# 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_dp_modch
_database_code_depnum_ccdc_archive 'CCDC 2519491'
loop_
_audit_author_name
_audit_author_address
'Dr. Subrata Das and Dr. Chris Franco'
;Associate Professor
India
;
_audit_update_record             
;
2025-12-30 deposited with the CCDC.	2026-04-24 downloaded from the CCDC.
;
_audit_creation_date             2025-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Cl N4 O2'
_chemical_formula_sum            'C15 H11 Cl N4 O2'
_chemical_formula_weight         314.73
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.1146(6)
_cell_length_b                   13.8220(10)
_cell_length_c                   13.2561(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.439(3)
_cell_angle_gamma                90
_cell_volume                     1470.71(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0539 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.9099.
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    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36436
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.107
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_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                2385
_reflns_number_total             2683
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.103
_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)+(0.0451P)²+0.7591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: N4(0.5) C13(0.5) N5(0.5) C16(0.5)
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C7(H7), C11(H11), C14(H14), C15(H15)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.31367(16) 0.86130(9) 0.67441(9) 0.0394(3) Uani 1 1 d . . . . .
O2 O -0.06529(17) 0.91809(10) 0.39471(10) 0.0472(4) Uani 1 1 d . . . . .
N1 N 0.11304(17) 0.79130(10) 0.38824(10) 0.0311(3) Uani 1 1 d . . . . .
N2 N 0.13054(19) 0.88944(11) 0.53201(11) 0.0361(3) Uani 1 1 d . . . . .
N3 N 0.31612(18) 0.67230(11) 0.37756(10) 0.0363(3) Uani 1 1 d . . . . .
H3 H 0.260438 0.652864 0.320969 0.044 Uiso 1 1 calc R U . . .
N4 N 0.8369(15) 0.5719(8) 0.5744(8) 0.074(2) Uani 0.5 1 d . . P . .
C1 C 0.0240(2) 0.76355(15) 0.28799(14) 0.0455(5) Uani 1 1 d . . . . .
H1A H 0.094596 0.774068 0.236923 0.068 Uiso 1 1 calc R U . . .
H1B H -0.075001 0.802030 0.272574 0.068 Uiso 1 1 calc R U . . .
H1C H -0.005929 0.696385 0.288881 0.068 Uiso 1 1 calc R U . . .
C2 C 0.25144(19) 0.74147(11) 0.43453(12) 0.0282(3) Uani 1 1 d . . . . .
C3 C 0.32416(19) 0.76069(11) 0.53200(12) 0.0291(3) Uani 1 1 d . . . . .
C4 C 0.4673(2) 0.70199(12) 0.58625(12) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.548979 0.746781 0.622505 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4140(2) 0.63142(12) 0.66377(12) 0.0319(4) Uani 1 1 d . . . . .
C6 C 0.5146(2) 0.61680(15) 0.75677(14) 0.0445(4) Uani 1 1 d . . . . .
H6 H 0.613413 0.651431 0.771949 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4699(3) 0.55141(16) 0.82723(15) 0.0499(5) Uani 1 1 d . . . . .
H7 H 0.538268 0.541758 0.889111 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3236(2) 0.50116(13) 0.80446(14) 0.0426(4) Uani 1 1 d . . . . .
C9 C 0.2602(2) 0.83799(11) 0.58588(12) 0.0295(3) Uani 1 1 d . . . . .
C10 C 0.0517(2) 0.86977(12) 0.43589(13) 0.0331(4) Uani 1 1 d . . . . .
C11 C 0.4708(2) 0.63417(14) 0.41161(14) 0.0406(4) Uani 1 1 d . . . . .
H11 H 0.522659 0.596691 0.367175 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5494(2) 0.64898(14) 0.50614(14) 0.0406(4) Uani 1 1 d . . . . .
C13 C 0.708(2) 0.6024(12) 0.5443(14) 0.047(2) Uani 0.5 1 d . . P . .
C14 C 0.2667(2) 0.57945(13) 0.64349(14) 0.0393(4) Uani 1 1 d . . . . .
