# Supplementary Information (SI) for CrystEngComm.
# 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_ELMAM2
_database_code_depnum_ccdc_archive 'CCDC 2386992'
loop_
_audit_author_name
_audit_author_address
'Dr. Maqsood Ahmed'
;Materials Chemistry Laboratory, Institute of Chemistry, The Islamia University of Bahawalpur,
Pakistan
;
#Added by publCIF



_audit_update_record             
;
2025-05-08 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;


_refine_ls_number_constraints    ?
#Added by publCIF




_cell_special_details            ?
#Added by publCIF


_publcif_datablock.id            {50be19ac-0151-4055-8df6-bc981922eddb}

_symmetry_space_group_name_H-M   'C 2/c'
# publcif _publ_body_element loop end
_audit_creation_method           'MoPro v21.06             '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H14 Cl N4, C7 H5 O3, H2 O'
_chemical_formula_sum            'C19 H21 Cl N4 O4'
_chemical_formula_weight         404.830
_chemical_absolute_configuration .

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M_alt 'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
H H 0.0000 0.0000 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
N N 0.0061 0.0033 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
O O 0.0106 0.0060 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
Cl Cl 0.1484 0.1585 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '

loop_
_symmetry_equiv_pos_as_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                   16.4563(6)
_cell_length_b                   14.2010(6)
_cell_length_c                   16.4360(8)
_cell_angle_alpha                90.
_cell_angle_beta                 97.994(2)
_cell_angle_gamma                90.
_cell_volume                     3803.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3865
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.25
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.745
_exptl_special_details           ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_reflns_Friedel_coverage         ?
_reflns_Friedel_fraction_full    ?
_reflns_Friedel_fraction_max     ?
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3865
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.05111
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3865
_reflns_number_gt                2933
_reflns_threshold_expression     'I > 2 σ(I)'
_computing_data_collection       
'Bruker BIS V6.2.16/2021-10-23 and APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B (2016)'
_computing_data_reduction        'SAINT V8.40B (2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w =1/[1.2561*σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     none
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         3865
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
# R_factor is R(F)  &  wR_factor is wR2(I) 
## Refinement was performed using a cutoff  I/sigmaI >    0.00
## R_factor_gt is computed  for  I/sigmaI > 2
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0465
_refine_ls_wR_factor_gt          0.0432
_refine_ls_goodness_of_fit_ref   1.000
# GOF(I) computed assuming all  773 parameters refined:     1.068
_refine_ls_restrained_S_all      0.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.39
_refine_diff_density_rms         ?


loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.53797(3) 0.39724(3) 1.12143(3) 0.026817(19) Uani 1 d . . . .
N N1 0.06438(9) 0.34753(10) 0.66444(10) 0.02005(7) Uani 1 d . . . .
N N2 0.17441(10) 0.31303(10) 0.93577(9) 0.02223(7) Uani 1 d . . . .
O O1 0.22190(6) 0.38111(7) 0.54097(7) 0.02116(5) Uani 1 d . . . .
O O3 0.21018(7) 0.38271(7) 0.15321(7) 0.01982(5) Uani 1 d . . . .
O O2 0.08691(6) 0.39324(7) 0.50301(7) 0.02017(5) Uani 1 d . . . .
O O4 0.07435(8) 0.41997(9) 0.04866(8) 0.02293(6) Uani 1 d . . . .
H H4A 0.0171(15) 0.4035(13) 0.0412(13) 0.040(7) Uiso 1 d D . . .
N N3 0.20255(7) 0.37557(8) 0.70203(9) 0.01368(6) Uani 1 d . . . .
N N4 0.11856(8) 0.33071(8) 0.80105(8) 0.01696(6) Uani 1 d . . . .
C C1 0.33392(9) 0.37303(9) 0.90826(10) 0.01425(7) Uani 1 d . . . .
C C2 0.32905(10) 0.43774(10) 0.97145(10) 0.01780(7) Uani 1 d . . . .
H H2 0.2756(10) 0.4826(9) 0.9695(11) 0.041(5) Uiso 1 d D . . .
C C3 0.39229(10) 0.44545(10) 1.03664(10) 0.01984(8) Uani 1 d . . . .
H H3A 0.3879(11) 0.4957(9) 1.0854(11) 0.043(6) Uiso 1 d D . . .
C C4 0.46076(9) 0.38810(10) 1.03886(10) 0.01757(7) Uani 1 d . . . .
C C5 0.46796(9) 0.32378(10) 0.97643(10) 0.01671(7) Uani 1 d . . . .
H H5 0.5223(10) 0.2804(9) 0.9781(11) 0.042(5) Uiso 1 d D . . .
C C6 0.40395(9) 0.31621(10) 0.91122(10) 0.01553(7) Uani 1 d . . . .
H H6 0.4085(10) 0.2659(8) 0.8625(10) 0.032(5) Uiso 1 d D . . .
C C7 0.26413(9) 0.36458(9) 0.84049(10) 0.01342(7) Uani 1 d . . . .
C C8 0.26985(9) 0.38486(9) 0.76019(10) 0.01351(7) Uani 1 d . . . .
C C9 0.12874(9) 0.35095(10) 0.72376(10) 0.01461(7) Uani 1 d . . . .
C C10 0.18451(9) 0.33609(10) 0.85845(10) 0.01607(7) Uani 1 d . . . .
C C11 0.34629(9) 0.42088(10) 0.73011(10) 0.01552(7) Uani 1 d . . . .
H H11A 0.3895(8) 0.4445(10) 0.7827(10) 0.036(5) Uiso 1 d D . . .
H H11B 0.3300(9) 0.4815(9) 0.6903(7) 0.031(5) Uiso 1 d D . . .
C C12 0.38893(10) 0.34758(11) 0.68206(11) 0.01978(8) Uani 1 d . . . .
H H12A 0.4456(9) 0.3779(9) 0.6655(10) 0.034(5) Uiso 1 d D . . .
H H12B 0.3481(9) 0.3277(11) 0.6263(11) 0.049(6) Uiso 1 d D . . .
H H12C 0.4038(10) 0.2854(10) 0.7206(9) 0.045(5) Uiso 1 d D . . .
C C13 0.17316(9) 0.38457(9) 0.39834(10) 0.01451(7) Uani 1 d . . . .
C C14 0.24799(10) 0.35645(10) 0.37540(10) 0.01637(7) Uani 1 d . . . .
H H14 0.2974(9) 0.3346(10) 0.4220(7) 0.033(5) Uiso 1 d D . . .
C C15 0.25995(9) 0.35596(10) 0.29321(10) 0.01627(7) Uani 1 d . . . .
H H15 0.3182(10) 0.3337(10) 0.2762(10) 0.033(5) Uiso 1 d D . . .
C C16 0.19627(9) 0.38464(10) 0.23259(10) 0.01573(7) Uani 1 d . . . .
C C17 0.12152(10) 0.41462(10) 0.25524(10) 0.01759(7) Uani 1 d . . . .
H H17 0.0725(10) 0.4381(11) 0.2089(8) 0.042(5) Uiso 1 d D . . .
C C18 0.11050(10) 0.41402(10) 0.33762(10) 0.01813(8) Uani 1 d . . . .
H H18 0.0525(10) 0.4372(10) 0.3548(10) 0.036(5) Uiso 1 d D . . .
C C19 0.16087(10) 0.38554(9) 0.48679(10) 0.01542(7) Uani 1 d . . . .
H H4B 0.0769(11) 0.4861(15) 0.0307(12) 0.034(6) Uiso 1 d D . . .
H H2A 0.2224(13) 0.3305(13) 0.9854(14) 0.038(6) Uiso 1 d D . . .
H H1A 0.0743(13) 0.3636(13) 0.6045(15) 0.038(7) Uiso 1 d D . . .
H H2B 0.1168(15) 0.3058(14) 0.9512(14) 0.045(7) Uiso 1 d D . . .
H H1B 0.0067(14) 0.3284(13) 0.6805(13) 0.040(7) Uiso 1 d D . . .
H H3B 0.1558(13) 0.3977(12) 0.1177(13) 0.031(6) Uiso 1 d D . . .
H H3 0.2072(11) 0.3835(11) 0.6363(13) 0.026(5) Uiso 1 d D . . .


