# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_dB2A34
_database_code_depnum_ccdc_archive 'CCDC 2533554'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2026-04-28 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl4 N2 O4'
_chemical_formula_weight         494.18

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      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                   20.664(6)
_cell_length_b                   7.984(2)
_cell_length_c                   13.230(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.428(9)
_cell_angle_gamma                90
_cell_volume                     2131.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    2646
_cell_measurement_theta_min      2.018
_cell_measurement_theta_max      26.562

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37847
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_av_R_equivalents  0.1322
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.018
_diffrn_reflns_theta_max         26.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4412
_reflns_number_gt                2646
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.3960P] 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         4412
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1905
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.25415(6) 0.29113(16) 0.25979(9) 0.0642(4) Uani 1 1 d . . . . .
Cl1 Cl 0.39604(6) 0.18662(16) 0.38860(9) 0.0665(4) Uani 1 1 d . . . . .
Cl4 Cl 0.44749(5) 0.83153(18) 0.93356(9) 0.0708(4) Uani 1 1 d . . . . .
Cl3 Cl 0.49942(5) 1.01085(16) 0.75222(10) 0.0707(4) Uani 1 1 d . . . . .
O4 O 0.07316(12) 0.9674(3) 0.64736(18) 0.0417(6) Uani 1 1 d . . . . .
O1 O 0.04472(12) 0.7469(3) 0.44885(19) 0.0417(6) Uani 1 1 d . . . . .
O3 O 0.09202(13) 0.7131(3) 0.7136(2) 0.0505(7) Uani 1 1 d . . . . .
O2 O 0.08031(13) 0.4845(3) 0.4550(2) 0.0583(8) Uani 1 1 d . . . . .
N1 N 0.05958(14) 0.1462(4) 0.4589(2) 0.0404(7) Uani 1 1 d . . . . .
H1A H 0.058265 0.256954 0.465982 0.061 Uiso 1 1 calc R U . . .
H1B H 0.073709 0.099255 0.520722 0.061 Uiso 1 1 calc R U . . .
H1C H 0.019196 0.108459 0.430825 0.061 Uiso 1 1 calc R U . . .
N2 N 0.02627(14) 0.0867(4) 0.2233(2) 0.0432(8) Uani 1 1 d . . . . .
H2A H 0.038557 -0.015696 0.208528 0.065 Uiso 1 1 calc R U . . .
H2B H 0.011050 0.142548 0.164831 0.065 Uiso 1 1 calc R U . . .
H2C H -0.005477 0.079191 0.259125 0.065 Uiso 1 1 calc R U . . .
C18 C 0.10760(16) 0.8336(4) 0.6649(3) 0.0338(8) Uani 1 1 d . . . . .
C4 C 0.25600(17) 0.4826(4) 0.5402(3) 0.0372(8) Uani 1 1 d . . . . .
C10 C 0.16841(16) 0.8209(4) 0.6180(3) 0.0342(8) Uani 1 1 d . . . . .
H10 H 0.184157 0.930849 0.600810 0.041 Uiso 1 1 calc R U . . .
C12 C 0.29417(17) 0.7830(5) 0.6939(3) 0.0380(8) Uani 1 1 d . . . . .
C11 C 0.22593(17) 0.7075(4) 0.6766(3) 0.0366(8) Uani 1 1 d . . . . .
H11 H 0.216534 0.667887 0.742082 0.044 Uiso 1 1 calc R U . . .
C2 C 0.15806(17) 0.6957(4) 0.5235(3) 0.0343(8) Uani 1 1 d . . . . .
H2 H 0.179101 0.742162 0.470019 0.041 Uiso 1 1 calc R U . . .
C17 C 0.33543(17) 0.7771(4) 0.7916(3) 0.0389(8) Uani 1 1 d . . . . .
H17 H 0.320404 0.726704 0.845591 0.047 Uiso 1 1 calc R U . . .
C19 C 0.10512(16) 0.1034(4) 0.3915(3) 0.0377(8) Uani 1 1 d . . . . .
H19A H 0.107821 -0.017508 0.386402 0.045 Uiso 1 1 calc R U . . .
H19B H 0.149041 0.144884 0.422416 0.045 Uiso 1 1 calc R U . . .
C1 C 0.20569(16) 0.5712(4) 0.5895(3) 0.0351(8) Uani 1 1 d . . . . .
H1 H 0.179148 0.485656 0.614976 0.042 Uiso 1 1 calc R U . . .
C6 C 0.28008(18) 0.3462(5) 0.3888(3) 0.0403(9) Uani 1 1 d . . . . .
C5 C 0.23775(17) 0.4383(5) 0.4353(3) 0.0413(9) Uani 1 1 d . . . . .
H5 H 0.196691 0.471233 0.396524 0.050 Uiso 1 1 calc R U . . .
C3 C 0.08872(17) 0.6368(4) 0.4735(3) 0.0372(8) Uani 1 1 d . . . . .
C16 C 0.39846(17) 0.8448(5) 0.8101(3) 0.0430(9) Uani 1 1 d . . . . .
C20 C 0.08346(18) 0.1756(5) 0.2851(3) 0.0400(9) Uani 1 1 d . . . . .
H20A H 0.072022 0.292587 0.290690 0.048 Uiso 1 1 calc R U . . .
H20B H 0.120022 0.170239 0.249928 0.048 Uiso 1 1 calc R U . . .
C15 C 0.42138(17) 0.9206(5) 0.7306(3) 0.0453(10) Uani 1 1 d . . . . .
C13 C 0.31793(19) 0.8580(5) 0.6138(3) 0.0473(10) Uani 1 1 d . . . . .
H13 H 0.291176 0.862899 0.547660 0.057 Uiso 1 1 calc R U . . .
C8 C 0.36076(19) 0.3464(5) 0.5480(3) 0.0478(10) Uani 1 1 d . . . . .
H8 H 0.402481 0.316817 0.585930 0.057 Uiso 1 1 calc R U . . .
C9 C 0.31820(18) 0.4357(5) 0.5944(3) 0.0448(9) Uani 1 1 d . . . . .
H9 H 0.331576 0.465243 0.663741 0.054 Uiso 1 1 calc R U . . .
C7 C 0.34166(19) 0.3004(5) 0.4447(3) 0.0435(9) Uani 1 1 d . . . . .
C14 C 0.38159(19) 0.9255(5) 0.6325(3) 0.0503(10) Uani 1 1 d . . . . .
H14 H 0.397321 0.974086 0.578572 0.060 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 C6 1.732(4) . ?
Cl1 C7 1.732(4) . ?
Cl4 C16 1.730(4) . ?
Cl3 C15 1.733(4) . ?
O4 C18 1.277(4) . ?
O1 C3 1.257(4) . ?
O3 C18 1.239(4) . ?
O2 C3 1.245(4) . ?
N1 C19 1.469(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C20 1.468(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C18 C10 1.520(5) . ?
C4 C9 1.381(5) . ?
C4 C5 1.403(5) . ?
C4 C1 1.516(5) . ?
C10 C11 1.561(5) . ?
C10 C2 1.578(5) . ?
C10 H10 0.9800 . ?
C12 C17 1.387(5) . ?
C12 C13 1.396(5) . ?
C12 C11 1.505(5) . ?
C11 C1 1.575(5) . ?
C11 H11 0.9800 . ?
C2 C3 1.518(5) . ?
C2 C1 1.533(5) . ?
C2 H2 0.9800 . ?
C17 C16 1.382(5) . ?
C17 H17 0.9300 . ?
C19 C20 1.498(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C1 H1 0.9800 . ?
C6 C7 1.376(5) . ?
C6 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C16 C15 1.383(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C15 C14 1.379(6) . ?
C13 C14 1.394(5) . ?
C13 H13 0.9300 . ?
C8 C9 1.375(5) . ?
C8 C7 1.388(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C14 H14 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
C19 N1 H1A 109.5 . . ?
C19 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C19 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C20 N2 H2A 109.5 . . ?
C20 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C20 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O3 C18 O4 123.2(3) . . ?
O3 C18 C10 119.4(3) . . ?
O4 C18 C10 117.4(3) . . ?
C9 C4 C5 117.8(3) . . ?
C9 C4 C1 123.4(3) . . ?
C5 C4 C1 118.7(3) . . ?
C18 C10 C11 116.3(3) . . ?
C18 C10 C2 112.5(3) . . ?
C11 C10 C2 89.2(2) . . ?
C18 C10 H10 112.3 . . ?
C11 C10 H10 112.3 . . ?
C2 C10 H10 112.3 . . ?
C17 C12 C13 118.4(3) . . ?
C17 C12 C11 119.8(3) . . ?
C13 C12 C11 121.8(3) . . ?
C12 C11 C10 115.6(3) . . ?
C12 C11 C1 118.7(3) . . ?
C10 C11 C1 89.0(2) . . ?
C12 C11 H11 110.6 . . ?
C10 C11 H11 110.6 . . ?
C1 C11 H11 110.6 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C10 119.7(3) . . ?
C1 C2 C10 90.0(3) . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C10 C2 H2 109.1 . . ?
C16 C17 C12 121.3(4) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
N1 C19 C20 112.3(3) . . ?
N1 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N1 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C4 C1 C2 118.3(3) . . ?
C4 C1 C11 122.6(3) . . ?
C2 C1 C11 90.3(3) . . ?
C4 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
C11 C1 H1 108.0 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 Cl2 121.1(3) . . ?
C5 C6 Cl2 118.8(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
O2 C3 O1 124.7(3) . . ?
O2 C3 C2 117.8(3) . . ?
O1 C3 C2 117.3(3) . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 Cl4 118.8(3) . . ?
C15 C16 Cl4 121.2(3) . . ?
N2 C20 C19 112.3(3) . . ?
N2 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
N2 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 Cl3 119.3(3) . . ?
C16 C15 Cl3 121.0(3) . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 121.5(4) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C6 C7 C8 119.5(3) . . ?
C6 C7 Cl1 121.3(3) . . ?
C8 C7 Cl1 119.2(3) . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_B4A24
_database_code_depnum_ccdc_archive 'CCDC 2533556'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2026-04-28 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cl2 N O2'
_chemical_formula_weight         261.12

