# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_tj14
_database_code_depnum_ccdc_archive 'CCDC 2070105'
loop_
_audit_author_name
_audit_author_address
'PALNATI MANOJKUMAR'
;Research scholar
India
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-11-19 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         ?
_chemical_formula_sum            'C16 H11 Cl2 N O5'
_chemical_formula_weight         368.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   22.9722(6)
_cell_length_b                   13.0888(3)
_cell_length_c                   5.09300(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1531.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2716
_cell_measurement_theta_min      2.359
_cell_measurement_theta_max      25.679

_exptl_crystal_description       Block
_exptl_crystal_colour            Grey
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.452
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13993
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             2716
_reflns_number_gt                2370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.849
_reflns_Friedel_fraction_full    0.859

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²] 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_abs_structure_details 
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2716
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.006
_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
Cl2 Cl 0.37684(5) 0.49107(8) 0.5872(3) 0.0460(3) Uani 1 1 d . . . . .
Cl1 Cl 0.40713(5) 0.84223(8) 1.4316(3) 0.0513(3) Uani 1 1 d . . . . .
O5 O 0.48300(12) 0.6604(2) 1.3456(7) 0.0452(8) Uani 1 1 d . . . . .
H5 H 0.4987 0.6048 1.3235 0.068 Uiso 1 1 calc R U . . .
O2 O 0.30984(11) 0.8108(2) 1.0586(7) 0.0488(8) Uani 1 1 d . . . . .
O4 O 0.46800(12) 0.5151(2) 1.0027(7) 0.0468(8) Uani 1 1 d . . . . .
O1 O 0.24661(12) 0.6177(3) 0.2528(7) 0.0543(9) Uani 1 1 d . . . . .
H1 H 0.2580 0.6157 0.4053 0.081 Uiso 1 1 calc R U . . .
O3 O 0.29473(12) 0.6656(2) 0.7009(7) 0.0499(8) Uani 1 1 d . . . . .
N1 N 0.19142(14) 0.7367(3) -0.0952(9) 0.0429(9) Uani 1 1 d . . . . .
H2A H 0.2286 0.7365 -0.0740 0.052 Uiso 1 1 calc R U . . .
C15 C 0.43009(15) 0.5825(3) 0.9934(9) 0.0348(9) Uani 1 1 d . . . . .
C14 C 0.43720(16) 0.6676(3) 1.1915(9) 0.0340(9) Uani 1 1 d . . . . .
C9 C 0.18846(18) 0.6115(3) 0.2478(10) 0.0455(11) Uani 1 1 d . . . . .
C16 C 0.38268(16) 0.5853(3) 0.8199(9) 0.0338(9) Uani 1 1 d . . . . .
C12 C 0.34799(16) 0.7454(3) 1.0416(9) 0.0368(10) Uani 1 1 d . . . . .
C11 C 0.33985(16) 0.6598(3) 0.8392(9) 0.0352(9) Uani 1 1 d . . . . .
C13 C 0.39911(16) 0.7446(3) 1.2050(9) 0.0348(9) Uani 1 1 d . . . . .
C3 C 0.1099(2) 0.7984(4) -0.3153(11) 0.0570(14) Uani 1 1 d . . . . .
H3 H 0.0933 0.8403 -0.4424 0.068 Uiso 1 1 calc R U . . .
C10 C 0.15936(18) 0.6729(3) 0.0611(11) 0.0440(10) Uani 1 1 d . . . . .
C2 C 0.16977(18) 0.7992(3) -0.2780(10) 0.0432(11) Uani 1 1 d . . . . .
C4 C 0.07526(19) 0.7365(4) -0.1664(12) 0.0601(15) Uani 1 1 d . . . . .
H4 H 0.0352 0.7368 -0.1941 0.072 Uiso 1 1 calc R U . . .
C8 C 0.1553(2) 0.5498(4) 0.4057(11) 0.0588(13) Uani 1 1 d . . . . .