_geom_special_details            
;                                    
;

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 C4 1.7303(15) . ?
N1 C9 1.337(2) . ?
N1 H1A 1.05(2) . ?
N1 H1B 1.06(2) . ?
N2 C10 1.345(2) . ?
N2 H2B 1.02(2) . ?
N2 H2A 1.08(2) . ?
O1 C19 1.2477(18) . ?
O3 C16 1.3558(19) . ?
O3 H3B 1.02(2) . ?
O2 C19 1.2863(17) . ?
O4 H4A 0.96(2) . ?
O4 H4B 0.99(2) . ?
N3 C9 1.3586(19) . ?
N3 C8 1.3650(19) . ?
N3 H3 1.10(2) . ?
N4 C9 1.336(2) . ?
N4 C10 1.3376(19) . ?
C1 C7 1.489(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.390(2) . ?
C2 H2 1.08300 . ?
C3 C4 1.387(2) . ?
C3 H3A 1.08300 . ?
C4 C5 1.391(2) . ?
C5 C6 1.399(2) . ?
C5 H5 1.08300 . ?
C6 H6 1.08300 . ?
C7 C10 1.441(2) . ?
C7 C8 1.367(2) . ?
C8 C11 1.504(2) . ?
C11 C12 1.534(2) . ?
C11 H11B 1.09200 . ?
C11 H11A 1.09200 . ?
C12 H12A 1.09500 . ?
C12 H12B 1.09500 . ?
C12 H12C 1.09500 . ?
C13 C19 1.495(2) . ?
C13 C14 1.395(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.392(2) . ?
C14 H14 1.08300 . ?
C15 C16 1.402(2) . ?
C15 H15 1.08300 . ?
C16 C17 1.400(2) . ?
C17 C18 1.391(2) . ?
C17 H17 1.08300 . ?
C18 H18 1.08300 . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 H1A 118.(1) . . . ?
C9 N1 H1B 118.(1) . . . ?
H1A N1 H1B 124.(2) . . . ?
C10 N2 H2B 120.(1) . . . ?
C10 N2 H2A 119.(1) . . . ?
H2B N2 H2A 116.(2) . . . ?
C16 O3 H3B 107.(1) . . . ?
H4A O4 H4B 106.(2) . . . ?
C9 N3 C8 120.58(12) . . . ?
C9 N3 H3 118.2(10) . . . ?
C8 N3 H3 121.1(10) . . . ?
C9 N4 C10 117.50(13) . . . ?
C7 C1 C2 119.40(12) . . . ?
C7 C1 C6 121.61(12) . . . ?
C2 C1 C6 118.98(12) . . . ?
C1 C2 C3 120.69(13) . . . ?
C1 C2 H2 119.7(9) . . . ?
C3 C2 H2 119.6(9) . . . ?
C4 C3 C2 119.50(14) . . . ?
C4 C3 H3A 120.4(9) . . . ?
C2 C3 H3A 120.1(9) . . . ?
Cl1 C4 C3 118.82(11) . . . ?
Cl1 C4 C5 119.95(11) . . . ?
C3 C4 C5 121.23(13) . . . ?
C4 C5 C6 118.91(13) . . . ?
C4 C5 H5 120.6(9) . . . ?
C6 C5 H5 120.5(9) . . . ?
C1 C6 C5 120.67(13) . . . ?
C1 C6 H6 119.7(8) . . . ?
C5 C6 H6 119.6(8) . . . ?
C10 C7 C8 116.34(13) . . . ?
C10 C7 C1 119.88(12) . . . ?
C8 C7 C1 123.76(13) . . . ?
N3 C8 C7 119.86(13) . . . ?
N3 C8 C11 115.90(12) . . . ?
C7 C8 C11 124.21(12) . . . ?
N3 C9 N4 122.71(13) . . . ?
N3 C9 N1 117.66(13) . . . ?
N4 C9 N1 119.62(13) . . . ?
N4 C10 N2 117.25(14) . . . ?
N4 C10 C7 122.92(12) . . . ?
N2 C10 C7 119.83(13) . . . ?
C8 C11 C12 113.70(12) . . . ?
C8 C11 H11B 108.5(8) . . . ?
C8 C11 H11A 109.0(7) . . . ?
C12 C11 H11B 108.6(7) . . . ?
C12 C11 H11A 108.8(8) . . . ?
H11B C11 H11A 108.(1) . . . ?
C11 C12 H12A 109.1(8) . . . ?
C11 C12 H12B 109.5(9) . . . ?
C11 C12 H12C 109.3(8) . . . ?
H12A C12 H12B 110.(1) . . . ?
H12A C12 H12C 109.(1) . . . ?
H12B C12 H12C 110.(1) . . . ?
C19 C13 C14 120.60(13) . . . ?
C19 C13 C18 120.41(13) . . . ?
C14 C13 C18 118.98(13) . . . ?
C13 C14 C15 120.86(13) . . . ?
C13 C14 H14 119.7(8) . . . ?
C15 C14 H14 119.5(7) . . . ?
C16 C15 C14 119.71(14) . . . ?
C16 C15 H15 120.2(8) . . . ?
C14 C15 H15 120.1(9) . . . ?
O3 C16 C17 122.28(13) . . . ?
O3 C16 C15 117.93(13) . . . ?
C17 C16 C15 119.79(13) . . . ?
C16 C17 C18 119.69(14) . . . ?
C16 C17 H17 120.2(9) . . . ?
C18 C17 H17 120.1(8) . . . ?
C13 C18 C17 120.97(13) . . . ?
C13 C18 H18 119.7(8) . . . ?
C17 C18 H18 119.4(10) . . . ?
O1 C19 O2 123.18(12) . . . ?
O1 C19 C13 119.29(12) . . . ?
O2 C19 C13 117.51(12) . . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C4 C3 C2 . . . . -178.84(16) ?