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.7040(8)
_cell_length_b                   8.4116(10)
_cell_length_c                   11.5801(13)
_cell_angle_alpha                71.576(7)
_cell_angle_beta                 80.805(7)
_cell_angle_gamma                79.641(8)
_cell_volume                     605.73(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    304(2)
_cell_measurement_reflns_used    2023
_cell_measurement_theta_min      3.108
_cell_measurement_theta_max      30.612

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             270
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.520
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      304(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8072
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.108
_diffrn_reflns_theta_max         30.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3692
_reflns_number_gt                2023
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.1404P] 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         3692
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1910
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_restrained_S_all      0.899
_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 0.53022(13) 1.09514(9) 0.20958(6) 0.0625(3) Uani 1 1 d . . . . .
Cl1 Cl 0.14073(11) 0.73696(11) 0.62548(7) 0.0658(3) Uani 1 1 d . . . . .
O2 O 0.8743(3) 0.1602(2) 0.83926(18) 0.0574(5) Uani 1 1 d . . . . .
O1 O 0.5588(3) 0.2533(3) 0.89962(19) 0.0680(6) Uani 1 1 d . . . . .
N1 N 0.1883(3) 0.1411(3) 0.9818(2) 0.0496(5) Uani 1 1 d . . . . .
H1A H 0.122220 0.143884 0.920198 0.074 Uiso 1 1 calc R U . . .
H1B H 0.201885 0.036656 1.033085 0.074 Uiso 1 1 calc R U . . .
H1C H 0.311087 0.171927 0.952432 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5468(4) 0.6609(3) 0.5617(2) 0.0397(5) Uani 1 1 d . . . . .
C1 C 0.7128(4) 0.2638(3) 0.8253(2) 0.0436(6) Uani 1 1 d . . . . .
C4 C 0.3675(4) 0.7679(3) 0.5297(2) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.5357(4) 0.9289(3) 0.3455(2) 0.0450(6) Uani 1 1 d . . . . .
C2 C 0.5551(4) 0.5198(3) 0.6759(2) 0.0437(6) Uani 1 1 d . . . . .
H2 H 0.435428 0.509218 0.729150 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3588(4) 0.9009(3) 0.4225(2) 0.0473(6) Uani 1 1 d . . . . .
H6 H 0.236225 0.969467 0.403157 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7172(4) 0.8276(4) 0.3721(2) 0.0507(7) Uani 1 1 d . . . . .
H8 H 0.835964 0.847568 0.319136 0.061 Uiso 1 1 calc R U . . .
C9 C 0.7196(4) 0.6961(3) 0.4789(2) 0.0493(6) Uani 1 1 d . . . . .
H9 H 0.842644 0.627343 0.496780 0.059 Uiso 1 1 calc R U . . .
C3 C 0.7137(4) 0.4078(3) 0.7102(2) 0.0480(6) Uani 1 1 d . . . . .
H3 H 0.835645 0.418839 0.659120 0.058 Uiso 1 1 calc R U . . .
C10 C 0.0718(4) 0.2585(3) 1.0474(3) 0.0526(7) Uani 1 1 d . . . . .
H10A H 0.135284 0.245553 1.120060 0.063 Uiso 1 1 calc R U . . .
H10B H -0.065767 0.230628 1.073298 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0630(5) 0.4397(3) 0.9676(3) 0.0553(7) Uani 1 1 d . . . . .
H11A H 0.004763 0.451481 0.893395 0.066 Uiso 1 1 calc R U . . .
H11B H 0.200439 0.468795 0.944385 0.066 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 C7 1.744(2) . ?
Cl1 C4 1.741(3) . ?
O2 C1 1.259(3) . ?
O1 C1 1.231(3) . ?
N1 C10 1.473(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C5 C4 1.390(3) . ?
C5 C9 1.392(4) . ?
C5 C2 1.473(3) . ?
C1 C3 1.491(3) . ?
C4 C6 1.385(3) . ?
C7 C8 1.372(4) . ?
C7 C6 1.374(4) . ?
C2 C3 1.309(3) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C10 C11 1.508(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C11 1.509(6) 2_567 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 H1A 109.5 . . ?
C10 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C10 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 C5 C9 115.7(2) . . ?
C4 C5 C2 122.5(2) . . ?
C9 C5 C2 121.7(2) . . ?
O1 C1 O2 124.5(2) . . ?
O1 C1 C3 119.3(2) . . ?
O2 C1 C3 116.3(2) . . ?
C6 C4 C5 122.8(2) . . ?
C6 C4 Cl1 117.06(19) . . ?
C5 C4 Cl1 120.15(19) . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 Cl2 118.9(2) . . ?
C6 C7 Cl2 119.6(2) . . ?
C3 C2 C5 126.7(2) . . ?
C3 C2 H2 116.6 . . ?
C5 C2 H2 116.6 . . ?
C7 C6 C4 118.3(2) . . ?
C7 C6 H6 120.8 . . ?
C4 C6 H6 120.8 . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C5 123.2(2) . . ?
C8 C9 H9 118.4 . . ?
C5 C9 H9 118.4 . . ?
C2 C3 C1 124.7(2) . . ?
C2 C3 H3 117.7 . . ?
C1 C3 H3 117.7 . . ?
N1 C10 C11 111.4(2) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C11 111.8(3) . 2_567 ?
C10 C11 H11A 109.3 . . ?
C11 C11 H11A 109.3 2_567 . ?
C10 C11 H11B 109.3 . . ?
C11 C11 H11B 109.3 2_567 . ?
H11A C11 H11B 107.9 . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_B4A34
_database_code_depnum_ccdc_archive 'CCDC 2533553'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2026-04-28 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cl2 N O2'
_chemical_formula_weight         261.12