H14 H 0.198036 0.588399 0.581595 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2199(2) 0.51454(14) 0.71350(15) 0.0449(4) Uani 1 1 d . . . . .
H15 H 0.120239 0.480570 0.699423 0.054 Uiso 1 1 calc R U . . .
N5 N 0.8602(17) 0.6119(10) 0.5463(10) 0.123(5) Uani 0.5 1 d . . P . .
C16 C 0.724(3) 0.6280(13) 0.5254(14) 0.065(4) Uani 0.5 1 d . . P . .
H2 H 0.101(2) 0.9408(16) 0.5599(15) 0.042(5) Uiso 1 1 d . . . . .
Cl3 Cl 0.26658(8) 0.41804(4) 0.89284(5) 0.0648(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2328(19) . ?
O2 C10 1.222(2) . ?
N1 C1 1.468(2) . ?
N1 C2 1.382(2) . ?
N1 C10 1.384(2) . ?
N2 C9 1.379(2) . ?
N2 C10 1.366(2) . ?
N2 H2 0.85(2) . ?
N3 H3 0.8600 . ?
N3 C2 1.370(2) . ?
N3 C11 1.375(2) . ?
N4 C13 1.15(2) . ?
N4 N5 0.708(17) . ?
N4 C16 1.30(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.365(2) . ?
C3 C4 1.510(2) . ?
C3 C9 1.425(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.525(2) . ?
C4 C12 1.522(2) . ?
C5 C6 1.390(2) . ?
C5 C14 1.387(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(3) . ?
C8 C15 1.378(3) . ?
C8 Cl3 1.7509(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.336(3) . ?
C12 C13 1.46(2) . ?
C12 C16 1.43(2) . ?
C13 N5 1.24(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
N5 C16 1.12(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 122.13(14) . . ?
C2 N1 C10 120.74(13) . . ?
C10 N1 C1 117.12(14) . . ?
C9 N2 H2 116.5(14) . . ?
C10 N2 C9 126.67(15) . . ?
C10 N2 H2 116.7(14) . . ?
C2 N3 H3 120.3 . . ?
C2 N3 C11 119.46(14) . . ?
C11 N3 H3 120.3 . . ?
C13 N4 C16 20.7(11) . . ?
N5 N4 C13 80.2(19) . . ?
N5 N4 C16 59.6(17) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 N1 117.09(14) . . ?
C3 C2 N1 122.23(14) . . ?
C3 C2 N3 120.67(14) . . ?
C2 C3 C4 122.80(14) . . ?
C2 C3 C9 118.80(14) . . ?
C9 C3 C4 118.39(13) . . ?
C3 C4 H4 108.2 . . ?
C3 C4 C5 113.00(13) . . ?
C3 C4 C12 108.15(13) . . ?
C5 C4 H4 108.2 . . ?
C12 C4 H4 108.2 . . ?
C12 C4 C5 111.02(14) . . ?
C6 C5 C4 120.21(16) . . ?
C14 C5 C4 121.49(14) . . ?
C14 C5 C6 118.30(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.99(18) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.09(17) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C15 121.52(17) . . ?
C7 C8 Cl3 119.39(15) . . ?
C15 C8 Cl3 119.09(16) . . ?
O1 C9 N2 119.55(15) . . ?
O1 C9 C3 124.76(15) . . ?
N2 C9 C3 115.69(14) . . ?
O2 C10 N1 122.16(15) . . ?
O2 C10 N2 122.31(15) . . ?
N2 C10 N1 115.53(14) . . ?
N3 C11 H11 118.8 . . ?
C12 C11 N3 122.44(16) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C4 122.04(15) . . ?
C11 C12 C13 122.2(8) . . ?
C11 C12 C16 117.4(8) . . ?
C13 C12 C4 115.1(8) . . ?
C16 C12 C4 119.8(8) . . ?
C16 C12 C13 18.4(8) . . ?
N4 C13 C12 175.4(14) . . ?
N4 C13 N5 34.2(9) . . ?
N5 C13 C12 141.7(11) . . ?
C5 C14 H14 119.3 . . ?
