# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_datam
_database_code_depnum_ccdc_archive 'CCDC 2272061'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.0782(7)
_cell_length_b                   12.8899(12)
_cell_length_c                   17.2503(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1573.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4636
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.417
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.952
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16778
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         27.465
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3605
_reflns_number_gt                3451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0394P)²+0.2115P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.4201(3) 0.39614(18) 0.41034(13) 0.0333(5) Uani 1 1 d . . . . .
C2 C 0.4850(3) 0.30786(19) 0.37101(13) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.3803(4) 0.21664(18) 0.37323(14) 0.0357(5) Uani 1 1 d . . . . .
C4 C 0.2135(4) 0.2110(2) 0.41460(15) 0.0419(6) Uani 1 1 d . . . . .
H4 H 0.144553 0.147805 0.417157 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1486(4) 0.2985(2) 0.45215(14) 0.0451(7) Uani 1 1 d . . . . .
H5 H 0.032610 0.295716 0.479806 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2496(4) 0.3903(2) 0.45017(14) 0.0412(6) Uani 1 1 d . . . . .
H6 H 0.202240 0.449783 0.476222 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4087(4) 0.7299(2) 0.39230(15) 0.0411(6) Uani 1 1 d . . . . .
H7 H 0.413955 0.696743 0.343143 0.049 Uiso 1 1 calc R U . . .
C8 C 0.3984(4) 0.8382(2) 0.39437(16) 0.0447(6) Uani 1 1 d . . . . .
H8 H 0.394473 0.877248 0.347676 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3942(4) 0.8870(2) 0.46468(16) 0.0413(5) Uani 1 1 d . . . . .
H9 H 0.388457 0.960517 0.467306 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3985(3) 0.82780(19) 0.53310(14) 0.0335(5) Uani 1 1 d . . . . .
C11 C 0.3938(4) 0.87375(19) 0.60883(15) 0.0392(6) Uani 1 1 d . . . . .
H11 H 0.391092 0.947145 0.613684 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3931(3) 0.8145(2) 0.67314(14) 0.0377(5) Uani 1 1 d . . . . .
H12 H 0.392190 0.846840 0.722636 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3938(3) 0.70358(18) 0.66816(14) 0.0328(5) Uani 1 1 d . . . . .
C14 C 0.3823(3) 0.6398(2) 0.73426(14) 0.0392(5) Uani 1 1 d . . . . .
H14 H 0.378911 0.669501 0.784657 0.047 Uiso 1 1 calc R U . . .
C15 C 0.3762(4) 0.5343(2) 0.72478(15) 0.0433(6) Uani 1 1 d . . . . .
H15 H 0.366039 0.489730 0.768419 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3850(4) 0.4936(2) 0.65003(16) 0.0424(6) Uani 1 1 d . . . . .
H16 H 0.380995 0.420297 0.644532 0.051 Uiso 1 1 calc R U . . .
C17 C 0.4006(3) 0.65460(17) 0.59477(14) 0.0306(5) Uani 1 1 d . . . . .
C18 C 0.4046(3) 0.71858(17) 0.52575(13) 0.0301(5) Uani 1 1 d . . . . .
N1 N 0.4113(3) 0.67090(16) 0.45527(11) 0.0352(4) Uani 1 1 d . . . . .
N2 N 0.3985(3) 0.55011(15) 0.58614(12) 0.0368(4) Uani 1 1 d . . . . .
O1 O 0.5275(3) 0.48182(15) 0.40720(13) 0.0489(5) Uani 1 1 d . . . . .
H1O H 0.477(6) 0.532(3) 0.432(2) 0.082(13) Uiso 1 1 d . . . . .
Cl1 Cl 0.69618(9) 0.31530(5) 0.32110(4) 0.04606(19) Uani 1 1 d . . . . .
Cl2 Cl 0.45669(12) 0.10788(5) 0.32281(5) 0.0549(2) 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 O1 1.342(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.390(3) . ?
C2 Cl1 1.728(2) . ?
C3 C4 1.382(4) . ?
C3 Cl2 1.736(3) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.326(3) . ?
C7 C8 1.399(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.366(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.406(4) . ?
C9 H9 0.9500 . ?
C10 C18 1.414(3) . ?
C10 C11 1.435(3) . ?
C11 C12 1.347(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.433(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.408(3) . ?
C13 C17 1.416(3) . ?
C14 C15 1.370(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 N2 1.325(3) . ?
C16 H16 0.9500 . ?
C17 N2 1.355(3) . ?
C17 C18 1.449(3) . ?
C18 N1 1.363(3) . ?
O1 H1O 0.85(4) . ?

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
O1 C1 C6 123.8(2) . . ?
O1 C1 C2 117.6(2) . . ?
C6 C1 C2 118.6(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 Cl1 121.45(18) . . ?
C1 C2 Cl1 118.65(18) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 Cl2 118.82(19) . . ?
C2 C3 Cl2 120.2(2) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C8 123.5(2) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C18 117.7(2) . . ?
C9 C10 C11 122.7(2) . . ?
C18 C10 C11 119.6(2) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C17 117.8(2) . . ?
C14 C13 C12 122.3(2) . . ?
C17 C13 C12 119.9(2) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N2 C16 C15 124.5(2) . . ?
N2 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
N2 C17 C13 122.8(2) . . ?
N2 C17 C18 118.4(2) . . ?
C13 C17 C18 118.8(2) . . ?
N1 C18 C10 122.0(2) . . ?
N1 C18 C17 118.5(2) . . ?
C10 C18 C17 119.5(2) . . ?
C7 N1 C18 118.2(2) . . ?
C16 N2 C17 117.1(2) . . ?
C1 O1 H1O 111(3) . . ?

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
O1 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
O1 C1 C2 Cl1 -0.4(3) . . . . ?
C6 C1 C2 Cl1 179.68(18) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
Cl1 C2 C3 C4 178.70(18) . . . . ?
C1 C2 C3 Cl2 178.46(18) . . . . ?
Cl1 C2 C3 Cl2 -2.0(3) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
Cl2 C3 C4 C5 -177.4(2) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
O1 C1 C6 C5 -178.6(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
N1 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C18 -0.8(3) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 178.3(2) . . . . ?
C18 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C11 C12 C13 C14 -176.3(2) . . . . ?
C11 C12 C13 C17 1.8(4) . . . . ?
C17 C13 C14 C15 -0.7(3) . . . . ?
C12 C13 C14 C15 177.4(2) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 N2 -0.2(4) . . . . ?
C14 C13 C17 N2 -0.7(3) . . . . ?
C12 C13 C17 N2 -178.9(2) . . . . ?
C14 C13 C17 C18 177.5(2) . . . . ?
C12 C13 C17 C18 -0.7(3) . . . . ?
C9 C10 C18 N1 1.7(3) . . . . ?
C11 C10 C18 N1 -179.2(2) . . . . ?
C9 C10 C18 C17 -177.3(2) . . . . ?
C11 C10 C18 C17 1.7(3) . . . . ?
N2 C17 C18 N1 -1.8(3) . . . . ?
C13 C17 C18 N1 179.93(19) . . . . ?
N2 C17 C18 C10 177.2(2) . . . . ?
C13 C17 C18 C10 -1.0(3) . . . . ?
C8 C7 N1 C18 -0.3(4) . . . . ?
C10 C18 N1 C7 -1.2(3) . . . . ?
C17 C18 N1 C7 177.8(2) . . . . ?
C15 C16 N2 C17 -1.1(4) . . . . ?
C13 C17 N2 C16 1.6(4) . . . . ?
C18 C17 N2 C16 -176.6(2) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_datam_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2272062'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17

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                   11.404(8)
_cell_length_b                   12.721(8)
_cell_length_c                   15.241(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.811(8)
_cell_angle_gamma                90
_cell_volume                     2080(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7406
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      33.8

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.592
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18584
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4077
_reflns_number_gt                3757
_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)+(0.0398P)²+0.8700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4077
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_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 -0.03010(17) 0.31110(14) 0.26128(12) 0.0260(4) Uani 1 1 d . . . . .
C2 C -0.10340(16) 0.30681(14) 0.16697(12) 0.0248(4) Uani 1 1 d . . . . .
C3 C -0.08653(18) 0.38085(15) 0.10543(13) 0.0287(4) Uani 1 1 d . . . . .
C4 C -0.0011(2) 0.46093(16) 0.13529(15) 0.0369(5) Uani 1 1 d . . . . .
H4 H 0.008396 0.511941 0.092658 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0707(2) 0.46547(16) 0.22878(15) 0.0375(5) Uani 1 1 d . . . . .
H5 H 0.130335 0.520119 0.250487 0.045 Uiso 1 1 calc R U . . .
C6 C 0.05691(19) 0.39145(16) 0.29118(13) 0.0325(4) Uani 1 1 d . . . . .
H6 H 0.107419 0.395655 0.355059 0.039 Uiso 1 1 calc R U . . .
C7 C 0.52594(18) 0.43391(14) 1.21674(12) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.60019(17) 0.43881(14) 1.31085(12) 0.0249(4) Uani 1 1 d . . . . .
C9 C 0.57391(17) 0.51240(15) 1.36858(12) 0.0272(4) Uani 1 1 d . . . . .
C10 C 0.47678(19) 0.58248(16) 1.33429(14) 0.0337(4) Uani 1 1 d . . . . .
H10 H 0.460390 0.633444 1.374213 0.040 Uiso 1 1 calc R U . . .
C11 C 0.40404(19) 0.57779(16) 1.24185(14) 0.0351(4) Uani 1 1 d . . . . .
H11 H 0.336989 0.625826 1.217804 0.042 Uiso 1 1 calc R U . . .
C12 C 0.42750(18) 0.50366(15) 1.18328(13) 0.0302(4) Uani 1 1 d . . . . .
H12 H 0.375670 0.500637 1.119664 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1772(2) 0.23210(19) 0.54000(15) 0.0438(5) Uani 1 1 d . . . . .
H13 H 0.203684 0.182313 0.504165 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2486(2) 0.24420(18) 0.63261(14) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.322621 0.204241 0.658843 0.048 Uiso 1 1 calc R U . . .
C15 C 0.21159(17) 0.31505(14) 0.68719(12) 0.0248(4) Uani 1 1 d . . . . .
C16 C 0.10365(18) 0.37133(16) 0.64297(13) 0.0318(4) Uani 1 1 d . . . . .
H16 H 0.074570 0.421545 0.676940 0.038 Uiso 1 1 calc R U . . .
C17 C 0.03849(19) 0.35461(16) 0.54993(14) 0.0342(4) Uani 1 1 d . . . . .
H17 H -0.035338 0.394116 0.521368 0.041 Uiso 1 1 calc R U . . .
C18 C 0.35039(19) 0.43555(16) 0.92505(13) 0.0315(4) Uani 1 1 d . . . . .
H18 H 0.343497 0.499556 0.955045 0.038 Uiso 1 1 calc R U . . .
C19 C 0.27781(18) 0.42322(15) 0.83279(12) 0.0280(4) Uani 1 1 d . . . . .
H19 H 0.222961 0.477726 0.800867 0.034 Uiso 1 1 calc R U . . .
C20 C 0.28532(17) 0.33054(14) 0.78670(12) 0.0249(4) Uani 1 1 d . . . . .
C21 C 0.3679(2) 0.25450(16) 0.83867(13) 0.0341(4) Uani 1 1 d . . . . .
H21 H 0.376271 0.189450 0.810766 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4370(2) 0.27390(17) 0.93041(14) 0.0371(5) Uani 1 1 d . . . . .
H22 H 0.493129 0.221059 0.964152 0.045 Uiso 1 1 calc R U . . .
N1 N 0.07382(16) 0.28581(14) 0.49802(11) 0.0335(4) Uani 1 1 d . . . . .
N2 N 0.42969(16) 0.36312(14) 0.97476(11) 0.0329(4) Uani 1 1 d . . . . .
O1 O -0.04699(14) 0.23655(11) 0.31818(9) 0.0324(3) Uani 1 1 d . . . . .
H1 H -0.008(2) 0.2524(12) 0.3729(18) 0.049 Uiso 1 1 calc R U . . .
O2 O 0.55490(14) 0.36102(11) 1.16365(10) 0.0340(3) Uani 1 1 d . . . . .
H2 H 0.516(2) 0.3705(13) 1.112(2) 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl -0.21068(4) 0.20731(4) 0.12843(3) 0.03356(14) Uani 1 1 d . . . . .
Cl2 Cl -0.17438(5) 0.37291(4) -0.01201(3) 0.03941(15) Uani 1 1 d . . . . .
Cl3 Cl 0.72445(5) 0.35445(4) 1.35111(4) 0.03879(15) Uani 1 1 d . . . . .
Cl4 Cl 0.66454(5) 0.51812(4) 1.48551(3) 0.04039(15) 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 O1 1.342(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.388(3) . ?
C2 Cl1 1.7195(19) . ?
C3 C4 1.376(3) . ?
C3 Cl2 1.733(2) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.343(2) . ?
C7 C12 1.386(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.385(3) . ?
C8 Cl3 1.717(2) . ?
C9 C10 1.379(3) . ?
C9 Cl4 1.732(2) . ?
C10 C11 1.373(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N1 1.325(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 C20 1.477(3) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 N1 1.331(3) . ?
C17 H17 0.9500 . ?
C18 N2 1.333(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C21 C22 1.375(3) . ?
C21 H21 0.9500 . ?
C22 N2 1.338(3) . ?
C22 H22 0.9500 . ?
O1 H1 0.83(3) . ?
O2 H2 0.78(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 123.42(17) . . ?
O1 C1 C2 118.04(17) . . ?
C6 C1 C2 118.53(17) . . ?
C3 C2 C1 119.80(17) . . ?
C3 C2 Cl1 120.95(15) . . ?
C1 C2 Cl1 119.23(14) . . ?
C4 C3 C2 121.58(18) . . ?
C4 C3 Cl2 118.78(15) . . ?
C2 C3 Cl2 119.64(15) . . ?
C3 C4 C5 118.50(18) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 120.91(19) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.66(19) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O2 C7 C12 123.66(17) . . ?
O2 C7 C8 117.49(17) . . ?
C12 C7 C8 118.84(17) . . ?
C9 C8 C7 119.70(17) . . ?
C9 C8 Cl3 121.71(14) . . ?
C7 C8 Cl3 118.57(14) . . ?
C10 C9 C8 121.00(17) . . ?
C10 C9 Cl4 119.02(15) . . ?
C8 C9 Cl4 119.98(15) . . ?
C11 C10 C9 119.28(18) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.62(18) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.54(18) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C13 C14 123.9(2) . . ?
N1 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 116.43(18) . . ?
C16 C15 C20 122.23(17) . . ?
C14 C15 C20 121.33(17) . . ?
C17 C16 C15 120.12(18) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N1 C17 C16 123.21(19) . . ?
N1 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
N2 C18 C19 123.96(18) . . ?
N2 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
C18 C19 C20 119.59(18) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 116.54(17) . . ?
C19 C20 C15 121.40(17) . . ?
C21 C20 C15 122.05(17) . . ?
C22 C21 C20 119.83(18) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
N2 C22 C21 123.60(19) . . ?
N2 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
C13 N1 C17 116.83(17) . . ?
C18 N2 C22 116.48(17) . . ?
C1 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_datam_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2272064'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20

