# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_CKHA_2_070823_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2289141'
loop_
_audit_author_name
_audit_author_address
'FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Cl N O3'
_chemical_formula_sum            'C19 H14 Cl N O3'
_chemical_formula_weight         339.76

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.782(19)
_cell_length_b                   15.878(18)
_cell_length_c                   8.643(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.91(5)
_cell_angle_gamma                90
_cell_volume                     1750(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2747
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      19.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.066
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_max          0.175
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6048
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15304
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.048
_diffrn_reflns_theta_max         27.073
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3779
_reflns_number_gt                1913
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0792P)²+0.8805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3779
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2068
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.47691(10) 0.69574(8) 0.83734(15) 0.1254(6) Uani 1 1 d . . . . .
O1 O 0.2220(2) 0.25817(16) 0.2635(4) 0.1062(9) Uani 1 1 d . . . . .
O2 O 0.20044(18) 0.42880(15) 0.1059(3) 0.0814(7) Uani 1 1 d . . . . .
O3 O 0.06543(18) 0.41153(16) 0.2604(3) 0.0870(8) Uani 1 1 d . . . . .
N1 N 0.3806(2) 0.36890(17) 0.5409(3) 0.0678(7) Uani 1 1 d . . . . .
C1 C 0.3401(2) 0.51933(19) 0.5582(3) 0.0568(8) Uani 1 1 d . . . . .
C2 C 0.3650(2) 0.5969(2) 0.6326(4) 0.0709(9) Uani 1 1 d . . . . .
H2 H 0.328191 0.645422 0.603012 0.085 Uiso 1 1 calc R U . . .
C3 C 0.4431(3) 0.6001(2) 0.7477(4) 0.0802(10) Uani 1 1 d . . . . .
C4 C 0.5016(3) 0.5283(3) 0.7959(4) 0.0798(10) Uani 1 1 d . . . . .
H4 H 0.554861 0.532447 0.874286 0.096 Uiso 1 1 calc R U . . .
C5 C 0.4791(3) 0.4532(2) 0.7265(4) 0.0732(9) Uani 1 1 d . . . . .
H5 H 0.517109 0.405633 0.758704 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3989(2) 0.4460(2) 0.6059(3) 0.0607(8) Uani 1 1 d . . . . .
C7 C 0.3050(2) 0.36289(19) 0.4274(4) 0.0656(8) Uani 1 1 d . . . . .
C8 C 0.2424(2) 0.43243(18) 0.3714(3) 0.0570(8) Uani 1 1 d . . . . .
C9 C 0.2589(2) 0.51113(18) 0.4362(3) 0.0549(7) Uani 1 1 d . . . . .
C10 C 0.2878(3) 0.2763(2) 0.3633(5) 0.0899(12) Uani 1 1 d . . . . .
H10 H 0.331065 0.233424 0.403774 0.108 Uiso 1 1 calc R U . . .
C11 C 0.1580(3) 0.42149(19) 0.2416(4) 0.0635(8) Uani 1 1 d . . . . .
C12 C 0.1262(3) 0.4209(3) -0.0309(5) 0.1037(13) Uani 1 1 d . . . . .
H12A H 0.114956 0.362034 -0.056744 0.124 Uiso 1 1 calc R U . . .
H12B H 0.059326 0.445838 -0.010068 0.124 Uiso 1 1 calc R U . . .
C13 C 0.1703(5) 0.4638(4) -0.1562(6) 0.159(2) Uani 1 1 d . . . . .
H13A H 0.126130 0.455817 -0.249400 0.239 Uiso 1 1 calc R U . . .
H13B H 0.238851 0.441587 -0.170531 0.239 Uiso 1 1 calc R U . . .
H13C H 0.175655 0.522840 -0.133057 0.239 Uiso 1 1 calc R U . . .
C14 C 0.1937(2) 0.58482(18) 0.3808(4) 0.0603(8) Uani 1 1 d . . . . .
C15 C 0.1001(3) 0.6040(2) 0.4448(4) 0.0770(10) Uani 1 1 d . . . . .
H15 H 0.078655 0.571294 0.526007 0.092 Uiso 1 1 calc R U . . .
C16 C 0.0371(3) 0.6711(3) 0.3909(5) 0.0936(12) Uani 1 1 d . . . . .
H16 H -0.025894 0.682524 0.434472 0.112 Uiso 1 1 calc R U . . .
C17 C 0.0696(4) 0.7194(3) 0.2737(6) 0.1024(14) Uani 1 1 d . . . . .
H17 H 0.030098 0.765854 0.239760 0.123 Uiso 1 1 calc R U . . .
C18 C 0.1610(4) 0.7002(3) 0.2042(7) 0.135(2) Uani 1 1 d . . . . .
H18 H 0.181128 0.732411 0.121410 0.162 Uiso 1 1 calc R U . . .
C19 C 0.2231(3) 0.6327(3) 0.2578(6) 0.1156(17) Uani 1 1 d . . . . .
H19 H 0.284457 0.619930 0.210620 0.139 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.746(4) . ?
O1 C10 1.198(4) . ?
O2 C11 1.331(4) . ?
O2 C12 1.470(4) . ?
O3 C11 1.215(4) . ?
N1 C7 1.333(4) . ?
N1 C6 1.360(4) . ?
C1 C2 1.415(4) . ?
C1 C6 1.432(4) . ?
C1 C9 1.433(4) . ?
C2 C3 1.362(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(5) . ?
C4 C5 1.357(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.429(4) . ?
C7 C10 1.493(5) . ?
C8 C9 1.380(4) . ?
C8 C11 1.513(4) . ?
C9 C14 1.497(4) . ?
C10 H10 0.9300 . ?
C12 C13 1.428(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.380(5) . ?
C14 C15 1.385(5) . ?
C15 C16 1.396(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 115.0(3) . . ?
C7 N1 C6 117.6(3) . . ?
C2 C1 C6 118.6(3) . . ?
C2 C1 C9 122.9(3) . . ?
C6 C1 C9 118.5(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 Cl1 120.2(3) . . ?
C4 C3 Cl1 117.5(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N1 C6 C5 118.2(3) . . ?
N1 C6 C1 122.8(3) . . ?
C5 C6 C1 119.1(3) . . ?
N1 C7 C8 123.7(3) . . ?
N1 C7 C10 114.8(3) . . ?
C8 C7 C10 121.4(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 C11 119.1(3) . . ?
C7 C8 C11 121.1(3) . . ?
C8 C9 C1 117.6(3) . . ?
C8 C9 C14 120.8(3) . . ?
C1 C9 C14 121.6(3) . . ?
O1 C10 C7 124.5(3) . . ?
O1 C10 H10 117.7 . . ?
C7 C10 H10 117.7 . . ?
O3 C11 O2 126.0(3) . . ?
O3 C11 C8 124.6(3) . . ?
O2 C11 C8 109.3(3) . . ?
C13 C12 O2 107.7(4) . . ?
C13 C12 H12A 110.2 . . ?
O2 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
O2 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.3(3) . . ?
C19 C14 C9 120.1(3) . . ?
C15 C14 C9 121.5(3) . . ?
C14 C15 C16 121.9(4) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.0(4) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(5) . . . . ?
C9 C1 C2 C3 -180.0(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 Cl1 178.5(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
Cl1 C3 C4 C5 -178.6(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C7 N1 C6 C5 -179.9(3) . . . . ?
C7 N1 C6 C1 0.5(4) . . . . ?
C4 C5 C6 N1 179.7(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C2 C1 C6 N1 -179.9(3) . . . . ?
C9 C1 C6 N1 -0.3(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C9 C1 C6 C5 -179.9(3) . . . . ?
C6 N1 C7 C8 -0.3(5) . . . . ?
C6 N1 C7 C10 -178.9(3) . . . . ?
N1 C7 C8 C9 -0.1(5) . . . . ?
C10 C7 C8 C9 178.3(3) . . . . ?
N1 C7 C8 C11 179.8(3) . . . . ?
C10 C7 C8 C11 -1.8(5) . . . . ?
C7 C8 C9 C1 0.3(4) . . . . ?
C11 C8 C9 C1 -179.6(3) . . . . ?
C7 C8 C9 C14 -179.4(3) . . . . ?
C11 C8 C9 C14 0.7(4) . . . . ?
C2 C1 C9 C8 179.4(3) . . . . ?
C6 C1 C9 C8 -0.2(4) . . . . ?
C2 C1 C9 C14 -0.9(4) . . . . ?
C6 C1 C9 C14 179.5(3) . . . . ?
N1 C7 C10 O1 178.3(4) . . . . ?
C8 C7 C10 O1 -0.3(6) . . . . ?
C12 O2 C11 O3 -2.1(5) . . . . ?
C12 O2 C11 C8 -179.0(3) . . . . ?
C9 C8 C11 O3 -82.9(4) . . . . ?
C7 C8 C11 O3 97.2(4) . . . . ?
C9 C8 C11 O2 94.0(3) . . . . ?
C7 C8 C11 O2 -85.9(3) . . . . ?
C11 O2 C12 C13 155.9(4) . . . . ?
C8 C9 C14 C19 -87.8(4) . . . . ?
C1 C9 C14 C19 92.5(4) . . . . ?
C8 C9 C14 C15 88.6(4) . . . . ?
C1 C9 C14 C15 -91.1(4) . . . . ?
C19 C14 C15 C16 -1.6(5) . . . . ?
C9 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 2.9(7) . . . . ?
C16 C17 C18 C19 -2.5(8) . . . . ?
C15 C14 C19 C18 2.1(7) . . . . ?
C9 C14 C19 C18 178.6(4) . . . . ?
C17 C18 C19 C14 -0.1(8) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_HA_3_2HPYI_240125_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2421395'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2025-02-04 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 N4 O'
_chemical_formula_sum            'C22 H14 N4 O'
_chemical_formula_weight         350.37

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'