C15 C14 C5 121.31(16) . . ?
C15 C14 H14 119.3 . . ?
C8 C15 C14 118.78(18) . . ?
C8 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N4 N5 C13 65.6(19) . . ?
N4 N5 C16 87(2) . . ?
C16 N5 C13 21.9(11) . . ?
N4 C16 C12 144.7(12) . . ?
N5 C16 N4 33.0(10) . . ?
N5 C16 C12 176.0(18) . . ?

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
N1 C2 C3 C4 175.30(14) . . . . ?
N1 C2 C3 C9 -3.2(2) . . . . ?
N3 C2 C3 C4 -6.0(2) . . . . ?
N3 C2 C3 C9 175.44(15) . . . . ?
N3 C11 C12 C4 5.4(3) . . . . ?
N3 C11 C12 C13 175.2(6) . . . . ?
N3 C11 C12 C16 -164.2(7) . . . . ?
N4 C13 N5 C16 178(6) . . . . ?
C1 N1 C2 N3 8.2(2) . . . . ?
C1 N1 C2 C3 -173.07(16) . . . . ?
C1 N1 C10 O2 -4.2(3) . . . . ?
C1 N1 C10 N2 175.64(16) . . . . ?
C2 N1 C10 O2 176.31(16) . . . . ?
C2 N1 C10 N2 -3.8(2) . . . . ?
C2 N3 C11 C12 11.9(3) . . . . ?
C2 C3 C4 C5 -103.13(18) . . . . ?
C2 C3 C4 C12 20.2(2) . . . . ?
C2 C3 C9 O1 178.90(15) . . . . ?
C2 C3 C9 N2 -1.9(2) . . . . ?
C3 C4 C5 C6 -140.60(16) . . . . ?
C3 C4 C5 C14 40.3(2) . . . . ?
C3 C4 C12 C11 -19.8(2) . . . . ?
C3 C4 C12 C13 169.6(6) . . . . ?
C3 C4 C12 C16 149.5(6) . . . . ?
C4 C3 C9 O1 0.3(2) . . . . ?
C4 C3 C9 N2 179.47(14) . . . . ?
C4 C5 C6 C7 -178.61(17) . . . . ?
C4 C5 C14 C15 179.15(16) . . . . ?
C4 C12 C13 N5 -104(3) . . . . ?
C4 C12 C16 N4 76(3) . . . . ?
C5 C4 C12 C11 104.7(2) . . . . ?
C5 C4 C12 C13 -65.9(6) . . . . ?
C5 C4 C12 C16 -86.0(6) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C14 C15 C8 -0.7(3) . . . . ?
C6 C5 C14 C15 0.0(3) . . . . ?
C6 C7 C8 C15 -0.3(3) . . . . ?
C6 C7 C8 Cl3 179.74(15) . . . . ?
C7 C8 C15 C14 0.8(3) . . . . ?
C9 N2 C10 O2 178.20(17) . . . . ?
C9 N2 C10 N1 -1.7(3) . . . . ?
C9 C3 C4 C5 75.42(18) . . . . ?
C9 C3 C4 C12 -161.27(15) . . . . ?
C10 N1 C2 N3 -172.38(15) . . . . ?
C10 N1 C2 C3 6.3(2) . . . . ?
C10 N2 C9 O1 -176.24(16) . . . . ?
C10 N2 C9 C3 4.5(2) . . . . ?
C11 N3 C2 N1 167.22(15) . . . . ?
C11 N3 C2 C3 -11.5(2) . . . . ?
C11 C12 C13 N5 85(3) . . . . ?
C11 C12 C16 N4 -114(3) . . . . ?
C12 C4 C5 C6 97.69(18) . . . . ?
C12 C4 C5 C14 -81.44(19) . . . . ?
C12 C13 N5 N4 176(3) . . . . ?
C12 C13 N5 C16 -5(3) . . . . ?
C13 N4 N5 C16 -1(2) . . . . ?
C13 N4 C16 C12 4(3) . . . . ?
C13 N4 C16 N5 178(6) . . . . ?
C13 C12 C16 N4 -4(2) . . . . ?
