# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KA533_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1954828'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 Cl N O3'
_chemical_formula_sum            'C17 H10 Cl N O3'
_chemical_formula_weight         311.71

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                   16.2453(4)
_cell_length_b                   8.9674(2)
_cell_length_c                   9.7074(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.2014(10)
_cell_angle_gamma                90
_cell_volume                     1411.95(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5884
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6429

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15624
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.511
_diffrn_reflns_theta_max         30.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4283
_reflns_number_gt                2705
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4283
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.441
_refine_ls_restrained_S_all      1.441
_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
C1 C 0.14664(10) 0.37152(18) 0.83447(16) 0.0400(4) Uani 1 1 d . . . . .
C2 C 0.08220(11) 0.3753(2) 0.9206(2) 0.0546(5) Uani 1 1 d . . . . .
H2 H 0.0687 0.4626 0.9659 0.065 Uiso 1 1 calc R U . . .
C3 C 0.03814(13) 0.2448(2) 0.9376(2) 0.0668(6) Uani 1 1 d . . . . .
H3 H -0.0065 0.2450 0.9936 0.080 Uiso 1 1 calc R U . . .
C4 C 0.05953(13) 0.1144(2) 0.8726(2) 0.0651(6) Uani 1 1 d . . . . .
H4 H 0.0291 0.0282 0.8859 0.078 Uiso 1 1 calc R U . . .
C5 C 0.12478(12) 0.1097(2) 0.78858(19) 0.0530(5) Uani 1 1 d . . . . .
H5 H 0.1395 0.0217 0.7457 0.064 Uiso 1 1 calc R U . . .
C6 C 0.16783(10) 0.24062(17) 0.77015(16) 0.0399(4) Uani 1 1 d . . . . .
C7 C 0.23623(10) 0.26992(17) 0.68043(15) 0.0379(4) Uani 1 1 d . . . . .
C8 C 0.20676(10) 0.49199(17) 0.80292(15) 0.0368(4) Uani 1 1 d . . . . .
C9 C 0.27247(10) 0.52093(17) 0.59342(15) 0.0386(4) Uani 1 1 d . . . . .
C10 C 0.22526(11) 0.64318(19) 0.60512(17) 0.0478(4) Uani 1 1 d . . . . .
H10 H 0.2238 0.7228 0.5436 0.057 Uiso 1 1 calc R U . . .
C11 C 0.17738(11) 0.63451(18) 0.72538(17) 0.0437(4) Uani 1 1 d . . . . .
C12 C 0.33147(10) 0.48914(19) 0.48960(15) 0.0405(4) Uani 1 1 d . . . . .
C13 C 0.39405(11) 0.3843(2) 0.51033(17) 0.0465(4) Uani 1 1 d . . . . .
H13 H 0.3971 0.3282 0.5911 0.056 Uiso 1 1 calc R U . . .
C14 C 0.45146(12) 0.3621(2) 0.41363(18) 0.0540(5) Uani 1 1 d . . . . .
H14 H 0.4924 0.2904 0.4282 0.065 Uiso 1 1 calc R U . . .
C15 C 0.44807(13) 0.4469(2) 0.29463(18) 0.0526(5) Uani 1 1 d . . . . .
C16 C 0.38650(13) 0.5503(2) 0.27040(18) 0.0594(5) Uani 1 1 d . . . . .
H16 H 0.3839 0.6056 0.1892 0.071 Uiso 1 1 calc R U . . .
C17 C 0.32857(13) 0.5715(2) 0.36723(18) 0.0542(5) Uani 1 1 d . . . . .
H17 H 0.2870 0.6417 0.3508 0.065 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52427(4) 0.42620(7) 0.17747(5) 0.0771(2) Uani 1 1 d . . . . .
N1 N 0.25987(8) 0.41873(13) 0.70332(12) 0.0347(3) Uani 1 1 d . . . . .
O1 O 0.26560(8) 0.18736(13) 0.59805(12) 0.0536(3) Uani 1 1 d . . . . .
O2 O 0.25248(8) 0.54562(13) 0.91988(12) 0.0447(3) Uani 1 1 d . . . . .
H2O H 0.2581(12) 0.475(2) 0.972(2) 0.062(6) Uiso 1 1 d . . . . .
O3 O 0.12874(8) 0.72178(14) 0.77025(14) 0.0611(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(2) . ?
C1 C6 1.382(2) . ?
C1 C8 1.499(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.473(2) . ?
C7 O1 1.2074(18) . ?
C7 N1 1.4029(19) . ?
C8 O2 1.4063(18) . ?
C8 N1 1.4847(19) . ?
C8 C11 1.545(2) . ?
C9 C10 1.346(2) . ?
C9 N1 1.4298(18) . ?
C9 C12 1.457(2) . ?
C10 C11 1.441(2) . ?
C10 H10 0.9300 . ?
C11 O3 1.210(2) . ?
C12 C13 1.391(2) . ?
C12 C17 1.398(2) . ?
C13 C14 1.374(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 Cl1 1.7371(18) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
O2 H2O 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.84(15) . . ?
C2 C1 C8 129.24(15) . . ?
C6 C1 C8 109.76(14) . . ?
C1 C2 C3 117.82(17) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.99(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 121.29(17) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 117.58(17) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 121.46(16) . . ?
C1 C6 C7 109.31(14) . . ?
C5 C6 C7 129.15(15) . . ?
O1 C7 N1 124.98(15) . . ?
O1 C7 C6 128.40(15) . . ?
N1 C7 C6 106.55(13) . . ?
O2 C8 N1 112.16(12) . . ?
O2 C8 C1 113.72(12) . . ?
N1 C8 C1 102.89(12) . . ?
O2 C8 C11 104.20(12) . . ?
N1 C8 C11 102.92(12) . . ?
C1 C8 C11 120.55(14) . . ?
C10 C9 N1 110.67(14) . . ?
C10 C9 C12 128.13(14) . . ?
N1 C9 C12 121.18(14) . . ?
C9 C10 C11 111.12(14) . . ?
C9 C10 H10 124.4 . . ?
C11 C10 H10 124.4 . . ?
O3 C11 C10 130.51(16) . . ?
O3 C11 C8 123.34(15) . . ?
C10 C11 C8 105.86(14) . . ?
C13 C12 C17 118.03(16) . . ?
C13 C12 C9 122.40(14) . . ?
C17 C12 C9 119.49(16) . . ?
C14 C13 C12 121.16(16) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.65(18) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.59(17) . . ?
C16 C15 Cl1 119.89(14) . . ?
C14 C15 Cl1 119.49(16) . . ?
C15 C16 C17 119.61(16) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 120.94(18) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C7 N1 C9 122.74(12) . . ?
C7 N1 C8 111.11(12) . . ?
C9 N1 C8 108.36(12) . . ?
C8 O2 H2O 105.7(14) . . ?