H8 H 0.1730 0.5094 0.5332 0.071 Uiso 1 1 calc R U . . .
C5 C 0.0989(2) 0.6718(4) 0.0290(11) 0.0517(13) Uani 1 1 d . . . . .
C7 C 0.0948(2) 0.5478(4) 0.3745(13) 0.0690(17) Uani 1 1 d . . . . .
H7 H 0.0731 0.5048 0.4821 0.083 Uiso 1 1 calc R U . . .
C1 C 0.2108(2) 0.8652(4) -0.4274(12) 0.0550(12) Uani 1 1 d . . . . .
H1A H 0.2501 0.8475 -0.3822 0.083 Uiso 1 1 calc R U . . .
H1B H 0.2039 0.9356 -0.3841 0.083 Uiso 1 1 calc R U . . .
H1C H 0.2050 0.8552 -0.6123 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0662(2) 0.6059(4) 0.1936(14) 0.0675(17) Uani 1 1 d . . . . .
H6 H 0.0259 0.6023 0.1784 0.081 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
Cl2 C16 1.716(4) . ?
Cl1 C13 1.732(4) . ?
O5 C14 1.316(5) . ?
O5 H5 0.8200 . ?
O2 C12 1.229(4) . ?
O4 C15 1.241(4) . ?
O1 C9 1.339(4) . ?
O1 H1 0.8200 . ?
O3 C11 1.255(5) . ?
N1 C2 1.335(6) . ?
N1 C10 1.369(6) . ?
N1 H2A 0.8600 . ?
C15 C16 1.403(6) . ?
C15 C14 1.512(6) . ?
C14 C13 1.336(5) . ?
C9 C8 1.370(7) . ?
C9 C10 1.413(7) . ?
C16 C11 1.389(5) . ?
C12 C13 1.440(5) . ?
C12 C11 1.534(6) . ?
C3 C4 1.366(8) . ?
C3 C2 1.389(5) . ?
C3 H3 0.9300 . ?
C10 C5 1.398(6) . ?
C2 C1 1.489(7) . ?
C4 C5 1.414(8) . ?
C4 H4 0.9300 . ?
C8 C7 1.399(7) . ?
C8 H8 0.9300 . ?
C5 C6 1.419(8) . ?
C7 C6 1.364(8) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 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
C14 O5 H5 109.5 . . ?
C9 O1 H1 109.5 . . ?
C2 N1 C10 125.4(4) . . ?
C2 N1 H2A 117.3 . . ?
C10 N1 H2A 117.3 . . ?
O4 C15 C16 126.0(4) . . ?
O4 C15 C14 115.0(4) . . ?
C16 C15 C14 119.0(3) . . ?
O5 C14 C13 123.2(4) . . ?
O5 C14 C15 115.6(3) . . ?
C13 C14 C15 121.3(4) . . ?
O1 C9 C8 125.4(4) . . ?
O1 C9 C10 116.7(4) . . ?
C8 C9 C10 117.9(4) . . ?
C11 C16 C15 121.6(4) . . ?
C11 C16 Cl2 119.9(3) . . ?
C15 C16 Cl2 118.5(3) . . ?
O2 C12 C13 123.1(4) . . ?
O2 C12 C11 118.0(4) . . ?
C13 C12 C11 118.9(3) . . ?
O3 C11 C16 126.0(4) . . ?
O3 C11 C12 115.7(3) . . ?
C16 C11 C12 118.3(3) . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 Cl1 121.4(3) . . ?
C12 C13 Cl1 117.8(3) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
N1 C10 C5 118.2(4) . . ?
N1 C10 C9 118.9(4) . . ?
C5 C10 C9 122.9(4) . . ?
N1 C2 C3 117.4(4) . . ?
N1 C2 C1 118.4(4) . . ?
C3 C2 C1 124.2(5) . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C5 C4 117.3(5) . . ?
C10 C5 C6 117.6(5) . . ?
C4 C5 C6 125.2(5) . . ?
C6 C7 C8 123.1(5) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.049