C13 N5 C16 N4 -2(6) . . . . ?
C14 C5 C6 C7 0.5(3) . . . . ?
N5 N4 C16 C12 -174(4) . . . . ?
C16 N4 C13 N5 -2(6) . . . . ?
C16 N4 N5 C13 1(2) . . . . ?
C16 C12 C13 N5 5(3) . . . . ?
Cl3 C8 C15 C14 -179.20(14) . . . . ?

_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. 
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#######################################################################

data_a2n2_a_modch
_database_code_depnum_ccdc_archive 'CCDC 2519497'
loop_
_audit_author_name
_audit_author_address
'Dr. Subrata Das and Dr. Chris Franco'
;Associate Professor
India
;
_audit_update_record             
;
2025-12-30 deposited with the CCDC.	2026-04-24 downloaded from the CCDC.
;
_audit_creation_date             2025-12-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Cl N6 O5, 1.5[H2O]'
_chemical_formula_sum            'C20 H25 Cl N6 O6.50'
_chemical_formula_weight         488.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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                   8.0227(11)
_cell_length_b                   20.042(3)
_cell_length_c                   15.413(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.697(14)
_cell_angle_gamma                90
_cell_volume                     2417.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3490
_cell_measurement_theta_min      2.4310
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.2513
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.143
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.1290
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9316
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.711
_diffrn_reflns_theta_max         24.711
_diffrn_reflns_theta_min         2.442
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.9953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  10.00   1.00   52.00    --  -16.64 -77.00 -30.00   50
  2  ω    -37.00   0.00   1.00   52.00    --  -16.64 -77.00-120.00   37
  3  ω    -32.00   9.00   1.00   52.00    --  -16.64 -77.00  90.00   41
  4  ω    -24.00  54.00   1.00   52.00    --  -16.64  19.00  90.00   78
  5  ω      6.00  32.00   1.00   52.00    --  -16.64  38.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0132379000
_diffrn_orient_matrix_UB_12      0.0333431000
_diffrn_orient_matrix_UB_13      0.0121875000
_diffrn_orient_matrix_UB_21      0.0794623000
_diffrn_orient_matrix_UB_22      -0.0005629000
_diffrn_orient_matrix_UB_23      0.0312020000
_diffrn_orient_matrix_UB_31      0.0414200000
_diffrn_orient_matrix_UB_32      0.0117816000
_diffrn_orient_matrix_UB_33      -0.0332571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1822
_reflns_number_total             4084
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1763
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      0.996
_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)+(0.1324P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2453
_refine_ls_wR_factor_ref         0.2961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: Cl1(0.57) Cl1A(0.43)
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N1(H1), C18(H18), C3(H3B), C7(H7), C4(H4), C6(H6)
3.c Tetrahedral OH refined with riding coordinates:
 O3(H3A)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.4101(8) 0.9206(3) 0.2309(4) 0.1013(16) Uani 0.57 1 d . . P . .
O5 O 0.0164(5) 0.5659(2) 0.0783(2) 0.0577(11) Uani 1 1 d . . . . .
O1 O -0.0531(5) 0.5664(2) 0.2812(2) 0.0610(11) Uani 1 1 d . . . . .
N5 N 0.5015(6) 0.6543(2) 0.3990(3) 0.0520(12) Uani 1 1 d . . . . .
H5 H 0.580080 0.635479 0.377579 0.062 Uiso 1 1 calc R U . . .
N1 N 0.2260(5) 0.4947(2) 0.0606(3) 0.0566(13) Uani 1 1 d . . . . .
H1 H 0.152754 0.477138 0.017526 0.068 Uiso 1 1 calc R U . . .
O4 O 0.4215(6) 0.4214(3) 0.0345(4) 0.1000(18) Uani 1 1 d . . . . .
N4 N 0.3458(6) 0.5922(3) 0.4842(3) 0.0608(14) Uani 1 1 d . . . . .
N3 N 0.0803(7) 0.5504(3) 0.4232(3) 0.0666(17) Uani 1 1 d . . . . .