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                   22.923(3)
_cell_length_b                   11.7148(14)
_cell_length_c                   11.6400(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.091(6)
_cell_angle_gamma                90
_cell_volume                     3123.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8175
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.421
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.902
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32124
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         0.889
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7171
_reflns_number_gt                6198
_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)+(0.0467P)²+0.9559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7171
_refine_ls_number_parameters     419
_refine_ls_number_restraints     642
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.072
_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
C1 C 0.34505(8) 0.15441(15) 0.48699(16) 0.0283(4) Uani 1 1 d . U . . .
C2 C 0.29310(8) 0.09285(15) 0.48705(16) 0.0276(4) Uani 1 1 d . U . . .
C3 C 0.25158(8) 0.10346(16) 0.39798(17) 0.0317(4) Uani 1 1 d . U . . .
H3 H 0.216241 0.061162 0.398753 0.038 Uiso 1 1 calc R U . . .
C4 C 0.26251(8) 0.17674(16) 0.30786(17) 0.0323(4) Uani 1 1 d . U . . .
C5 C 0.31359(9) 0.23745(18) 0.30497(18) 0.0378(5) Uani 1 1 d . U . . .
H5 H 0.320768 0.286749 0.242241 0.045 Uiso 1 1 calc R U . . .
C6 C 0.35454(8) 0.22602(17) 0.39454(18) 0.0370(5) Uani 1 1 d . U . . .
H6 H 0.389921 0.268097 0.392707 0.044 Uiso 1 1 calc R U . . .
C7 C 0.83615(8) 0.16040(17) 1.02158(17) 0.0344(4) Uani 1 1 d . U . . .
C8 C 0.79117(8) 0.08119(16) 1.00995(16) 0.0299(4) Uani 1 1 d . U . . .
C9 C 0.75207(8) 0.08341(16) 0.91658(17) 0.0322(4) Uani 1 1 d . U . . .
H9 H 0.721641 0.028536 0.909350 0.039 Uiso 1 1 calc R U . . .
C10 C 0.75812(8) 0.16723(17) 0.83376(17) 0.0332(4) Uani 1 1 d . U . . .
C11 C 0.80176(9) 0.24777(17) 0.84350(18) 0.0374(5) Uani 1 1 d . U . . .
H11 H 0.805159 0.305361 0.786678 0.045 Uiso 1 1 calc R U . . .
C12 C 0.84067(9) 0.24361(18) 0.93745(19) 0.0410(5) Uani 1 1 d . U . . .
H12 H 0.870992 0.298733 0.944376 0.049 Uiso 1 1 calc R U . . .
C13 C 0.51938(9) 0.14510(16) 0.45434(17) 0.0336(4) Uani 1 1 d . U . . .
H13 H 0.496103 0.085609 0.421397 0.040 Uiso 1 1 calc R U . . .
C14 C 0.57904(9) 0.14358(17) 0.43616(17) 0.0361(4) Uani 1 1 d . U . . .
H14 H 0.595732 0.084837 0.391667 0.043 Uiso 1 1 calc R U . . .
C15 C 0.61326(8) 0.22848(17) 0.48370(16) 0.0328(4) Uani 1 1 d . U . . .
H15 H 0.654172 0.228694 0.473281 0.039 Uiso 1 1 calc R U . . .
C16 C 0.58734(8) 0.31547(15) 0.54814(15) 0.0274(4) Uani 1 1 d . U . . .
C17 C 0.62041(8) 0.40683(16) 0.60133(16) 0.0319(4) Uani 1 1 d . U . . .
H17 H 0.661628 0.408262 0.595471 0.038 Uiso 1 1 calc R U . . .
C18 C 0.59386(9) 0.49037(16) 0.65930(16) 0.0322(4) Uani 1 1 d . U . . .
H18 H 0.616603 0.550036 0.693372 0.039 Uiso 1 1 calc R U . . .
C19 C 0.53188(8) 0.49058(15) 0.67034(15) 0.0276(4) Uani 1 1 d . U . . .
C20 C 0.50271(9) 0.57893(16) 0.72680(16) 0.0340(4) Uani 1 1 d . U . . .
H20 H 0.523766 0.642725 0.756970 0.041 Uiso 1 1 calc R U . . .
C21 C 0.44376(9) 0.57160(17) 0.73755(17) 0.0373(5) Uani 1 1 d . U . . .
H21 H 0.423027 0.630661 0.774316 0.045 Uiso 1 1 calc R U . . .
C22 C 0.41427(9) 0.47523(18) 0.69332(18) 0.0376(4) Uani 1 1 d . U . . .
H22 H 0.373459 0.470044 0.703901 0.045 Uiso 1 1 calc R U . . .
C23 C 0.49790(8) 0.39943(14) 0.62488(14) 0.0252(4) Uani 1 1 d . U . . .
C24 C 0.52643(8) 0.31036(14) 0.56112(14) 0.0244(3) Uani 1 1 d . U . . .
C25 C 1.01357(10) 0.14764(18) 0.95269(19) 0.0421(5) Uani 1 1 d . U . . .
H25 H 0.991140 0.086543 0.920558 0.051 Uiso 1 1 calc R U . . .
C26 C 1.07298(10) 0.15140(19) 0.93055(18) 0.0426(5) Uani 1 1 d . U . . .
H26 H 1.090301 0.094056 0.885229 0.051 Uiso 1 1 calc R U . . .
C27 C 1.10577(9) 0.23947(18) 0.97551(16) 0.0357(4) Uani 1 1 d . U . . .
H27 H 1.146327 0.243738 0.961965 0.043 Uiso 1 1 calc R U . . .
C28 C 1.07902(8) 0.32361(16) 1.04192(15) 0.0289(4) Uani 1 1 d . U . . .
C29 C 1.11019(8) 0.41924(17) 1.09157(16) 0.0335(4) Uani 1 1 d . U . . .
H29 H 1.150998 0.425766 1.081585 0.040 Uiso 1 1 calc R U . . .
C30 C 1.08264(9) 0.49966(16) 1.15190(16) 0.0333(4) Uani 1 1 d . U . . .
H30 H 1.104166 0.562628 1.182606 0.040 Uiso 1 1 calc R U . . .
C31 C 1.02146(9) 0.49172(15) 1.17047(15) 0.0291(4) Uani 1 1 d . U . . .
C32 C 0.99134(10) 0.57522(17) 1.23139(17) 0.0380(5) Uani 1 1 d . U . . .
H32 H 1.010948 0.641847 1.258770 0.046 Uiso 1 1 calc R U . . .
C33 C 0.93349(10) 0.55942(19) 1.25076(18) 0.0423(5) Uani 1 1 d . U . . .
H33 H 0.912017 0.615568 1.290233 0.051 Uiso 1 1 calc R U . . .
C34 C 0.90625(9) 0.45828(19) 1.21111(17) 0.0393(5) Uani 1 1 d . U . . .
H34 H 0.866511 0.446516 1.228343 0.047 Uiso 1 1 calc R U . . .
C35 C 0.98965(8) 0.39595(15) 1.12889(15) 0.0263(4) Uani 1 1 d . U . . .
C36 C 1.01880(8) 0.31131(15) 1.06044(15) 0.0261(4) Uani 1 1 d . U . . .
N1 N 0.43965(7) 0.39091(14) 0.63770(14) 0.0318(3) Uani 1 1 d . U . . .
N2 N 0.49303(6) 0.22462(13) 0.51491(13) 0.0275(3) Uani 1 1 d . U . . .
N3 N 0.93275(7) 0.37849(14) 1.15118(14) 0.0321(3) Uani 1 1 d . U . . .
N4 N 0.98651(7) 0.22399(14) 1.01576(14) 0.0342(4) Uani 1 1 d . U . . .
O1 O 0.38445(6) 0.14189(12) 0.57612(12) 0.0348(3) Uani 1 1 d . U . . .
H1 H 0.4124(10) 0.182(2) 0.5660(11) 0.052 Uiso 1 1 calc R U . . .
O2 O 0.87340(7) 0.15527(16) 1.11394(14) 0.0549(5) Uani 1 1 d . U . . .
H2 H 0.8980(13) 0.203(3) 1.1084(13) 0.082 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27964(2) 0.00187(5) 0.60067(5) 0.03986(14) Uani 1 1 d . U . . .
Cl2 Cl 0.21023(2) 0.19210(5) 0.19596(5) 0.04956(16) Uani 1 1 d . U . . .
Cl3 Cl 0.78295(2) -0.02096(5) 1.11633(5) 0.04145(15) Uani 1 1 d . U . . .
Cl4 Cl 0.70932(3) 0.17101(6) 0.71496(5) 0.05335(17) Uani 1 1 d . 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
C1 O1 1.358(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.392(2) . ?
C2 C3 1.387(3) . ?
C2 Cl1 1.7349(18) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(3) . ?
C4 Cl2 1.7468(19) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.349(2) . ?
C7 C12 1.388(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.384(3) . ?
C8 Cl3 1.7371(19) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 Cl4 1.7471(19) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N2 1.327(2) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.410(3) . ?
C15 H15 0.9500 . ?
C16 C24 1.411(2) . ?
C16 C17 1.439(2) . ?
C17 C18 1.347(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.431(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.408(3) . ?
C19 C23 1.413(2) . ?
C20 C21 1.364(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.404(3) . ?
C21 H21 0.9500 . ?
C22 N1 1.327(2) . ?
C22 H22 0.9500 . ?
C23 N1 1.353(2) . ?
C23 C24 1.450(2) . ?
C24 N2 1.362(2) . ?
C25 N4 1.326(3) . ?
C25 C26 1.396(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.369(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.407(3) . ?
C27 H27 0.9500 . ?
C28 C36 1.412(2) . ?
C28 C29 1.439(3) . ?
C29 C30 1.346(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.430(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.404(3) . ?
C31 C35 1.414(2) . ?
C32 C33 1.366(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.409(3) . ?
C33 H33 0.9500 . ?
C34 N3 1.327(3) . ?
C34 H34 0.9500 . ?
C35 N3 1.355(2) . ?
C35 C36 1.450(3) . ?
C36 N4 1.355(2) . ?
O1 H1 0.81(2) . ?
O2 H2 0.80(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 122.60(16) . . ?
O1 C1 C2 119.25(16) . . ?
C6 C1 C2 118.14(17) . . ?
C3 C2 C1 121.12(17) . . ?
C3 C2 Cl1 119.25(14) . . ?
C1 C2 Cl1 119.63(14) . . ?
C4 C3 C2 118.91(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 121.20(18) . . ?
C5 C4 Cl2 119.43(16) . . ?
C3 C4 Cl2 119.36(15) . . ?
C4 C5 C6 119.19(18) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 121.43(18) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O2 C7 C12 122.13(18) . . ?
O2 C7 C8 119.56(17) . . ?
C12 C7 C8 118.30(18) . . ?
C9 C8 C7 121.40(17) . . ?
C9 C8 Cl3 119.26(14) . . ?
C7 C8 Cl3 119.33(15) . . ?
C8 C9 C10 118.76(17) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.25(18) . . ?
C11 C10 Cl4 119.35(15) . . ?
C9 C10 Cl4 119.40(15) . . ?
C10 C11 C12 119.04(18) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 121.24(18) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
N2 C13 C14 123.97(17) . . ?
N2 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C15 C14 C13 118.70(18) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.56(18) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C24 117.67(16) . . ?
C15 C16 C17 122.77(17) . . ?
C24 C16 C17 119.56(17) . . ?
C18 C17 C16 121.05(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.96(17) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C23 117.74(17) . . ?
C20 C19 C18 122.22(17) . . ?
C23 C19 C18 120.04(17) . . ?
C21 C20 C19 119.04(18) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 118.83(18) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
N1 C22 C21 124.3(2) . . ?
N1 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
N1 C23 C19 123.19(17) . . ?
N1 C23 C24 117.96(15) . . ?
C19 C23 C24 118.86(16) . . ?
N2 C24 C16 122.22(16) . . ?
N2 C24 C23 118.38(16) . . ?
C16 C24 C23 119.39(16) . . ?
N4 C25 C26 124.08(19) . . ?
N4 C25 H25 118.0 . . ?
C26 C25 H25 118.0 . . ?
C27 C26 C25 118.61(19) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C28 119.59(19) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C36 117.41(17) . . ?
C27 C28 C29 123.11(18) . . ?
C36 C28 C29 119.48(17) . . ?
C30 C29 C28 121.27(18) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C31 120.98(17) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C32 C31 C35 117.94(18) . . ?
C32 C31 C30 122.28(18) . . ?
C35 C31 C30 119.76(17) . . ?
C33 C32 C31 119.16(19) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 118.76(19) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
N3 C34 C33 124.0(2) . . ?
N3 C34 H34 118.0 . . ?
C33 C34 H34 118.0 . . ?
N3 C35 C31 122.85(17) . . ?
N3 C35 C36 117.91(16) . . ?
C31 C35 C36 119.24(17) . . ?
N4 C36 C28 122.80(17) . . ?
N4 C36 C35 118.08(16) . . ?
C28 C36 C35 119.12(16) . . ?
C22 N1 C23 116.81(17) . . ?
C13 N2 C24 117.87(16) . . ?
C34 N3 C35 117.18(17) . . ?
C25 N4 C36 117.50(17) . . ?
C1 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.058