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.2940(11)
_cell_length_b                   7.3566(10)
_cell_length_c                   11.7557(19)
_cell_angle_alpha                88.446(5)
_cell_angle_beta                 84.280(5)
_cell_angle_gamma                72.170(4)
_cell_volume                     597.51(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    11557
_cell_measurement_theta_min      2.947
_cell_measurement_theta_max      27.246

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             270
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.527
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5114
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11557
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         27.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2668
_reflns_number_gt                1536
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0948P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.062(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2668
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Cl1 Cl 0.55110(15) 0.07971(15) 0.85009(8) 0.0612(4) Uani 1 1 d . . . . .
Cl2 Cl 0.89902(13) 0.06907(16) 0.66340(9) 0.0643(4) Uani 1 1 d . . . . .
O1 O 0.3581(3) 0.4766(4) 0.1424(2) 0.0524(7) Uani 1 1 d . . . . .
O2 O 0.0538(3) 0.4777(4) 0.1688(2) 0.0574(7) Uani 1 1 d . . . . .
N1 N 0.7481(4) 0.4124(4) 0.0762(2) 0.0404(7) Uani 1 1 d . . . . .
H1C H 0.841157 0.452626 0.100079 0.061 Uiso 1 1 calc R U . . .
H1B H 0.638659 0.461990 0.120673 0.061 Uiso 1 1 calc R U . . .
H1A H 0.730460 0.449413 0.004382 0.061 Uiso 1 1 calc R U . . .
C4 C 0.4379(4) 0.2782(4) 0.4884(3) 0.0387(8) Uani 1 1 d . . . . .
C9 C 0.2170(5) 0.4490(4) 0.2025(3) 0.0397(8) Uani 1 1 d . . . . .
C2 C 0.6619(4) 0.1486(5) 0.6299(3) 0.0405(8) Uani 1 1 d . . . . .
C1 C 0.5098(5) 0.1558(5) 0.7118(3) 0.0410(8) Uani 1 1 d . . . . .
C3 C 0.6251(5) 0.2115(5) 0.5197(3) 0.0412(8) Uani 1 1 d . . . . .
H3 H 0.728225 0.208975 0.465776 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4046(4) 0.3425(4) 0.3705(3) 0.0409(8) Uani 1 1 d . . . . .
H7 H 0.511202 0.356480 0.324891 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8044(5) 0.2028(4) 0.0822(3) 0.0436(8) Uani 1 1 d . . . . .
H10B H 0.695535 0.160904 0.066581 0.052 Uiso 1 1 calc R U . . .
H10A H 0.835718 0.162735 0.159048 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2429(5) 0.3824(5) 0.3221(3) 0.0438(8) Uani 1 1 d . . . . .
H8 H 0.135206 0.367882 0.366279 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9754(5) 0.1080(4) -0.0013(3) 0.0438(8) Uani 1 1 d . . . . .
H11A H 1.086579 0.143820 0.016891 0.053 Uiso 1 1 calc R U . . .
H11B H 0.947026 0.153066 -0.077861 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2883(5) 0.2827(5) 0.5724(3) 0.0485(9) Uani 1 1 d . . . . .
H5 H 0.161320 0.327597 0.553678 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3221(5) 0.2230(5) 0.6820(3) 0.0503(9) Uani 1 1 d . . . . .
H6 H 0.218877 0.227759 0.736308 0.060 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
Cl1 C1 1.730(3) . ?
Cl2 C2 1.730(3) . ?
O1 C9 1.255(4) . ?
O2 C9 1.246(4) . ?
N1 C10 1.471(4) . ?
N1 H1C 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1A 0.8900 . ?
C4 C3 1.386(4) . ?
C4 C5 1.390(5) . ?
C4 C7 1.472(5) . ?
C9 C8 1.488(5) . ?
C2 C1 1.383(4) . ?
C2 C3 1.388(5) . ?
C1 C6 1.383(5) . ?
C3 H3 0.9300 . ?
C7 C8 1.309(4) . ?
C7 H7 0.9300 . ?
C10 C11 1.505(4) . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C8 H8 0.9300 . ?
C11 C11 1.519(6) 2_755 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
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
C10 N1 H1C 109.5 . . ?
C10 N1 H1B 109.5 . . ?
H1C N1 H1B 109.5 . . ?
C10 N1 H1A 109.5 . . ?
H1C N1 H1A 109.5 . . ?
H1B N1 H1A 109.5 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C7 119.8(3) . . ?
C5 C4 C7 122.9(3) . . ?
O2 C9 O1 123.9(3) . . ?
O2 C9 C8 117.5(3) . . ?
O1 C9 C8 118.5(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 Cl2 121.2(3) . . ?
C3 C2 Cl2 118.9(2) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 Cl1 119.6(3) . . ?
C2 C1 Cl1 121.0(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C8 C7 C4 127.7(3) . . ?
C8 C7 H7 116.1 . . ?
C4 C7 H7 116.1 . . ?
N1 C10 C11 112.6(3) . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
H10B C10 H10A 107.8 . . ?
C7 C8 C9 125.5(3) . . ?
C7 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
C10 C11 C11 111.9(3) . 2_755 ?
C10 C11 H11A 109.2 . . ?
C11 C11 H11A 109.2 2_755 . ?
C10 C11 H11B 109.2 . . ?
C11 C11 H11B 109.2 2_755 . ?
H11A C11 H11B 107.9 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_B3A24
_database_code_depnum_ccdc_archive 'CCDC 2533552'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2026-04-28 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl4 N2 O4'
_chemical_formula_weight         502.16