_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                   13.3290(6)
_cell_length_b                   6.8873(3)
_cell_length_c                   19.3643(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.513(2)
_cell_angle_gamma                90
_cell_volume                     1747.82(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8457
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.83
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32586
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_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         2.404
_diffrn_reflns_theta_max         28.303
_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             4325
_reflns_number_gt                2478
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0579P)²+0.3566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4325
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O2 O 0.82504(8) 0.5603(2) 0.29483(6) 0.0651(4) Uani 1 1 d . . . . .
N1 N 0.76699(9) 0.54365(19) 0.17846(7) 0.0489(3) Uani 1 1 d . . . . .
N2 N 0.69332(11) 0.5376(2) 0.11908(7) 0.0572(4) Uani 1 1 d . . . . .
N3 N 0.46829(10) 0.54748(19) 0.19566(8) 0.0561(4) Uani 1 1 d . . . . .
N5 N 0.89482(11) 0.3678(3) 0.13875(9) 0.0726(5) Uani 1 1 d . . . . .
C1 C 0.98976(15) 0.3578(4) 0.12474(13) 0.0878(7) Uani 1 1 d . . . . .
H1 H 1.009808 0.242543 0.106242 0.105 Uiso 1 1 calc R U . . .
C2 C 1.05771(16) 0.5044(4) 0.13583(12) 0.0837(7) Uani 1 1 d . . . . .
H2 H 1.122275 0.490255 0.124652 0.100 Uiso 1 1 calc R U . . .
C3 C 1.03045(15) 0.6722(4) 0.16346(12) 0.0848(7) Uani 1 1 d . . . . .
H3 H 1.076130 0.775302 0.171774 0.102 Uiso 1 1 calc R U . . .
C4 C 0.93367(14) 0.6886(3) 0.17922(11) 0.0704(5) Uani 1 1 d . . . . .
H4 H 0.912826 0.801526 0.198826 0.084 Uiso 1 1 calc R U . . .
C5 C 0.75170(12) 0.5527(2) 0.24717(8) 0.0460(4) Uani 1 1 d . . . . .
C6 C 0.64451(11) 0.5502(2) 0.25591(8) 0.0441(4) Uani 1 1 d . . . . .
C7 C 0.56800(11) 0.5474(2) 0.19501(9) 0.0483(4) Uani 1 1 d . . . . .
C8 C 0.59999(13) 0.5420(2) 0.12814(9) 0.0568(4) Uani 1 1 d . . . . .
H8 H 0.549268 0.541704 0.088179 0.068 Uiso 1 1 calc R U . . .
C9 C 0.61648(12) 0.5491(2) 0.32174(9) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.51094(13) 0.5481(2) 0.32357(10) 0.0536(4) Uani 1 1 d . . . . .
C11 C 0.43976(12) 0.5489(2) 0.25951(11) 0.0556(4) Uani 1 1 d . . . . .
C12 C 0.69188(13) 0.5468(2) 0.38855(9) 0.0534(4) Uani 1 1 d . . . . .
C13 C 0.72296(15) 0.7168(3) 0.42408(10) 0.0700(5) Uani 1 1 d . . . . .
H13 H 0.695263 0.834921 0.406768 0.084 Uiso 1 1 calc R U . . .
C14 C 0.79508(18) 0.7120(4) 0.48527(11) 0.0849(7) Uani 1 1 d . . . . .
H14 H 0.816600 0.826792 0.508660 0.102 Uiso 1 1 calc R U . . .
C15 C 0.83467(19) 0.5381(4) 0.51129(12) 0.0908(7) Uani 1 1 d . . . . .
H15 H 0.884520 0.535168 0.551719 0.109 Uiso 1 1 calc R U . . .
C16 C 0.80157(19) 0.3701(4) 0.47843(12) 0.0952(8) Uani 1 1 d . . . . .
H16 H 0.827347 0.252119 0.497212 0.114 Uiso 1 1 calc R U . . .
C17 C 0.73022(16) 0.3730(3) 0.41755(10) 0.0765(6) Uani 1 1 d . . . . .
H17 H 0.707508 0.256775 0.395672 0.092 Uiso 1 1 calc R U . . .
C18 C 0.47315(15) 0.5469(3) 0.38760(12) 0.0710(6) Uani 1 1 d . . . . .
H18 H 0.518782 0.544255 0.430104 0.085 Uiso 1 1 calc R U . . .
C19 C 0.37126(18) 0.5496(3) 0.38752(15) 0.0842(7) Uani 1 1 d . . . . .
H19 H 0.347675 0.549410 0.429855 0.101 Uiso 1 1 calc R U . . .
C20 C 0.30159(17) 0.5528(3) 0.32400(16) 0.0839(7) Uani 1 1 d . . . . .
H20 H 0.232012 0.555992 0.324639 0.101 Uiso 1 1 calc R U . . .
C21 C 0.33392(14) 0.5512(3) 0.26153(13) 0.0711(6) Uani 1 1 d . . . . .
H21 H 0.286498 0.551564 0.219845 0.085 Uiso 1 1 calc R U . . .
C23 C 0.87024(12) 0.5337(2) 0.16500(8) 0.0499(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C5 1.2169(18) . ?
N1 N2 1.3697(18) . ?
N1 C5 1.384(2) . ?
N1 C23 1.4482(19) . ?
N2 C8 1.288(2) . ?
N3 C7 1.331(2) . ?
N3 C11 1.358(2) . ?
N5 C23 1.316(2) . ?
N5 C1 1.343(2) . ?
C1 C2 1.347(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.351(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C23 1.358(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.469(2) . ?
C6 C9 1.392(2) . ?
C6 C7 1.411(2) . ?
C7 C8 1.436(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.414(2) . ?
C9 C12 1.486(2) . ?
C10 C11 1.418(3) . ?
C10 C18 1.421(3) . ?
C11 C21 1.418(2) . ?
C12 C17 1.380(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.355(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.358(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 126.86(13) . . ?
N2 N1 C23 114.00(12) . . ?
C5 N1 C23 119.12(13) . . ?
C8 N2 N1 116.56(14) . . ?
C7 N3 C11 117.02(15) . . ?
C23 N5 C1 115.62(16) . . ?
N5 C1 C2 124.1(2) . . ?
N5 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 118.86(19) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.08(19) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C23 C4 C3 117.55(19) . . ?
C23 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
O2 C5 N1 119.49(14) . . ?
O2 C5 C6 125.22(14) . . ?
N1 C5 C6 115.29(13) . . ?
C9 C6 C7 119.43(14) . . ?
C9 C6 C5 122.31(14) . . ?
C7 C6 C5 118.26(14) . . ?
N3 C7 C6 124.23(16) . . ?
N3 C7 C8 118.01(15) . . ?
C6 C7 C8 117.76(14) . . ?
N2 C8 C7 125.21(15) . . ?
N2 C8 H8 117.4 . . ?
C7 C8 H8 117.4 . . ?
C6 C9 C10 117.22(15) . . ?
C6 C9 C12 123.04(13) . . ?
C10 C9 C12 119.74(14) . . ?
C9 C10 C11 119.22(16) . . ?
C9 C10 C18 122.32(18) . . ?
C11 C10 C18 118.46(16) . . ?
N3 C11 C10 122.87(14) . . ?
N3 C11 C21 118.05(18) . . ?
C10 C11 C21 119.08(18) . . ?
C17 C12 C13 118.49(18) . . ?
C17 C12 C9 120.31(16) . . ?
C13 C12 C9 121.18(16) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C10 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C10 C18 H18 119.6 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 121.06(19) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C11 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C11 C21 H21 119.9 . . ?
N5 C23 C4 124.80(16) . . ?
N5 C23 N1 114.97(14) . . ?
C4 C23 N1 120.23(16) . . ?

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
C5 N1 N2 C8 0.5(2) . . . . ?
C23 N1 N2 C8 178.65(14) . . . . ?
C23 N5 C1 C2 -0.2(3) . . . . ?
N5 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C23 -0.8(3) . . . . ?
N2 N1 C5 O2 -178.88(15) . . . . ?
C23 N1 C5 O2 3.0(2) . . . . ?
N2 N1 C5 C6 1.8(2) . . . . ?
C23 N1 C5 C6 -176.37(13) . . . . ?
O2 C5 C6 C9 -2.5(2) . . . . ?
N1 C5 C6 C9 176.88(13) . . . . ?
O2 C5 C6 C7 177.99(15) . . . . ?
N1 C5 C6 C7 -2.7(2) . . . . ?
C11 N3 C7 C6 -0.5(2) . . . . ?
C11 N3 C7 C8 178.78(14) . . . . ?
C9 C6 C7 N3 1.3(2) . . . . ?
C5 C6 C7 N3 -179.09(14) . . . . ?
C9 C6 C7 C8 -177.94(14) . . . . ?
C5 C6 C7 C8 1.6(2) . . . . ?
N1 N2 C8 C7 -1.8(2) . . . . ?
N3 C7 C8 N2 -178.62(16) . . . . ?
C6 C7 C8 N2 0.7(3) . . . . ?
C7 C6 C9 C10 -0.9(2) . . . . ?
C5 C6 C9 C10 179.56(14) . . . . ?
C7 C6 C9 C12 178.41(14) . . . . ?
C5 C6 C9 C12 -1.1(2) . . . . ?
C6 C9 C10 C11 -0.2(2) . . . . ?
C12 C9 C10 C11 -179.57(14) . . . . ?
C6 C9 C10 C18 180.00(15) . . . . ?
C12 C9 C10 C18 0.7(2) . . . . ?
C7 N3 C11 C10 -0.7(2) . . . . ?
C7 N3 C11 C21 179.31(14) . . . . ?
C9 C10 C11 N3 1.1(2) . . . . ?
C18 C10 C11 N3 -179.12(15) . . . . ?
C9 C10 C11 C21 -178.94(14) . . . . ?
C18 C10 C11 C21 0.8(2) . . . . ?
C6 C9 C12 C17 -86.9(2) . . . . ?
C10 C9 C12 C17 92.38(19) . . . . ?
C6 C9 C12 C13 95.02(19) . . . . ?
C10 C9 C12 C13 -85.7(2) . . . . ?
C17 C12 C13 C14 3.5(3) . . . . ?
C9 C12 C13 C14 -178.41(16) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C14 C15 C16 C17 1.9(4) . . . . ?
C15 C16 C17 C12 0.6(3) . . . . ?
C13 C12 C17 C16 -3.3(3) . . . . ?
C9 C12 C17 C16 178.55(19) . . . . ?
C9 C10 C18 C19 178.74(17) . . . . ?
C11 C10 C18 C19 -1.0(3) . . . . ?
C10 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C19 C20 C21 C11 -0.9(3) . . . . ?
N3 C11 C21 C20 -179.96(16) . . . . ?
C10 C11 C21 C20 0.1(2) . . . . ?
C1 N5 C23 C4 -1.0(3) . . . . ?
C1 N5 C23 N1 178.78(17) . . . . ?
C3 C4 C23 N5 1.5(3) . . . . ?
C3 C4 C23 N1 -178.28(17) . . . . ?
N2 N1 C23 N5 -66.41(19) . . . . ?
C5 N1 C23 N5 111.94(17) . . . . ?
N2 N1 C23 C4 113.43(17) . . . . ?
C5 N1 C23 C4 -68.2(2) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_ckcy_1_270724_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2376044'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER NAWAZ KHAN FAZLUR RAHMAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_audit_creation_date             2024-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H12 Cl3 N3 O'
_chemical_formula_sum            'C23 H12 Cl3 N3 O'
_chemical_formula_weight         452.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.925(3)
_cell_length_b                   11.551(3)
_cell_length_c                   14.849(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.201(8)
_cell_angle_gamma                90
_cell_volume                     2029.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.140
_cell_measurement_theta_min      2.465
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.179
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35920
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3582
_reflns_number_total             4300
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0911P)²+0.7847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1500
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.53387(7) 0.71997(8) 1.09707(4) 0.0839(3) Uani 1 1 d . . . . .
Cl2 Cl 0.14202(7) 0.50660(10) 0.97770(5) 0.0930(3) Uani 1 1 d . . . . .
Cl3 Cl 0.88152(5) 0.55284(6) 0.34703(4) 0.0591(2) Uani 1 1 d . . . . .
O1 O 0.58255(14) 0.53789(15) 0.79498(10) 0.0541(4) Uani 1 1 d . . . . .
N1 N 0.41837(13) 0.63502(14) 0.75981(10) 0.0380(4) Uani 1 1 d . . . . .
N2 N 0.33369(14) 0.68318(15) 0.69949(12) 0.0422(4) Uani 1 1 d . . . . .
N3 N 0.46493(13) 0.68154(14) 0.49543(11) 0.0377(4) Uani 1 1 d . . . . .
C1 C 0.39198(16) 0.62644(17) 0.85149(13) 0.0391(4) Uani 1 1 d . . . . .
C2 C 0.46776(18) 0.66946(19) 0.92187(14) 0.0456(5) Uani 1 1 d . . . . .
H2 H 0.535664 0.702522 0.910428 0.055 Uiso 1 1 calc R U . . .
C3 C 0.44053(19) 0.6623(2) 1.00903(14) 0.0485(5) Uani 1 1 d . . . . .
C4 C 0.34090(19) 0.6119(2) 1.02849(14) 0.0501(5) Uani 1 1 d . . . . .
H4 H 0.323841 0.606367 1.087755 0.060 Uiso 1 1 calc R U . . .
C5 C 0.26823(19) 0.5704(2) 0.95638(15) 0.0500(5) Uani 1 1 d . . . . .
C6 C 0.29134(17) 0.5770(2) 0.86751(14) 0.0461(5) Uani 1 1 d . . . . .
H6 H 0.240395 0.548819 0.820014 0.055 Uiso 1 1 calc R U . . .
C7 C 0.52004(15) 0.58870(16) 0.73825(13) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.54265(14) 0.60923(15) 0.64411(12) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.45640(15) 0.66096(15) 0.58217(12) 0.0336(4) Uani 1 1 d . . . . .
C10 C 0.35256(16) 0.69399(18) 0.61662(13) 0.0407(4) Uani 1 1 d . . . . .
H10 H 0.295239 0.725390 0.575629 0.049 Uiso 1 1 calc R U . . .
C11 C 0.64447(15) 0.57930(15) 0.61407(12) 0.0329(4) Uani 1 1 d . . . . .
C12 C 0.65636(15) 0.60121(15) 0.52167(12) 0.0345(4) Uani 1 1 d . . . . .
C13 C 0.56369(16) 0.65140(15) 0.46491(13) 0.0351(4) Uani 1 1 d . . . . .
C14 C 0.74068(16) 0.52514(16) 0.67348(13) 0.0356(4) Uani 1 1 d . . . . .
C15 C 0.75250(18) 0.40638(19) 0.67509(15) 0.0471(5) Uani 1 1 d . . . . .
H15 H 0.700976 0.360325 0.639026 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8409(2) 0.3559(2) 0.73029(18) 0.0565(6) Uani 1 1 d . . . . .
H16 H 0.848891 0.275811 0.730802 0.068 Uiso 1 1 calc R U . . .
C17 C 0.91732(19) 0.4229(2) 0.78456(17) 0.0564(6) Uani 1 1 d . . . . .
H17 H 0.974952 0.388233 0.823325 0.068 Uiso 1 1 calc R U . . .
C18 C 0.9079(2) 0.5402(2) 0.78102(19) 0.0624(7) Uani 1 1 d . . . . .
H18 H 0.960307 0.585917 0.816491 0.075 Uiso 1 1 calc R U . . .
C19 C 0.82037(18) 0.5920(2) 0.72477(17) 0.0523(5) Uani 1 1 d . . . . .
H19 H 0.815497 0.672314 0.721678 0.063 Uiso 1 1 calc R U . . .
C20 C 0.75590(17) 0.57210(17) 0.48362(14) 0.0408(4) Uani 1 1 d . . . . .
H20 H 0.817388 0.540061 0.519826 0.049 Uiso 1 1 calc R U . . .
C21 C 0.76093(17) 0.59125(19) 0.39399(14) 0.0434(5) Uani 1 1 d . . . . .
C22 C 0.66987(19) 0.64003(19) 0.33678(14) 0.0480(5) Uani 1 1 d . . . . .
H22 H 0.675530 0.651993 0.275578 0.058 Uiso 1 1 calc R U . . .
C23 C 0.57384(18) 0.66944(19) 0.37165(14) 0.0451(5) Uani 1 1 d . . . . .
H23 H 0.513855 0.701850 0.333945 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.740(2) . ?
Cl2 C5 1.740(2) . ?
Cl3 C21 1.733(2) . ?
O1 C7 1.205(2) . ?
N1 N2 1.380(2) . ?
N1 C1 1.439(2) . ?
N1 C7 1.399(2) . ?
N2 C10 1.285(3) . ?
N3 C9 1.326(2) . ?
N3 C13 1.359(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.476(3) . ?
C8 C9 1.423(2) . ?
C8 C11 1.389(2) . ?
C9 C10 1.449(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.420(3) . ?
C11 C14 1.494(2) . ?
C12 C13 1.426(3) . ?
C12 C20 1.418(3) . ?
C13 C23 1.421(3) . ?
C14 C15 1.379(3) . ?
C14 C19 1.378(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.360(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.358(3) . ?
C21 C22 1.410(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.358(3) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 114.39(15) . . ?
N2 N1 C7 126.19(15) . . ?
C7 N1 C1 119.27(15) . . ?
C10 N2 N1 117.33(16) . . ?
C9 N3 C13 116.94(16) . . ?
C2 C1 N1 119.33(18) . . ?
C6 C1 N1 119.40(18) . . ?
C6 C1 C2 121.26(18) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 Cl1 118.66(18) . . ?
C2 C3 C4 122.1(2) . . ?
C4 C3 Cl1 119.26(17) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.19(19) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 Cl2 118.73(17) . . ?
C4 C5 C6 122.8(2) . . ?
C6 C5 Cl2 118.49(18) . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
O1 C7 N1 120.28(17) . . ?
O1 C7 C8 124.75(17) . . ?
N1 C7 C8 114.95(15) . . ?
C9 C8 C7 118.48(16) . . ?
C11 C8 C7 122.36(16) . . ?
C11 C8 C9 119.16(16) . . ?
N3 C9 C8 124.47(17) . . ?
N3 C9 C10 117.94(16) . . ?
C8 C9 C10 117.58(16) . . ?
N2 C10 C9 124.94(17) . . ?
N2 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
C8 C11 C12 117.60(16) . . ?
C8 C11 C14 123.52(16) . . ?
C12 C11 C14 118.87(16) . . ?
C11 C12 C13 118.67(16) . . ?
C20 C12 C11 122.21(17) . . ?
C20 C12 C13 119.10(17) . . ?
N3 C13 C12 123.14(17) . . ?
N3 C13 C23 118.08(17) . . ?
C23 C13 C12 118.77(18) . . ?
C15 C14 C11 119.74(18) . . ?
C19 C14 C11 121.13(18) . . ?
C19 C14 C15 119.10(18) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.3(2) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C12 C20 H20 120.2 . . ?
C21 C20 C12 119.61(19) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 Cl3 119.57(17) . . ?
C20 C21 C22 122.03(19) . . ?
C22 C21 Cl3 118.38(16) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.54(19) . . ?
C23 C22 H22 120.2 . . ?
C13 C23 H23 119.5 . . ?
C22 C23 C13 120.9(2) . . ?
C22 C23 H23 119.5 . . ?