N2 N 0.4986(6) 0.4974(3) 0.1464(3) 0.0650(14) Uani 1 1 d . . . . .
O3 O 0.5791(6) 0.5714(3) 0.2640(3) 0.0918(16) Uani 1 1 d . . . . .
H3A H 0.668810 0.552663 0.261614 0.138 Uiso 1 1 calc R U . . .
C1 C 0.2258(6) 0.6275(3) 0.2328(3) 0.0408(12) Uani 1 1 d . . . . .
H1A H 0.103240 0.629380 0.205972 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1685(7) 0.5472(3) 0.1053(3) 0.0455(13) Uani 1 1 d . . . . .
C16 C 0.0769(7) 0.5738(3) 0.3394(3) 0.0449(13) Uani 1 1 d . . . . .
N6 N 0.6601(7) 0.7490(3) 0.4269(3) 0.0741(16) Uani 1 1 d . . . . .
C13 C 0.2292(6) 0.6065(3) 0.3275(3) 0.0441(13) Uani 1 1 d . . . . .
C8 C 0.2896(6) 0.5744(3) 0.1781(3) 0.0443(13) Uani 1 1 d . . . . .
C14 C 0.3547(7) 0.6187(3) 0.4019(4) 0.0497(14) Uani 1 1 d . . . . .
C9 C 0.4528(7) 0.5500(3) 0.1960(4) 0.0504(14) Uani 1 1 d . . . . .
C2 C 0.2841(7) 0.7008(3) 0.2249(4) 0.0539(15) Uani 1 1 d . . . . .
C18 C 0.5233(8) 0.7141(3) 0.4273(4) 0.0578(16) Uani 1 1 d . . . . .
H18 H 0.436621 0.734018 0.449532 0.069 Uiso 1 1 calc R U . . .
O2 O 0.2090(7) 0.5271(4) 0.5663(3) 0.129(3) Uani 1 1 d . . . . .
C10 C 0.3825(8) 0.4690(4) 0.0776(4) 0.0654(17) Uani 1 1 d . . . . .
C15 C 0.2116(8) 0.5538(4) 0.4948(4) 0.080(2) Uani 1 1 d . . . . .
C3 C 0.4015(10) 0.7193(4) 0.1813(5) 0.083(2) Uani 1 1 d . . . . .
H3B H 0.458236 0.687949 0.153900 0.100 Uiso 1 1 calc R U . . .
C7 C 0.1997(10) 0.7494(4) 0.2632(5) 0.082(2) Uani 1 1 d . . . . .
H7 H 0.112978 0.736312 0.290817 0.098 Uiso 1 1 calc R U . . .
C5 C 0.3546(13) 0.8352(4) 0.2220(6) 0.091(3) Uani 1 1 d . . . . .
C4 C 0.4404(11) 0.7925(5) 0.1773(5) 0.098(3) Uani 1 1 d . . . . .
H4 H 0.519031 0.808201 0.145891 0.117 Uiso 1 1 calc R U . . .
C6 C 0.2399(13) 0.8164(4) 0.2616(6) 0.103(3) Uani 1 1 d . . . . .
H6 H 0.183209 0.847503 0.289473 0.124 Uiso 1 1 calc R U . . .
C12 C 0.6741(8) 0.4708(5) 0.1671(6) 0.113(3) Uani 1 1 d . . . . .
H12A H 0.753127 0.506209 0.163779 0.169 Uiso 1 1 calc R U . . .
H12B H 0.684631 0.436680 0.124933 0.169 Uiso 1 1 calc R U . . .
H12C H 0.698781 0.452337 0.225947 0.169 Uiso 1 1 calc R U . . .
C17 C 0.4913(9) 0.5970(5) 0.5617(4) 0.101(3) Uani 1 1 d . . . . .
H17A H 0.596166 0.598935 0.541445 0.152 Uiso 1 1 calc R U . . .
H17B H 0.492467 0.558608 0.599028 0.152 Uiso 1 1 calc R U . . .
H17C H 0.479872 0.636646 0.594876 0.152 Uiso 1 1 calc R U . . .