# start Validation Reply Form
_vrf_PLAT110_datam               
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Performed Platon AddSymm. No change suggested.
;
_vrf_PLAT112_datam               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         B        100 %Fit  
RESPONSE: Performed Platon AddSymm. No change suggested.
;
_vrf_PLAT113_datam               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/c Check 
RESPONSE: Performed Platon AddSymm. No change suggested.
;
# 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_datam_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2272065'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   18.809(3)
_cell_length_b                   3.8575(6)
_cell_length_c                   29.184(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.486(7)
_cell_angle_gamma                90
_cell_volume                     2094.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10352
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.8

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.588
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.944
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9003
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.308
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2377
_reflns_number_gt                1982
_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)+(0.0380P)²+1.2452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C 0.66476(9) 0.6828(5) 0.61260(5) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.59689(8) 0.6449(4) 0.58635(6) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.58295(8) 0.7521(4) 0.54073(5) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.536340 0.726007 0.523456 0.026 Uiso 1 1 calc R U . . .
C4 C 0.63805(9) 0.8980(4) 0.52066(6) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.70605(9) 0.9377(5) 0.54538(6) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.743639 1.036405 0.531198 0.029 Uiso 1 1 calc R U . . .
C6 C 0.71853(9) 0.8314(5) 0.59112(6) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.765109 0.860813 0.608319 0.030 Uiso 1 1 calc R U . . .
C7 C 0.83661(9) 0.6618(5) 0.74201(6) 0.0303(4) Uani 1 1 d . . . . .
H7 H 0.799917 0.728277 0.759385 0.036 Uiso 1 1 calc R U . . .
C8 C 0.90695(9) 0.6660(5) 0.76389(6) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.917798 0.733139 0.795469 0.030 Uiso 1 1 calc R U . . .
C9 C 0.96173(8) 0.5709(4) 0.73916(5) 0.0208(4) Uani 1 1 d . . . . .
C10 C 0.94191(9) 0.4737(5) 0.69310(6) 0.0254(4) Uani 1 1 d . . . . .
H10 H 0.977439 0.407296 0.674808 0.031 Uiso 1 1 calc R U . . .
C11 C 0.87032(10) 0.4747(5) 0.67432(6) 0.0296(4) Uani 1 1 d . . . . .
H11 H 0.857841 0.404076 0.642975 0.035 Uiso 1 1 calc R U . . .
N1 N 0.81720(8) 0.5694(4) 0.69765(5) 0.0310(4) Uani 1 1 d . . . . .
O1 O 0.67476(7) 0.5727(4) 0.65715(4) 0.0309(3) Uani 1 1 d . . . . .
H1 H 0.7168(12) 0.584(6) 0.6675(4) 0.046 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52773(2) 0.45934(12) 0.61139(2) 0.02653(13) Uani 1 1 d . . . . .
Cl2 Cl 0.62004(2) 1.03844(13) 0.46321(2) 0.03093(14) 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 O1 1.3542(19) . ?
C1 C6 1.390(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.382(2) . ?
C2 Cl1 1.7376(16) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 Cl2 1.7469(17) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.340(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 C9 1.485(3) 2_756 ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.340(2) . ?
C11 H11 0.9500 . ?
O1 H1 0.80(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
O1 C1 C6 123.72(14) . . ?
O1 C1 C2 118.71(15) . . ?
C6 C1 C2 117.58(15) . . ?
C3 C2 C1 121.70(15) . . ?
C3 C2 Cl1 118.76(12) . . ?
C1 C2 Cl1 119.54(13) . . ?
C2 C3 C4 118.84(15) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.19(15) . . ?
C5 C4 Cl2 120.03(13) . . ?
C3 C4 Cl2 118.78(12) . . ?
C4 C5 C6 118.92(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 121.77(15) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N1 C7 C8 123.73(16) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.27(15) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.29(15) . . ?
C8 C9 C9 121.64(17) . 2_756 ?
C10 C9 C9 121.07(17) . 2_756 ?
C11 C10 C9 119.37(15) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.85(16) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C7 N1 C11 116.49(15) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.91(16) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
O1 C1 C2 Cl1 0.0(2) . . . . ?
C6 C1 C2 Cl1 179.78(14) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
Cl1 C2 C3 C4 -179.62(13) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl2 -179.19(13) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
Cl2 C4 C5 C6 178.59(14) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
O1 C1 C6 C5 179.46(17) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
N1 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C9 179.92(14) . . . 2_756 ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C9 C10 C11 179.55(13) 2_756 . . . ?
C9 C10 C11 N1 1.0(3) . . . . ?
C8 C7 N1 C11 0.5(3) . . . . ?
C10 C11 N1 C7 -1.1(3) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_datam_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2272063'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C16 H12 Cl2 N2 O'
_chemical_formula_weight         319.18