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
Cl1 C3 C4 C5 178.23(18) . . . . ?
Cl2 C5 C6 C1 -179.31(17) . . . . ?
Cl3 C21 C22 C23 179.12(17) . . . . ?
O1 C7 C8 C9 174.14(19) . . . . ?
O1 C7 C8 C11 -5.5(3) . . . . ?
N1 N2 C10 C9 -0.9(3) . . . . ?
N1 C1 C2 C3 178.98(19) . . . . ?
N1 C1 C6 C5 -179.77(19) . . . . ?
N1 C7 C8 C9 -6.9(2) . . . . ?
N1 C7 C8 C11 173.47(16) . . . . ?
N2 N1 C1 C2 -128.8(2) . . . . ?
N2 N1 C1 C6 50.4(2) . . . . ?
N2 N1 C7 O1 -172.12(19) . . . . ?
N2 N1 C7 C8 8.9(3) . . . . ?
N3 C9 C10 N2 -177.47(19) . . . . ?
N3 C13 C23 C22 -179.32(19) . . . . ?
C1 N1 N2 C10 179.48(18) . . . . ?
C1 N1 C7 O1 3.1(3) . . . . ?
C1 N1 C7 C8 -175.89(16) . . . . ?
C1 C2 C3 Cl1 -178.23(16) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 Cl2 -179.90(18) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 N1 N2 C10 -5.1(3) . . . . ?
C7 N1 C1 C2 55.4(3) . . . . ?
C7 N1 C1 C6 -125.4(2) . . . . ?
C7 C8 C9 N3 -178.36(17) . . . . ?
C7 C8 C9 C10 2.1(2) . . . . ?
C7 C8 C11 C12 178.94(16) . . . . ?
C7 C8 C11 C14 -0.7(3) . . . . ?
C8 C9 C10 N2 2.1(3) . . . . ?
C8 C11 C12 C13 -0.5(3) . . . . ?
C8 C11 C12 C20 -178.83(17) . . . . ?
C8 C11 C14 C15 94.7(2) . . . . ?
C8 C11 C14 C19 -87.4(3) . . . . ?
C9 N3 C13 C12 -0.8(3) . . . . ?
C9 N3 C13 C23 178.22(17) . . . . ?
C9 C8 C11 C12 -0.7(3) . . . . ?
C9 C8 C11 C14 179.70(16) . . . . ?
C11 C8 C9 N3 1.3(3) . . . . ?
C11 C8 C9 C10 -178.29(17) . . . . ?
C11 C12 C13 N3 1.3(3) . . . . ?
C11 C12 C13 C23 -177.69(17) . . . . ?
C11 C12 C20 C21 177.62(18) . . . . ?
C11 C14 C15 C16 -179.6(2) . . . . ?
C11 C14 C19 C18 178.6(2) . . . . ?
C12 C11 C14 C15 -84.9(2) . . . . ?
C12 C11 C14 C19 93.0(2) . . . . ?
C12 C13 C23 C22 -0.2(3) . . . . ?
C12 C20 C21 Cl3 -178.65(15) . . . . ?
C12 C20 C21 C22 0.3(3) . . . . ?
C13 N3 C9 C8 -0.5(3) . . . . ?
C13 N3 C9 C10 179.07(16) . . . . ?
C13 C12 C20 C21 -0.7(3) . . . . ?
C14 C11 C12 C13 179.12(16) . . . . ?
C14 C11 C12 C20 0.8(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C14 C19 C18 -3.5(3) . . . . ?
C15 C16 C17 C18 -2.5(4) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C17 C18 C19 C14 1.5(4) . . . . ?
C19 C14 C15 C16 2.5(3) . . . . ?
C20 C12 C13 N3 179.71(17) . . . . ?
C20 C12 C13 C23 0.7(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C13 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2B_140824_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2381375'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2024-09-02 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Cl N3 O'
_chemical_formula_sum            'C20 H14 Cl N3 O'
_chemical_formula_weight         347.79

