# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_acpb9_070324_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2374871'
loop_
_audit_author_name
_audit_author_address
'Nawaz khan F'
;VIT, Vellore
India
;
_audit_update_record             
;
2024-08-29 deposited with the CCDC.	2024-10-30 downloaded from the CCDC.
;
_audit_creation_date             2024-08-29
_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         'C25 H18 Cl N O3'
_chemical_formula_sum            'C25 H18 Cl N O3'
_chemical_formula_weight         415.85
_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                   16.624(2)
_cell_length_b                   5.2910(8)
_cell_length_c                   23.770(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.602(5)
_cell_angle_gamma                90
_cell_volume                     2040.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7401
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.144
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28713
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.681
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2796
_reflns_number_total             5037
_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       SHELXL
_computing_data_collection       APEX
_computing_data_reduction        SAINT
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.033
_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)+(0.0700P)²+0.7098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl1B)=1-FVAR(1)
 Sof(Cl1A)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1A Cl 0.3066(5) 1.081(2) 0.8680(3) 0.0860(17) Uani 0.49(5) 1 d . . P A 1
Cl1B Cl 0.3016(7) 1.025(5) 0.8664(4) 0.103(2) Uani 0.51(5) 1 d . . P A 2
O1 O 0.40152(12) 0.3307(3) 0.63905(7) 0.0783(6) Uani 1 1 d . . . . .
O2 O 0.66592(12) 0.0627(4) 0.82224(8) 0.0776(6) Uani 1 1 d . . . . .
O15 O 0.60381(11) 0.3856(4) 0.69386(6) 0.0744(5) Uani 1 1 d . . . . .
N1 N 0.50233(11) 0.6452(3) 0.70991(7) 0.0494(5) Uani 1 1 d . . . . .
C1 C 0.39637(13) 0.5402(4) 0.55115(8) 0.0463(5) Uani 1 1 d . . . . .
C2 C 0.42568(18) 0.7261(5) 0.52093(10) 0.0743(8) Uani 1 1 d . . . . .
H2 H 0.463198 0.844082 0.540278 0.089 Uiso 1 1 calc R U . . .
C3 C 0.74772(16) 0.4126(5) 0.80880(12) 0.0692(7) Uani 1 1 d . . . . .
H3A H 0.792840 0.299680 0.822865 0.104 Uiso 1 1 calc R U . . .
H3B H 0.752370 0.557962 0.833466 0.104 Uiso 1 1 calc R U . . .
H3C H 0.749051 0.465183 0.770366 0.104 Uiso 1 1 calc R U . . .
C4 C 0.39933(19) 0.7386(6) 0.46120(11) 0.0809(9) Uani 1 1 d . . . . .
H4 H 0.420185 0.863894 0.440917 0.097 Uiso 1 1 calc R U . . .
C5 C 0.34406(15) 0.5719(5) 0.43235(9) 0.0621(7) Uani 1 1 d . . . . .
H5 H 0.327110 0.581101 0.392450 0.075 Uiso 1 1 calc R U . . .
C6 C 0.31334(17) 0.3899(6) 0.46229(10) 0.0728(8) Uani 1 1 d . . . . .
H6 H 0.274224 0.276810 0.442739 0.087 Uiso 1 1 calc R U . . .
C7 C 0.33966(16) 0.3716(5) 0.52138(10) 0.0629(6) Uani 1 1 d . . . . .
H7 H 0.318930 0.244351 0.541209 0.075 Uiso 1 1 calc R U . . .
C8 C 0.42413(14) 0.5093(4) 0.61452(8) 0.0490(5) Uani 1 1 d . . . . .
C9 C 0.48277(15) 0.7009(4) 0.64812(8) 0.0528(6) Uani 1 1 d . . . . .
H9A H 0.533271 0.702171 0.633981 0.063 Uiso 1 1 calc R U . . .
H9B H 0.458247 0.867709 0.641919 0.063 Uiso 1 1 calc R U . . .
C10 C 0.56702(14) 0.4813(5) 0.72814(9) 0.0527(6) Uani 1 1 d . . . . .
C11 C 0.59106(13) 0.4339(4) 0.79004(8) 0.0454(5) Uani 1 1 d . . . . .
C12 C 0.54838(12) 0.5295(4) 0.82730(8) 0.0411(5) Uani 1 1 d . . . . .