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'
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                   10.5285(11)
_cell_length_b                   7.0970(7)
_cell_length_c                   19.468(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.747(7)
_cell_angle_gamma                90
_cell_volume                     1433.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11915
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.452
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.948
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14484
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.060
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3277
_reflns_number_gt                2492
_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)+(0.0300P)²+0.8439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3277
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.1737(2) 0.6319(3) 0.54489(11) 0.0309(5) Uani 1 1 d . . . . .
C2 C 0.11347(19) 0.5814(3) 0.60117(11) 0.0289(5) Uani 1 1 d . . . . .
C3 C 0.08882(19) 0.3935(3) 0.61278(11) 0.0308(5) Uani 1 1 d . . . . .
C4 C 0.1189(2) 0.2538(3) 0.56890(12) 0.0350(5) Uani 1 1 d . . . . .
H4 H 0.100494 0.125488 0.577006 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1764(2) 0.3049(3) 0.51288(12) 0.0372(5) Uani 1 1 d . . . . .
H5 H 0.197092 0.210339 0.482054 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2042(2) 0.4906(3) 0.50094(11) 0.0357(5) Uani 1 1 d . . . . .
H6 H 0.244437 0.522276 0.462365 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2743(2) 0.9236(3) 0.37083(13) 0.0394(6) Uani 1 1 d . . . . .
H7 H 0.186478 0.958311 0.368075 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3265(2) 0.9282(3) 0.31027(11) 0.0326(5) Uani 1 1 d . . . . .
H8 H 0.274934 0.963246 0.267312 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4555(2) 0.8810(3) 0.31301(10) 0.0267(4) Uani 1 1 d . . . . .
C10 C 0.5246(2) 0.8311(3) 0.37760(11) 0.0339(5) Uani 1 1 d . . . . .
H10 H 0.613133 0.798602 0.382284 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4633(3) 0.8292(3) 0.43515(12) 0.0423(6) Uani 1 1 d . . . . .
H11 H 0.512155 0.794360 0.478885 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6992(3) 0.9137(3) 0.19232(14) 0.0459(6) Uani 1 1 d . . . . .
H12 H 0.789046 0.935695 0.195849 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6478(2) 0.9138(3) 0.25337(12) 0.0361(5) Uani 1 1 d . . . . .
H13 H 0.701505 0.935355 0.297000 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5167(2) 0.8820(3) 0.24988(11) 0.0283(5) Uani 1 1 d . . . . .
C15 C 0.4449(2) 0.8509(3) 0.18414(10) 0.0343(5) Uani 1 1 d . . . . .
H15 H 0.354884 0.827773 0.178817 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5057(3) 0.8542(3) 0.12667(12) 0.0470(7) Uani 1 1 d . . . . .
H16 H 0.454541 0.833075 0.082251 0.056 Uiso 1 1 calc R U . . .
N1 N 0.3395(2) 0.8735(3) 0.43261(10) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.6312(2) 0.8848(3) 0.12925(11) 0.0496(6) Uani 1 1 d . . . . .
O1 O 0.20076(17) 0.8161(2) 0.53703(9) 0.0417(4) Uani 1 1 d . . . . .
H1 H 0.240(3) 0.8285(7) 0.5037(14) 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07155(6) 0.75813(8) 0.65458(3) 0.03951(16) Uani 1 1 d . . . . .
Cl2 Cl 0.02118(6) 0.32961(9) 0.68512(3) 0.04803(19) 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 O1 1.352(2) . ?
C1 C6 1.391(3) . ?
C1 C2 1.403(3) . ?
C2 C3 1.385(3) . ?
C2 Cl1 1.733(2) . ?
C3 C4 1.380(3) . ?
C3 Cl2 1.742(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.328(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 C14 1.482(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 N1 1.334(3) . ?
C11 H11 0.9500 . ?
C12 N2 1.329(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 N2 1.331(3) . ?
C16 H16 0.9500 . ?
O1 H1 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 123.57(18) . . ?
O1 C1 C2 117.86(18) . . ?
C6 C1 C2 118.56(19) . . ?
C3 C2 C1 119.73(18) . . ?
C3 C2 Cl1 121.69(16) . . ?
C1 C2 Cl1 118.58(16) . . ?
C4 C3 C2 121.45(19) . . ?
C4 C3 Cl2 118.80(17) . . ?
C2 C3 Cl2 119.74(16) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C8 124.0(2) . . ?
N1 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.05(19) . . ?
C10 C9 C14 121.2(2) . . ?
C8 C9 C14 121.77(19) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.6(2) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N2 C12 C13 124.4(2) . . ?
N2 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C14 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 116.90(19) . . ?
C13 C14 C9 121.9(2) . . ?
C15 C14 C9 121.2(2) . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N2 C16 C15 124.4(2) . . ?
N2 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C7 N1 C11 116.64(19) . . ?
C12 N2 C16 115.9(2) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.4(2) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
O1 C1 C2 Cl1 2.7(3) . . . . ?
C6 C1 C2 Cl1 -178.26(17) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
Cl1 C2 C3 C4 178.03(17) . . . . ?
C1 C2 C3 Cl2 176.86(16) . . . . ?
Cl1 C2 C3 Cl2 -3.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
Cl2 C3 C4 C5 -177.93(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
O1 C1 C6 C5 178.5(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
N1 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 C14 179.55(19) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C14 C9 C10 C11 -179.0(2) . . . . ?
C9 C10 C11 N1 -0.2(4) . . . . ?
N2 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C9 -179.7(2) . . . . ?
C10 C9 C14 C13 -28.1(3) . . . . ?
C8 C9 C14 C13 152.5(2) . . . . ?
C10 C9 C14 C15 152.0(2) . . . . ?
C8 C9 C14 C15 -27.5(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C9 C14 C15 C16 179.6(2) . . . . ?
C14 C15 C16 N2 0.2(4) . . . . ?
C8 C7 N1 C11 1.3(3) . . . . ?
C10 C11 N1 C7 -0.7(3) . . . . ?
C13 C12 N2 C16 -0.1(4) . . . . ?
C15 C16 N2 C12 0.0(4) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_datam_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2272069'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17

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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.3339(14)
_cell_length_b                   7.2993(10)
_cell_length_c                   14.5440(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.972(7)
_cell_angle_gamma                90
_cell_volume                     1059.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9438
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.581
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.944
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10358
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2436
_reflns_number_gt                2119
_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)+(0.0411P)²+0.4455P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     138
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.012
_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
C1 C 0.37540(14) 0.2483(2) 0.16482(10) 0.0247(3) Uani 1 1 d . U . . .
C2 C 0.37778(15) 0.0724(2) 0.20260(10) 0.0268(3) Uani 1 1 d . U . . .
C3 C 0.26855(17) -0.0449(2) 0.17768(12) 0.0345(4) Uani 1 1 d . U . . .
H3 H 0.274047 -0.165058 0.203551 0.041 Uiso 1 1 calc R U . . .
C4 C 0.15209(18) 0.0144(3) 0.11509(13) 0.0400(4) Uani 1 1 d . U . . .
H4 H 0.076784 -0.064877 0.097977 0.048 Uiso 1 1 calc R U . . .
C5 C 0.14439(16) 0.1888(3) 0.07712(12) 0.0362(4) Uani 1 1 d . U . . .
H5 H 0.063756 0.230285 0.034572 0.043 Uiso 1 1 calc R U . . .
C6 C 0.25490(15) 0.3024(2) 0.10154(10) 0.0280(3) Uani 1 1 d . U . . .
C7 C 0.80444(16) 0.2485(2) 0.36033(11) 0.0326(3) Uani 1 1 d . U . . .
H7 H 0.795066 0.126597 0.336660 0.039 Uiso 1 1 calc R U . . .
C8 C 0.92124(15) 0.2942(2) 0.42752(11) 0.0300(3) Uani 1 1 d . U . . .
H8 H 0.989318 0.204944 0.448850 0.036 Uiso 1 1 calc R U . . .
C9 C 0.93842(14) 0.4714(2) 0.46365(10) 0.0243(3) Uani 1 1 d . U . . .
C10 C 0.83389(15) 0.5940(2) 0.42818(11) 0.0308(3) Uani 1 1 d . U . . .
H10 H 0.840575 0.717157 0.449960 0.037 Uiso 1 1 calc R U . . .
C11 C 0.72046(16) 0.5357(2) 0.36124(12) 0.0330(3) Uani 1 1 d . U . . .
H11 H 0.650340 0.621494 0.338558 0.040 Uiso 1 1 calc R U . . .
N1 N 0.70430(13) 0.36539(19) 0.32683(9) 0.0310(3) Uani 1 1 d . U . . .
O1 O 0.47814(11) 0.36644(15) 0.18424(8) 0.0318(3) Uani 1 1 d . U . . .
H1 H 0.5351(18) 0.3295(17) 0.2280(15) 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52075(4) -0.00083(5) 0.28616(3) 0.03656(13) Uani 1 1 d . U . . .
Cl2 Cl 0.24259(4) 0.52284(6) 0.05569(3) 0.03937(13) Uani 1 1 d . 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
C1 O1 1.3399(16) . ?
C1 C2 1.395(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.388(2) . ?
C2 Cl1 1.7371(16) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 Cl2 1.7339(16) . ?
C7 N1 1.333(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 C9 1.489(3) 3_766 ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.334(2) . ?
C11 H11 0.9500 . ?
O1 H1 0.79(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
O1 C1 C2 125.25(13) . . ?
O1 C1 C6 118.61(13) . . ?
C2 C1 C6 116.14(13) . . ?
C3 C2 C1 122.33(15) . . ?
C3 C2 Cl1 118.69(13) . . ?
C1 C2 Cl1 118.96(11) . . ?
C4 C3 C2 119.40(16) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.27(15) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.46(16) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 122.39(15) . . ?
C5 C6 Cl2 118.98(13) . . ?
C1 C6 Cl2 118.59(11) . . ?
N1 C7 C8 123.89(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.61(15) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 116.48(13) . . ?
C8 C9 C9 122.10(17) . 3_766 ?
C10 C9 C9 121.41(17) . 3_766 ?
C11 C10 C9 119.85(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.48(15) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C7 N1 C11 116.69(13) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.42(14) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
O1 C1 C2 Cl1 3.3(2) . . . . ?
C6 C1 C2 Cl1 -176.84(11) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
Cl1 C2 C3 C4 176.80(13) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 Cl2 -178.42(13) . . . . ?
O1 C1 C6 C5 179.57(14) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
O1 C1 C6 Cl2 -2.79(19) . . . . ?
C2 C1 C6 Cl2 177.35(11) . . . . ?
N1 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C9 179.73(17) . . . 3_766 ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C9 C10 C11 -179.47(17) 3_766 . . . ?
C9 C10 C11 N1 -0.5(3) . . . . ?
C8 C7 N1 C11 0.1(2) . . . . ?
C10 C11 N1 C7 0.1(2) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_datam_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2272067'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17

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                   5.789(7)
_cell_length_b                   14.243(19)
_cell_length_c                   12.602(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.64(3)
_cell_angle_gamma                90
_cell_volume                     1027(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    809
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.8