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7967(16)
_cell_length_b                   9.9850(17)
_cell_length_c                   10.4267(18)
_cell_angle_alpha                100.814(5)
_cell_angle_beta                 104.185(5)
_cell_angle_gamma                117.719(5)
_cell_volume                     819.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7021
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6683
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20366
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.152
_diffrn_reflns_theta_max         28.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4054
_reflns_number_gt                2542
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0413P)²+0.3932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.09888(8) 0.64503(9) 0.84767(7) 0.0739(2) Uani 1 1 d . . . . .
O1 O 0.45289(17) 0.17488(18) 0.48391(15) 0.0564(4) Uani 1 1 d . . . . .
N1 N -0.0882(2) 0.1036(2) 0.35990(18) 0.0474(4) Uani 1 1 d . . . . .
N2 N 0.2304(2) -0.0278(2) 0.29313(17) 0.0466(4) Uani 1 1 d . . . . .
N3 N 0.0706(2) -0.1080(2) 0.19748(18) 0.0553(5) Uani 1 1 d . . . . .
C2 C 0.1267(2) 0.3243(2) 0.5792(2) 0.0385(4) Uani 1 1 d . . . . .
C3 C -0.0390(2) 0.2290(2) 0.4753(2) 0.0428(5) Uani 1 1 d . . . . .
C4 C -0.1584(3) 0.2654(3) 0.4933(2) 0.0529(5) Uani 1 1 d . . . . .
H4 H -0.267135 0.202712 0.426489 0.064 Uiso 1 1 calc R U . . .
C5 C -0.1173(3) 0.3891(3) 0.6054(2) 0.0541(6) Uani 1 1 d . . . . .
H5 H -0.196808 0.411887 0.615587 0.065 Uiso 1 1 calc R U . . .
C6 C 0.0471(3) 0.4834(3) 0.7069(2) 0.0482(5) Uani 1 1 d . . . . .
C7 C 0.1659(2) 0.4529(2) 0.6961(2) 0.0442(5) Uani 1 1 d . . . . .
H7 H 0.273082 0.516435 0.765551 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2455(2) 0.2855(2) 0.56373(19) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.1930(2) 0.1574(2) 0.44394(19) 0.0382(4) Uani 1 1 d . . . . .
C10 C 0.0259(2) 0.0718(2) 0.3461(2) 0.0424(5) Uani 1 1 d . . . . .
C11 C 0.3045(2) 0.1066(2) 0.4130(2) 0.0415(4) Uani 1 1 d . . . . .
C12 C -0.0234(3) -0.0594(3) 0.2231(2) 0.0546(6) Uani 1 1 d . . . . .
H12 H -0.131991 -0.113062 0.157030 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4145(2) 0.3774(2) 0.67820(19) 0.0378(4) Uani 1 1 d . . . . .
C14 C 0.5347(3) 0.5304(3) 0.6928(2) 0.0534(5) Uani 1 1 d . . . . .
H14 H 0.512561 0.577471 0.628044 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6885(3) 0.6144(3) 0.8038(3) 0.0624(6) Uani 1 1 d . . . . .
H15 H 0.770429 0.716226 0.811288 0.075 Uiso 1 1 calc R U . . .
C16 C 0.7211(3) 0.5493(3) 0.9024(2) 0.0565(6) Uani 1 1 d . . . . .
H16 H 0.823521 0.607391 0.978092 0.068 Uiso 1 1 calc R U . . .
C17 C 0.6015(3) 0.3979(3) 0.8887(2) 0.0560(6) Uani 1 1 d . . . . .
H17 H 0.622832 0.352979 0.955567 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4498(3) 0.3113(3) 0.7767(2) 0.0481(5) Uani 1 1 d . . . . .
H18 H 0.370484 0.207328 0.767309 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3311(3) -0.0884(3) 0.2569(2) 0.0556(6) Uani 1 1 d . . . . .
H19A H 0.258201 -0.203004 0.201846 0.067 Uiso 1 1 calc R U . . .
H19B H 0.408707 -0.076004 0.343365 0.067 Uiso 1 1 calc R U . . .
C20 C 0.4261(3) -0.0068(3) 0.1764(3) 0.0693(7) Uani 1 1 d . . . . .
H20 H 0.514527 -0.018743 0.175468 0.083 Uiso 1 1 calc R U . . .
C21 C 0.4020(5) 0.0766(4) 0.1091(4) 0.1038(11) Uani 1 1 d . . . . .
H21A H 0.315280 0.092755 0.106266 0.125 Uiso 1 1 calc R U . . .
H21B H 0.470684 0.122475 0.061986 0.125 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.733(2) . ?
O1 C11 1.220(2) . ?
N1 C10 1.328(3) . ?
N1 C3 1.355(3) . ?
N2 N3 1.362(2) . ?
N2 C11 1.382(2) . ?
N2 C19 1.461(3) . ?
N3 C12 1.282(3) . ?
C2 C7 1.417(3) . ?
C2 C8 1.421(2) . ?
C2 C3 1.424(3) . ?
C3 C4 1.419(3) . ?
C4 C5 1.349(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.356(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(3) . ?
C8 C13 1.488(2) . ?
C9 C10 1.415(3) . ?
C9 C11 1.476(3) . ?
C10 C12 1.439(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 C18 1.380(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.472(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.250(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9300 . ?
C21 H21B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C3 117.06(16) . . ?
N3 N2 C11 126.27(17) . . ?
N3 N2 C19 114.66(16) . . ?
C11 N2 C19 118.97(17) . . ?
C12 N3 N2 117.49(17) . . ?
C7 C2 C8 122.38(17) . . ?
C7 C2 C3 118.43(17) . . ?
C8 C2 C3 119.17(17) . . ?
N1 C3 C4 118.39(18) . . ?
N1 C3 C2 122.70(18) . . ?
C4 C3 C2 118.91(19) . . ?
C5 C4 C3 121.38(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.23(19) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 122.0(2) . . ?
C7 C6 Cl1 119.43(16) . . ?
C5 C6 Cl1 118.56(16) . . ?
C6 C7 C2 120.04(18) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 C8 C2 117.23(16) . . ?
C9 C8 C13 123.86(16) . . ?
C2 C8 C13 118.84(16) . . ?
C8 C9 C10 119.07(17) . . ?
C8 C9 C11 122.90(17) . . ?
C10 C9 C11 118.03(17) . . ?
N1 C10 C9 124.75(18) . . ?
N1 C10 C12 117.81(18) . . ?
C9 C10 C12 117.44(18) . . ?
O1 C11 N2 119.63(18) . . ?
O1 C11 C9 124.86(17) . . ?
N2 C11 C9 115.50(17) . . ?
N3 C12 C10 125.07(19) . . ?
N3 C12 H12 117.5 . . ?
C10 C12 H12 117.5 . . ?
C14 C13 C18 118.81(18) . . ?
C14 C13 C8 121.79(17) . . ?
C18 C13 C8 119.32(17) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.5(2) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
N2 C19 C20 114.2(2) . . ?
N2 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
N2 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C19 127.7(3) . . ?
C21 C20 H20 116.1 . . ?
C19 C20 H20 116.1 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?

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
C11 N2 N3 C12 -3.2(3) . . . . ?
C19 N2 N3 C12 -179.5(2) . . . . ?
C10 N1 C3 C4 -179.68(18) . . . . ?
C10 N1 C3 C2 -0.2(3) . . . . ?
C7 C2 C3 N1 -179.97(18) . . . . ?
C8 C2 C3 N1 -1.2(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C8 C2 C3 C4 178.24(18) . . . . ?
N1 C3 C4 C5 -179.68(19) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 Cl1 178.32(17) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
Cl1 C6 C7 C2 -177.99(15) . . . . ?
C8 C2 C7 C6 -179.04(19) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C7 C2 C8 C9 -179.53(17) . . . . ?
C3 C2 C8 C9 1.7(3) . . . . ?
C7 C2 C8 C13 3.4(3) . . . . ?
C3 C2 C8 C13 -175.34(17) . . . . ?
C2 C8 C9 C10 -1.0(3) . . . . ?
C13 C8 C9 C10 175.96(17) . . . . ?
C2 C8 C9 C11 178.56(17) . . . . ?
C13 C8 C9 C11 -4.5(3) . . . . ?
C3 N1 C10 C9 1.1(3) . . . . ?
C3 N1 C10 C12 -179.03(18) . . . . ?
C8 C9 C10 N1 -0.5(3) . . . . ?
C11 C9 C10 N1 179.95(18) . . . . ?
C8 C9 C10 C12 179.64(18) . . . . ?
C11 C9 C10 C12 0.1(3) . . . . ?
N3 N2 C11 O1 -174.02(19) . . . . ?
C19 N2 C11 O1 2.1(3) . . . . ?
N3 N2 C11 C9 5.3(3) . . . . ?
C19 N2 C11 C9 -178.51(17) . . . . ?
C8 C9 C11 O1 -3.7(3) . . . . ?
C10 C9 C11 O1 175.84(19) . . . . ?
C8 C9 C11 N2 176.97(17) . . . . ?
C10 C9 C11 N2 -3.5(3) . . . . ?
N2 N3 C12 C10 -1.0(3) . . . . ?
N1 C10 C12 N3 -177.5(2) . . . . ?
C9 C10 C12 N3 2.4(3) . . . . ?
C9 C8 C13 C14 104.9(2) . . . . ?
C2 C8 C13 C14 -78.2(2) . . . . ?
C9 C8 C13 C18 -78.2(2) . . . . ?
C2 C8 C13 C18 98.6(2) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
C8 C13 C14 C15 177.64(19) . . . . ?
C13 C14 C15 C16 -2.2(4) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C13 -1.5(3) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C8 C13 C18 C17 -175.91(18) . . . . ?
N3 N2 C19 C20 92.0(2) . . . . ?
C11 N2 C19 C20 -84.6(2) . . . . ?
N2 C19 C20 C21 -18.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C19 H19B O1 0.97 2.60 3.507(3) 155.0 2_656 yes

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_CKCY_2_270724_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2388359'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2024-10-02 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H13 Br F N3 O, C H Cl3'
_chemical_formula_sum            'C24 H14 Br Cl3 F N3 O'
_chemical_formula_weight         565.64

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.9616(9)
_cell_length_b                   10.8396(10)
_cell_length_c                   11.1734(10)
_cell_angle_alpha                92.854(4)
_cell_angle_beta                 99.122(4)
_cell_angle_gamma                92.843(4)
_cell_volume                     1187.74(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6892
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      22.24

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    2.098
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5746
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31645
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         27.180
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5289
_reflns_number_gt                2691
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1656P)²+0.6067P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5289
_refine_ls_number_parameters     299
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2954
_refine_ls_wR_factor_gt          0.2472
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.007