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   8.365(10)
_cell_length_b                   13.846(18)
_cell_length_c                   41.35(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4788(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2010
_cell_measurement_theta_min      1.970
_cell_measurement_theta_max      24.719

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             2048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.523
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5111
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24896
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.627
_diffrn_reflns_theta_max         24.719
_diffrn_reflns_theta_full        24.719
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4048
_reflns_number_gt                2009
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1274P)²+1.0328P] 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         4048
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2484
_refine_ls_wR_factor_gt          0.1902
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Cl1 Cl 0.0255(3) 0.33167(13) 0.64768(4) 0.1002(7) Uani 1 1 d . . . . .
Cl3 Cl 0.7189(2) 0.56693(14) 0.63496(4) 0.1041(7) Uani 1 1 d . . . . .
Cl4 Cl 0.8261(3) 0.79644(15) 0.73666(4) 0.1136(8) Uani 1 1 d . . . . .
Cl2 Cl 0.0103(3) 0.54526(16) 0.75556(4) 0.1136(8) Uani 1 1 d . . . . .
O1 O 0.2773(5) 0.4712(3) 0.55078(9) 0.0692(11) Uani 1 1 d . . . . .
O4 O 1.1118(5) 0.7777(3) 0.52149(9) 0.0791(12) Uani 1 1 d . . . . .
O2 O 0.4165(5) 0.6073(3) 0.55104(9) 0.0795(12) Uani 1 1 d . . . . .
O3 O 0.9255(5) 0.6687(3) 0.52876(9) 0.0863(14) Uani 1 1 d . . . . .
N1 N 0.6817(5) 0.5449(3) 0.51657(10) 0.0599(12) Uani 1 1 d . . . . .
H1A H 0.743711 0.596388 0.519486 0.072 Uiso 1 1 calc R U . . .
H1B H 0.590705 0.553419 0.505771 0.072 Uiso 1 1 calc R U . . .
N2 N 1.0613(5) 0.3064(3) 0.53900(10) 0.0604(12) Uani 1 1 d . . . . .
H2A H 1.054392 0.306800 0.517519 0.091 Uiso 1 1 calc R U . . .
H2B H 1.089336 0.247700 0.545695 0.091 Uiso 1 1 calc R U . . .
H2C H 1.134557 0.349044 0.545312 0.091 Uiso 1 1 calc R U . . .
C4 C 0.1717(6) 0.5082(4) 0.65145(12) 0.0517(13) Uani 1 1 d . . . . .
C3 C 0.2133(6) 0.4982(4) 0.61755(12) 0.0523(13) Uani 1 1 d . . . . .
H3 H 0.182685 0.440834 0.607613 0.063 Uiso 1 1 calc R U . . .
C10 C 1.0193(6) 0.7324(4) 0.53934(13) 0.0554(14) Uani 1 1 d . . . . .
C1 C 0.3287(6) 0.5441(4) 0.56438(13) 0.0561(14) Uani 1 1 d . . . . .
C13 C 0.9010(6) 0.7293(4) 0.63001(13) 0.0601(14) Uani 1 1 d . . . . .
C11 C 1.0125(6) 0.7554(4) 0.57452(13) 0.0584(14) Uani 1 1 d . . . . .
H11 H 1.077595 0.804882 0.582101 0.070 Uiso 1 1 calc R U . . .
C12 C 0.9214(7) 0.7108(4) 0.59556(13) 0.0610(14) Uani 1 1 d . . . . .
H12 H 0.861011 0.660001 0.587312 0.073 Uiso 1 1 calc R U . . .
C2 C 0.2889(6) 0.5604(4) 0.59939(13) 0.0611(15) Uani 1 1 d . . . . .
H2 H 0.320048 0.618484 0.608734 0.073 Uiso 1 1 calc R U . . .
C14 C 0.8108(7) 0.6701(4) 0.65029(14) 0.0648(16) Uani 1 1 d . . . . .
C9 C 0.2136(7) 0.5890(4) 0.66989(13) 0.0658(15) Uani 1 1 d . . . . .
H9 H 0.275386 0.637069 0.660360 0.079 Uiso 1 1 calc R U . . .
C5 C 0.0814(7) 0.4380(4) 0.66754(13) 0.0651(15) Uani 1 1 d . . . . .
C8 C 0.1671(7) 0.6002(5) 0.70140(13) 0.0748(17) Uani 1 1 d . . . . .
H8 H 0.197258 0.655006 0.712901 0.090 Uiso 1 1 calc R U . . .
C15 C 0.7893(7) 0.6891(5) 0.68280(15) 0.0742(17) Uani 1 1 d . . . . .
H15 H 0.728935 0.647532 0.695572 0.089 Uiso 1 1 calc R U . . .
C16 C 0.8576(8) 0.7694(5) 0.69596(13) 0.0740(17) Uani 1 1 d . . . . .
C7 C 0.0753(7) 0.5298(5) 0.71606(13) 0.0750(18) Uani 1 1 d . . . . .
C22 C 0.8309(16) 0.4255(8) 0.5530(3) 0.058(3) Uani 0.5 1 d . . P . .
C18 C 0.9675(8) 0.8101(4) 0.64513(15) 0.0780(18) Uani 1 1 d . . . . .
H18 H 1.027518 0.852497 0.632589 0.094 Uiso 1 1 calc R U . . .
C6 C 0.0313(7) 0.4473(5) 0.69933(14) 0.0797(19) Uani 1 1 d . . . . .
H6 H -0.030036 0.399533 0.709149 0.096 Uiso 1 1 calc R U . . .
C17 C 0.9493(8) 0.8308(5) 0.67756(15) 0.0823(19) Uani 1 1 d . . . . .
H17 H 0.997687 0.884719 0.686714 0.099 Uiso 1 1 calc R U . . .
C19 C 0.6996(13) 0.4626(8) 0.5373(3) 0.052(3) Uani 0.5 1 d . . P . .
C20 C 0.8708(14) 0.4293(7) 0.5300(4) 0.053(3) Uani 0.5 1 d . . P . .
C21 C 0.9036(6) 0.3326(4) 0.55316(16) 0.0737(18) Uani 1 1 d . . . . .
H21 H 0.824280 0.282155 0.548753 0.088 Uiso 1 1 calc R U . . .
C25 C 0.760(2) 0.4346(8) 0.5195(3) 0.058(3) Uani 0.5 1 d . . P . .