C13 C 0.47627(12) 0.6818(4) 0.80580(8) 0.0430(5) Uani 1 1 d . . . . .
C14 C 0.45416(13) 0.7389(4) 0.74639(8) 0.0464(5) Uani 1 1 d . . . . .
C16 C 0.57795(12) 0.4938(4) 0.89125(8) 0.0414(5) Uani 1 1 d . . . . .
C17 C 0.55016(19) 0.3031(6) 0.92024(10) 0.0833(9) Uani 1 1 d . . . . .
H17 H 0.511764 0.189011 0.900261 0.100 Uiso 1 1 calc R U . . .
C18 C 0.5784(2) 0.2766(6) 0.97935(11) 0.0908(10) Uani 1 1 d . . . . .
H18 H 0.558749 0.144568 0.998418 0.109 Uiso 1 1 calc R U . . .
C19 C 0.63375(15) 0.4385(5) 1.00948(9) 0.0612(7) Uani 1 1 d . . . . .
H19 H 0.651974 0.420734 1.049147 0.073 Uiso 1 1 calc R U . . .
C20 C 0.66225(19) 0.6267(6) 0.98119(10) 0.0783(8) Uani 1 1 d . . . . .
H20 H 0.700972 0.739161 1.001449 0.094 Uiso 1 1 calc R U . . .
C21 C 0.63457(17) 0.6551(5) 0.92214(9) 0.0710(8) Uani 1 1 d . . . . .
H21 H 0.655032 0.786499 0.903345 0.085 Uiso 1 1 calc R U . . .
C22 C 0.42815(13) 0.7793(4) 0.84222(9) 0.0513(5) Uani 1 1 d . . . . .
H22 H 0.441777 0.741768 0.881378 0.062 Uiso 1 1 calc R U . . .
C23 C 0.36146(14) 0.9287(5) 0.82104(10) 0.0591(6) Uani 1 1 d . . . . .
C24 C 0.33972(16) 0.9847(5) 0.76271(11) 0.0648(7) Uani 1 1 d . . . . .
H24 H 0.294352 1.087224 0.748610 0.078 Uiso 1 1 calc R U . . .
C25 C 0.38490(15) 0.8895(5) 0.72586(10) 0.0581(6) Uani 1 1 d . . . . .
H25 H 0.369337 0.925439 0.686689 0.070 Uiso 1 1 calc R U . . .
C26 C 0.66865(14) 0.2808(4) 0.80837(8) 0.0508(6) 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
Cl1A C23 1.779(9) . ?
Cl1B C23 1.697(9) . ?
O1 C8 1.212(3) . ?
O2 C26 1.204(3) . ?
O15 C10 1.230(3) . ?
N1 C9 1.463(2) . ?
N1 C10 1.376(3) . ?
N1 C14 1.393(3) . ?
C1 C2 1.369(3) . ?
C1 C7 1.376(3) . ?
C1 C8 1.485(3) . ?
C2 H2 0.9300 . ?
C2 C4 1.393(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C26 1.486(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.348(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.361(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.509(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.460(3) . ?
C11 C12 1.348(3) . ?
C11 C26 1.505(3) . ?
C12 C13 1.442(3) . ?
C12 C16 1.504(2) . ?
C13 C14 1.412(3) . ?
C13 C22 1.399(3) . ?
C14 C25 1.398(3) . ?
C16 C17 1.359(3) . ?
C16 C21 1.361(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.344(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.345(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.365(3) . ?
C23 C24 1.386(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.368(3) . ?
C25 H25 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 C9 115.48(18) . . ?
C10 N1 C14 122.95(16) . . ?
C14 N1 C9 121.40(18) . . ?
C2 C1 C7 118.6(2) . . ?
C2 C1 C8 123.0(2) . . ?
C7 C1 C8 118.5(2) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C4 120.0(2) . . ?
C4 C2 H2 120.0 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C26 C3 H3A 109.5 . . ?
C26 C3 H3B 109.5 . . ?
C26 C3 H3C 109.5 . . ?
C2 C4 H4 119.5 . . ?
C5 C4 C2 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C1 C7 C6 120.5(2) . . ?
C1 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O1 C8 C1 120.9(2) . . ?
O1 C8 C9 120.10(18) . . ?
C1 C8 C9 119.00(18) . . ?
N1 C9 C8 111.87(18) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O15 C10 N1 121.24(19) . . ?
O15 C10 C11 122.1(2) . . ?