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
Br1 Br 0.00681(8) 0.20154(7) 0.14492(7) 0.0907(5) Uani 1 1 d . . . . .
Cl1 Cl 0.6180(6) 0.0321(3) 0.1836(4) 0.206(2) Uani 1 1 d . . . . .
Cl2 Cl 0.5879(4) 0.1113(3) 0.4236(4) 0.1673(15) Uani 1 1 d . . . . .
Cl4 Cl 0.8085(5) -0.0304(4) 0.3872(6) 0.207(2) Uani 1 1 d . . . . .
F2 F 0.4509(4) 0.3595(5) 0.4289(4) 0.1087(16) Uani 1 1 d . . . . .
O2 O 0.4558(4) 0.2805(4) 0.6537(4) 0.0601(10) Uani 1 1 d . . . . .
N1 N 0.5136(5) 0.6585(4) 0.9034(5) 0.0564(12) Uani 1 1 d . . . . .
N2 N 0.3261(4) 0.4434(4) 0.6133(4) 0.0492(11) Uani 1 1 d . . . . .
N3 N 0.2744(5) 0.5549(5) 0.6437(5) 0.0610(13) Uani 1 1 d . . . . .
C1 C 0.6411(13) -0.0077(8) 0.3376(12) 0.136(4) Uani 1 1 d . . . . .
H1 H 0.586139 -0.083708 0.344524 0.164 Uiso 1 1 calc R U . . .
C2 C 0.6969(5) 0.5149(5) 0.9451(5) 0.0494(13) Uani 1 1 d . . . . .
C3 C 0.6324(6) 0.6274(5) 0.9712(5) 0.0533(14) Uani 1 1 d . . . . .
C4 C 0.6935(7) 0.7083(6) 1.0664(6) 0.0656(17) Uani 1 1 d . . . . .
H4 H 0.652896 0.781757 1.081262 0.079 Uiso 1 1 calc R U . . .
C5 C 0.8112(7) 0.6833(7) 1.1388(6) 0.0737(18) Uani 1 1 d . . . . .
H5 H 0.848895 0.737210 1.204192 0.088 Uiso 1 1 calc R U . . .
C6 C 0.8748(7) 0.5741(8) 1.1125(6) 0.077(2) Uani 1 1 d . . . . .
H6 H 0.956555 0.557670 1.160186 0.093 Uiso 1 1 calc R U . . .
C7 C 0.8201(6) 0.4920(6) 1.0193(6) 0.0618(15) Uani 1 1 d . . . . .
H7 H 0.864242 0.420452 1.004668 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6332(5) 0.4331(5) 0.8468(5) 0.0468(12) Uani 1 1 d . . . . .
C9 C 0.5110(5) 0.4671(5) 0.7815(5) 0.0437(12) Uani 1 1 d . . . . .
C10 C 0.4586(5) 0.5801(5) 0.8118(5) 0.0491(13) Uani 1 1 d . . . . .
C11 C 0.4338(5) 0.3879(5) 0.6803(5) 0.0466(13) Uani 1 1 d . . . . .
C12 C 0.3373(6) 0.6165(6) 0.7387(6) 0.0600(15) Uani 1 1 d . . . . .
H12 H 0.301681 0.690095 0.761829 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7005(5) 0.3199(5) 0.8164(5) 0.0523(14) Uani 1 1 d . . . . .
C14 C 0.7695(6) 0.3138(7) 0.7167(6) 0.0673(17) Uani 1 1 d . . . . .
H14 H 0.770521 0.380976 0.668173 0.081 Uiso 1 1 calc R U . . .
C15 C 0.8345(7) 0.2127(7) 0.6894(8) 0.081(2) Uani 1 1 d . . . . .
H15 H 0.880684 0.210129 0.623294 0.097 Uiso 1 1 calc R U . . .
C16 C 0.8314(9) 0.1135(8) 0.7609(10) 0.097(3) Uani 1 1 d . . . . .
H16 H 0.872966 0.042344 0.739938 0.117 Uiso 1 1 calc R U . . .
C17 C 0.7715(9) 0.1153(7) 0.8584(8) 0.083(2) Uani 1 1 d . . . . .
H17 H 0.776261 0.048378 0.907622 0.100 Uiso 1 1 calc R U . . .
C18 C 0.7008(7) 0.2185(6) 0.8873(6) 0.0664(17) Uani 1 1 d . . . . .
H18 H 0.654560 0.219002 0.953364 0.080 Uiso 1 1 calc R U . . .
C19 C 0.2513(5) 0.3802(5) 0.5063(5) 0.0501(13) Uani 1 1 d . . . . .
C20 C 0.1091(6) 0.3621(6) 0.4911(6) 0.0639(16) Uani 1 1 d . . . . .
H20 H 0.063257 0.386555 0.553857 0.077 Uiso 1 1 calc R U . . .
C21 C 0.0372(6) 0.3091(6) 0.3853(6) 0.0660(17) Uani 1 1 d . . . . .
H21 H -0.057247 0.298554 0.375262 0.079 Uiso 1 1 calc R U . . .
C22 C 0.1055(6) 0.2717(6) 0.2945(6) 0.0626(16) Uani 1 1 d . . . . .
C23 C 0.2458(6) 0.2834(6) 0.3074(6) 0.0624(16) Uani 1 1 d . . . . .
H23 H 0.291783 0.254341 0.246420 0.075 Uiso 1 1 calc R U . . .
C24 C 0.3147(7) 0.3395(6) 0.4136(6) 0.0603(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
Br1 C22 1.902(6) . ?
Cl1 C1 1.778(14) . ?
Cl2 C1 1.724(10) . ?
Cl4 C1 1.705(13) . ?
F2 C24 1.346(8) . ?
O2 C11 1.226(7) . ?
N1 C10 1.326(8) . ?
N1 C3 1.367(7) . ?
N2 N3 1.386(6) . ?
N2 C11 1.388(6) . ?
N2 C19 1.428(7) . ?
N3 C12 1.282(8) . ?
C1 H1 0.9800 . ?
C2 C7 1.409(8) . ?
C2 C8 1.422(8) . ?
C2 C3 1.445(8) . ?
C3 C4 1.385(9) . ?
C4 C5 1.363(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(10) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.392(7) . ?
C8 C13 1.478(8) . ?
C9 C10 1.402(7) . ?
C9 C11 1.473(8) . ?
C10 C12 1.432(8) . ?
C12 H12 0.9300 . ?
C13 C18 1.386(8) . ?
C13 C14 1.399(9) . ?
C14 C15 1.346(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.322(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.363(8) . ?
C19 C20 1.402(8) . ?
C20 C21 1.366(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(8) . ?
C23 C24 1.370(9) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C3 117.0(5) . . ?
N3 N2 C11 126.2(5) . . ?
N3 N2 C19 113.7(4) . . ?
C11 N2 C19 119.9(4) . . ?
C12 N3 N2 116.9(5) . . ?
Cl2 C1 Cl4 110.2(7) . . ?
Cl2 C1 Cl1 108.4(6) . . ?
Cl4 C1 Cl1 110.1(6) . . ?
Cl2 C1 H1 109.4 . . ?
Cl4 C1 H1 109.4 . . ?
Cl1 C1 H1 109.4 . . ?
C7 C2 C8 123.5(5) . . ?
C7 C2 C3 117.9(5) . . ?
C8 C2 C3 118.7(5) . . ?
N1 C3 C4 118.4(6) . . ?
N1 C3 C2 122.2(5) . . ?
C4 C3 C2 119.4(5) . . ?
C5 C4 C3 121.9(6) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.6(6) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 121.9(7) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C2 120.2(6) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C2 117.3(5) . . ?
C9 C8 C13 123.4(5) . . ?
C2 C8 C13 119.2(5) . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 C11 122.1(5) . . ?
C10 C9 C11 118.2(5) . . ?
N1 C10 C9 125.1(5) . . ?
N1 C10 C12 116.3(5) . . ?
C9 C10 C12 118.7(5) . . ?
O2 C11 N2 119.6(5) . . ?
O2 C11 C9 125.8(5) . . ?
N2 C11 C9 114.6(5) . . ?
N3 C12 C10 124.6(6) . . ?
N3 C12 H12 117.7 . . ?
C10 C12 H12 117.7 . . ?
C18 C13 C14 118.1(5) . . ?
C18 C13 C8 121.3(5) . . ?
C14 C13 C8 120.6(5) . . ?
C15 C14 C13 121.4(7) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 118.8(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 122.4(7) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C16 C17 C18 119.7(7) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 119.3(6) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C24 C19 C20 117.7(6) . . ?
C24 C19 N2 121.3(5) . . ?
C20 C19 N2 121.0(5) . . ?
C21 C20 C19 120.8(6) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.2(6) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 121.9(6) . . ?
C21 C22 Br1 119.8(5) . . ?
C23 C22 Br1 118.3(5) . . ?
C24 C23 C22 117.4(6) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
F2 C24 C19 116.8(6) . . ?
F2 C24 C23 120.1(6) . . ?
C19 C24 C23 123.0(6) . . ?

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
C11 N2 N3 C12 4.7(8) . . . . ?
C19 N2 N3 C12 -179.7(5) . . . . ?
C10 N1 C3 C4 179.0(5) . . . . ?
C10 N1 C3 C2 0.4(8) . . . . ?
C7 C2 C3 N1 179.2(5) . . . . ?
C8 C2 C3 N1 -1.0(8) . . . . ?
C7 C2 C3 C4 0.5(8) . . . . ?
C8 C2 C3 C4 -179.7(5) . . . . ?
N1 C3 C4 C5 179.4(6) . . . . ?
C2 C3 C4 C5 -1.9(9) . . . . ?
C3 C4 C5 C6 2.5(10) . . . . ?
C4 C5 C6 C7 -1.8(11) . . . . ?
C5 C6 C7 C2 0.4(10) . . . . ?
C8 C2 C7 C6 -179.6(6) . . . . ?
C3 C2 C7 C6 0.2(9) . . . . ?
C7 C2 C8 C9 179.6(5) . . . . ?
C3 C2 C8 C9 -0.2(7) . . . . ?
C7 C2 C8 C13 -2.4(8) . . . . ?
C3 C2 C8 C13 177.9(5) . . . . ?
C2 C8 C9 C10 2.1(7) . . . . ?
C13 C8 C9 C10 -175.9(5) . . . . ?
C2 C8 C9 C11 -178.1(4) . . . . ?
C13 C8 C9 C11 3.9(8) . . . . ?
C3 N1 C10 C9 1.7(8) . . . . ?
C3 N1 C10 C12 -177.5(5) . . . . ?
C8 C9 C10 N1 -3.0(8) . . . . ?
C11 C9 C10 N1 177.2(5) . . . . ?
C8 C9 C10 C12 176.2(5) . . . . ?
C11 C9 C10 C12 -3.6(7) . . . . ?
N3 N2 C11 O2 168.4(5) . . . . ?
C19 N2 C11 O2 -6.9(7) . . . . ?
N3 N2 C11 C9 -10.3(7) . . . . ?
C19 N2 C11 C9 174.3(4) . . . . ?
C8 C9 C11 O2 10.8(8) . . . . ?
C10 C9 C11 O2 -169.4(5) . . . . ?
C8 C9 C11 N2 -170.6(4) . . . . ?
C10 C9 C11 N2 9.3(7) . . . . ?
N2 N3 C12 C10 2.3(9) . . . . ?
N1 C10 C12 N3 176.7(5) . . . . ?
C9 C10 C12 N3 -2.6(9) . . . . ?
C9 C8 C13 C18 -106.9(7) . . . . ?
C2 C8 C13 C18 75.1(7) . . . . ?
C9 C8 C13 C14 75.0(7) . . . . ?
C2 C8 C13 C14 -103.0(6) . . . . ?
C18 C13 C14 C15 0.1(10) . . . . ?
C8 C13 C14 C15 178.2(6) . . . . ?
C13 C14 C15 C16 0.6(11) . . . . ?
C14 C15 C16 C17 -2.7(13) . . . . ?
C15 C16 C17 C18 4.0(13) . . . . ?
C14 C13 C18 C17 1.2(9) . . . . ?
C8 C13 C18 C17 -177.0(6) . . . . ?
C16 C17 C18 C13 -3.2(11) . . . . ?
N3 N2 C19 C24 128.3(5) . . . . ?
C11 N2 C19 C24 -55.9(7) . . . . ?
N3 N2 C19 C20 -49.3(7) . . . . ?
C11 N2 C19 C20 126.6(6) . . . . ?
C24 C19 C20 C21 -2.1(9) . . . . ?
N2 C19 C20 C21 175.6(5) . . . . ?
C19 C20 C21 C22 1.1(9) . . . . ?
C20 C21 C22 C23 1.5(9) . . . . ?
C20 C21 C22 Br1 -178.4(5) . . . . ?
C21 C22 C23 C24 -2.9(9) . . . . ?
Br1 C22 C23 C24 177.0(4) . . . . ?
C20 C19 C24 F2 178.9(5) . . . . ?
N2 C19 C24 F2 1.3(8) . . . . ?
C20 C19 C24 C23 0.6(8) . . . . ?
N2 C19 C24 C23 -177.1(5) . . . . ?
C22 C23 C24 F2 -176.4(6) . . . . ?
C22 C23 C24 C19 1.8(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.98 2.15 3.076(9) 156.0 2_656 yes
C4 H4 Cl1 0.93 2.95 3.836(8) 160.0 1_566 yes

_refine_diff_density_max         2.469
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_N_H2Cl_260924_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2l4v0m
_database_code_depnum_ccdc_archive 'CCDC 2387930'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER  FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 Cl N3 O'
_chemical_formula_sum            'C23 H14 Cl N3 O'
_chemical_formula_weight         383.82