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.599
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.942
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10520
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.270
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2349
_reflns_number_gt                2149
_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)+(0.0362P)²+0.3610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2349
_refine_ls_number_parameters     138
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      0.991
_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
C1 C 0.4324(2) 0.58052(10) 0.30853(11) 0.0187(3) Uani 1 1 d . U . . .
C2 C 0.6219(2) 0.54125(10) 0.26845(11) 0.0187(3) Uani 1 1 d . U . . .
C3 C 0.6787(3) 0.44756(10) 0.28381(12) 0.0228(3) Uani 1 1 d . U . . .
H3 H 0.809629 0.422610 0.256068 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5467(3) 0.38987(10) 0.33916(13) 0.0250(3) Uani 1 1 d . U . . .
H4 H 0.583107 0.325134 0.349191 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3601(3) 0.42935(10) 0.37947(11) 0.0217(3) Uani 1 1 d . U . . .
C6 C 0.3009(2) 0.52293(10) 0.36539(11) 0.0204(3) Uani 1 1 d . U . . .
H6 H 0.171331 0.547707 0.394340 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2820(3) 0.82245(10) 0.46949(12) 0.0239(3) Uani 1 1 d . U . . .
H7 H 0.430648 0.794543 0.491231 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2400(3) 0.90982(10) 0.51064(12) 0.0222(3) Uani 1 1 d . U . . .
H8 H 0.357129 0.940112 0.559725 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0256(2) 0.95283(9) 0.47968(10) 0.0156(3) Uani 1 1 d . U . . .
C10 C -0.1365(2) 0.90323(10) 0.40904(12) 0.0200(3) Uani 1 1 d . U . . .
H10 H -0.286288 0.929470 0.385555 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0809(3) 0.81556(10) 0.37255(12) 0.0223(3) Uani 1 1 d . U . . .
H11 H -0.195878 0.782732 0.324885 0.027 Uiso 1 1 calc R U . . .
N1 N 0.1265(2) 0.77529(8) 0.40130(10) 0.0213(3) Uani 1 1 d . U . . .
O1 O 0.38654(19) 0.67179(7) 0.28909(9) 0.0255(2) Uani 1 1 d . U . . .
H1 H 0.282(4) 0.6894(6) 0.3238(16) 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.78854(6) 0.61289(2) 0.19851(3) 0.02438(12) Uani 1 1 d . U . . .
Cl2 Cl 0.19202(7) 0.35821(3) 0.45035(3) 0.03083(13) Uani 1 1 d . 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
C1 O1 1.342(2) . ?
C1 C6 1.389(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.381(3) . ?
C2 Cl1 1.7332(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 Cl2 1.742(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.330(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 C9 1.484(3) 3_576 ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.331(2) . ?
C11 H11 0.9500 . ?
O1 H1 0.84(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
O1 C1 C6 123.88(13) . . ?
O1 C1 C2 117.91(13) . . ?
C6 C1 C2 118.21(15) . . ?
C3 C2 C1 121.42(14) . . ?
C3 C2 Cl1 120.08(12) . . ?
C1 C2 Cl1 118.49(13) . . ?
C4 C3 C2 120.52(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 117.81(15) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 122.60(14) . . ?
C4 C5 Cl2 118.70(14) . . ?
C6 C5 Cl2 118.71(13) . . ?
C5 C6 C1 119.44(14) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 123.81(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.49(14) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 116.53(14) . . ?
C10 C9 C9 122.16(16) . 3_576 ?
C8 C9 C9 121.31(16) . 3_576 ?
C11 C10 C9 120.27(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N1 C11 C10 122.90(14) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C7 N1 C11 116.99(14) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.14(13) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
O1 C1 C2 Cl1 1.12(18) . . . . ?
C6 C1 C2 Cl1 -179.40(10) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
Cl1 C2 C3 C4 -179.83(11) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 Cl2 -179.60(11) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
Cl2 C5 C6 C1 -179.64(11) . . . . ?
O1 C1 C6 C5 178.87(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C8 C9 C9 -178.94(15) . . . 3_576 ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C9 C10 C11 179.59(15) 3_576 . . . ?
C9 C10 C11 N1 -0.8(2) . . . . ?
C8 C7 N1 C11 -0.4(2) . . . . ?
C10 C11 N1 C7 1.1(2) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_datam_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2272068'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20

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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5269(11)
_cell_length_b                   12.0193(12)
_cell_length_c                   13.2546(14)
_cell_angle_alpha                90
_cell_angle_beta                 113.080(5)
_cell_angle_gamma                90
_cell_volume                     1542.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14666
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.426
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.959
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13283
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.158
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3531
_reflns_number_gt                2944
_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)+(0.0380P)²+0.4667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3531
_refine_ls_number_parameters     210
_refine_ls_number_restraints     321
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.008
_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
C1 C 0.42347(14) 0.26153(12) 0.37138(11) 0.0220(3) Uani 1 1 d . U . . .
C2 C 0.38105(16) 0.17026(13) 0.41522(12) 0.0250(3) Uani 1 1 d . U . . .
C3 C 0.29455(16) 0.08858(13) 0.34990(13) 0.0293(3) Uani 1 1 d . U . . .
H3 H 0.268554 0.027098 0.382635 0.035 Uiso 1 1 calc R U . . .
C4 C 0.24636(16) 0.09694(14) 0.23714(13) 0.0313(4) Uani 1 1 d . U . . .
H4 H 0.183659 0.043059 0.192100 0.038 Uiso 1 1 calc R U . . .
C5 C 0.28965(15) 0.18415(13) 0.18968(12) 0.0279(3) Uani 1 1 d . U . . .
H5 H 0.258241 0.189875 0.112198 0.034 Uiso 1 1 calc R U . . .
C6 C 0.37954(14) 0.26286(12) 0.25716(12) 0.0229(3) Uani 1 1 d . U . . .
C7 C 0.70225(17) 0.56196(13) 0.41876(12) 0.0289(3) Uani 1 1 d . U . . .
H7 H 0.632263 0.593014 0.438555 0.035 Uiso 1 1 calc R U . . .
C8 C 0.79216(17) 0.63467(13) 0.39628(13) 0.0314(4) Uani 1 1 d . U . . .
H8 H 0.783560 0.712907 0.401627 0.038 Uiso 1 1 calc R U . . .
C9 C 0.89231(16) 0.59100(14) 0.36656(12) 0.0305(4) Uani 1 1 d . U . . .
H9 H 0.953520 0.638719 0.350057 0.037 Uiso 1 1 calc R U . . .
C10 C 0.90403(15) 0.47488(13) 0.36060(11) 0.0259(3) Uani 1 1 d . U . . .
C11 C 1.00760(16) 0.42311(15) 0.33108(13) 0.0330(4) Uani 1 1 d . U . . .
H11 H 1.067656 0.468322 0.310653 0.040 Uiso 1 1 calc R U . . .
C12 C 1.02111(16) 0.31179(15) 0.33182(13) 0.0331(4) Uani 1 1 d . U . . .
H12 H 1.091391 0.279634 0.313079 0.040 Uiso 1 1 calc R U . . .
C13 C 0.93094(15) 0.24117(13) 0.36049(11) 0.0275(3) Uani 1 1 d . U . . .
C14 C 0.94374(17) 0.12432(14) 0.36587(13) 0.0340(4) Uani 1 1 d . U . . .
H14 H 1.016316 0.089205 0.352246 0.041 Uiso 1 1 calc R U . . .
C15 C 0.85190(18) 0.06190(14) 0.39062(13) 0.0345(4) Uani 1 1 d . U . . .
H15 H 0.859959 -0.016837 0.395327 0.041 Uiso 1 1 calc R U . . .
C16 C 0.74492(17) 0.11656(13) 0.40905(12) 0.0303(3) Uani 1 1 d . U . . .
H16 H 0.679423 0.072292 0.423820 0.036 Uiso 1 1 calc R U . . .
C17 C 0.82311(14) 0.28803(12) 0.38451(11) 0.0229(3) Uani 1 1 d . U . . .
C18 C 0.81057(14) 0.40808(13) 0.38615(11) 0.0225(3) Uani 1 1 d . U . . .
N1 N 0.71000(13) 0.45238(10) 0.41378(10) 0.0246(3) Uani 1 1 d . U . . .
N2 N 0.72995(13) 0.22563(10) 0.40709(10) 0.0263(3) Uani 1 1 d . U . . .
O1 O 0.49689(12) 0.34329(9) 0.43801(8) 0.0270(2) Uani 1 1 d . U . . .
H1 H 0.5583(19) 0.3649(12) 0.4176(11) 0.041 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43985(5) 0.15841(3) 0.55719(3) 0.03722(12) Uani 1 1 d . U . . .
Cl2 Cl 0.44275(4) 0.36593(3) 0.19755(3) 0.03103(11) Uani 1 1 d . 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
C1 O1 1.3446(17) . ?
C1 C2 1.394(2) . ?
C1 C6 1.399(2) . ?
C2 C3 1.387(2) . ?
C2 Cl1 1.7411(15) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 Cl2 1.7361(15) . ?
C7 N1 1.3229(19) . ?
C7 C8 1.403(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.367(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.406(2) . ?
C9 H9 0.9500 . ?
C10 C18 1.410(2) . ?
C10 C11 1.436(2) . ?
C11 C12 1.345(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.431(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(2) . ?
C13 C17 1.411(2) . ?
C14 C15 1.362(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.405(2) . ?
C15 H15 0.9500 . ?
C16 N2 1.319(2) . ?
C16 H16 0.9500 . ?
C17 N2 1.3579(19) . ?
C17 C18 1.450(2) . ?
C18 N1 1.3573(19) . ?
O1 H1 0.83(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
O1 C1 C2 119.79(13) . . ?
O1 C1 C6 124.30(13) . . ?
C2 C1 C6 115.85(13) . . ?
C3 C2 C1 122.40(14) . . ?
C3 C2 Cl1 119.01(12) . . ?
C1 C2 Cl1 118.59(11) . . ?
C4 C3 C2 119.79(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.92(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 118.98(14) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 122.83(14) . . ?
C5 C6 Cl2 118.63(11) . . ?
C1 C6 Cl2 118.53(11) . . ?
N1 C7 C8 123.33(15) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C9 C8 C7 118.86(15) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.48(15) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C18 117.83(14) . . ?
C9 C10 C11 122.55(15) . . ?
C18 C10 C11 119.62(14) . . ?
C12 C11 C10 121.22(15) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.83(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C17 117.10(15) . . ?
C14 C13 C12 122.95(15) . . ?
C17 C13 C12 119.95(15) . . ?
C15 C14 C13 119.88(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 118.51(16) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N2 C16 C15 123.96(16) . . ?
N2 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
N2 C17 C13 122.94(14) . . ?
N2 C17 C18 117.94(13) . . ?
C13 C17 C18 119.12(13) . . ?
N1 C18 C10 122.19(14) . . ?
N1 C18 C17 118.66(13) . . ?
C10 C18 C17 119.14(13) . . ?
C7 N1 C18 118.29(13) . . ?
C16 N2 C17 117.52(14) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 173.90(13) . . . . ?
C6 C1 C2 C3 -3.4(2) . . . . ?
O1 C1 C2 Cl1 -6.45(19) . . . . ?
C6 C1 C2 Cl1 176.29(10) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
Cl1 C2 C3 C4 179.67(12) . . . . ?
C2 C3 C4 C5 3.0(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C1 -3.3(2) . . . . ?
C4 C5 C6 Cl2 175.47(11) . . . . ?
O1 C1 C6 C5 -171.74(14) . . . . ?
C2 C1 C6 C5 5.4(2) . . . . ?
O1 C1 C6 Cl2 9.49(19) . . . . ?
C2 C1 C6 Cl2 -173.39(11) . . . . ?
N1 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C9 C10 C18 -0.1(2) . . . . ?
C8 C9 C10 C11 -179.34(14) . . . . ?
C9 C10 C11 C12 176.35(15) . . . . ?
C18 C10 C11 C12 -2.9(2) . . . . ?
C10 C11 C12 C13 1.0(2) . . . . ?
C11 C12 C13 C14 -177.91(15) . . . . ?
C11 C12 C13 C17 2.3(2) . . . . ?
C17 C13 C14 C15 1.7(2) . . . . ?
C12 C13 C14 C15 -178.11(15) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C14 C15 C16 N2 -2.1(2) . . . . ?
C14 C13 C17 N2 -3.0(2) . . . . ?
C12 C13 C17 N2 176.74(13) . . . . ?
C14 C13 C17 C18 176.53(13) . . . . ?
C12 C13 C17 C18 -3.7(2) . . . . ?
C9 C10 C18 N1 1.2(2) . . . . ?
C11 C10 C18 N1 -179.50(13) . . . . ?
C9 C10 C18 C17 -177.85(13) . . . . ?
C11 C10 C18 C17 1.4(2) . . . . ?
N2 C17 C18 N1 2.28(19) . . . . ?
C13 C17 C18 N1 -177.31(12) . . . . ?
N2 C17 C18 C10 -178.59(12) . . . . ?
C13 C17 C18 C10 1.81(19) . . . . ?
C8 C7 N1 C18 0.4(2) . . . . ?
C10 C18 N1 C7 -1.4(2) . . . . ?
C17 C18 N1 C7 177.71(13) . . . . ?
C15 C16 N2 C17 0.8(2) . . . . ?
C13 C17 N2 C16 1.8(2) . . . . ?
C18 C17 N2 C16 -177.77(13) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_datam_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2272071'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17