N1 C10 C11 116.68(19) . . ?
C10 C11 C26 114.40(18) . . ?
C12 C11 C10 122.01(19) . . ?
C12 C11 C26 123.54(17) . . ?
C11 C12 C13 119.52(17) . . ?
C11 C12 C16 120.94(18) . . ?
C13 C12 C16 119.42(17) . . ?
C14 C13 C12 119.25(19) . . ?
C22 C13 C12 122.00(17) . . ?
C22 C13 C14 118.74(19) . . ?
N1 C14 C13 119.13(18) . . ?
N1 C14 C25 121.80(18) . . ?
C25 C14 C13 119.1(2) . . ?
C17 C16 C12 122.24(19) . . ?
C17 C16 C21 117.63(19) . . ?
C21 C16 C12 120.13(18) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.7(2) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 121.1(2) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C13 C22 H22 119.6 . . ?
C23 C22 C13 120.9(2) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 Cl1A 121.1(3) . . ?
C22 C23 Cl1B 118.8(4) . . ?
C22 C23 C24 120.4(2) . . ?
C24 C23 Cl1A 118.2(4) . . ?
C24 C23 Cl1B 120.6(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C14 C25 H25 119.6 . . ?
C24 C25 C14 120.8(2) . . ?
C24 C25 H25 119.6 . . ?
O2 C26 C3 122.3(2) . . ?
O2 C26 C11 120.9(2) . . ?
C3 C26 C11 116.8(2) . . ?

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
Cl1A C23 C24 C25 174.3(5) . . . . ?
Cl1B C23 C24 C25 -174.9(10) . . . . ?
O1 C8 C9 N1 -2.6(3) . . . . ?
O15 C10 C11 C12 -176.9(2) . . . . ?
O15 C10 C11 C26 5.7(3) . . . . ?
N1 C10 C11 C12 5.0(3) . . . . ?
N1 C10 C11 C26 -172.5(2) . . . . ?
N1 C14 C25 C24 -178.3(2) . . . . ?
C1 C2 C4 C5 1.0(5) . . . . ?
C1 C8 C9 N1 178.77(19) . . . . ?
C2 C1 C7 C6 0.2(4) . . . . ?
C2 C1 C8 O1 -174.2(3) . . . . ?
C2 C1 C8 C9 4.4(3) . . . . ?
C2 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 C1 1.2(4) . . . . ?
C7 C1 C2 C4 -1.3(4) . . . . ?
C7 C1 C8 O1 4.6(3) . . . . ?
C7 C1 C8 C9 -176.8(2) . . . . ?
C8 C1 C2 C4 177.6(3) . . . . ?
C8 C1 C7 C6 -178.7(2) . . . . ?
C9 N1 C10 O15 -1.6(3) . . . . ?
C9 N1 C10 C11 176.51(19) . . . . ?
C9 N1 C14 C13 -179.33(19) . . . . ?
C9 N1 C14 C25 0.2(3) . . . . ?
C10 N1 C9 C8 86.8(2) . . . . ?
C10 N1 C14 C13 5.5(3) . . . . ?
C10 N1 C14 C25 -175.0(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C10 C11 C12 C16 -175.46(19) . . . . ?
C10 C11 C26 O2 -105.6(2) . . . . ?
C10 C11 C26 C3 74.8(3) . . . . ?
C11 C12 C13 C14 -3.3(3) . . . . ?
C11 C12 C13 C22 178.0(2) . . . . ?
C11 C12 C16 C17 -95.2(3) . . . . ?
C11 C12 C16 C21 84.6(3) . . . . ?
C12 C11 C26 O2 77.0(3) . . . . ?
C12 C11 C26 C3 -102.6(3) . . . . ?
C12 C13 C14 N1 0.4(3) . . . . ?
C12 C13 C14 C25 -179.1(2) . . . . ?
C12 C13 C22 C23 178.2(2) . . . . ?
C12 C16 C17 C18 -179.6(3) . . . . ?
C12 C16 C21 C20 179.6(3) . . . . ?
C13 C12 C16 C17 88.8(3) . . . . ?
C13 C12 C16 C21 -91.4(3) . . . . ?
C13 C14 C25 C24 1.2(3) . . . . ?
C13 C22 C23 Cl1A -173.2(5) . . . . ?
C13 C22 C23 Cl1B 175.9(10) . . . . ?