_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
Cl1 C5 1.749(6) . ?
Cl3 C14 1.742(6) . ?
Cl4 C16 1.744(6) . ?
Cl2 C7 1.735(6) . ?
O1 C1 1.233(6) . ?
O4 C10 1.239(6) . ?
O2 C1 1.268(6) . ?
O3 C10 1.259(6) . ?
N1 C19 1.433(11) . ?
N1 C25 1.666(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C21 1.488(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C4 C9 1.399(8) . ?
C4 C5 1.400(7) . ?
C4 C3 1.451(7) . ?
C3 C2 1.305(7) . ?
C3 H3 0.9300 . ?
C10 C11 1.490(8) . ?
C1 C2 1.502(7) . ?
C13 C14 1.395(7) . ?
C13 C18 1.397(8) . ?
C13 C12 1.457(8) . ?
C11 C12 1.311(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C14 C15 1.381(8) . ?
C9 C8 1.368(7) . ?
C9 H9 0.9300 . ?
C5 C6 1.386(8) . ?
C8 C7 1.381(8) . ?
C8 H8 0.9300 . ?
C15 C16 1.363(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(9) . ?
C7 C6 1.386(8) . ?
C22 C20 1.012(13) . ?
C22 C19 1.376(15) . ?
C22 C21 1.423(12) . ?
C22 C25 1.513(17) . ?
C18 C17 1.380(8) . ?
C18 H18 0.9300 . ?
C6 H6 0.9300 . ?
C17 H17 0.9300 . ?
C19 C25 0.972(14) . ?
C19 C20 1.534(16) . ?
C20 C25 1.025(14) . ?
C20 C21 1.670(14) . ?
C21 H21 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
C19 N1 C25 35.6(5) . . ?
C19 N1 H1A 119.6 . . ?
C25 N1 H1A 119.6 . . ?
C19 N1 H1B 119.6 . . ?
C25 N1 H1B 119.6 . . ?
H1A N1 H1B 117.4 . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C9 C4 C5 115.6(5) . . ?
C9 C4 C3 122.9(5) . . ?
C5 C4 C3 121.5(5) . . ?
C2 C3 C4 127.5(5) . . ?
C2 C3 H3 116.2 . . ?
C4 C3 H3 116.2 . . ?
O4 C10 O3 122.4(5) . . ?
O4 C10 C11 119.8(5) . . ?
O3 C10 C11 117.7(5) . . ?
O1 C1 O2 124.6(5) . . ?
O1 C1 C2 119.0(5) . . ?
O2 C1 C2 116.4(5) . . ?
C14 C13 C18 114.6(6) . . ?
C14 C13 C12 123.2(5) . . ?
C18 C13 C12 122.1(5) . . ?
C12 C11 C10 124.7(5) . . ?
C12 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C11 C12 C13 129.3(6) . . ?
C11 C12 H12 115.4 . . ?
C13 C12 H12 115.4 . . ?
C3 C2 C1 124.2(5) . . ?
C3 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C15 C14 C13 122.9(5) . . ?
C15 C14 Cl3 116.9(5) . . ?
C13 C14 Cl3 120.1(5) . . ?
C8 C9 C4 122.6(5) . . ?
C8 C9 H9 118.7 . . ?
C4 C9 H9 118.7 . . ?
C6 C5 C4 123.3(5) . . ?
C6 C5 Cl1 116.3(5) . . ?
C4 C5 Cl1 120.4(4) . . ?
C9 C8 C7 119.7(6) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C16 C15 C14 119.3(6) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.1(6) . . ?
C15 C16 Cl4 119.8(5) . . ?
C17 C16 Cl4 119.1(5) . . ?
C8 C7 C6 120.7(6) . . ?
C8 C7 Cl2 120.0(5) . . ?
C6 C7 Cl2 119.2(5) . . ?
C20 C22 C19 78.3(10) . . ?
C20 C22 C21 84.8(12) . . ?
C19 C22 C21 132.9(10) . . ?
C20 C22 C25 42.4(9) . . ?
C19 C22 C25 39.0(6) . . ?
C21 C22 C25 104.2(10) . . ?
C17 C18 C13 123.9(6) . . ?
C17 C18 H18 118.1 . . ?
C13 C18 H18 118.1 . . ?
C5 C6 C7 118.0(6) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C16 C17 C18 118.1(6) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C25 C19 C22 78.1(11) . . ?
C25 C19 N1 85.4(13) . . ?
C22 C19 N1 131.6(10) . . ?
C25 C19 C20 41.1(10) . . ?
C22 C19 C20 40.2(6) . . ?
N1 C19 C20 102.7(10) . . ?
C22 C20 C25 95.9(15) . . ?
C22 C20 C19 61.5(10) . . ?
C25 C20 C19 38.5(10) . . ?
C22 C20 C21 58.1(10) . . ?
C25 C20 C21 116.6(11) . . ?
C19 C20 C21 106.3(8) . . ?
C22 C21 N2 126.7(7) . . ?
C22 C21 C20 37.1(5) . . ?
N2 C21 C20 96.6(5) . . ?
C22 C21 H21 110.7 . . ?
N2 C21 H21 110.7 . . ?
C20 C21 H21 110.7 . . ?
C19 C25 C20 100.4(17) . . ?
C19 C25 C22 62.9(11) . . ?
C20 C25 C22 41.7(9) . . ?
C19 C25 N1 59.0(11) . . ?
C20 C25 N1 116.9(11) . . ?
C22 C25 N1 107.3(9) . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_B2A24
_database_code_depnum_ccdc_archive 'CCDC 2533551'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2026-04-28 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Cl4 N2 O6'
_chemical_formula_weight         530.21

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                   7.739(2)
_cell_length_b                   38.409(11)
_cell_length_c                   8.028(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.796(10)
_cell_angle_gamma                90
_cell_volume                     2385.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    306(2)
_cell_measurement_reflns_used    2208
_cell_measurement_theta_min      2.593
_cell_measurement_theta_max      25.499