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
C6 C1 C2 C3 -1.7(3) . . . . ?
C8 C1 C2 C3 -176.53(17) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C8 C1 C6 C5 176.49(15) . . . . ?
C2 C1 C6 C7 177.76(15) . . . . ?
C8 C1 C6 C7 -6.47(18) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -175.91(17) . . . . ?
C1 C6 C7 O1 -171.87(16) . . . . ?
C5 C6 C7 O1 4.9(3) . . . . ?
C1 C6 C7 N1 5.31(17) . . . . ?
C5 C6 C7 N1 -177.94(16) . . . . ?
C2 C1 C8 O2 58.7(2) . . . . ?
C6 C1 C8 O2 -116.58(15) . . . . ?
C2 C1 C8 N1 -179.72(16) . . . . ?
C6 C1 C8 N1 4.96(16) . . . . ?
C2 C1 C8 C11 -66.0(2) . . . . ?
C6 C1 C8 C11 118.64(16) . . . . ?
N1 C9 C10 C11 0.7(2) . . . . ?
C12 C9 C10 C11 -177.64(14) . . . . ?
C9 C10 C11 O3 179.63(18) . . . . ?
C9 C10 C11 C8 5.77(19) . . . . ?
O2 C8 C11 O3 -66.7(2) . . . . ?
N1 C8 C11 O3 176.10(16) . . . . ?
C1 C8 C11 O3 62.4(2) . . . . ?
O2 C8 C11 C10 107.72(14) . . . . ?
N1 C8 C11 C10 -9.48(16) . . . . ?
C1 C8 C11 C10 -123.14(16) . . . . ?
C10 C9 C12 C13 159.57(17) . . . . ?
N1 C9 C12 C13 -18.6(2) . . . . ?
C10 C9 C12 C17 -17.0(3) . . . . ?
N1 C9 C12 C17 164.86(15) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C9 C12 C13 C14 -176.56(15) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C13 C14 C15 Cl1 176.22(14) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
Cl1 C15 C16 C17 -176.69(15) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C9 C12 C17 C16 176.17(16) . . . . ?
O1 C7 N1 C9 44.7(2) . . . . ?
C6 C7 N1 C9 -132.57(14) . . . . ?
O1 C7 N1 C8 175.25(14) . . . . ?
C6 C7 N1 C8 -2.06(16) . . . . ?
C10 C9 N1 C7 124.42(16) . . . . ?
C12 C9 N1 C7 -57.1(2) . . . . ?
C10 C9 N1 C8 -7.22(17) . . . . ?
C12 C9 N1 C8 171.25(13) . . . . ?
O2 C8 N1 C7 120.99(14) . . . . ?
C1 C8 N1 C7 -1.60(16) . . . . ?
C11 C8 N1 C7 -127.59(13) . . . . ?
O2 C8 N1 C9 -101.37(14) . . . . ?
C1 C8 N1 C9 136.04(12) . . . . ?
C11 C8 N1 C9 10.05(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.82(2) 1.90(2) 2.7131(17) 177(2) 4_566

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.048