C13 C22 C23 C24 0.6(4) . . . . ?
C14 N1 C9 C8 -88.7(2) . . . . ?
C14 N1 C10 O15 173.8(2) . . . . ?
C14 N1 C10 C11 -8.1(3) . . . . ?
C14 C13 C22 C23 -0.6(3) . . . . ?
C16 C12 C13 C14 172.77(18) . . . . ?
C16 C12 C13 C22 -6.0(3) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C16 C21 C20 -0.6(4) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C21 C16 C17 C18 0.5(4) . . . . ?
C22 C13 C14 N1 179.20(19) . . . . ?
C22 C13 C14 C25 -0.3(3) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C14 -1.2(4) . . . . ?
C26 C11 C12 C13 177.8(2) . . . . ?
C26 C11 C12 C16 1.8(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_acpb_290324_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2388694'
loop_
_audit_author_name
_audit_author_address
'Nawaz khan F'
;VIT, Vellore
India
;
_audit_update_record             
;
2024-10-04 deposited with the CCDC.	2024-10-30 downloaded from the CCDC.
;
_audit_creation_date             2024-10-03
_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         'C39 H23 Cl4 N O3, 1.25[H2O]'
_chemical_formula_sum            'C39 H25.50 Cl4 N O4.25'
_chemical_formula_weight         717.90
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   31.3651(17)
_cell_length_b                   11.6284(6)
_cell_length_c                   20.2570(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.297(2)
_cell_angle_gamma                90
_cell_volume                     7328.4(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9369
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0958 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8656.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2948
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.149
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            71644
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_min         2.027
_diffrn_ambient_temperature      302.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4761
_reflns_number_total             9085
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         9085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+7.2345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1662
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39)
;
_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 0.26903(4) 0.52531(9) 0.42451(6) 0.1232(4) Uani 1 1 d . . . . .
Cl2 Cl 0.07928(3) 0.82527(10) 0.14072(6) 0.1178(4) Uani 1 1 d . . . . .
Cl3 Cl 0.46521(3) 0.37709(8) 0.16525(5) 0.1054(3) Uani 1 1 d . . . . .
Cl4 Cl 0.31533(4) 0.73285(11) -0.00277(4) 0.1231(4) Uani 1 1 d . . . . .
O1 O 0.40654(7) 0.91792(17) 0.39835(10) 0.0832(6) Uani 1 1 d . . . . .
O2 O 0.31167(6) 0.83796(15) 0.30306(8) 0.0684(5) Uani 1 1 d . . . . .
O3 O 0.26701(6) 0.57888(16) 0.24976(10) 0.0802(6) Uani 1 1 d . . . . .
N1 N 0.33638(6) 0.71075(16) 0.23317(8) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.31024(9) 0.6819(2) 0.50703(13) 0.0684(7) Uani 1 1 d . . . . .
C2 C 0.27996(10) 0.5955(3) 0.50001(16) 0.0817(9) Uani 1 1 d . . . . .
C3 C 0.25687(13) 0.5654(4) 0.5515(2) 0.1105(13) Uani 1 1 d . . . . .
H3 H 0.236658 0.506554 0.545728 0.158(19) Uiso 1 1 calc R . . . .
C4 C 0.26397(16) 0.6223(5) 0.6101(2) 0.1215(17) Uani 1 1 d . . . . .
H4 H 0.248708 0.602033 0.644832 0.161(17) Uiso 1 1 calc R . . . .
C5 C 0.29303(17) 0.7083(4) 0.61859(19) 0.1212(15) Uani 1 1 d . . . . .
H5 H 0.297305 0.747742 0.658829 0.136(15) Uiso 1 1 calc R . . . .
C6 C 0.31630(13) 0.7380(3) 0.56830(14) 0.0943(11) Uani 1 1 d . . . . .
H6 H 0.336525 0.796648 0.575187 0.105(13) Uiso 1 1 calc R . . . .
C7 C 0.33500(9) 0.7133(2) 0.45319(12) 0.0624(6) Uani 1 1 d . . . . .
H7 H 0.332727 0.664619 0.416472 0.073(8) Uiso 1 1 calc R . . . .
C8 C 0.36017(9) 0.8035(2) 0.45157(13) 0.0702(7) Uani 1 1 d . . . . .
H8 H 0.362849 0.852561 0.488140 0.094(10) Uiso 1 1 calc R . . . .