Cl1 C4 C3 H3A . . . . 1.(1) ?
Cl1 C4 C5 C6 . . . . 178.61(16) ?
Cl1 C4 C5 H5 . . . . -2.(1) ?
N1 C9 N3 C8 . . . . 176.78(17) ?
N1 C9 N3 H3 . . . . -6.8(10) ?
N1 C9 N4 C10 . . . . -179.26(17) ?
N2 C10 N4 C9 . . . . -178.14(17) ?
N2 C10 C7 C8 . . . . 178.58(18) ?
N2 C10 C7 C1 . . . . -3.07(18) ?
O1 C19 C13 C14 . . . . 15.48(17) ?
O1 C19 C13 C18 . . . . -162.95(17) ?
O3 C16 C17 C18 . . . . 179.25(17) ?
O3 C16 C17 H17 . . . . -0.6(10) ?
O3 C16 C15 C14 . . . . -179.67(17) ?
O3 C16 C15 H15 . . . . 0.5(9) ?
O2 C19 C13 C14 . . . . -166.13(17) ?
O2 C19 C13 C18 . . . . 15.44(17) ?
N3 C9 N4 C10 . . . . 0.52(16) ?
N3 C9 N1 H1A . . . . 0.(1) ?
N3 C9 N1 H1B . . . . 180.(1) ?
N3 C8 C7 C10 . . . . -1.40(16) ?
N3 C8 C7 C1 . . . . -179.68(17) ?
N3 C8 C11 C12 . . . . -74.72(17) ?
N3 C8 C11 H11B . . . . 46.2(7) ?
N3 C8 C11 H11A . . . . 163.7(8) ?
N4 C9 N3 C8 . . . . -3.01(16) ?
N4 C9 N3 H3 . . . . 173.(1) ?
N4 C9 N1 H1A . . . . -180.(1) ?
N4 C9 N1 H1B . . . . 0.(1) ?
N4 C10 N2 H2B . . . . -13.(1) ?
N4 C10 N2 H2A . . . . -167.(1) ?
N4 C10 C7 C8 . . . . -1.07(17) ?
N4 C10 C7 C1 . . . . 177.28(17) ?
C1 C7 C8 C11 . . . . -1.84(18) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C1 C2 C3 H3A . . . . -180.(1) ?
C1 C6 C5 C4 . . . . 0.58(19) ?
C1 C6 C5 H5 . . . . -179.(1) ?
C2 C1 C7 C10 . . . . -61.6(2) ?
C2 C1 C7 C8 . . . . 116.7(2) ?
C2 C1 C6 C5 . . . . 0.2(2) ?
C2 C1 C6 H6 . . . . -179.8(10) ?
C2 C3 C4 C5 . . . . 0.9(2) ?
H2 C2 C1 C7 . . . . -2.(1) ?
H2 C2 C1 C6 . . . . 179.(1) ?
H2 C2 C3 C4 . . . . -180.(1) ?
H2 C2 C3 H3A . . . . 0.(2) ?
C3 C4 C5 C6 . . . . -1.1(2) ?
C3 C4 C5 H5 . . . . 179.(1) ?
C3 C2 C1 C7 . . . . 178.3(2) ?
C3 C2 C1 C6 . . . . -0.4(2) ?
H3A C3 C4 C5 . . . . -179.(1) ?
C4 C5 C6 H6 . . . . -179.4(10) ?
C5 C6 C1 C7 . . . . -178.51(19) ?
H5 C5 C6 H6 . . . . 1.(2) ?
C6 C1 C7 C10 . . . . 117.1(2) ?
C6 C1 C7 C8 . . . . -64.6(2) ?
H6 C6 C1 C7 . . . . 1.(1) ?
C7 C10 N4 C9 . . . . 1.52(17) ?
C7 C10 N2 H2B . . . . 168.(1) ?
C7 C10 N2 H2A . . . . 13.(1) ?
C7 C8 N3 C9 . . . . 3.39(17) ?
C7 C8 N3 H3 . . . . -173.(1) ?
C7 C8 C11 C12 . . . . 107.36(18) ?
C7 C8 C11 H11B . . . . -131.7(8) ?
C7 C8 C11 H11A . . . . -14.2(9) ?
C8 C11 C12 H12A . . . . -176.8(8) ?
C8 C11 C12 H12B . . . . 63.1(9) ?
C8 C11 C12 H12C . . . . -57.2(8) ?
C9 N3 C8 C11 . . . . -174.63(16) ?
C10 C7 C8 C11 . . . . 176.44(18) ?
C11 C8 N3 H3 . . . . 9.1(10) ?
H11A C11 C12 H12A . . . . -55.(1) ?
H11A C11 C12 H12B . . . . -175.(1) ?
H11A C11 C12 H12C . . . . 64.(1) ?
H11B C11 C12 H12A . . . . 62.(1) ?
H11B C11 C12 H12B . . . . -58.(1) ?
H11B C11 C12 H12C . . . . -178.(1) ?
C13 C14 C15 C16 . . . . 0.41(18) ?
C13 C14 C15 H15 . . . . -179.7(9) ?
C13 C18 C17 C16 . . . . 0.49(19) ?
C13 C18 C17 H17 . . . . -179.6(10) ?
C14 C13 C18 C17 . . . . 0.69(19) ?
C14 C13 C18 H18 . . . . -178.9(9) ?
C14 C15 C16 C17 . . . . 0.78(19) ?
H14 C14 C13 C19 . . . . 1.(1) ?
H14 C14 C13 C18 . . . . 179.(1) ?
H14 C14 C15 C16 . . . . -180.(1) ?
H14 C14 C15 H15 . . . . 0.(1) ?
C15 C16 O3 H3B . . . . 173.(1) ?
C15 C16 C17 C18 . . . . -1.22(19) ?
C15 C16 C17 H17 . . . . 178.9(10) ?
C15 C14 C13 C19 . . . . -179.60(18) ?
C15 C14 C13 C18 . . . . -1.14(18) ?
H15 C15 C16 C17 . . . . -179.(1) ?
C16 C17 C18 H18 . . . . -179.9(9) ?
C17 C16 O3 H3B . . . . -7.(1) ?
C17 C18 C13 C19 . . . . 179.15(19) ?
H17 C17 C18 H18 . . . . 0.(2) ?
H18 C18 C13 C19 . . . . 0.(1) ?