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.535
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4279
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      306(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24536
_diffrn_reflns_av_unetI/netI     0.1244
_diffrn_reflns_av_R_equivalents  0.1599
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             4252
_reflns_number_gt                2208
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4252
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1897
_refine_ls_R_factor_gt           0.1044
_refine_ls_wR_factor_ref         0.2608
_refine_ls_wR_factor_gt          0.2356
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.210
_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
Cl1A Cl 0.7979(3) 0.10111(5) 0.1561(3) 0.0736(7) Uani 1 1 d . . . . .
Cl2A Cl 0.8938(3) -0.00122(5) -0.2799(3) 0.0707(7) Uani 1 1 d . . . . .
O1A O 0.4420(6) 0.21848(11) -0.3093(6) 0.0468(12) Uani 1 1 d . . . . .
O2A O 0.6103(6) 0.21756(11) -0.0862(5) 0.0537(13) Uani 1 1 d . . . . .
C1A C 0.7263(8) 0.10915(17) -0.1749(10) 0.0496(18) Uani 1 1 d . . . . .
C2A C 0.7844(9) 0.08662(18) -0.0471(8) 0.0497(18) Uani 1 1 d . . . . .
C3A C 0.8345(8) 0.05234(17) -0.0793(9) 0.0501(17) Uani 1 1 d . . . . .
H3A H 0.872148 0.037851 0.007307 0.060 Uiso 1 1 calc R U . . .
C4A C 0.8273(9) 0.04063(16) -0.2374(9) 0.0484(17) Uani 1 1 d . . . . .
C5A C 0.7726(10) 0.06225(19) -0.3659(11) 0.066(2) Uani 1 1 d . . . . .
H5A H 0.771055 0.054042 -0.474940 0.079 Uiso 1 1 calc R U . . .
C6A C 0.7210(10) 0.09544(18) -0.3349(10) 0.060(2) Uani 1 1 d . . . . .
H6A H 0.681269 0.109275 -0.423142 0.072 Uiso 1 1 calc R U . . .
C7A C 0.6806(9) 0.14577(17) -0.1437(8) 0.0476(17) Uani 1 1 d . . . . .
H7A H 0.733889 0.156524 -0.051907 0.057 Uiso 1 1 calc R U . . .
C8A C 0.5703(9) 0.16470(17) -0.2347(8) 0.0507(18) Uani 1 1 d . . . . .
H8A H 0.508516 0.153722 -0.320974 0.061 Uiso 1 1 calc R U . . .
C9A C 0.5387(9) 0.20286(16) -0.2072(8) 0.0405(15) Uani 1 1 d . . . . .
Cl2B Cl 0.3924(3) 0.49851(5) -0.7903(3) 0.0670(6) Uani 1 1 d . . . . .
Cl1B Cl 0.3327(3) 0.41475(5) -0.2648(2) 0.0764(7) Uani 1 1 d . . . . .
O1B O 0.0580(7) 0.27411(12) -0.5831(5) 0.0593(14) Uani 1 1 d . . . . .
O2B O 0.0521(5) 0.30241(11) -0.3422(5) 0.0429(11) Uani 1 1 d . . . . .
C1B C 0.2313(8) 0.39546(16) -0.5775(8) 0.0412(16) Uani 1 1 d . . . . .
C2B C 0.3041(9) 0.42096(16) -0.4814(8) 0.0445(16) Uani 1 1 d . . . . .
C3B C 0.3491(9) 0.45234(18) -0.5437(8) 0.0500(18) Uani 1 1 d . . . . .
H3B H 0.394366 0.469478 -0.473145 0.060 Uiso 1 1 calc R U . . .
C4B C 0.3274(8) 0.45885(17) -0.7134(8) 0.0467(17) Uani 1 1 d . . . . .
C5B C 0.2577(9) 0.43387(16) -0.8181(9) 0.0514(18) Uani 1 1 d . . . . .
H5B H 0.242095 0.438149 -0.931547 0.062 Uiso 1 1 calc R U . . .
C6B C 0.2106(9) 0.40160(18) -0.7492(9) 0.0516(18) Uani 1 1 d . . . . .
H6B H 0.165289 0.384203 -0.818358 0.062 Uiso 1 1 calc R U . . .
C7B C 0.1718(8) 0.36228(16) -0.5053(9) 0.0445(16) Uani 1 1 d . . . . .
H7B H 0.160010 0.361882 -0.390440 0.053 Uiso 1 1 calc R U . . .
C8B C 0.1331(9) 0.33272(18) -0.5870(8) 0.0504(18) Uani 1 1 d . . . . .
H8B H 0.141412 0.332028 -0.702281 0.060 Uiso 1 1 calc R U . . .
C9B C 0.0767(8) 0.30085(16) -0.4967(8) 0.0404(15) Uani 1 1 d . . . . .
O1W O -0.0583(7) 0.28211(12) -0.9088(6) 0.0658(15) Uani 1 1 d . . . . .
O2W O 1.0559(11) 0.15491(16) -0.5428(8) 0.114(3) Uani 1 1 d . . . . .
N1 N 0.3482(7) 0.28048(13) -0.1503(7) 0.0438(14) Uani 1 1 d . . . . .
H1A H 0.388040 0.260551 -0.190637 0.066 Uiso 1 1 calc R U . . .
H1B H 0.237044 0.282845 -0.180005 0.066 Uiso 1 1 calc R U . . .
H1C H 0.359617 0.280333 -0.039624 0.066 Uiso 1 1 calc R U . . .
N2 N 0.7259(6) 0.27852(13) -0.2573(6) 0.0403(13) Uani 1 1 d . . . . .
H2A H 0.692196 0.258557 -0.212290 0.060 Uiso 1 1 calc R U . . .
H2B H 0.839962 0.280670 -0.244032 0.060 Uiso 1 1 calc R U . . .
H2C H 0.697095 0.278632 -0.365522 0.060 Uiso 1 1 calc R U . . .
C1 C 0.4489(8) 0.31025(16) -0.2185(8) 0.0452(17) Uani 1 1 d . . . . .
H1D H 0.404992 0.331891 -0.174068 0.054 Uiso 1 1 calc R U . . .
H1E H 0.431956 0.310888 -0.338715 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6412(8) 0.30749(16) -0.1756(8) 0.0438(17) Uani 1 1 d . . . . .
H2D H 0.697094 0.329006 -0.207079 0.053 Uiso 1 1 calc R U . . .
H2E H 0.656850 0.304867 -0.055892 0.053 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
Cl1A C2A 1.724(7) . ?
Cl2A C4A 1.725(6) . ?
O1A C9A 1.246(8) . ?
O2A C9A 1.240(8) . ?
C1A C6A 1.387(10) . ?
C1A C2A 1.406(10) . ?
C1A C7A 1.474(9) . ?
C2A C3A 1.399(9) . ?
C3A C4A 1.346(9) . ?
C4A C5A 1.380(10) . ?
C5A C6A 1.361(10) . ?
C7A C8A 1.324(9) . ?
C8A C9A 1.503(9) . ?
Cl2B C4B 1.725(7) . ?
Cl1B C2B 1.762(7) . ?
O1B C9B 1.245(7) . ?
O2B C9B 1.262(7) . ?
C1B C2B 1.358(9) . ?
C1B C6B 1.403(9) . ?
C1B C7B 1.479(9) . ?
C2B C3B 1.355(9) . ?
C3B C4B 1.390(9) . ?
C4B C5B 1.375(9) . ?
C5B C6B 1.410(9) . ?
C7B C8B 1.340(9) . ?
C8B C9B 1.495(9) . ?
N1 C1 1.497(8) . ?
N2 C2 1.458(7) . ?
C1 C2 1.521(9) . ?