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   14.9493(11)
_cell_length_b                   7.5272(6)
_cell_length_c                   16.2680(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.674(3)
_cell_angle_gamma                90
_cell_volume                     1828.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8619
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34398
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.895
_diffrn_reflns_theta_max         28.306
_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             4535
_reflns_number_gt                2727
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0454P)²+1.0106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0141(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4535
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.57358(8) 0.91647(10) 0.87625(5) 0.1091(4) Uani 1 1 d . . . . .
O1 O 0.43504(10) 0.5872(2) 0.76508(9) 0.0626(5) Uani 1 1 d . . . . .
N1 N 0.58498(11) 0.7512(2) 0.52147(10) 0.0470(5) Uani 1 1 d . . . . .
N2 N 0.58439(11) 0.6096(3) 0.76134(10) 0.0472(5) Uani 1 1 d . . . . .
N3 N 0.66403(12) 0.6439(3) 0.72522(11) 0.0617(6) Uani 1 1 d . . . . .
C1 C 0.59482(13) 0.5675(3) 0.84714(12) 0.0460(5) Uani 1 1 d . . . . .
C2 C 0.61066(18) 0.3960(3) 0.87236(14) 0.0646(7) Uani 1 1 d . . . . .
H2 H 0.612980 0.305766 0.833485 0.077 Uiso 1 1 calc R U . . .
C3 C 0.6232(2) 0.3563(4) 0.95492(15) 0.0729(8) Uani 1 1 d . . . . .
H3 H 0.633976 0.239642 0.971403 0.087 Uiso 1 1 calc R U . . .
C4 C 0.61976(16) 0.4885(4) 1.01269(14) 0.0602(6) Uani 1 1 d . . . . .
H4 H 0.627741 0.461252 1.068309 0.072 Uiso 1 1 calc R U . . .
C5 C 0.60463(17) 0.6604(4) 0.98864(14) 0.0592(6) Uani 1 1 d . . . . .
H5 H 0.602701 0.750368 1.027699 0.071 Uiso 1 1 calc R U . . .
C6 C 0.59221(16) 0.6995(3) 0.90586(13) 0.0531(6) Uani 1 1 d . . . . .
C7 C 0.65879(15) 0.6862(4) 0.64890(14) 0.0610(7) Uani 1 1 d . . . . .
H7 H 0.712186 0.708281 0.623590 0.073 Uiso 1 1 calc R U . . .
C8 C 0.57734(13) 0.7023(3) 0.59921(12) 0.0431(5) Uani 1 1 d . . . . .
C9 C 0.49543(13) 0.6669(3) 0.63617(11) 0.0376(4) Uani 1 1 d . . . . .
C10 C 0.49915(14) 0.6181(3) 0.72417(12) 0.0429(5) Uani 1 1 d . . . . .
C11 C 0.50826(14) 0.7676(3) 0.47452(12) 0.0418(5) Uani 1 1 d . . . . .
C12 C 0.42229(13) 0.7323(3) 0.50499(11) 0.0397(5) Uani 1 1 d . . . . .
C13 C 0.41590(13) 0.6806(3) 0.58843(11) 0.0381(4) Uani 1 1 d . . . . .
C14 C 0.51503(16) 0.8239(3) 0.39195(12) 0.0519(6) Uani 1 1 d . . . . .
H14 H 0.570979 0.847122 0.371669 0.062 Uiso 1 1 calc R U . . .
C15 C 0.44056(17) 0.8439(3) 0.34255(14) 0.0604(6) Uani 1 1 d . . . . .
H15 H 0.445866 0.881547 0.288543 0.072 Uiso 1 1 calc R U . . .
C16 C 0.35568(17) 0.8090(4) 0.37126(14) 0.0621(7) Uani 1 1 d . . . . .
H16 H 0.305218 0.822818 0.336202 0.075 Uiso 1 1 calc R U . . .
C17 C 0.34642(15) 0.7548(3) 0.45023(13) 0.0540(6) Uani 1 1 d . . . . .
H17 H 0.289536 0.732175 0.468574 0.065 Uiso 1 1 calc R U . . .
C18 C 0.32542(13) 0.6504(3) 0.62098(11) 0.0399(5) Uani 1 1 d . . . . .
C19 C 0.28505(15) 0.7829(3) 0.66465(13) 0.0545(6) Uani 1 1 d . . . . .
H19 H 0.315134 0.889509 0.674580 0.065 Uiso 1 1 calc R U . . .
C20 C 0.20073(17) 0.7595(4) 0.69376(14) 0.0621(7) Uani 1 1 d . . . . .
H20 H 0.174279 0.849698 0.723212 0.074 Uiso 1 1 calc R U . . .
C21 C 0.15628(15) 0.6041(4) 0.67934(13) 0.0620(7) Uani 1 1 d . . . . .
H21 H 0.099613 0.588054 0.699430 0.074 Uiso 1 1 calc R U . . .
C22 C 0.19462(15) 0.4702(4) 0.63517(14) 0.0588(6) Uani 1 1 d . . . . .
H22 H 0.163919 0.364281 0.625376 0.071 Uiso 1 1 calc R U . . .
C23 C 0.27917(14) 0.4942(3) 0.60538(13) 0.0486(5) Uani 1 1 d . . . . .
H23 H 0.304847 0.404801 0.574815 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.722(2) . ?
O1 C10 1.214(2) . ?
N1 C8 1.327(2) . ?
N1 C11 1.354(3) . ?
N2 N3 1.377(2) . ?
N2 C10 1.386(3) . ?
N2 C1 1.433(2) . ?
N3 C7 1.281(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.380(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.435(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(3) . ?
C9 C13 1.393(3) . ?
C9 C10 1.477(3) . ?
C11 C14 1.417(3) . ?
C11 C12 1.424(3) . ?
C12 C17 1.419(3) . ?
C12 C13 1.420(3) . ?
C13 C18 1.493(3) . ?
C14 C15 1.351(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.380(3) . ?
C18 C23 1.382(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.360(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C11 117.03(17) . . ?
N3 N2 C10 126.94(16) . . ?
N3 N2 C1 113.60(16) . . ?
C10 N2 C1 119.42(17) . . ?
C7 N3 N2 116.46(18) . . ?
C2 C1 C6 118.7(2) . . ?
C2 C1 N2 120.6(2) . . ?
C6 C1 N2 120.7(2) . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.9(2) . . ?
C1 C6 Cl1 119.91(17) . . ?
C5 C6 Cl1 119.15(19) . . ?
N3 C7 C8 125.4(2) . . ?
N3 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
N1 C8 C9 124.89(18) . . ?
N1 C8 C7 116.86(18) . . ?
C9 C8 C7 118.25(18) . . ?
C13 C9 C8 118.83(17) . . ?
C13 C9 C10 123.46(17) . . ?
C8 C9 C10 117.70(17) . . ?
O1 C10 N2 119.01(18) . . ?
O1 C10 C9 125.73(18) . . ?
N2 C10 C9 115.25(17) . . ?
N1 C11 C14 117.78(19) . . ?
N1 C11 C12 122.78(17) . . ?
C14 C11 C12 119.44(19) . . ?
C17 C12 C13 123.06(18) . . ?
C17 C12 C11 117.83(18) . . ?
C13 C12 C11 119.09(17) . . ?
C9 C13 C12 117.36(17) . . ?
C9 C13 C18 123.70(17) . . ?
C12 C13 C18 118.90(16) . . ?
C15 C14 C11 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C11 C14 H14 119.9 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C23 118.87(19) . . ?
C19 C18 C13 119.87(19) . . ?
C23 C18 C13 121.20(18) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 120.2(2) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?

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
C10 N2 N3 C7 -0.9(4) . . . . ?
C1 N2 N3 C7 -178.5(2) . . . . ?
N3 N2 C1 C2 -87.1(3) . . . . ?
C10 N2 C1 C2 95.1(3) . . . . ?
N3 N2 C1 C6 90.7(2) . . . . ?
C10 N2 C1 C6 -87.2(3) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
N2 C1 C2 C3 178.2(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N2 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 Cl1 179.36(19) . . . . ?
N2 C1 C6 Cl1 1.6(3) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 Cl1 -179.8(2) . . . . ?
N2 N3 C7 C8 0.8(4) . . . . ?
C11 N1 C8 C9 -0.2(3) . . . . ?
C11 N1 C8 C7 -179.6(2) . . . . ?
N3 C7 C8 N1 178.6(3) . . . . ?
N3 C7 C8 C9 -0.9(4) . . . . ?
N1 C8 C9 C13 1.1(3) . . . . ?
C7 C8 C9 C13 -179.5(2) . . . . ?
N1 C8 C9 C10 -178.5(2) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
N3 N2 C10 O1 -178.5(2) . . . . ?
C1 N2 C10 O1 -1.0(3) . . . . ?
N3 N2 C10 C9 1.0(3) . . . . ?
C1 N2 C10 C9 178.49(18) . . . . ?
C13 C9 C10 O1 -1.1(3) . . . . ?
C8 C9 C10 O1 178.5(2) . . . . ?
C13 C9 C10 N2 179.45(19) . . . . ?
C8 C9 C10 N2 -1.0(3) . . . . ?
C8 N1 C11 C14 178.5(2) . . . . ?
C8 N1 C11 C12 -0.9(3) . . . . ?
N1 C11 C12 C17 179.7(2) . . . . ?
C14 C11 C12 C17 0.3(3) . . . . ?
N1 C11 C12 C13 1.1(3) . . . . ?
C14 C11 C12 C13 -178.31(19) . . . . ?
C8 C9 C13 C12 -0.8(3) . . . . ?
C10 C9 C13 C12 178.74(19) . . . . ?
C8 C9 C13 C18 -178.57(19) . . . . ?
C10 C9 C13 C18 1.0(3) . . . . ?
C17 C12 C13 C9 -178.7(2) . . . . ?
C11 C12 C13 C9 -0.1(3) . . . . ?
C17 C12 C13 C18 -0.8(3) . . . . ?
C11 C12 C13 C18 177.69(18) . . . . ?
N1 C11 C14 C15 -179.4(2) . . . . ?
C12 C11 C14 C15 0.0(3) . . . . ?
C11 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C12 -0.1(4) . . . . ?
C13 C12 C17 C16 178.3(2) . . . . ?
C11 C12 C17 C16 -0.2(3) . . . . ?
C9 C13 C18 C19 79.8(3) . . . . ?
C12 C13 C18 C19 -97.9(2) . . . . ?
C9 C13 C18 C23 -102.9(2) . . . . ?
C12 C13 C18 C23 79.4(2) . . . . ?
C23 C18 C19 C20 1.2(3) . . . . ?
C13 C18 C19 C20 178.60(19) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C19 C18 C23 C22 -1.7(3) . . . . ?
C13 C18 C23 C22 -178.99(19) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_CY_2_Phma_081124_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2402442'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2024-11-13 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 N3 O3'
_chemical_formula_sum            'C27 H19 N3 O3'
_chemical_formula_weight         433.45

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'