C20 C 0.6638(14) 0.8216(4) 0.4476(6) 0.130(4) Uani 1 1 d . . . . .
H20A H 0.651170 0.846747 0.393491 0.195 Uiso 1 1 calc R U . . .
H20B H 0.770800 0.832683 0.486681 0.195 Uiso 1 1 calc R U . . .
H20C H 0.571896 0.832257 0.475910 0.195 Uiso 1 1 calc R U . . .
C19 C 0.8040(11) 0.7195(5) 0.3949(7) 0.122(4) Uani 1 1 d . . . . .
H19A H 0.843414 0.680272 0.428896 0.184 Uiso 1 1 calc R U . . .
H19B H 0.895338 0.751365 0.401606 0.184 Uiso 1 1 calc R U . . .
H19C H 0.766833 0.707812 0.333239 0.184 Uiso 1 1 calc R U . . .
Cl1A Cl 0.452(2) 0.9098(6) 0.1791(9) 0.271(10) Uani 0.43 1 d . . P . .
H3 H 0.001(7) 0.537(3) 0.427(4) 0.048(19) Uiso 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
Cl1 C5 1.767(10) . ?
Cl1 Cl1A 0.955(19) . ?
O5 C11 1.256(6) . ?
O1 C16 1.226(6) . ?
N5 H5 0.8600 . ?
N5 C14 1.386(7) . ?
N5 C18 1.275(7) . ?
N1 H1 0.8600 . ?
N1 C11 1.390(7) . ?
N1 C10 1.329(7) . ?
O4 C10 1.240(7) . ?
N4 C14 1.392(7) . ?
N4 C15 1.361(7) . ?
N4 C17 1.478(7) . ?
N3 C16 1.369(7) . ?
N3 C15 1.350(8) . ?
N3 H3 0.71(6) . ?
N2 C9 1.398(7) . ?
N2 C10 1.371(7) . ?
N2 C12 1.472(8) . ?
O3 H3A 0.8200 . ?
O3 C9 1.358(6) . ?
C1 H1A 0.9800 . ?
C1 C13 1.512(7) . ?
C1 C8 1.516(7) . ?
C1 C2 1.554(7) . ?
C11 C8 1.422(7) . ?
C16 C13 1.434(7) . ?
N6 C18 1.302(7) . ?
N6 C20 1.490(9) . ?
N6 C19 1.474(10) . ?
C13 C14 1.371(7) . ?
C8 C9 1.368(7) . ?
C2 C3 1.326(9) . ?
C2 C7 1.388(9) . ?
C18 H18 0.9300 . ?
O2 C15 1.229(7) . ?
C3 H3B 0.9300 . ?
C3 C4 1.503(11) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(10) . ?
C5 C4 1.374(12) . ?
C5 C6 1.269(12) . ?
C5 Cl1A 1.872(14) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
Cl1A Cl1 C5 81.0(9) . . ?
C14 N5 H5 119.1 . . ?
C18 N5 H5 119.1 . . ?
C18 N5 C14 121.8(5) . . ?
C11 N1 H1 116.6 . . ?
C10 N1 H1 116.6 . . ?
C10 N1 C11 126.8(5) . . ?
C14 N4 C17 121.4(5) . . ?
C15 N4 C14 121.7(5) . . ?
C15 N4 C17 116.5(5) . . ?
C16 N3 H3 112(5) . . ?
C15 N3 C16 127.2(5) . . ?
C15 N3 H3 120(5) . . ?
C9 N2 C12 120.5(5) . . ?
C10 N2 C9 121.3(5) . . ?
C10 N2 C12 118.2(5) . . ?
C9 O3 H3A 109.5 . . ?
C13 C1 H1A 102.8 . . ?
C13 C1 C8 113.9(4) . . ?
C13 C1 C2 113.3(4) . . ?
C8 C1 H1A 102.8 . . ?
C8 C1 C2 118.4(4) . . ?
C2 C1 H1A 102.8 . . ?
O5 C11 N1 117.7(5) . . ?
O5 C11 C8 126.4(5) . . ?
N1 C11 C8 115.9(5) . . ?