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
C6A C1A C2A 116.2(6) . . ?
C6A C1A C7A 121.3(6) . . ?
C2A C1A C7A 122.4(7) . . ?
C3A C2A C1A 121.9(6) . . ?
C3A C2A Cl1A 118.0(6) . . ?
C1A C2A Cl1A 120.0(5) . . ?
C2A C3A C4A 119.0(7) . . ?
C3A C4A C5A 120.4(6) . . ?
C3A C4A Cl2A 119.6(6) . . ?
C5A C4A Cl2A 119.9(6) . . ?
C6A C5A C4A 120.8(7) . . ?
C5A C6A C1A 121.6(7) . . ?
C8A C7A C1A 125.8(7) . . ?
C7A C8A C9A 124.0(6) . . ?
O2A C9A O1A 122.8(6) . . ?
O2A C9A C8A 119.2(6) . . ?
O1A C9A C8A 118.0(6) . . ?
C2B C1B C6B 118.0(6) . . ?
C2B C1B C7B 121.8(6) . . ?
C6B C1B C7B 120.2(6) . . ?
C1B C2B C3B 122.6(6) . . ?
C1B C2B Cl1B 120.0(5) . . ?
C3B C2B Cl1B 117.3(5) . . ?
C4B C3B C2B 119.8(7) . . ?
C5B C4B C3B 120.4(6) . . ?
C5B C4B Cl2B 120.7(5) . . ?
C3B C4B Cl2B 118.8(5) . . ?
C4B C5B C6B 118.4(7) . . ?
C1B C6B C5B 120.7(7) . . ?
C8B C7B C1B 127.3(6) . . ?
C7B C8B C9B 121.4(6) . . ?
O1B C9B O2B 124.6(6) . . ?
O1B C9B C8B 115.8(6) . . ?
O2B C9B C8B 119.5(6) . . ?
N1 C1 C2 112.4(5) . . ?
N2 C2 C1 113.7(5) . . ?

_refine_diff_density_max         1.213
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.107


# start Validation Reply Form
_vrf_PLAT306_B2A24               
;
PROBLEM: Isolated Oxygen Atom(s) (H-atoms Missing ?) ....          2 Check
RESPONSE: ...The H-atoms can not be located.
;
_vrf_PLAT430_B2A24               
;
PROBLEM: Short Inter D...A Contact  O1B      ..O1W      .       2.74 Ang.
RESPONSE: ...Due to the hydrogen bonding.
;
_vrf_PLAT041_B2A24               
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE:...H atoms of water molecules could not be located.
;
# end Validation Reply Form



####################################################################### 
# 
# 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_dB2A24
_database_code_depnum_ccdc_archive 'CCDC 2533555'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2026-04-28 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl4 N2 O4'
_chemical_formula_weight         494.18

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      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                   19.923(2)
_cell_length_b                   7.8306(8)
_cell_length_c                   14.0052(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.688(3)
_cell_angle_gamma                90
_cell_volume                     2153.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    2389
_cell_measurement_theta_min      2.074
_cell_measurement_theta_max      26.469