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      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                   7.4028(9)
_cell_length_b                   7.9597(10)
_cell_length_c                   9.3490(12)
_cell_angle_alpha                100.674(7)
_cell_angle_beta                 94.021(7)
_cell_angle_gamma                100.270(7)
_cell_volume                     529.64(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2429
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.581
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.955
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5656
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.105
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2429
_reflns_number_gt                1934
_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)+(0.0462P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2429
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.5959(3) 0.5232(3) 0.7801(2) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.4074(3) 0.4549(3) 0.7629(2) 0.0263(4) Uani 1 1 d . . . . .
H2 H 0.331868 0.495603 0.834412 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3299(3) 0.3279(3) 0.6420(2) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.4391(3) 0.2653(2) 0.5373(2) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.6257(3) 0.3346(3) 0.5535(2) 0.0264(4) Uani 1 1 d . . . . .
H5 H 0.700601 0.293754 0.481472 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7050(3) 0.4626(3) 0.6734(2) 0.0253(4) Uani 1 1 d . . . . .
H6 H 0.833583 0.509489 0.683221 0.030 Uiso 1 1 calc R U . . .
C7 C 1.1440(3) 0.7476(3) 1.0276(2) 0.0324(5) Uani 1 1 d . . . . .
H7 H 1.094289 0.668350 1.085834 0.039 Uiso 1 1 calc R U . . .
C8 C 1.3259(3) 0.8326(3) 1.0629(2) 0.0284(5) Uani 1 1 d . . . . .
H8 H 1.398030 0.809757 1.142557 0.034 Uiso 1 1 calc R U . . .
C9 C 1.4031(3) 0.9513(2) 0.9820(2) 0.0232(4) Uani 1 1 d . . . . .
C10 C 1.2895(3) 0.9735(3) 0.8652(3) 0.0389(6) Uani 1 1 d . . . . .
H10 H 1.335540 1.051348 0.804600 0.047 Uiso 1 1 calc R U . . .
C11 C 1.1097(3) 0.8825(3) 0.8372(3) 0.0428(6) Uani 1 1 d . . . . .
H11 H 1.035235 0.900679 0.756639 0.051 Uiso 1 1 calc R U . . .
N1 N 1.0341(2) 0.7707(2) 0.9162(2) 0.0322(4) Uani 1 1 d . . . . .
O1 O 0.6657(2) 0.6450(2) 0.90153(16) 0.0335(4) Uani 1 1 d . . . . .
H1 H 0.781(4) 0.682(3) 0.8973(14) 0.050 Uiso 1 1 calc R U . . .
Cl1 Cl 0.09394(7) 0.24649(8) 0.62200(7) 0.04021(18) Uani 1 1 d . . . . .
Cl2 Cl 0.34386(8) 0.10396(7) 0.38614(6) 0.03702(17) 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 O1 1.352(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.397(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 Cl1 1.735(2) . ?
C4 C5 1.380(3) . ?
C4 Cl2 1.735(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.336(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 C9 1.487(4) 2_877 ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 N1 1.333(3) . ?
C11 H11 0.9500 . ?
O1 H1 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 117.89(18) . . ?
O1 C1 C6 122.88(18) . . ?
C2 C1 C6 119.23(18) . . ?
C3 C2 C1 120.14(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.58(18) . . ?
C2 C3 Cl1 119.25(15) . . ?
C4 C3 Cl1 120.17(16) . . ?
C5 C4 C3 119.26(18) . . ?
C5 C4 Cl2 119.69(16) . . ?
C3 C4 Cl2 121.04(15) . . ?
C4 C5 C6 120.78(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.99(18) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C8 123.7(2) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 116.22(18) . . ?
C8 C9 C9 121.9(2) . 2_877 ?
C10 C9 C9 121.9(2) . 2_877 ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N1 C11 C10 124.0(2) . . ?
N1 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C11 N1 C7 116.12(18) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.86(18) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 Cl1 -179.27(15) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
Cl1 C3 C4 C5 178.54(15) . . . . ?
C2 C3 C4 Cl2 179.20(16) . . . . ?
Cl1 C3 C4 Cl2 -0.7(2) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
Cl2 C4 C5 C6 -179.68(15) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
O1 C1 C6 C5 178.33(18) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
N1 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C7 C8 C9 C9 178.6(2) . . . 2_877 ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C9 C10 C11 -179.0(3) 2_877 . . . ?
C9 C10 C11 N1 -0.2(4) . . . . ?
C10 C11 N1 C7 -0.6(4) . . . . ?
C8 C7 N1 C11 0.2(3) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_datam_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2272072'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   3.8427(6)
_cell_length_b                   17.047(3)
_cell_length_c                   11.6457(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.752(7)
_cell_angle_gamma                90
_cell_volume                     755.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7142
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.435
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.958
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7797
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3440
_reflns_number_gt                2941
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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)+(0.0240P)²+0.1881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     210
_refine_ls_number_restraints     322
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      0.984
_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 0.5463(9) 0.3976(2) 0.2177(3) 0.0192(8) Uani 1 1 d . U . . .
C2 C 0.5134(10) 0.3334(2) 0.1431(3) 0.0201(8) Uani 1 1 d . U . . .
H2 H 0.611668 0.284087 0.167742 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3367(10) 0.3425(2) 0.0334(3) 0.0216(8) Uani 1 1 d . U . . .
C4 C 0.1946(10) 0.4130(2) -0.0075(3) 0.0215(8) Uani 1 1 d . U . . .
H4 H 0.073315 0.418151 -0.083754 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2373(9) 0.4758(2) 0.0681(3) 0.0208(8) Uani 1 1 d . U . . .
C6 C 0.4112(9) 0.4704(2) 0.1789(3) 0.0204(8) Uani 1 1 d . U . . .
H6 H 0.438836 0.515110 0.227898 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4805(10) 0.4202(2) 0.5762(3) 0.0254(9) Uani 1 1 d . U . . .
H7 H 0.423598 0.370574 0.541479 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4287(11) 0.4305(2) 0.6915(3) 0.0278(9) Uani 1 1 d . U . . .
H8 H 0.345089 0.388774 0.734431 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5020(10) 0.5027(2) 0.7414(3) 0.0238(8) Uani 1 1 d . U . . .
H9 H 0.464760 0.511855 0.819225 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6322(9) 0.5628(2) 0.6766(3) 0.0189(7) Uani 1 1 d . U . . .
C11 C 0.7143(10) 0.6390(2) 0.7238(3) 0.0213(8) Uani 1 1 d . U . . .
H11 H 0.678980 0.649904 0.801351 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8408(10) 0.6957(2) 0.6603(3) 0.0215(8) Uani 1 1 d . U . . .
H12 H 0.893156 0.745957 0.693362 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8972(10) 0.68059(19) 0.5428(3) 0.0197(8) Uani 1 1 d . U . . .
C14 C 1.0341(9) 0.7384(2) 0.4748(3) 0.0226(8) Uani 1 1 d . U . . .
H14 H 1.098624 0.788444 0.506689 0.027 Uiso 1 1 calc R U . . .
C15 C 1.0728(10) 0.7215(2) 0.3627(3) 0.0243(8) Uani 1 1 d . U . . .
H15 H 1.161795 0.759778 0.314997 0.029 Uiso 1 1 calc R U . . .
C16 C 0.9784(10) 0.6465(2) 0.3191(3) 0.0268(9) Uani 1 1 d . U . . .
H16 H 1.007234 0.635467 0.240944 0.032 Uiso 1 1 calc R U . . .
C17 C 0.8146(9) 0.6069(2) 0.4919(3) 0.0184(8) Uani 1 1 d . U . . .
C18 C 0.6799(9) 0.54626(19) 0.5610(3) 0.0193(8) Uani 1 1 d . U . . .
N1 N 0.6039(8) 0.47510(16) 0.5119(3) 0.0221(7) Uani 1 1 d . U . . .
N2 N 0.8519(8) 0.59022(16) 0.3801(2) 0.0217(7) Uani 1 1 d . U . . .
O1 O 0.7193(8) 0.38672(15) 0.3258(2) 0.0291(7) Uani 1 1 d . U . . .
H1 H 0.682(10) 0.426(2) 0.368(3) 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2945(3) 0.26131(6) -0.05890(8) 0.0417(3) Uani 1 1 d . U . . .
Cl2 Cl 0.0757(3) 0.56727(5) 0.01866(7) 0.0299(2) Uani 1 1 d . 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
C1 O1 1.355(4) . ?
C1 C2 1.393(5) . ?
C1 C6 1.396(5) . ?
C2 C3 1.372(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(5) . ?
C3 Cl1 1.747(4) . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(5) . ?
C5 Cl2 1.747(4) . ?
C6 H6 0.9500 . ?
C7 N1 1.326(5) . ?
C7 C8 1.396(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(5) . ?
C9 H9 0.9500 . ?
C10 C18 1.411(5) . ?
C10 C11 1.430(5) . ?
C11 C12 1.346(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.437(5) . ?
C12 H12 0.9500 . ?
C13 C17 1.407(5) . ?
C13 C14 1.409(5) . ?
C14 C15 1.365(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.405(5) . ?
C15 H15 0.9500 . ?
C16 N2 1.325(4) . ?
C16 H16 0.9500 . ?
C17 N2 1.359(4) . ?
C17 C18 1.448(5) . ?
C18 N1 1.356(4) . ?
O1 H1 0.86(5) . ?

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
O1 C1 C2 117.6(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 119.9(3) . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 Cl1 118.4(3) . . ?
C4 C3 Cl1 118.6(3) . . ?
C3 C4 C5 116.6(3) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C6 C5 C4 123.2(3) . . ?
C6 C5 Cl2 118.4(3) . . ?
C4 C5 Cl2 118.4(3) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
N1 C7 C8 124.3(3) . . ?
N1 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C9 C8 C7 118.2(4) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C18 117.9(3) . . ?
C9 C10 C11 122.2(3) . . ?
C18 C10 C11 119.9(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C17 C13 C14 117.9(3) . . ?
C17 C13 C12 120.4(3) . . ?
C14 C13 C12 121.7(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N2 C16 C15 124.1(3) . . ?
N2 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
N2 C17 C13 122.9(3) . . ?
N2 C17 C18 118.4(3) . . ?
C13 C17 C18 118.7(3) . . ?
N1 C18 C10 122.2(3) . . ?
N1 C18 C17 118.5(3) . . ?
C10 C18 C17 119.3(3) . . ?
C7 N1 C18 117.8(3) . . ?
C16 N2 C17 117.1(3) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 -2.2(5) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C2 C3 Cl1 -179.5(3) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
Cl1 C3 C4 C5 -179.4(3) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C3 C4 C5 Cl2 177.7(3) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
Cl2 C5 C6 C1 -178.8(3) . . . . ?
O1 C1 C6 C5 -179.5(3) . . . . ?
C2 C1 C6 C5 2.2(5) . . . . ?
N1 C7 C8 C9 1.6(6) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C18 0.5(5) . . . . ?
C8 C9 C10 C11 -179.8(3) . . . . ?
C9 C10 C11 C12 179.6(3) . . . . ?
C18 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C17 1.2(5) . . . . ?
C11 C12 C13 C14 -179.1(4) . . . . ?
C17 C13 C14 C15 1.6(5) . . . . ?
C12 C13 C14 C15 -178.1(4) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 N2 0.2(6) . . . . ?
C14 C13 C17 N2 -1.9(5) . . . . ?
C12 C13 C17 N2 177.8(3) . . . . ?
C14 C13 C17 C18 178.9(3) . . . . ?
C12 C13 C17 C18 -1.4(5) . . . . ?
C9 C10 C18 N1 0.1(5) . . . . ?
C11 C10 C18 N1 -179.6(3) . . . . ?
C9 C10 C18 C17 -179.8(3) . . . . ?
C11 C10 C18 C17 0.5(5) . . . . ?
N2 C17 C18 N1 1.4(5) . . . . ?
C13 C17 C18 N1 -179.4(3) . . . . ?
N2 C17 C18 C10 -178.7(3) . . . . ?
C13 C17 C18 C10 0.6(5) . . . . ?
C8 C7 N1 C18 -1.0(6) . . . . ?
C10 C18 N1 C7 0.1(5) . . . . ?
C17 C18 N1 C7 -180.0(3) . . . . ?
C15 C16 N2 C17 -0.4(5) . . . . ?
C13 C17 N2 C16 1.3(5) . . . . ?
C18 C17 N2 C16 -179.5(3) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_datam_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 2272066'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C24 H16 Cl4 N2 O2'
_chemical_formula_weight         506.19