C9 C 0.38415(9) 0.8324(2) 0.39678(12) 0.0600(6) Uani 1 1 d . . . . .
C10 C 0.37989(8) 0.75600(19) 0.33617(10) 0.0512(5) Uani 1 1 d . . . . .
C11 C 0.34043(8) 0.77131(19) 0.29203(11) 0.0517(6) Uani 1 1 d . . . . .
C12 C 0.36703(7) 0.63260(19) 0.21642(11) 0.0484(5) Uani 1 1 d . . . . .
C13 C 0.40545(7) 0.61991(19) 0.25945(10) 0.0478(5) Uani 1 1 d . . . . .
C14 C 0.41191(7) 0.68624(19) 0.32057(10) 0.0488(5) Uani 1 1 d . . . . .
C15 C 0.29605(7) 0.7264(2) 0.19140(11) 0.0527(6) Uani 1 1 d . . . . .
C16 C 0.25950(8) 0.6639(2) 0.21548(12) 0.0553(6) Uani 1 1 d . . . . .
C17 C 0.21498(7) 0.7059(2) 0.19631(11) 0.0511(5) Uani 1 1 d . . . . .
C18 C 0.20554(8) 0.8224(2) 0.19453(11) 0.0557(6) Uani 1 1 d . . . . .
H18 H 0.227503 0.876017 0.203585 0.057(7) Uiso 1 1 calc R . . . .
C19 C 0.16356(9) 0.8589(2) 0.17934(13) 0.0670(7) Uani 1 1 d . . . . .
H19 H 0.157020 0.936869 0.179096 0.087(9) Uiso 1 1 calc R . . . .
C20 C 0.13171(9) 0.7793(3) 0.16465(13) 0.0698(7) Uani 1 1 d . . . . .
C21 C 0.14019(9) 0.6633(3) 0.16705(14) 0.0713(7) Uani 1 1 d . . . . .
H21 H 0.118075 0.610265 0.157643 0.072(8) Uiso 1 1 calc R . . . .
C22 C 0.18201(8) 0.6270(2) 0.18361(13) 0.0630(7) Uani 1 1 d . . . . .
H22 H 0.188084 0.548712 0.186261 0.079(8) Uiso 1 1 calc R . . . .
C23 C 0.35997(8) 0.5679(2) 0.15823(12) 0.0617(6) Uani 1 1 d . . . . .
H23 H 0.334586 0.577119 0.129588 0.064(7) Uiso 1 1 calc R . . . .
C24 C 0.39014(8) 0.4911(2) 0.14302(13) 0.0698(7) Uani 1 1 d . . . . .
H24 H 0.385316 0.448375 0.103965 0.086(9) Uiso 1 1 calc R . . . .
C25 C 0.42773(8) 0.4766(2) 0.18542(13) 0.0649(7) Uani 1 1 d . . . . .
C26 C 0.43558(8) 0.5391(2) 0.24287(12) 0.0579(6) Uani 1 1 d . . . . .
H26 H 0.461026 0.527998 0.271104 0.071(8) Uiso 1 1 calc R . . . .
C27 C 0.45344(8) 0.6802(2) 0.36544(12) 0.0578(6) Uani 1 1 d . . . . .
C28 C 0.45540(11) 0.6387(3) 0.42928(14) 0.0827(9) Uani 1 1 d . . . . .
H28 H 0.430868 0.608975 0.444393 0.073(8) Uiso 1 1 calc R . . . .
C29 C 0.49426(14) 0.6411(4) 0.47146(18) 0.1081(12) Uani 1 1 d . . . . .
H29 H 0.495408 0.614423 0.514936 0.122(13) Uiso 1 1 calc R . . . .
C30 C 0.53041(14) 0.6823(4) 0.4492(2) 0.1138(13) Uani 1 1 d . . . . .
H30 H 0.556248 0.682998 0.477312 0.168(18) Uiso 1 1 calc R . . . .
C31 C 0.52897(11) 0.7222(4) 0.3865(2) 0.1060(12) Uani 1 1 d . . . . .
H31 H 0.553802 0.749617 0.371224 0.138(15) Uiso 1 1 calc R . . . .
C32 C 0.49038(9) 0.7221(3) 0.34474(15) 0.0830(9) Uani 1 1 d . . . . .
H32 H 0.489522 0.751061 0.301801 0.097(10) Uiso 1 1 calc R . . . .