_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                   10.4666(6)
_cell_length_b                   13.6900(8)
_cell_length_c                   14.9463(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.902(2)
_cell_angle_gamma                90
_cell_volume                     2103.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9576
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.37
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61731
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         28.296
_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             5213
_reflns_number_gt                3664
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0470P)²+0.6559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5213
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O1 O 0.35283(14) 0.30319(14) 0.24759(12) 0.0963(5) Uani 1 1 d . . . . .
O2 O 0.66126(10) 0.59428(9) 0.20275(7) 0.0517(3) Uani 1 1 d . . . . .
O3 O 0.56436(13) 0.29095(10) 0.30523(9) 0.0646(3) Uani 1 1 d . . . . .
N1 N 1.06448(11) 0.59439(10) 0.41511(9) 0.0455(3) Uani 1 1 d . . . . .
N2 N 0.83925(11) 0.51475(9) 0.17428(8) 0.0410(3) Uani 1 1 d . . . . .
N3 N 0.97241(12) 0.50262(10) 0.18857(9) 0.0484(3) Uani 1 1 d . . . . .
C1 C 0.87365(14) 0.63724(10) 0.47905(9) 0.0390(3) Uani 1 1 d . . . . .
C2 C 1.01091(14) 0.62753(11) 0.48499(10) 0.0415(3) Uani 1 1 d . . . . .
C3 C 1.09486(16) 0.65213(12) 0.56773(11) 0.0521(4) Uani 1 1 d . . . . .
H3 H 1.184426 0.647212 0.571955 0.063 Uiso 1 1 calc R U . . .
C4 C 1.04648(18) 0.68275(13) 0.64085(11) 0.0573(4) Uani 1 1 d . . . . .
H4 H 1.103135 0.700455 0.694082 0.069 Uiso 1 1 calc R U . . .
C5 C 0.91154(18) 0.68798(13) 0.63697(11) 0.0555(4) Uani 1 1 d . . . . .
H5 H 0.879512 0.706344 0.688435 0.067 Uiso 1 1 calc R U . . .
C6 C 0.82731(16) 0.66636(12) 0.55838(10) 0.0475(4) Uani 1 1 d . . . . .
H6 H 0.738192 0.670721 0.556602 0.057 Uiso 1 1 calc R U . . .
C7 C 0.78998(13) 0.61855(10) 0.39461(9) 0.0363(3) Uani 1 1 d . . . . .
C8 C 0.84700(13) 0.58655(10) 0.32310(9) 0.0366(3) Uani 1 1 d . . . . .
C9 C 0.98360(13) 0.57322(11) 0.33808(10) 0.0400(3) Uani 1 1 d . . . . .
C10 C 0.77217(13) 0.56827(11) 0.23069(10) 0.0386(3) Uani 1 1 d . . . . .
C11 C 1.03816(14) 0.53224(13) 0.26514(11) 0.0492(4) Uani 1 1 d . . . . .
H11 H 1.128247 0.526715 0.274093 0.059 Uiso 1 1 calc R U . . .
C12 C 0.64660(13) 0.63063(11) 0.38662(9) 0.0375(3) Uani 1 1 d . . . . .
C13 C 0.56639(16) 0.55021(13) 0.38353(13) 0.0571(4) Uani 1 1 d . . . . .
H13 H 0.601715 0.487722 0.385749 0.069 Uiso 1 1 calc R U . . .
C14 C 0.43407(17) 0.56203(16) 0.37716(15) 0.0682(5) Uani 1 1 d . . . . .
H14 H 0.380901 0.507389 0.375605 0.082 Uiso 1 1 calc R U . . .
C15 C 0.38027(16) 0.65362(15) 0.37309(12) 0.0602(5) Uani 1 1 d . . . . .
H15 H 0.290917 0.661120 0.368277 0.072 Uiso 1 1 calc R U . . .
C16 C 0.45882(16) 0.73393(14) 0.37616(11) 0.0524(4) Uani 1 1 d . . . . .
H16 H 0.422589 0.796154 0.372982 0.063 Uiso 1 1 calc R U . . .
C17 C 0.59192(15) 0.72300(12) 0.38397(10) 0.0446(3) Uani 1 1 d . . . . .
H17 H 0.644915 0.777922 0.387468 0.054 Uiso 1 1 calc R U . . .
C18 C 0.77354(14) 0.48626(11) 0.08474(10) 0.0404(3) Uani 1 1 d . . . . .
C19 C 0.82235(16) 0.51777(13) 0.00985(11) 0.0507(4) Uani 1 1 d . . . . .
H19 H 0.897216 0.555865 0.017835 0.061 Uiso 1 1 calc R U . . .
C20 C 0.75947(18) 0.49242(14) -0.07679(11) 0.0569(4) Uani 1 1 d . . . . .
H20 H 0.792629 0.512885 -0.127177 0.068 Uiso 1 1 calc R U . . .
C21 C 0.64774(18) 0.43687(13) -0.08875(11) 0.0551(4) Uani 1 1 d . . . . .
H21 H 0.604145 0.421410 -0.147174 0.066 Uiso 1 1 calc R U . . .
C22 C 0.60079(16) 0.40432(12) -0.01405(11) 0.0484(4) Uani 1 1 d . . . . .
H22 H 0.525513 0.366653 -0.022832 0.058 Uiso 1 1 calc R U . . .
C23 C 0.66343(14) 0.42649(11) 0.07453(10) 0.0403(3) Uani 1 1 d . . . . .
C24 C 0.61962(14) 0.38495(11) 0.15383(10) 0.0429(3) Uani 1 1 d . . . . .
H24 H 0.679924 0.383942 0.208201 0.051 Uiso 1 1 calc R U . . .
C25 C 0.50302(16) 0.34869(12) 0.15614(12) 0.0508(4) Uani 1 1 d . . . . .
H25 H 0.442472 0.346287 0.101928 0.061 Uiso 1 1 calc R U . . .
C26 C 0.46377(17) 0.31220(13) 0.23878(13) 0.0557(4) Uani 1 1 d . . . . .
C27 C 0.5323(2) 0.26052(17) 0.39043(14) 0.0801(6) Uani 1 1 d . . . . .
H27A H 0.608342 0.234041 0.428857 0.120 Uiso 1 1 calc R U . . .
H27B H 0.465561 0.211539 0.379342 0.120 Uiso 1 1 calc R U . . .
H27C H 0.501667 0.315691 0.419959 0.120 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
O1 C26 1.199(2) . ?
O2 C10 1.2104(16) . ?
O3 C26 1.336(2) . ?
O3 C27 1.438(2) . ?
N1 C9 1.3258(18) . ?
N1 C2 1.354(2) . ?
N2 N3 1.3796(16) . ?
N2 C10 1.4017(18) . ?
N2 C18 1.4379(18) . ?
N3 C11 1.285(2) . ?
C1 C7 1.4168(19) . ?
C1 C6 1.420(2) . ?
C1 C2 1.429(2) . ?
C2 C3 1.416(2) . ?
C3 C4 1.355(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3898(19) . ?
C7 C12 1.4920(19) . ?
C8 C9 1.4165(19) . ?
C8 C10 1.4747(19) . ?
C9 C11 1.437(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(2) . ?
C12 C17 1.385(2) . ?
C13 C14 1.380(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.384(2) . ?
C18 C23 1.398(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.464(2) . ?
C24 C25 1.324(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.461(2) . ?
C25 H25 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C26 O3 C27 116.00(15) . . ?
C9 N1 C2 116.98(12) . . ?
N3 N2 C10 125.18(12) . . ?
N3 N2 C18 113.75(11) . . ?
C10 N2 C18 119.72(11) . . ?
C11 N3 N2 117.09(12) . . ?
C7 C1 C6 122.91(13) . . ?
C7 C1 C2 118.90(13) . . ?
C6 C1 C2 118.19(13) . . ?
N1 C2 C3 118.33(14) . . ?
N1 C2 C1 122.79(13) . . ?
C3 C2 C1 118.87(14) . . ?
C4 C3 C2 120.89(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.58(15) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.45(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.91(15) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 117.33(12) . . ?
C8 C7 C12 123.03(12) . . ?
C1 C7 C12 119.61(12) . . ?
C7 C8 C9 119.11(12) . . ?
C7 C8 C10 122.99(12) . . ?
C9 C8 C10 117.88(12) . . ?
N1 C9 C8 124.66(13) . . ?
N1 C9 C11 117.65(13) . . ?
C8 C9 C11 117.68(13) . . ?
O2 C10 N2 120.20(13) . . ?
O2 C10 C8 125.31(13) . . ?
N2 C10 C8 114.48(12) . . ?
N3 C11 C9 125.19(13) . . ?
N3 C11 H11 117.4 . . ?
C9 C11 H11 117.4 . . ?
C13 C12 C17 118.80(14) . . ?
C13 C12 C7 120.70(14) . . ?
C17 C12 C7 120.49(13) . . ?
C14 C13 C12 120.34(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.58(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.61(15) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.32(16) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.33(15) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 121.11(14) . . ?
C19 C18 N2 118.91(13) . . ?
C23 C18 N2 119.97(13) . . ?
C20 C19 C18 119.77(15) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.16(16) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 119.87(15) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 121.58(15) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C22 C23 C18 117.43(14) . . ?
C22 C23 C24 121.39(14) . . ?
C18 C23 C24 121.12(13) . . ?
C25 C24 C23 126.73(15) . . ?
C25 C24 H24 116.6 . . ?
C23 C24 H24 116.6 . . ?
C24 C25 C26 123.92(16) . . ?
C24 C25 H25 118.0 . . ?
C26 C25 H25 118.0 . . ?
O1 C26 O3 122.63(18) . . ?
O1 C26 C25 124.10(18) . . ?
O3 C26 C25 113.26(15) . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C10 N2 N3 C11 9.2(2) . . . . ?
C18 N2 N3 C11 175.82(14) . . . . ?
C9 N1 C2 C3 -179.09(14) . . . . ?
C9 N1 C2 C1 1.9(2) . . . . ?
C7 C1 C2 N1 -4.9(2) . . . . ?
C6 C1 C2 N1 175.76(14) . . . . ?
C7 C1 C2 C3 176.07(14) . . . . ?
C6 C1 C2 C3 -3.3(2) . . . . ?
N1 C2 C3 C4 -177.91(15) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 -2.8(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C7 C1 C6 C5 -176.90(15) . . . . ?
C2 C1 C6 C5 2.4(2) . . . . ?
C6 C1 C7 C8 -177.36(14) . . . . ?
C2 C1 C7 C8 3.3(2) . . . . ?
C6 C1 C7 C12 0.8(2) . . . . ?
C2 C1 C7 C12 -178.56(13) . . . . ?
C1 C7 C8 C9 0.8(2) . . . . ?
C12 C7 C8 C9 -177.30(13) . . . . ?
C1 C7 C8 C10 -177.42(13) . . . . ?
C12 C7 C8 C10 4.5(2) . . . . ?
C2 N1 C9 C8 2.6(2) . . . . ?
C2 N1 C9 C11 -176.21(14) . . . . ?
C7 C8 C9 N1 -4.0(2) . . . . ?
C10 C8 C9 N1 174.24(14) . . . . ?
C7 C8 C9 C11 174.83(14) . . . . ?
C10 C8 C9 C11 -6.9(2) . . . . ?
N3 N2 C10 O2 162.54(14) . . . . ?
C18 N2 C10 O2 -3.4(2) . . . . ?
N3 N2 C10 C8 -18.5(2) . . . . ?
C18 N2 C10 C8 175.60(12) . . . . ?
C7 C8 C10 O2 13.6(2) . . . . ?
C9 C8 C10 O2 -164.64(15) . . . . ?
C7 C8 C10 N2 -165.34(13) . . . . ?
C9 C8 C10 N2 16.46(19) . . . . ?
N2 N3 C11 C9 2.6(3) . . . . ?
N1 C9 C11 N3 175.72(16) . . . . ?
C8 C9 C11 N3 -3.2(3) . . . . ?
C8 C7 C12 C13 73.2(2) . . . . ?
C1 C7 C12 C13 -104.82(17) . . . . ?
C8 C7 C12 C17 -108.09(17) . . . . ?
C1 C7 C12 C17 73.90(18) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C7 C12 C13 C14 179.27(16) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C12 1.5(2) . . . . ?
C13 C12 C17 C16 -1.5(2) . . . . ?
C7 C12 C17 C16 179.72(13) . . . . ?
N3 N2 C18 C19 -46.80(19) . . . . ?
C10 N2 C18 C19 120.63(16) . . . . ?
N3 N2 C18 C23 132.24(14) . . . . ?
C10 N2 C18 C23 -60.33(19) . . . . ?
C23 C18 C19 C20 2.0(2) . . . . ?
N2 C18 C19 C20 -179.01(14) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C19 C20 C21 C22 -1.8(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C18 2.3(2) . . . . ?
C21 C22 C23 C24 -174.75(15) . . . . ?
C19 C18 C23 C22 -3.4(2) . . . . ?
N2 C18 C23 C22 177.58(13) . . . . ?
C19 C18 C23 C24 173.65(14) . . . . ?
N2 C18 C23 C24 -5.4(2) . . . . ?
C22 C23 C24 C25 -21.1(2) . . . . ?
C18 C23 C24 C25 161.97(16) . . . . ?
C23 C24 C25 C26 -177.16(15) . . . . ?
C27 O3 C26 O1 -2.8(3) . . . . ?
C27 O3 C26 C25 176.20(16) . . . . ?
C24 C25 C26 O1 159.78(19) . . . . ?
C24 C25 C26 O3 -19.2(2) . . . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_C_HOLF_260924_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2387931'
loop_
_audit_author_name
_audit_author_address
'KAMESHWARAN CHINNAGOUNDER FAZLUR RAHMAN NAWAZ KHAN'
;Vellore Institute of Technology (Vellore)
India
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 Cl N3 O3'
_chemical_formula_sum            'C27 H18 Cl N3 O3'
_chemical_formula_weight         467.89

