1.000000 R
C00D C 0.51888(19) 1.1447(6) 0.6823(3) 0.0449(8) Uani 1.000000 .
H00e H 0.51702(19) 1.2860(6) 0.7051(3) 0.0539(10) Uiso 1.000000 R
C00E C 0.76581(19) 0.1876(6) 0.8523(2) 0.0438(8) Uani 1.000000 .
H00f H 0.74411(19) 0.3031(6) 0.8711(2) 0.0526(10) Uiso 1.000000 R
C00F C 0.9127(2) 0.0325(6) 0.5891(2) 0.0451(8) Uani 1.000000 .
H00g H 0.8859(2) 0.1601(6) 0.5648(2) 0.0541(10) Uiso 1.000000 R
C00G C 0.58108(18) 0.7964(6) 0.6890(3) 0.0435(8) Uani 1.000000 .
C00H C 0.67723(17) 0.4898(5) 0.6735(3) 0.0421(8) Uani 1.000000 .
H00H H 0.65668(17) 0.5434(5) 0.6165(3) 0.0505(10) Uiso 1.000000 R
C00I C 0.9942(2) -0.3445(7) 0.6608(3) 0.0617(11) Uani 1.000000 .
H00I H 1.0215(2) -0.4710(7) 0.6854(3) 0.0741(13) Uiso 1.000000 R
C00J C 0.8384(2) -0.1516(6) 0.8834(3) 0.0497(9) Uani 1.000000 .
H00J H 0.8645(2) -0.2597(6) 0.9236(3) 0.0596(11) Uiso 1.000000 R
C00K C 0.57807(19) 1.0076(5) 0.7232(3) 0.0445(8) Uani 1.000000 .
H00K H 0.61568(19) 1.0567(5) 0.7734(3) 0.0534(10) Uiso 1.000000 R
C00L C 0.5249(2) 0.7243(6) 0.6148(3) 0.0502(9) Uani 1.000000 .
H00L H 0.5268(2) 0.5827(6) 0.5922(3) 0.0602(11) Uiso 1.000000 R
C00M C 0.8044(2) 0.0185(6) 0.9102(2) 0.0498(9) Uani 1.000000 .
H00M H 0.8073(2) 0.0205(6) 0.9677(2) 0.0598(11) Uiso 1.000000 R
C00N C 0.9849(2) 0.0213(7) 0.6012(3) 0.0590(11) Uani 1.000000 .
H00N H 1.0063(2) 0.1431(7) 0.5855(3) 0.0708(13) Uiso 1.000000 R
C00O C 0.46291(18) 1.0734(6) 0.6082(3) 0.0455(8) Uani 1.000000 .
C00P C 1.0250(2) -0.1649(8) 0.6356(3) 0.0645(12) Uani 1.000000 .
H00P H 1.0731(2) -0.1709(8) 0.6421(3) 0.0774(14) Uiso 1.000000 R
C00Q C 0.4646(2) 0.8627(6) 0.5728(3) 0.0534(9) Uani 1.000000 .
H00Q H 0.4269(2) 0.8146(6) 0.5225(3) 0.0641(11) Uiso 1.000000 R


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
S01 C00G 1.781(4) . ?
S01 C00H 1.707(4) . ?
Cl02 C00O 1.745(3) . ?
O003 C005 1.220(4) . ?
N004 C005 1.387(4) . ?
N004 C008 1.409(4) . ?
N004 C00B 1.473(4) . ?
C005 C009 1.524(5) . ?
C006 C00B 1.518(4) . ?
C006 C00C 1.377(5) . ?
C006 C00F 1.394(5) . ?
C007 C008 1.414(4) . ?
C007 C009 1.450(5) . ?
C007 C00E 1.392(5) . ?
C008 C00A 1.385(5) . ?
C009 C00H 1.355(4) . ?
C00A H00A 0.9300 . ?
C00A C00J 1.399(5) . ?
C00B H00b 0.9700 . ?
C00B H00c 0.9700 . ?
C00C H00d 0.9300 . ?
C00C C00I 1.394(5) . ?
C00D H00e 0.9300 . ?
C00D C00K 1.386(5) . ?
C00D C00O 1.375(5) . ?
C00E H00f 0.9300 . ?
C00E C00M 1.403(5) . ?
C00F H00g 0.9300 . ?
C00F C00N 1.386(5) . ?
C00G C00K 1.391(5) . ?
C00G C00L 1.380(5) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00P 1.379(6) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.385(5) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.408(5) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00P 1.361(6) . ?
C00O C00Q 1.392(5) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 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
C00H S01 C00G 103.52(18) . . ?
C008 N004 C005 111.2(2) . . ?
C00B N004 C005 123.0(3) . . ?
C00B N004 C008 125.4(3) . . ?
N004 C005 O003 126.3(3) . . ?
C009 C005 O003 128.4(3) . . ?
C009 C005 N004 105.3(3) . . ?
C00C C006 C00B 120.8(3) . . ?
C00F C006 C00B 120.5(3) . . ?
C00F C006 C00C 118.6(3) . . ?
C009 C007 C008 107.1(3) . . ?
C00E C007 C008 119.3(3) . . ?
C00E C007 C009 133.5(3) . . ?