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      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                   7.9894(16)
_cell_length_b                   9.4955(19)
_cell_length_c                   15.762(3)
_cell_angle_alpha                85.572(6)
_cell_angle_beta                 79.226(6)
_cell_angle_gamma                71.653(5)
_cell_volume                     1114.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7444
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.557
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.946
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11845
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5112
_reflns_number_gt                2953
_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)+(0.0446P)²+0.2599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5112
_refine_ls_number_parameters     293
_refine_ls_number_restraints     432
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      0.979
_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 1.0024(4) 0.6738(4) 0.2662(2) 0.0218(7) Uani 1 1 d . U . . .
C2 C 1.1357(4) 0.5745(4) 0.2104(2) 0.0247(7) Uani 1 1 d . U . . .
C3 C 1.2497(4) 0.6226(4) 0.1464(2) 0.0271(8) Uani 1 1 d . U . . .
H3 H 1.337649 0.553003 0.108265 0.032 Uiso 1 1 calc R U . . .
C4 C 1.2368(5) 0.7706(4) 0.1376(2) 0.0304(8) Uani 1 1 d . U . . .
H4 H 1.315681 0.804374 0.094000 0.036 Uiso 1 1 calc R U . . .
C5 C 1.1070(5) 0.8687(4) 0.1933(2) 0.0281(8) Uani 1 1 d . U . . .
C6 C 0.9875(4) 0.8242(4) 0.2572(2) 0.0247(7) Uani 1 1 d . U . . .
H6 H 0.897641 0.894861 0.293910 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6420(4) 0.7760(4) 0.1842(2) 0.0221(7) Uani 1 1 d . U . . .
C8 C 0.6729(5) 0.8545(4) 0.1070(2) 0.0277(8) Uani 1 1 d . U . . .
C9 C 0.7376(5) 0.7827(4) 0.0297(2) 0.0374(9) Uani 1 1 d . U . . .
H9 H 0.760679 0.837622 -0.021684 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7696(5) 0.6311(4) 0.0260(2) 0.0371(9) Uani 1 1 d . U . . .
H10 H 0.812533 0.581326 -0.027436 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7375(4) 0.5543(4) 0.1021(2) 0.0271(8) Uani 1 1 d . U . . .
C12 C 0.6768(4) 0.6235(4) 0.1799(2) 0.0234(7) Uani 1 1 d . U . . .
H12 H 0.658244 0.567016 0.231196 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8111(5) 0.8737(4) 0.4857(2) 0.0317(8) Uani 1 1 d . U . . .
H13 H 0.905901 0.892185 0.444905 0.038 Uiso 1 1 calc R U . . .
C14 C 0.7924(5) 0.9129(4) 0.5711(2) 0.0356(9) Uani 1 1 d . U . . .
H14 H 0.872531 0.957195 0.587573 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6578(5) 0.8868(4) 0.6308(2) 0.0320(8) Uani 1 1 d . U . . .
H15 H 0.643372 0.912214 0.689436 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5398(5) 0.8216(4) 0.6044(2) 0.0276(8) Uani 1 1 d . U . . .
C17 C 0.3989(5) 0.7879(4) 0.6647(2) 0.0353(9) Uani 1 1 d . U . . .
H17 H 0.380575 0.813582 0.723546 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2927(5) 0.7208(4) 0.6393(2) 0.0336(9) Uani 1 1 d . U . . .
H18 H 0.202742 0.696311 0.680651 0.040 Uiso 1 1 calc R U . . .
C19 C 0.3137(4) 0.6854(4) 0.5498(2) 0.0250(7) Uani 1 1 d . U . . .
C20 C 0.2060(4) 0.6120(4) 0.5216(2) 0.0292(8) Uani 1 1 d . U . . .
H20 H 0.117993 0.583026 0.562023 0.035 Uiso 1 1 calc R U . . .
C21 C 0.2289(4) 0.5829(4) 0.4361(2) 0.0308(8) Uani 1 1 d . U . . .
H21 H 0.159166 0.532059 0.416074 0.037 Uiso 1 1 calc R U . . .
C22 C 0.3573(4) 0.6297(4) 0.3788(2) 0.0282(8) Uani 1 1 d . U . . .
H22 H 0.368810 0.612659 0.319111 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4459(4) 0.7211(3) 0.4879(2) 0.0206(7) Uani 1 1 d . U . . .
C24 C 0.5666(4) 0.7883(3) 0.5164(2) 0.0224(7) Uani 1 1 d . U . . .
N1 N 0.7035(4) 0.8118(3) 0.45813(17) 0.0233(6) Uani 1 1 d . U . . .
N2 N 0.4645(3) 0.6966(3) 0.40191(17) 0.0232(6) Uani 1 1 d . U . . .
O1 O 0.8944(3) 0.6196(2) 0.32761(14) 0.0265(6) Uani 1 1 d . U . . .
H1 H 0.822(4) 0.691(3) 0.3592(19) 0.040 Uiso 1 1 calc R U . . .
O2 O 0.5783(3) 0.8522(2) 0.25815(14) 0.0291(6) Uani 1 1 d . U . . .
H2 H 0.558(5) 0.796(3) 0.2980(19) 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 1.15709(13) 0.38556(9) 0.22251(6) 0.0369(3) Uani 1 1 d . U . . .
Cl2 Cl 1.08840(14) 1.05748(10) 0.18607(6) 0.0425(3) Uani 1 1 d . U . . .
Cl3 Cl 0.62907(15) 1.04582(10) 0.11016(6) 0.0446(3) Uani 1 1 d . U . . .
Cl4 Cl 0.77283(13) 0.36348(10) 0.09912(6) 0.0412(3) Uani 1 1 d . 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
C1 O1 1.356(3) . ?
C1 C6 1.393(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.379(4) . ?
C2 Cl1 1.747(3) . ?
C3 C4 1.375(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 Cl2 1.748(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.348(4) . ?
C7 C12 1.391(4) . ?
C7 C8 1.401(4) . ?
C8 C9 1.372(5) . ?
C8 Cl3 1.742(3) . ?
C9 C10 1.384(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(4) . ?
C11 Cl4 1.747(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.331(4) . ?
C13 C14 1.393(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(5) . ?
C15 H15 0.9500 . ?
C16 C24 1.409(4) . ?
C16 C17 1.432(5) . ?
C17 C18 1.339(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.443(5) . ?
C18 H18 0.9500 . ?
C19 C23 1.404(4) . ?
C19 C20 1.411(4) . ?
C20 C21 1.364(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(4) . ?
C21 H21 0.9500 . ?
C22 N2 1.328(4) . ?
C22 H22 0.9500 . ?
C23 N2 1.366(4) . ?
C23 C24 1.459(4) . ?
C24 N1 1.355(4) . ?
O1 H1 0.86(3) . ?
O2 H2 0.82(4) . ?

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
O1 C1 C6 122.8(3) . . ?
O1 C1 C2 118.5(3) . . ?
C6 C1 C2 118.6(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 Cl1 119.9(3) . . ?
C1 C2 Cl1 118.8(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 Cl2 120.1(3) . . ?
C6 C5 Cl2 117.3(3) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
O2 C7 C12 123.7(3) . . ?
O2 C7 C8 118.5(3) . . ?
C12 C7 C8 117.8(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 Cl3 120.1(3) . . ?
C7 C8 Cl3 118.9(3) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 Cl4 118.9(3) . . ?
C10 C11 Cl4 119.1(3) . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N1 C13 C14 123.6(3) . . ?
N1 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C24 C16 C15 117.7(3) . . ?
C24 C16 C17 120.6(3) . . ?
C15 C16 C17 121.7(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C23 C19 C20 117.9(3) . . ?
C23 C19 C18 120.3(3) . . ?
C20 C19 C18 121.8(3) . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
N2 C22 C21 124.6(3) . . ?
N2 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?
N2 C23 C19 122.3(3) . . ?
N2 C23 C24 118.9(3) . . ?
C19 C23 C24 118.9(3) . . ?
N1 C24 C16 122.4(3) . . ?
N1 C24 C23 119.1(3) . . ?
C16 C24 C23 118.5(3) . . ?
C13 N1 C24 117.9(3) . . ?
C22 N2 C23 117.2(3) . . ?
C1 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.9(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
O1 C1 C2 Cl1 -0.1(4) . . . . ?
C6 C1 C2 Cl1 179.0(2) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
Cl1 C2 C3 C4 -178.5(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C3 C4 C5 Cl2 178.6(3) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
Cl2 C5 C6 C1 -178.1(3) . . . . ?
O1 C1 C6 C5 178.7(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
O2 C7 C8 C9 -180.0(3) . . . . ?
C12 C7 C8 C9 -0.8(5) . . . . ?
O2 C7 C8 Cl3 0.4(4) . . . . ?
C12 C7 C8 Cl3 179.5(2) . . . . ?
C7 C8 C9 C10 1.7(6) . . . . ?
Cl3 C8 C9 C10 -178.7(3) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C9 C10 C11 Cl4 178.9(3) . . . . ?
C10 C11 C12 C7 1.2(5) . . . . ?
Cl4 C11 C12 C7 -178.0(3) . . . . ?
O2 C7 C12 C11 178.5(3) . . . . ?
C8 C7 C12 C11 -0.6(5) . . . . ?
N1 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C24 -0.8(5) . . . . ?
C14 C15 C16 C17 178.3(3) . . . . ?
C24 C16 C17 C18 1.7(5) . . . . ?
C15 C16 C17 C18 -177.3(3) . . . . ?
C16 C17 C18 C19 -2.2(5) . . . . ?
C17 C18 C19 C23 -0.1(5) . . . . ?
C17 C18 C19 C20 178.7(3) . . . . ?
C23 C19 C20 C21 -2.2(5) . . . . ?
C18 C19 C20 C21 179.0(3) . . . . ?
C19 C20 C21 C22 -1.1(5) . . . . ?
C20 C21 C22 N2 2.6(5) . . . . ?
C20 C19 C23 N2 4.6(5) . . . . ?
C18 C19 C23 N2 -176.6(3) . . . . ?
C20 C19 C23 C24 -176.0(3) . . . . ?
C18 C19 C23 C24 2.8(5) . . . . ?
C15 C16 C24 N1 2.3(5) . . . . ?
C17 C16 C24 N1 -176.7(3) . . . . ?
C15 C16 C24 C23 -179.9(3) . . . . ?
C17 C16 C24 C23 1.0(5) . . . . ?
N2 C23 C24 N1 -6.0(4) . . . . ?
C19 C23 C24 N1 174.6(3) . . . . ?
N2 C23 C24 C16 176.2(3) . . . . ?
C19 C23 C24 C16 -3.2(4) . . . . ?
C14 C13 N1 C24 1.2(5) . . . . ?
C16 C24 N1 C13 -2.5(5) . . . . ?
C23 C24 N1 C13 179.8(3) . . . . ?
C21 C22 N2 C23 -0.3(5) . . . . ?
C19 C23 N2 C22 -3.3(5) . . . . ?
C24 C23 N2 C22 177.3(3) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.367
_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_datam_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 2272073'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17