C33 C 0.29398(8) 0.7860(2) 0.13542(12) 0.0620(6) Uani 1 1 d . . . . .
H33 H 0.267714 0.788357 0.108392 0.073(8) Uiso 1 1 calc R . . . .
C34 C 0.33037(9) 0.8490(3) 0.11269(13) 0.0692(7) Uani 1 1 d . . . . .
C35 C 0.34228(10) 0.8332(3) 0.04980(15) 0.0880(10) Uani 1 1 d . . . . .
C36 C 0.37561(13) 0.8925(4) 0.0287(2) 0.1122(14) Uani 1 1 d . . . . .
H36 H 0.382965 0.880231 -0.013844 0.138(15) Uiso 1 1 calc R . . . .
C37 C 0.39776(14) 0.9687(4) 0.0697(3) 0.1244(17) Uani 1 1 d . . . . .
H37 H 0.420777 1.007875 0.055482 0.123(13) Uiso 1 1 calc R . . . .
C38 C 0.38682(13) 0.9898(4) 0.1329(3) 0.1146(13) Uani 1 1 d . . . . .
H38 H 0.402194 1.043386 0.160559 0.144(17) Uiso 1 1 calc R . . . .
C39 C 0.35271(10) 0.9303(3) 0.15470(19) 0.0882(9) Uani 1 1 d . . . . .
H39 H 0.344855 0.944411 0.196710 0.061(8) Uiso 1 1 calc R . . . .


_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 C2 1.729(4) . ?
Cl2 C20 1.738(3) . ?
Cl3 C25 1.735(2) . ?
Cl4 C35 1.727(4) . ?
O1 C9 1.216(3) . ?
O2 C11 1.231(3) . ?
O3 C16 1.214(3) . ?
N1 C11 1.377(3) . ?
N1 C12 1.396(3) . ?
N1 C15 1.441(3) . ?
C1 C2 1.378(4) . ?
C1 C6 1.394(4) . ?
C1 C7 1.463(4) . ?
C2 C3 1.388(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.353(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.349(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.317(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.457(4) . ?
C9 C10 1.508(3) . ?
C10 C11 1.443(3) . ?
C10 C14 1.359(3) . ?
C12 C13 1.402(3) . ?
C12 C23 1.392(3) . ?
C13 C14 1.451(3) . ?
C13 C26 1.403(3) . ?
C14 C27 1.492(3) . ?
C15 C16 1.490(3) . ?
C15 C33 1.323(3) . ?
C16 C17 1.484(3) . ?
C17 C18 1.386(3) . ?
C17 C22 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(4) . ?
C20 C21 1.374(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.365(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C25 C26 1.367(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(4) . ?
C27 C32 1.371(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.397(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.360(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.347(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.385(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.478(4) . ?
C34 C35 1.385(4) . ?
C34 C39 1.399(4) . ?
C35 C36 1.366(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.347(6) . ?
C37 H37 0.9300 . ?
C37 C38 1.390(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.392(5) . ?
C39 H39 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 N1 C12 123.58(19) . . ?
C11 N1 C15 114.91(18) . . ?
C12 N1 C15 121.32(18) . . ?
C2 C1 C6 116.6(3) . . ?
C2 C1 C7 122.0(3) . . ?
C6 C1 C7 121.4(3) . . ?
C1 C2 Cl1 119.5(2) . . ?
C1 C2 C3 121.7(4) . . ?
C3 C2 Cl1 118.8(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 116.8 . . ?
C8 C7 C1 126.5(2) . . ?
C8 C7 H7 116.8 . . ?
C7 C8 H8 117.6 . . ?
C7 C8 C9 124.9(2) . . ?
C9 C8 H8 117.6 . . ?
O1 C9 C8 121.4(2) . . ?
O1 C9 C10 119.6(2) . . ?
C8 C9 C10 118.9(2) . . ?
C11 C10 C9 114.3(2) . . ?
C14 C10 C9 123.3(2) . . ?
C14 C10 C11 122.0(2) . . ?
O2 C11 N1 119.4(2) . . ?
O2 C11 C10 123.8(2) . . ?
N1 C11 C10 116.8(2) . . ?
N1 C12 C13 118.78(19) . . ?
C23 C12 N1 121.2(2) . . ?
C23 C12 C13 120.1(2) . . ?
C12 C13 C14 119.35(19) . . ?
C12 C13 C26 118.3(2) . . ?