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   24.6996(9)
_cell_length_b                   12.4147(4)
_cell_length_c                   18.1999(6)
_cell_angle_alpha                90
_cell_angle_beta                 126.0450(10)
_cell_angle_gamma                90
_cell_volume                     4512.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      25.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54414
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5622
_reflns_number_gt                3733
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0509P)²+2.6975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5622
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.43452(3) 0.87695(5) 0.49406(4) 0.0833(2) Uani 1 1 d . . . . .
O1 O 0.62736(6) 0.39546(10) 0.84451(8) 0.0568(3) Uani 1 1 d . . . . .
O2 O 0.86809(7) 0.37465(12) 0.84741(11) 0.0762(5) Uani 1 1 d . . . . .
O3 O 0.76107(7) 0.41409(14) 0.74474(11) 0.0756(4) Uani 1 1 d . . . . .
N1 N 0.58925(7) 0.24585(12) 0.75619(10) 0.0472(3) Uani 1 1 d . . . . .
N2 N 0.53915(8) 0.19062(13) 0.68032(11) 0.0572(4) Uani 1 1 d . . . . .
N3 N 0.43871(7) 0.40804(14) 0.53388(10) 0.0520(4) Uani 1 1 d . . . . .
C1 C 0.43910(8) 0.51684(16) 0.53048(11) 0.0489(4) Uani 1 1 d . . . . .
C2 C 0.63812(9) 0.17802(14) 0.83099(12) 0.0470(4) Uani 1 1 d . . . . .
C3 C 0.61634(11) 0.10201(16) 0.86344(15) 0.0591(5) Uani 1 1 d . . . . .
H3 H 0.570886 0.094422 0.836973 0.071 Uiso 1 1 calc R U . . .
C4 C 0.66264(12) 0.03710(16) 0.93570(15) 0.0663(6) Uani 1 1 d . . . . .
H4 H 0.648170 -0.014699 0.957471 0.080 Uiso 1 1 calc R U . . .
C5 C 0.72983(11) 0.04881(17) 0.97539(14) 0.0648(5) Uani 1 1 d . . . . .
H5 H 0.760833 0.006000 1.024660 0.078 Uiso 1 1 calc R U . . .
C6 C 0.75104(10) 0.12366(15) 0.94224(12) 0.0557(5) Uani 1 1 d . . . . .
H6 H 0.796641 0.130885 0.969566 0.067 Uiso 1 1 calc R U . . .
C7 C 0.70599(8) 0.18943(14) 0.86850(11) 0.0450(4) Uani 1 1 d . . . . .
C8 C 0.49262(9) 0.24634(16) 0.61309(13) 0.0566(5) Uani 1 1 d . . . . .
H8 H 0.458055 0.208893 0.562677 0.068 Uiso 1 1 calc R U . . .
C9 C 0.48948(8) 0.36180(15) 0.60921(11) 0.0465(4) Uani 1 1 d . . . . .
C10 C 0.54224(7) 0.41879(14) 0.68617(11) 0.0418(4) Uani 1 1 d . . . . .
C11 C 0.58974(8) 0.35678(14) 0.76940(11) 0.0442(4) Uani 1 1 d . . . . .
C12 C 0.72883(8) 0.26526(15) 0.83105(11) 0.0485(4) Uani 1 1 d . . . . .
H12 H 0.695466 0.305397 0.781573 0.058 Uiso 1 1 calc R U . . .
C13 C 0.79023(9) 0.28457(16) 0.85777(13) 0.0579(5) Uani 1 1 d . . . . .
H13 H 0.825959 0.247731 0.907347 0.069 Uiso 1 1 calc R U . . .
C14 C 0.80264(9) 0.36464(15) 0.80924(13) 0.0519(4) Uani 1 1 d . . . . .
C15 C 0.88418(12) 0.4508(2) 0.80250(18) 0.0812(7) Uani 1 1 d . . . . .
H15A H 0.931889 0.454790 0.834784 0.122 Uiso 1 1 calc R U . . .
H15B H 0.867096 0.520617 0.801704 0.122 Uiso 1 1 calc R U . . .
H15C H 0.864196 0.427514 0.741284 0.122 Uiso 1 1 calc R U . . .
C16 C 0.49338(8) 0.58102(15) 0.60048(11) 0.0448(4) Uani 1 1 d . . . . .
C17 C 0.54621(8) 0.52968(14) 0.68132(10) 0.0418(4) Uani 1 1 d . . . . .
C18 C 0.38399(9) 0.5685(2) 0.45244(12) 0.0613(5) Uani 1 1 d . . . . .
H18 H 0.348026 0.527499 0.407241 0.074 Uiso 1 1 calc R U . . .
C19 C 0.38299(10) 0.6764(2) 0.44281(13) 0.0656(6) Uani 1 1 d . . . . .
H19 H 0.346230 0.709440 0.391656 0.079 Uiso 1 1 calc R U . . .
C20 C 0.43752(10) 0.73861(17) 0.51009(13) 0.0578(5) Uani 1 1 d . . . . .
C21 C 0.49182(9) 0.69375(16) 0.58643(12) 0.0518(4) Uani 1 1 d . . . . .
H21 H 0.527756 0.736674 0.629231 0.062 Uiso 1 1 calc R U . . .
C22 C 0.60477(8) 0.59427(13) 0.75372(10) 0.0418(4) Uani 1 1 d . . . . .
C23 C 0.66552(9) 0.58340(16) 0.76682(12) 0.0529(4) Uani 1 1 d . . . . .
H23 H 0.670090 0.533202 0.732870 0.063 Uiso 1 1 calc R U . . .
C24 C 0.71956(9) 0.64636(18) 0.82987(13) 0.0623(5) Uani 1 1 d . . . . .
H24 H 0.760238 0.638442 0.838064 0.075 Uiso 1 1 calc R U . . .
C25 C 0.71348(10) 0.72038(17) 0.88034(13) 0.0636(5) Uani 1 1 d . . . . .
H25 H 0.749680 0.763604 0.922038 0.076 Uiso 1 1 calc R U . . .
C26 C 0.65388(11) 0.73044(18) 0.86912(13) 0.0650(5) Uani 1 1 d . . . . .
H26 H 0.649943 0.779663 0.904252 0.078 Uiso 1 1 calc R U . . .
C27 C 0.59963(9) 0.66819(16) 0.80616(12) 0.0560(5) Uani 1 1 d . . . . .
H27 H 0.559281 0.675955 0.798886 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.736(2) . ?
O1 C11 1.211(2) . ?
O2 C14 1.338(2) . ?
O2 C15 1.450(3) . ?
O3 C14 1.179(2) . ?
N1 N2 1.377(2) . ?
N1 C11 1.397(2) . ?
N1 C2 1.444(2) . ?
N2 C8 1.281(2) . ?
N3 C9 1.326(2) . ?
N3 C1 1.352(2) . ?
C1 C18 1.416(2) . ?
C1 C16 1.430(2) . ?
C2 C3 1.379(3) . ?
C2 C7 1.396(2) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(2) . ?
C6 H6 0.9300 . ?
C7 C12 1.457(2) . ?
C8 C9 1.435(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(2) . ?
C10 C17 1.387(2) . ?
C10 C11 1.474(2) . ?
C12 C13 1.314(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.477(3) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.419(3) . ?
C16 C17 1.419(2) . ?
C17 C22 1.493(2) . ?
C18 C19 1.349(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.359(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(2) . ?
C22 C27 1.383(3) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 C15 114.59(17) . . ?
N2 N1 C11 125.10(14) . . ?
N2 N1 C2 114.48(14) . . ?
C11 N1 C2 119.66(14) . . ?
C8 N2 N1 117.42(16) . . ?
C9 N3 C1 116.85(15) . . ?
N3 C1 C18 118.00(17) . . ?
N3 C1 C16 122.95(15) . . ?
C18 C1 C16 119.02(18) . . ?
C3 C2 C7 121.24(17) . . ?
C3 C2 N1 118.84(16) . . ?
C7 C2 N1 119.92(15) . . ?
C2 C3 C4 119.52(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.33(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.83(19) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.71(19) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 117.33(17) . . ?
C6 C7 C12 121.27(16) . . ?
C2 C7 C12 121.39(15) . . ?
N2 C8 C9 125.34(17) . . ?
N2 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
N3 C9 C10 124.43(17) . . ?
N3 C9 C8 118.30(16) . . ?
C10 C9 C8 117.25(16) . . ?
C17 C10 C9 119.38(15) . . ?
C17 C10 C11 122.72(15) . . ?
C9 C10 C11 117.88(16) . . ?
O1 C11 N1 120.54(16) . . ?
O1 C11 C10 124.81(16) . . ?
N1 C11 C10 114.64(14) . . ?
C13 C12 C7 128.70(17) . . ?
C13 C12 H12 115.7 . . ?
C7 C12 H12 115.7 . . ?
C12 C13 C14 120.13(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O3 C14 O2 123.15(18) . . ?
O3 C14 C13 125.47(17) . . ?
O2 C14 C13 111.38(16) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 122.72(16) . . ?
C21 C16 C1 118.50(16) . . ?
C17 C16 C1 118.78(17) . . ?
C10 C17 C16 117.10(15) . . ?
C10 C17 C22 123.04(14) . . ?
C16 C17 C22 119.74(15) . . ?
C19 C18 C1 120.87(19) . . ?
C19 C18 H18 119.6 . . ?
C1 C18 H18 119.6 . . ?
C18 C19 C20 119.90(18) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 122.0(2) . . ?
C21 C20 Cl1 119.74(17) . . ?
C19 C20 Cl1 118.28(15) . . ?
C20 C21 C16 119.62(18) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C23 C22 C27 118.53(16) . . ?
C23 C22 C17 119.35(15) . . ?
C27 C22 C17 122.07(15) . . ?
C22 C23 C24 120.61(18) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.24(19) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 119.65(18) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.46(18) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?

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
C11 N1 N2 C8 7.1(3) . . . . ?
C2 N1 N2 C8 176.99(16) . . . . ?
C9 N3 C1 C18 -177.30(16) . . . . ?
C9 N3 C1 C16 4.8(2) . . . . ?
N2 N1 C2 C3 -55.0(2) . . . . ?
C11 N1 C2 C3 115.53(19) . . . . ?
N2 N1 C2 C7 124.43(17) . . . . ?
C11 N1 C2 C7 -65.1(2) . . . . ?
C7 C2 C3 C4 1.3(3) . . . . ?
N1 C2 C3 C4 -179.37(17) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C2 1.7(3) . . . . ?
C5 C6 C7 C12 -177.06(18) . . . . ?
C3 C2 C7 C6 -2.3(3) . . . . ?
N1 C2 C7 C6 178.30(16) . . . . ?
C3 C2 C7 C12 176.40(17) . . . . ?
N1 C2 C7 C12 -3.0(2) . . . . ?
N1 N2 C8 C9 2.0(3) . . . . ?
C1 N3 C9 C10 1.9(2) . . . . ?
C1 N3 C9 C8 -176.53(16) . . . . ?
N2 C8 C9 N3 178.56(18) . . . . ?
N2 C8 C9 C10 0.0(3) . . . . ?
N3 C9 C10 C17 -6.9(3) . . . . ?
C8 C9 C10 C17 171.62(16) . . . . ?
N3 C9 C10 C11 171.42(15) . . . . ?
C8 C9 C10 C11 -10.1(2) . . . . ?
N2 N1 C11 O1 163.71(16) . . . . ?
C2 N1 C11 O1 -5.7(2) . . . . ?
N2 N1 C11 C10 -16.7(2) . . . . ?
C2 N1 C11 C10 173.94(14) . . . . ?
C17 C10 C11 O1 15.3(3) . . . . ?
C9 C10 C11 O1 -162.95(16) . . . . ?
C17 C10 C11 N1 -164.32(15) . . . . ?
C9 C10 C11 N1 17.4(2) . . . . ?
C6 C7 C12 C13 -0.6(3) . . . . ?
C2 C7 C12 C13 -179.31(19) . . . . ?
C7 C12 C13 C14 179.24(18) . . . . ?
C15 O2 C14 O3 -0.6(3) . . . . ?
C15 O2 C14 C13 179.06(18) . . . . ?
C12 C13 C14 O3 -1.6(3) . . . . ?
C12 C13 C14 O2 178.72(18) . . . . ?
N3 C1 C16 C21 174.06(16) . . . . ?
C18 C1 C16 C21 -3.9(2) . . . . ?
N3 C1 C16 C17 -6.5(2) . . . . ?
C18 C1 C16 C17 175.59(16) . . . . ?
C9 C10 C17 C16 4.7(2) . . . . ?
C11 C10 C17 C16 -173.47(14) . . . . ?
C9 C10 C17 C22 -171.22(15) . . . . ?
C11 C10 C17 C22 10.6(2) . . . . ?
C21 C16 C17 C10 -179.20(15) . . . . ?
C1 C16 C17 C10 1.4(2) . . . . ?
C21 C16 C17 C22 -3.1(2) . . . . ?
C1 C16 C17 C22 177.47(14) . . . . ?
N3 C1 C18 C19 -176.55(18) . . . . ?
C16 C1 C18 C19 1.5(3) . . . . ?
C1 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C18 C19 C20 Cl1 179.13(16) . . . . ?
C19 C20 C21 C16 -1.6(3) . . . . ?
Cl1 C20 C21 C16 178.37(13) . . . . ?
C17 C16 C21 C20 -175.50(16) . . . . ?
C1 C16 C21 C20 3.9(2) . . . . ?
C10 C17 C22 C23 68.7(2) . . . . ?
C16 C17 C22 C23 -107.12(19) . . . . ?
C10 C17 C22 C27 -113.8(2) . . . . ?
C16 C17 C22 C27 70.3(2) . . . . ?
C27 C22 C23 C24 -1.1(3) . . . . ?
C17 C22 C23 C24 176.44(17) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 1.1(3) . . . . ?
C24 C25 C26 C27 -1.3(3) . . . . ?
C25 C26 C27 C22 0.3(3) . . . . ?
C23 C22 C27 C26 0.9(3) . . . . ?
C17 C22 C27 C26 -176.58(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C18 H18 O3 0.93 2.58 3.260(2) 130.0 5_666 yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.036