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
C11 H11A C1 1.092 2.579 3.040(2) 104 1
C11 H11A C6 1.092 2.775 3.344(2) 112 1
C12 H12B O1 1.095 2.459 3.374(2) 140 1
N2 H2A C1 1.08(2) 2.45(2) 2.855(2) 101.(1) 1
N2 H2A C2 1.08(2) 2.36(2) 3.089(2) 123.(1) 1
N1 H1A O2 1.05(2) 1.76(2) 2.8058(19) 177.53(13) 1
N1 H1A C19 1.05(2) 2.58(2) 3.554(2) 155.3(8) 1
O3 H3B O4 1.02(2) 1.66(2) 2.6760(17) 172.0(4) 1
N3 H3 O1 1.10(2) 1.62(2) 2.7109(18) 171.6(4) 1
N3 H3 C19 1.10(2) 2.47(2) 3.511(2) 157.6(6) 1
O4 H4A O2 0.96(2) 1.77(2) 2.6984(16) 161.2(8) 2
N2 H2B O4 1.02(2) 2.45(2) 3.0513(19) 117.(1) 1_556
N1 H1B N4 1.06(2) 2.12(2) 3.1490(19) 162.9(6) 2_556
C15 H15 C9 1.083 2.763 3.494(2) 125 7_556
N2 H2B C5 1.02(2) 2.68(2) 3.505(2) 137.(1) 7_557
O4 H4B O2 0.99(2) 1.79(2) 2.7723(16) 176.48(16) 6_565
O4 H4B C19 0.99(2) 2.46(2) 3.3305(19) 148.(1) 6_565
C2 H2 O1 1.083 2.489 3.4048(18) 142 6_566
C2 H2 C14 1.083 2.762 3.497(2) 125 6_566
C15 H15 Cl1 1.083 2.853 3.4746(16) 117 2_656
####################################################################### 
# 
# 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_IAM_MoPro
_database_code_depnum_ccdc_archive 'CCDC 2386993'
loop_
_audit_author_name
_audit_author_address
'Dr. Maqsood Ahmed'
;Materials Chemistry Laboratory, Institute of Chemistry, The Islamia University of Bahawalpur,
Pakistan
;
_audit_update_record             
;
2025-05-08 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;