C26 C13 C14 122.3(2) . . ?
C10 C14 C13 119.2(2) . . ?
C10 C14 C27 120.0(2) . . ?
C13 C14 C27 120.7(2) . . ?
N1 C15 C16 113.60(19) . . ?
C33 C15 N1 120.9(2) . . ?
C33 C15 C16 125.4(2) . . ?
O3 C16 C15 118.9(2) . . ?
O3 C16 C17 121.7(2) . . ?
C17 C16 C15 119.4(2) . . ?
C18 C17 C16 121.3(2) . . ?
C22 C17 C16 119.2(2) . . ?
C22 C17 C18 119.5(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 Cl2 119.5(2) . . ?
C19 C20 C21 121.6(3) . . ?
C21 C20 Cl2 118.9(2) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 118.9(3) . . ?
C22 C21 H21 120.5 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C12 C23 H23 119.8 . . ?
C24 C23 C12 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 Cl3 119.09(19) . . ?
C26 C25 Cl3 120.0(2) . . ?
C26 C25 C24 120.9(2) . . ?
C13 C26 H26 119.8 . . ?
C25 C26 C13 120.4(2) . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C14 121.4(2) . . ?
C32 C27 C14 120.2(2) . . ?
C32 C27 C28 118.3(3) . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.2(4) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.3(4) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.8(4) . . ?
C32 C31 H31 120.1 . . ?
C27 C32 C31 121.4(3) . . ?
C27 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C15 C33 H33 117.6 . . ?
C15 C33 C34 124.8(2) . . ?
C34 C33 H33 117.6 . . ?
C35 C34 C33 122.0(3) . . ?
C35 C34 C39 118.5(3) . . ?
C39 C34 C33 119.5(3) . . ?
C34 C35 Cl4 119.3(3) . . ?
C36 C35 Cl4 118.8(3) . . ?
C36 C35 C34 121.9(4) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 C35 119.6(4) . . ?
C37 C36 H36 120.2 . . ?
C36 C37 H37 119.4 . . ?
C36 C37 C38 121.2(4) . . ?
C38 C37 H37 119.4 . . ?
C37 C38 H38 120.2 . . ?
C37 C38 C39 119.6(4) . . ?
C39 C38 H38 120.2 . . ?
C34 C39 H39 120.4 . . ?
C38 C39 C34 119.3(4) . . ?
C38 C39 H39 120.4 . . ?

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 C2 C3 C4 -177.7(3) . . . . ?
Cl2 C20 C21 C22 177.6(2) . . . . ?
Cl3 C25 C26 C13 179.89(19) . . . . ?
Cl4 C35 C36 C37 -178.1(3) . . . . ?
O1 C9 C10 C11 -101.6(3) . . . . ?
O1 C9 C10 C14 72.5(3) . . . . ?
O3 C16 C17 C18 140.8(3) . . . . ?
O3 C16 C17 C22 -35.6(3) . . . . ?
N1 C12 C13 C14 1.3(3) . . . . ?
N1 C12 C13 C26 178.5(2) . . . . ?
N1 C12 C23 C24 -179.3(2) . . . . ?
N1 C15 C16 O3 -25.5(3) . . . . ?
N1 C15 C16 C17 155.32(19) . . . . ?
N1 C15 C33 C34 -5.2(4) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C7 C8 C9 -179.6(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C7 C8 170.2(3) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C6 C1 C2 Cl1 177.5(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C1 C7 C8 -10.1(4) . . . . ?
C7 C1 C2 Cl1 -2.7(4) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
C7 C1 C6 C5 180.0(3) . . . . ?
C7 C8 C9 O1 179.3(3) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C8 C9 C10 C11 76.6(3) . . . . ?
C8 C9 C10 C14 -109.3(3) . . . . ?
C9 C10 C11 O2 -2.2(3) . . . . ?
C9 C10 C11 N1 174.7(2) . . . . ?
C9 C10 C14 C13 -177.1(2) . . . . ?
C9 C10 C14 C27 1.7(3) . . . . ?
C10 C14 C27 C28 64.1(3) . . . . ?
C10 C14 C27 C32 -112.4(3) . . . . ?
C11 N1 C12 C13 -4.4(3) . . . . ?
C11 N1 C12 C23 175.6(2) . . . . ?
C11 N1 C15 C16 -75.2(2) . . . . ?
C11 N1 C15 C33 108.5(3) . . . . ?