C007 C008 N004 109.6(3) . . ?
C00A C008 N004 128.0(3) . . ?
C00A C008 C007 122.3(3) . . ?
C007 C009 C005 106.7(3) . . ?
C00H C009 C005 119.9(3) . . ?
C00H C009 C007 133.3(3) . . ?
H00A C00A C008 121.29(19) . . ?
C00J C00A C008 117.4(3) . . ?
C00J C00A H00A 121.3(2) . . ?
C006 C00B N004 113.9(3) . . ?
H00b C00B N004 108.77(16) . . ?
H00b C00B C006 108.77(18) . . ?
H00c C00B N004 108.77(18) . . ?
H00c C00B C006 108.77(18) . . ?
H00c C00B H00b 107.7 . . ?
H00d C00C C006 119.4(2) . . ?
C00I C00C C006 121.1(4) . . ?
C00I C00C H00d 119.4(2) . . ?
C00K C00D H00e 119.7(2) . . ?
C00O C00D H00e 119.74(19) . . ?
C00O C00D C00K 120.5(3) . . ?
H00f C00E C007 120.75(19) . . ?
C00M C00E C007 118.5(3) . . ?
C00M C00E H00f 120.7(2) . . ?
H00g C00F C006 120.1(2) . . ?
C00N C00F C006 119.8(3) . . ?
C00N C00F H00g 120.1(2) . . ?
C00K C00G S01 116.9(3) . . ?
C00L C00G S01 123.1(3) . . ?
C00L C00G C00K 119.7(3) . . ?
C009 C00H S01 124.6(3) . . ?
H00H C00H S01 117.69(12) . . ?
H00H C00H C009 117.7(2) . . ?
H00I C00I C00C 120.3(2) . . ?
C00P C00I C00C 119.5(4) . . ?
C00P C00I H00I 120.3(2) . . ?
H00J C00J C00A 119.4(2) . . ?
C00M C00J C00A 121.2(3) . . ?
C00M C00J H00J 119.4(2) . . ?
C00G C00K C00D 119.8(4) . . ?
H00K C00K C00D 120.1(2) . . ?
H00K C00K C00G 120.1(2) . . ?
H00L C00L C00G 119.6(2) . . ?
C00Q C00L C00G 120.8(3) . . ?
C00Q C00L H00L 119.6(2) . . ?
C00J C00M C00E 121.2(3) . . ?
H00M C00M C00E 119.4(2) . . ?
H00M C00M C00J 119.4(2) . . ?
H00N C00N C00F 119.4(2) . . ?
C00P C00N C00F 121.2(4) . . ?
C00P C00N H00N 119.4(2) . . ?
C00D C00O Cl02 119.4(3) . . ?
C00Q C00O Cl02 119.8(3) . . ?
C00Q C00O C00D 120.7(3) . . ?
C00N C00P C00I 119.8(3) . . ?
H00P C00P C00I 120.1(2) . . ?
H00P C00P C00N 120.1(2) . . ?
C00O C00Q C00L 118.4(4) . . ?
H00Q C00Q C00L 120.8(2) . . ?
H00Q C00Q C00O 120.8(2) . . ?

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
S01 C00G C00K C00D -174.1(2) . . . . ?
S01 C00G C00L C00Q 173.8(3) . . . . ?
S01 C00H C009 C005 179.9(3) . . . . ?
S01 C00H C009 C007 4.6(4) . . . . ?
Cl02 C00O C00D C00K 179.8(3) . . . . ?
Cl02 C00O C00Q C00L -179.7(3) . . . . ?
O003 C005 N004 C008 179.0(3) . . . . ?
O003 C005 N004 C00B -7.8(4) . . . . ?
O003 C005 C009 C007 -178.4(4) . . . . ?
O003 C005 C009 C00H 5.1(4) . . . . ?
N004 C005 C009 C007 2.2(3) . . . . ?
N004 C005 C009 C00H -174.2(3) . . . . ?
N004 C008 C007 C009 1.1(3) . . . . ?
N004 C008 C007 C00E 178.6(3) . . . . ?
N004 C008 C00A C00J -178.3(3) . . . . ?
N004 C00B C006 C00C 115.4(3) . . . . ?
N004 C00B C006 C00F -68.1(3) . . . . ?
C005 C009 C007 C008 -2.0(3) . . . . ?
C005 C009 C007 C00E -179.0(3) . . . . ?
C006 C00C C00I C00P -0.8(4) . . . . ?
C006 C00F C00N C00P 0.9(4) . . . . ?
C007 C008 C00A C00J 0.7(4) . . . . ?
C007 C00E C00M C00J 1.5(4) . . . . ?
C008 C00A C00J C00M 0.3(4) . . . . ?
C00A C00J C00M C00E -1.4(5) . . . . ?
C00C C00I C00P C00N 1.3(5) . . . . ?
C00D C00K C00G C00L -0.4(4) . . . . ?
C00D C00O C00Q C00L 0.3(4) . . . . ?
C00F C00N C00P C00I -1.4(5) . . . . ?
C00G C00L C00Q C00O -0.4(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
(E)-1-benzyl-3-(((4-chlorophenyl)thio)methylene)indolin-2-one
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