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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

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

_cell_length_a                   8.0784(6)
_cell_length_b                   8.0784(6)
_cell_length_c                   32.831(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2142.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2449
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.410

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.575
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.945
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18582
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         27.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2449
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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)+(0.0338P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2449
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
C1 C 0.7486(3) 0.5394(3) 0.70670(6) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.8808(3) 0.4867(3) 0.68249(6) 0.0266(4) Uani 1 1 d . . . . .
H2 H 0.875099 0.494494 0.653650 0.032 Uiso 1 1 calc R U . . .
C3 C 1.0204(3) 0.4228(3) 0.70137(6) 0.0272(4) Uani 1 1 d . . . . .
C4 C 1.0344(3) 0.4085(3) 0.74358(6) 0.0294(5) Uani 1 1 d . . . . .
H4 H 1.131607 0.365516 0.755983 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8998(3) 0.4599(3) 0.76662(6) 0.0267(4) Uani 1 1 d . . . . .
C6 C 0.7577(3) 0.5251(3) 0.74933(6) 0.0269(4) Uani 1 1 d . . . . .
H6 H 0.667978 0.559634 0.765982 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7260(3) 0.6997(3) 0.58743(7) 0.0342(5) Uani 1 1 d . . . . .
H7 H 0.808731 0.757686 0.602247 0.041 Uiso 1 1 calc R U . . .
C8 C 0.7344(3) 0.7028(3) 0.54522(7) 0.0299(5) Uani 1 1 d . . . . .
H8 H 0.820292 0.761880 0.531823 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6147(3) 0.6177(3) 0.52271(6) 0.0234(4) Uani 1 1 d . . . . .
C10 C 0.4919(3) 0.5350(3) 0.54470(7) 0.0308(5) Uani 1 1 d . . . . .
H10 H 0.407311 0.475837 0.530834 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4943(3) 0.5400(3) 0.58712(7) 0.0339(5) Uani 1 1 d . . . . .
H11 H 0.409743 0.482908 0.601517 0.041 Uiso 1 1 calc R U . . .
Cl1 Cl 1.18453(7) 0.35649(9) 0.67096(2) 0.03730(17) Uani 1 1 d . . . . .
Cl2 Cl 0.90676(8) 0.43672(8) 0.81952(2) 0.03635(16) Uani 1 1 d . . . . .
N1 N 0.6090(2) 0.6205(3) 0.60858(5) 0.0315(4) Uani 1 1 d . . . . .
O1 O 0.6076(2) 0.6036(2) 0.69113(5) 0.0370(4) Uani 1 1 d . . . . .
H1 H 0.6169(16) 0.612(4) 0.6652(11) 0.055 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
C1 O1 1.352(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 Cl1 1.744(2) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 Cl2 1.748(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.336(3) . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(3) . ?
C9 C9 1.492(4) 7_556 ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 N1 1.333(3) . ?
C11 H11 0.9500 . ?
O1 H1 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 123.06(19) . . ?
O1 C1 C6 116.88(19) . . ?
C2 C1 C6 120.06(19) . . ?
C3 C2 C1 118.72(19) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 Cl1 118.46(16) . . ?
C4 C3 Cl1 118.79(17) . . ?
C5 C4 C3 116.9(2) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C6 C5 C4 122.67(19) . . ?
C6 C5 Cl2 118.36(17) . . ?
C4 C5 Cl2 118.95(17) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 124.2(2) . . ?
N1 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 116.95(19) . . ?
C10 C9 C9 121.36(13) . 7_556 ?
C8 C9 C9 121.69(13) . 7_556 ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 123.5(2) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C11 N1 C7 116.79(19) . . ?
C1 O1 H1 109.5 . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_datam_CCDC12
_database_code_depnum_ccdc_archive 'CCDC 2272070'
loop_
_audit_author_name
_audit_author_address
'Ritesh Dubey'
;University of Petroleum and Energy Studies, Dehradun
India
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2023-08-28 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            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20

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      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                   8.1270(15)
_cell_length_b                   8.5365(15)
_cell_length_c                   11.656(2)
_cell_angle_alpha                75.042(5)
_cell_angle_beta                 86.122(6)
_cell_angle_gamma                78.916(6)
_cell_volume                     766.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5854
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.428
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.967
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6447
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3379
_reflns_number_gt                2853
_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)+(0.0453P)²+0.2295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3379
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.7564(2) 0.5685(2) 0.18290(14) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.6046(2) 0.51091(19) 0.20090(14) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.592395 0.417271 0.263630 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4720(2) 0.5917(2) 0.12636(14) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.4881(2) 0.7289(2) 0.03411(13) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.6390(2) 0.7851(2) 0.01755(14) 0.0273(4) Uani 1 1 d . . . . .
H5 H 0.650794 0.879279 -0.044860 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7728(2) 0.7058(2) 0.09078(15) 0.0272(4) Uani 1 1 d . . . . .
H6 H 0.875854 0.745189 0.078184 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5956(2) 0.2602(2) 0.58187(16) 0.0336(4) Uani 1 1 d . . . . .
H7 H 0.560528 0.370958 0.587008 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5391(2) 0.1367(3) 0.67050(15) 0.0349(4) Uani 1 1 d . . . . .
H8 H 0.468069 0.163515 0.733441 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5880(2) -0.0233(2) 0.66487(15) 0.0322(4) Uani 1 1 d . . . . .
H9 H 0.550744 -0.109614 0.723754 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6947(2) -0.0594(2) 0.57056(14) 0.0266(4) Uani 1 1 d . . . . .
C11 C 0.7494(2) -0.2240(2) 0.55925(15) 0.0316(4) Uani 1 1 d . . . . .
H11 H 0.715227 -0.312948 0.617423 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8489(2) -0.2555(2) 0.46705(16) 0.0307(4) Uani 1 1 d . . . . .
H12 H 0.883109 -0.365890 0.460751 0.037 Uiso 1 1 calc R U . . .
C13 C 0.9029(2) -0.1240(2) 0.37913(14) 0.0250(3) Uani 1 1 d . . . . .
C14 C 1.0065(2) -0.1536(2) 0.28218(16) 0.0293(4) Uani 1 1 d . . . . .
H14 H 1.041831 -0.262741 0.273563 0.035 Uiso 1 1 calc R U . . .
C15 C 1.0557(2) -0.0235(2) 0.20062(16) 0.0319(4) Uani 1 1 d . . . . .
H15 H 1.124173 -0.040489 0.133980 0.038 Uiso 1 1 calc R U . . .
C16 C 1.0033(2) 0.1343(2) 0.21736(15) 0.0285(4) Uani 1 1 d . . . . .
H16 H 1.040388 0.223495 0.161228 0.034 Uiso 1 1 calc R U . . .
C17 C 0.85400(19) 0.0402(2) 0.38753(13) 0.0218(3) Uani 1 1 d . . . . .
C18 C 0.7449(2) 0.0743(2) 0.48575(13) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.69484(18) 0.23376(18) 0.49081(12) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.90492(17) 0.16821(17) 0.30672(11) 0.0238(3) Uani 1 1 d . . . . .
O1 O 0.88921(15) 0.49542(16) 0.25413(11) 0.0317(3) Uani 1 1 d . . . . .
H1 H 0.8769(14) 0.401(3) 0.2903(18) 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.28229(5) 0.52247(5) 0.15127(4) 0.03029(12) Uani 1 1 d . . . . .
Cl2 Cl 0.32387(6) 0.82880(5) -0.06078(4) 0.03099(13) 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 O1 1.356(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 Cl1 1.7353(17) . ?
C4 C5 1.385(2) . ?
C4 Cl2 1.7340(17) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.329(2) . ?
C7 C8 1.396(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.364(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.414(2) . ?
C9 H9 0.9500 . ?
C10 C18 1.410(2) . ?
C10 C11 1.428(3) . ?
C11 C12 1.353(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.428(2) . ?
C12 H12 0.9500 . ?
C13 C17 1.409(2) . ?
C13 C14 1.409(2) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C16 N2 1.327(2) . ?
C16 H16 0.9500 . ?
C17 N2 1.357(2) . ?
C17 C18 1.455(2) . ?
C18 N1 1.360(2) . ?
O1 H1 0.83(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
O1 C1 C6 118.47(15) . . ?
O1 C1 C2 121.77(15) . . ?
C6 C1 C2 119.75(16) . . ?
C3 C2 C1 119.41(15) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.94(15) . . ?
C2 C3 Cl1 119.19(12) . . ?
C4 C3 Cl1 119.85(13) . . ?
C5 C4 C3 119.07(15) . . ?
C5 C4 Cl2 119.70(13) . . ?
C3 C4 Cl2 121.23(13) . . ?
C6 C5 C4 120.78(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.05(16) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C8 124.65(17) . . ?
N1 C7 H7 117.7 . . ?
C8 C7 H7 117.7 . . ?
C9 C8 C7 118.63(16) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 119.35(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C18 C10 C9 117.56(16) . . ?
C18 C10 C11 120.40(15) . . ?
C9 C10 C11 122.04(16) . . ?
C12 C11 C10 121.07(16) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.44(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C17 C13 C14 118.01(16) . . ?
C17 C13 C12 120.47(15) . . ?
C14 C13 C12 121.52(16) . . ?
C15 C14 C13 119.33(16) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.58(16) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N2 C16 C15 124.20(16) . . ?
N2 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
N2 C17 C13 122.17(14) . . ?
N2 C17 C18 118.76(14) . . ?
C13 C17 C18 119.07(15) . . ?
N1 C18 C10 123.04(15) . . ?
N1 C18 C17 118.41(15) . . ?
C10 C18 C17 118.54(15) . . ?
C7 N1 C18 116.75(15) . . ?
C16 N2 C17 117.70(14) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.12(14) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 Cl1 -178.52(12) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
Cl1 C3 C4 C5 178.25(12) . . . . ?
C2 C3 C4 Cl2 179.07(12) . . . . ?
Cl1 C3 C4 Cl2 -2.39(19) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
Cl2 C4 C5 C6 -178.89(12) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
O1 C1 C6 C5 -178.96(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
N1 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C18 -0.3(2) . . . . ?
C8 C9 C10 C11 -179.55(17) . . . . ?
C18 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 178.74(17) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C17 0.3(3) . . . . ?
C11 C12 C13 C14 -179.94(16) . . . . ?
C17 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C15 -179.63(16) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 N2 -1.5(3) . . . . ?
C14 C13 C17 N2 -0.8(2) . . . . ?
C12 C13 C17 N2 178.96(15) . . . . ?
C14 C13 C17 C18 179.04(14) . . . . ?
C12 C13 C17 C18 -1.2(2) . . . . ?
C9 C10 C18 N1 -0.3(2) . . . . ?
C11 C10 C18 N1 178.93(15) . . . . ?
C9 C10 C18 C17 -179.67(14) . . . . ?
C11 C10 C18 C17 -0.4(2) . . . . ?
N2 C17 C18 N1 1.7(2) . . . . ?
C13 C17 C18 N1 -178.13(14) . . . . ?
N2 C17 C18 C10 -178.93(14) . . . . ?
C13 C17 C18 C10 1.2(2) . . . . ?
C8 C7 N1 C18 -0.7(3) . . . . ?
C10 C18 N1 C7 0.8(2) . . . . ?
C17 C18 N1 C7 -179.87(15) . . . . ?
C15 C16 N2 C17 0.8(3) . . . . ?
C13 C17 N2 C16 0.3(2) . . . . ?
C18 C17 N2 C16 -179.49(14) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.050