C11 C10 C14 C13 -3.5(3) . . . . ?
C11 C10 C14 C27 175.3(2) . . . . ?
C12 N1 C11 O2 -179.4(2) . . . . ?
C12 N1 C11 C10 3.5(3) . . . . ?
C12 N1 C15 C16 100.0(2) . . . . ?
C12 N1 C15 C33 -76.3(3) . . . . ?
C12 C13 C14 C10 2.5(3) . . . . ?
C12 C13 C14 C27 -176.3(2) . . . . ?
C12 C13 C26 C25 1.4(3) . . . . ?
C12 C23 C24 C25 0.3(4) . . . . ?
C13 C12 C23 C24 0.7(4) . . . . ?
C13 C14 C27 C28 -117.1(3) . . . . ?
C13 C14 C27 C32 66.4(3) . . . . ?
C14 C10 C11 O2 -176.3(2) . . . . ?
C14 C10 C11 N1 0.6(3) . . . . ?
C14 C13 C26 C25 178.5(2) . . . . ?
C14 C27 C28 C29 -175.8(3) . . . . ?
C14 C27 C32 C31 177.1(3) . . . . ?
C15 N1 C11 O2 -4.4(3) . . . . ?
C15 N1 C11 C10 178.53(19) . . . . ?
C15 N1 C12 C13 -179.2(2) . . . . ?
C15 N1 C12 C23 0.9(3) . . . . ?
C15 C16 C17 C18 -40.1(3) . . . . ?
C15 C16 C17 C22 143.5(2) . . . . ?
C15 C33 C34 C35 127.8(3) . . . . ?
C15 C33 C34 C39 -54.5(4) . . . . ?
C16 C15 C33 C34 179.0(2) . . . . ?
C16 C17 C18 C19 -177.2(2) . . . . ?
C16 C17 C22 C21 178.7(2) . . . . ?
C17 C18 C19 C20 -1.5(4) . . . . ?
C18 C17 C22 C21 2.2(4) . . . . ?
C18 C19 C20 Cl2 -176.2(2) . . . . ?
C18 C19 C20 C21 2.5(4) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C20 C21 C22 C17 -1.3(4) . . . . ?
C22 C17 C18 C19 -0.8(4) . . . . ?
C23 C12 C13 C14 -178.7(2) . . . . ?
C23 C12 C13 C26 -1.5(3) . . . . ?
C23 C24 C25 Cl3 179.2(2) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C13 -0.4(4) . . . . ?
C26 C13 C14 C10 -174.6(2) . . . . ?
C26 C13 C14 C27 6.6(3) . . . . ?
C27 C28 C29 C30 -1.3(6) . . . . ?
C28 C27 C32 C31 0.5(5) . . . . ?
C28 C29 C30 C31 0.6(7) . . . . ?
C29 C30 C31 C32 0.6(6) . . . . ?
C30 C31 C32 C27 -1.2(6) . . . . ?
C32 C27 C28 C29 0.7(5) . . . . ?
C33 C15 C16 O3 150.5(3) . . . . ?
C33 C15 C16 C17 -28.6(4) . . . . ?
C33 C34 C35 Cl4 -2.6(4) . . . . ?
C33 C34 C35 C36 179.3(3) . . . . ?
C33 C34 C39 C38 -179.7(3) . . . . ?
C34 C35 C36 C37 0.0(5) . . . . ?
C35 C34 C39 C38 -1.9(4) . . . . ?
C35 C36 C37 C38 -1.2(6) . . . . ?
C36 C37 C38 C39 0.8(6) . . . . ?
C37 C38 C39 C34 0.8(5) . . . . ?
C39 C34 C35 Cl4 179.7(2) . . . . ?
C39 C34 C35 C36 1.6(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.610 502.7 52.3 '5 H2O'
2 0.121 -0.032 0.024 17.9 0.0 ?
3 0.121 0.032 0.524 17.9 0.0 ?
4 0.379 0.468 0.476 17.9 0.0 ?
5 0.379 0.532 0.976 17.9 0.0 ?
6 0.500 0.000 -0.627 502.7 52.3 '5 H2O'
7 0.621 0.468 0.024 17.9 0.0 ?
8 0.621 0.532 0.524 17.9 0.0 ?
9 0.879 0.032 -0.024 17.9 0.0 ?
10 0.879 -0.032 0.476 17.9 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