_symmetry_space_group_name_H-M   'C 2/c'
#Added by publCIF


_publcif_datablock.id            {dfb70316-336d-43a2-826b-5fa161fde704}

_audit_creation_method           'MoPro v21.06             '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H14 Cl N4, C7 H5 O3, H2 O '
_chemical_formula_sum            'C19 H21 Cl N4 O4'
_chemical_formula_weight         404.830
_chemical_absolute_configuration .

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M_alt C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
H H 0.0000 0.0000 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
N N 0.0061 0.0033 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
O O 0.0106 0.0060 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
Cl Cl 0.1484 0.1585 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '

loop_
_symmetry_equiv_pos_as_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                   16.4563(6)
_cell_length_b                   14.2010(6)
_cell_length_c                   16.4360(8)
_cell_angle_alpha                90.
_cell_angle_beta                 97.994(2)
_cell_angle_gamma                90.
_cell_volume                     3803.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3865
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.4
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.745
_exptl_special_details           ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_reflns_Friedel_coverage         ?
_reflns_Friedel_fraction_full    ?
_reflns_Friedel_fraction_max     ?
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3865
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.05111
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3865
_reflns_number_gt                2633
_reflns_threshold_expression     'I > 2 σ(I)'
_computing_data_collection       
'Bruker BIS V6.2.16/2021-10-23 and APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B (2016)'
_computing_data_reduction        'SAINT V8.40B (2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w =1/[2.6628*σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     none
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         3865
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
# R_factor is R(F)  &  wR_factor is wR2(I) 
## Refinement was performed using a cutoff  I/sigmaI >    0.00
## R_factor_gt is computed  for  I/sigmaI > 2
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   0.977
# GOF(I) computed assuming all  583 parameters refined:     1.037
_refine_ls_restrained_S_all      0.000
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