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.580
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5938
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABD
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38275
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_av_R_equivalents  0.1559
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         26.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4424
_reflns_number_gt                2389
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.2637P] 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         4424
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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
Cl1 Cl 0.28066(6) 0.43485(16) 0.87670(7) 0.0528(3) Uani 1 1 d . . . . .
Cl4 Cl 0.26344(7) 0.76165(16) 0.69556(9) 0.0645(4) Uani 1 1 d . . . . .
Cl2 Cl 0.50638(6) 0.1501(2) 0.78816(11) 0.0902(5) Uani 1 1 d . . . . .
Cl3 Cl 0.43968(8) 0.7969(2) 0.44920(14) 0.1100(7) Uani 1 1 d . . . . .
O2 O 0.04281(13) 0.2426(3) 0.44490(18) 0.0394(7) Uani 1 1 d . . . . .
O4 O 0.07565(13) 0.0221(3) 0.63131(18) 0.0382(7) Uani 1 1 d . . . . .
O3 O 0.07573(13) 0.2794(4) 0.6958(2) 0.0452(7) Uani 1 1 d . . . . .
O1 O 0.07192(15) 0.5136(4) 0.4340(2) 0.0544(8) Uani 1 1 d . . . . .
N2 N 0.06033(15) 0.8624(4) 0.4437(2) 0.0352(8) Uani 1 1 d . . . . .
H2A H 0.020050 0.904795 0.417175 0.053 Uiso 1 1 calc R U . . .
H2B H 0.074229 0.912344 0.500706 0.053 Uiso 1 1 calc R U . . .
H2C H 0.056557 0.750384 0.452266 0.053 Uiso 1 1 calc R U . . .
N1 N 0.03157(15) 0.8798(4) 0.2214(2) 0.0413(8) Uani 1 1 d . . . . .
H1A H -0.003827 0.873293 0.252472 0.062 Uiso 1 1 calc R U . . .
H1B H 0.022326 0.822421 0.165916 0.062 Uiso 1 1 calc R U . . .
H1C H 0.039664 0.988738 0.209188 0.062 Uiso 1 1 calc R U . . .
C17 C 0.10167(18) 0.1675(5) 0.6491(2) 0.0296(8) Uani 1 1 d . . . . .
C18 C 0.08357(19) 0.3648(5) 0.4619(2) 0.0331(9) Uani 1 1 d . . . . .
C16 C 0.16580(18) 0.2109(5) 0.6098(3) 0.0316(9) Uani 1 1 d . . . . .
H16 H 0.192028 0.108099 0.600540 0.038 Uiso 1 1 calc R U . . .
C14 C 0.19335(18) 0.4739(5) 0.5733(3) 0.0328(9) Uani 1 1 d . . . . .
H14 H 0.160579 0.559929 0.587135 0.039 Uiso 1 1 calc R U . . .
C12 C 0.28541(18) 0.3057(5) 0.6967(3) 0.0329(9) Uani 1 1 d . . . . .
C13 C 0.21198(17) 0.3524(5) 0.6648(3) 0.0323(9) Uani 1 1 d . . . . .
H13 H 0.192191 0.395984 0.719524 0.039 Uiso 1 1 calc R U . . .
C15 C 0.15451(18) 0.3268(5) 0.5159(3) 0.0321(9) Uani 1 1 d . . . . .
H15 H 0.182173 0.281873 0.470001 0.039 Uiso 1 1 calc R U . . .
C1 C 0.25088(19) 0.5618(5) 0.5365(3) 0.0364(9) Uani 1 1 d . . . . .
C11 C 0.32083(19) 0.3372(5) 0.7902(3) 0.0359(9) Uani 1 1 d . . . . .
C19 C 0.11044(18) 0.8950(5) 0.3790(2) 0.0349(9) Uani 1 1 d . . . . .
H19A H 0.155021 0.857244 0.410697 0.042 Uiso 1 1 calc R U . . .
H19B H 0.112930 1.016921 0.367800 0.042 Uiso 1 1 calc R U . . .
C20 C 0.09252(19) 0.8048(5) 0.2826(3) 0.0362(9) Uani 1 1 d . . . . .
H20A H 0.130878 0.811620 0.248371 0.043 Uiso 1 1 calc R U . . .
H20B H 0.084034 0.685070 0.293884 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2886(2) 0.6894(5) 0.5905(3) 0.0429(10) Uani 1 1 d . . . . .
C7 C 0.3235(2) 0.2299(5) 0.6329(3) 0.0417(10) Uani 1 1 d . . . . .
H7 H 0.302268 0.207914 0.569773 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3909(2) 0.1862(6) 0.6593(3) 0.0482(11) Uani 1 1 d . . . . .
H8 H 0.414793 0.138238 0.614310 0.058 Uiso 1 1 calc R U . . .
C10 C 0.3883(2) 0.2915(6) 0.8183(3) 0.0509(11) Uani 1 1 d . . . . .
H10 H 0.410341 0.312591 0.881109 0.061 Uiso 1 1 calc R U . . .
C9 C 0.4224(2) 0.2142(6) 0.7522(3) 0.0487(11) Uani 1 1 d . . . . .
C5 C 0.3459(2) 0.7596(6) 0.5640(4) 0.0552(12) Uani 1 1 d . . . . .
H5 H 0.370180 0.843129 0.602542 0.066 Uiso 1 1 calc R U . . .
C2 C 0.2722(2) 0.5175(6) 0.4502(3) 0.0507(11) Uani 1 1 d . . . . .
H2 H 0.247038 0.437702 0.409902 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3673(2) 0.7070(7) 0.4816(4) 0.0613(14) Uani 1 1 d . . . . .
C3 C 0.3303(3) 0.5891(7) 0.4220(4) 0.0636(14) Uani 1 1 d . . . . .
H3 H 0.343584 0.557343 0.363941 0.076 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
Cl1 C11 1.737(4) . ?
Cl4 C6 1.727(4) . ?
Cl2 C9 1.738(4) . ?
Cl3 C4 1.733(5) . ?
O2 C18 1.252(4) . ?
O4 C17 1.259(4) . ?
O3 C17 1.255(4) . ?
O1 C18 1.238(4) . ?
N2 C19 1.480(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N1 C20 1.485(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C17 C16 1.513(5) . ?
C18 C15 1.516(5) . ?
C16 C13 1.559(5) . ?
C16 C15 1.582(5) . ?
C16 H16 0.9800 . ?
C14 C1 1.501(5) . ?
C14 C15 1.537(5) . ?
C14 C13 1.589(5) . ?
C14 H14 0.9800 . ?
C12 C7 1.398(5) . ?
C12 C11 1.401(5) . ?
C12 C13 1.501(5) . ?
C13 H13 0.9800 . ?
C15 H15 0.9800 . ?
C1 C2 1.390(5) . ?
C1 C6 1.394(5) . ?
C11 C10 1.382(6) . ?
C19 C20 1.512(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C6 C5 1.374(6) . ?
C7 C8 1.375(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(6) . ?
C8 H8 0.9300 . ?
C10 C9 1.377(6) . ?
C10 H10 0.9300 . ?
C5 C4 1.359(7) . ?
C5 H5 0.9300 . ?
C2 C3 1.402(6) . ?
C2 H2 0.9300 . ?
C4 C3 1.373(7) . ?
C3 H3 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
C19 N2 H2A 109.5 . . ?
C19 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C19 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C20 N1 H1A 109.5 . . ?
C20 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C20 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O3 C17 O4 122.9(3) . . ?
O3 C17 C16 118.7(3) . . ?
O4 C17 C16 118.4(3) . . ?
O1 C18 O2 125.3(4) . . ?
O1 C18 C15 116.8(3) . . ?
O2 C18 C15 117.7(3) . . ?
C17 C16 C13 116.3(3) . . ?
C17 C16 C15 114.9(3) . . ?
C13 C16 C15 89.6(3) . . ?
C17 C16 H16 111.5 . . ?
C13 C16 H16 111.5 . . ?
C15 C16 H16 111.5 . . ?
C1 C14 C15 120.7(3) . . ?
C1 C14 C13 117.6(3) . . ?
C15 C14 C13 90.1(3) . . ?
C1 C14 H14 109.0 . . ?
C15 C14 H14 109.0 . . ?
C13 C14 H14 109.0 . . ?
C7 C12 C11 115.4(3) . . ?
C7 C12 C13 121.3(3) . . ?
C11 C12 C13 123.2(3) . . ?
C12 C13 C16 116.0(3) . . ?
C12 C13 C14 118.0(3) . . ?
C16 C13 C14 89.3(3) . . ?
C12 C13 H13 110.6 . . ?
C16 C13 H13 110.6 . . ?
C14 C13 H13 110.6 . . ?
C18 C15 C14 117.3(3) . . ?
C18 C15 C16 121.2(3) . . ?
C14 C15 C16 90.4(3) . . ?
C18 C15 H15 108.8 . . ?
C14 C15 H15 108.8 . . ?
C16 C15 H15 108.8 . . ?
C2 C1 C6 115.8(4) . . ?
C2 C1 C14 123.1(4) . . ?
C6 C1 C14 121.0(3) . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 Cl1 117.1(3) . . ?
C12 C11 Cl1 120.7(3) . . ?
N2 C19 C20 112.6(3) . . ?
N2 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N2 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N1 C20 C19 112.2(3) . . ?
N1 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
N1 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C5 C6 C1 122.5(4) . . ?
C5 C6 Cl4 118.2(4) . . ?
C1 C6 Cl4 119.3(3) . . ?
C8 C7 C12 123.0(4) . . ?
C8 C7 H7 118.5 . . ?
C12 C7 H7 118.5 . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C9 C10 C11 119.3(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 Cl2 119.7(4) . . ?
C10 C9 Cl2 119.5(3) . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C2 C3 122.2(4) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 Cl3 119.5(4) . . ?
C3 C4 Cl3 119.9(4) . . ?
C4 C3 C2 118.8(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.072