O1 C16 N3 119.1(5) . . ?
O1 C16 C13 125.0(5) . . ?
N3 C16 C13 115.9(5) . . ?
C18 N6 C20 120.0(7) . . ?
C18 N6 C19 120.7(6) . . ?
C19 N6 C20 118.8(6) . . ?
C16 C13 C1 114.6(4) . . ?
C14 C13 C1 127.7(5) . . ?
C14 C13 C16 117.6(5) . . ?
C11 C8 C1 116.9(5) . . ?
C9 C8 C1 124.4(5) . . ?
C9 C8 C11 118.7(5) . . ?
N5 C14 N4 116.1(5) . . ?
C13 C14 N5 122.5(5) . . ?
C13 C14 N4 121.3(5) . . ?
O3 C9 N2 114.8(5) . . ?
O3 C9 C8 124.1(5) . . ?
C8 C9 N2 121.0(5) . . ?
C3 C2 C1 124.3(6) . . ?
C3 C2 C7 119.1(7) . . ?
C7 C2 C1 116.5(5) . . ?
N5 C18 N6 123.7(6) . . ?
N5 C18 H18 118.1 . . ?
N6 C18 H18 118.1 . . ?
N1 C10 N2 116.3(5) . . ?
O4 C10 N1 122.1(5) . . ?
O4 C10 N2 121.6(6) . . ?
N3 C15 N4 115.2(6) . . ?
O2 C15 N4 121.5(6) . . ?
O2 C15 N3 123.1(6) . . ?
C2 C3 H3B 120.9 . . ?
C2 C3 C4 118.1(8) . . ?
C4 C3 H3B 120.9 . . ?
C2 C7 H7 118.8 . . ?
C6 C7 C2 122.5(8) . . ?
C6 C7 H7 118.8 . . ?
Cl1 C5 Cl1A 30.2(6) . . ?
C4 C5 Cl1 119.8(8) . . ?
C4 C5 Cl1A 91.6(10) . . ?
C6 C5 Cl1 116.5(9) . . ?
C6 C5 C4 123.6(8) . . ?
C6 C5 Cl1A 143.9(11) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 C3 117.1(7) . . ?
C5 C4 H4 121.5 . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.5(9) . . ?
C5 C6 H6 120.3 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C19 H19A 109.5 . . ?
N6 C19 H19B 109.5 . . ?
N6 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Cl1 Cl1A C5 68.7(10) . . ?

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 C5 C4 C3 172.9(5) . . . . ?
Cl1 C5 C6 C7 -175.0(6) . . . . ?
O5 C11 C8 C1 5.0(8) . . . . ?
O5 C11 C8 C9 -177.0(5) . . . . ?
O1 C16 C13 C1 -5.0(8) . . . . ?
O1 C16 C13 C14 171.4(5) . . . . ?
N1 C11 C8 C1 -174.8(4) . . . . ?
N1 C11 C8 C9 3.2(8) . . . . ?
N3 C16 C13 C1 176.0(5) . . . . ?
N3 C16 C13 C14 -7.7(8) . . . . ?
C1 C13 C14 N5 0.6(9) . . . . ?
C1 C13 C14 N4 -175.5(5) . . . . ?
C1 C8 C9 N2 175.1(5) . . . . ?
C1 C8 C9 O3 -1.5(9) . . . . ?
C1 C2 C3 C4 178.2(5) . . . . ?
C1 C2 C7 C6 179.4(6) . . . . ?
C11 N1 C10 O4 179.2(6) . . . . ?
C11 N1 C10 N2 -0.1(10) . . . . ?
C11 C8 C9 N2 -2.8(8) . . . . ?
C11 C8 C9 O3 -179.4(5) . . . . ?
C16 N3 C15 N4 9.0(12) . . . . ?
C16 N3 C15 O2 -174.3(7) . . . . ?
C16 C13 C14 N5 -175.1(5) . . . . ?
C16 C13 C14 N4 8.7(8) . . . . ?
C13 C1 C8 C11 114.3(5) . . . . ?
C13 C1 C8 C9 -63.6(7) . . . . ?
C13 C1 C2 C3 129.3(6) . . . . ?
C13 C1 C2 C7 -53.9(7) . . . . ?
C8 C1 C13 C16 -88.8(6) . . . . ?
C8 C1 C13 C14 95.3(6) . . . . ?
C8 C1 C2 C3 -8.0(8) . . . . ?
C8 C1 C2 C7 168.8(5) . . . . ?
C14 N5 C18 N6 179.1(6) . . . . ?
C14 N4 C15 N3 -7.8(11) . . . . ?
C14 N4 C15 O2 175.4(7) . . . . ?
C9 N2 C10 N1 0.7(10) . . . . ?
C9 N2 C10 O4 -178.6(6) . . . . ?
C2 C1 C13 C16 131.9(5) . . . . ?
C2 C1 C13 C14 -44.0(7) . . . . ?
C2 C1 C8 C11 -108.6(5) . . . . ?
C2 C1 C8 C9 73.5(7) . . . . ?
C2 C3 C4 C5 2.1(10) . . . . ?
C2 C7 C6 C5 2.0(12) . . . . ?
C18 N5 C14 N4 -78.3(7) . . . . ?
C18 N5 C14 C13 105.3(7) . . . . ?
C10 N1 C11 O5 178.3(6) . . . . ?
C10 N1 C11 C8 -1.9(9) . . . . ?
C10 N2 C9 O3 177.6(6) . . . . ?
C10 N2 C9 C8 0.7(9) . . . . ?
C15 N4 C14 N5 -177.1(6) . . . . ?
C15 N4 C14 C13 -0.7(10) . . . . ?
C15 N3 C16 O1 179.6(7) . . . . ?
C15 N3 C16 C13 -1.3(10) . . . . ?
C3 C2 C7 C6 -3.6(10) . . . . ?
C7 C2 C3 C4 1.4(9) . . . . ?
C4 C5 C6 C7 1.9(14) . . . . ?
C4 C5 Cl1A Cl1 -159.9(12) . . . . ?
C6 C5 C4 C3 -3.8(13) . . . . ?
C6 C5 Cl1A Cl1 31.8(18) . . . . ?
C12 N2 C9 O3 -2.2(9) . . . . ?
C12 N2 C9 C8 -179.1(7) . . . . ?
C12 N2 C10 N1 -179.4(7) . . . . ?
C12 N2 C10 O4 1.3(11) . . . . ?
C17 N4 C14 N5 -5.2(9) . . . . ?
C17 N4 C14 C13 171.2(6) . . . . ?
C17 N4 C15 N3 179.8(7) . . . . ?
C17 N4 C15 O2 3.1(12) . . . . ?
C20 N6 C18 N5 170.3(7) . . . . ?
C19 N6 C18 N5 -1.8(10) . . . . ?
Cl1A Cl1 C5 C4 23.3(13) . . . . ?
Cl1A Cl1 C5 C6 -159.7(13) . . . . ?
Cl1A C5 C4 C3 -175.6(6) . . . . ?
Cl1A C5 C6 C7 167.8(10) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 64 electrons were 
found in a volume of 340Å³ in 1 void per unit cell. 
This is consistent with the presence of 
1.5[H2O] per Formula Unit 
which account for 60 electrons 
per unit cell.
;
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 0.219 0.261 0.882 84.6 15.5 '1.5 H2O'
2 -0.281 0.239 0.382 84.6 15.5 '1.5 H2O'
3 -0.219 0.739 0.118 84.6 15.5 '1.5 H2O'
4 0.281 0.761 0.618 84.6 15.5 '1.5 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.560

# start Validation Reply Form
_vrf_PLAT213_a2n2_a_modch        
;
PROBLEM: Atom Cl1A            has ADP max/min Ratio .....        4.2 prolat  
RESPONSE: These alerts are generated because there is a degree of disorder
in the chlorine atom in the structure.
;
_vrf_PLAT242_a2n2_a_modch        
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C5 Check  
RESPONSE: These alerts are generated because there is a degree of disorder
in the chlorine atom in the structure.
;
# end Validation Reply Form