_diffrn_measured_fraction_theta_max 0.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.39
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.53797 0.39718 1.12148 0.03083(3) Uani 1 d . . . .
N N1 0.06465 0.34768 0.66438 0.02127(8) Uani 1 d . . . .
N N2 0.17470 0.31317 0.93547 0.02388(9) Uani 1 d . . . .
O O1 0.22192 0.38113 0.54102 0.02248(7) Uani 1 d . . . .
O O3 0.21032 0.38274 0.15329 0.02212(7) Uani 1 d . . . .
O O2 0.08682 0.39322 0.50292 0.02220(7) Uani 1 d . . . .
O O4 0.07449 0.41969 0.04878 0.02500(7) Uani 1 d . . . .
H H4A 0.01921 0.40382 0.04237 0.03800 Uiso 1 d R U . .
N N3 0.20247 0.37559 0.70199 0.01585(8) Uani 1 d . . . .
N N4 0.11826 0.33059 0.80110 0.01805(8) Uani 1 d . . . .
C C1 0.33385 0.37290 0.90834 0.01562(9) Uani 1 d . . . .
C C2 0.32923 0.43762 0.97146 0.01930(10) Uani 1 d . . . .
H H2 0.27579 0.48251 0.96952 0.02400 Uiso 1 d R U . .
C C3 0.39224 0.44539 1.03641 0.02143(10) Uani 1 d . . . .
H H3A 0.38780 0.49565 1.08516 0.02600 Uiso 1 d R U . .
C C4 0.46031 0.38801 1.03823 0.01989(10) Uani 1 d . . . .
C C5 0.46782 0.32383 0.97642 0.01810(10) Uani 1 d . . . .
H H5 0.52214 0.28043 0.97810 0.02300 Uiso 1 d R U . .
C C6 0.40403 0.31611 0.91131 0.01713(9) Uani 1 d . . . .
H H6 0.40862 0.26582 0.86262 0.02200 Uiso 1 d R U . .
C C7 0.26405 0.36466 0.84037 0.01458(9) Uani 1 d . . . .
C C8 0.27023 0.38501 0.76061 0.01585(9) Uani 1 d . . . .
C C9 0.12857 0.35092 0.72393 0.01669(9) Uani 1 d . . . .
C C10 0.18466 0.33622 0.85839 0.01744(10) Uani 1 d . . . .
C C11 0.34632 0.42120 0.73004 0.01777(9) Uani 1 d . . . .
H H11A 0.38950 0.44480 0.78259 0.02200 Uiso 1 d R U . .
H H11B 0.33001 0.48185 0.69027 0.02200 Uiso 1 d R U . .
C C12 0.38891 0.34746 0.68190 0.02126(10) Uani 1 d . . . .
H H12A 0.44553 0.37781 0.66531 0.03300 Uiso 1 d R U . .
H H12B 0.34810 0.32761 0.62615 0.03300 Uiso 1 d R U . .
H H12C 0.40379 0.28525 0.72048 0.03300 Uiso 1 d R U . .
C C13 0.17315 0.38458 0.39843 0.01608(9) Uani 1 d . . . .
C C14 0.24796 0.35645 0.37523 0.01815(10) Uani 1 d . . . .
H H14 0.29740 0.33455 0.42187 0.02300 Uiso 1 d R U . .
C C15 0.25982 0.35599 0.29333 0.01785(10) Uani 1 d . . . .
H H15 0.31810 0.33368 0.27631 0.02300 Uiso 1 d R U . .
C C16 0.19609 0.38465 0.23294 0.01812(9) Uani 1 d . . . .
C C17 0.12156 0.41458 0.25543 0.01931(10) Uani 1 d . . . .
H H17 0.07249 0.43803 0.20905 0.02500 Uiso 1 d R U . .
C C18 0.11059 0.41399 0.33744 0.01987(10) Uani 1 d . . . .
H H18 0.05260 0.43713 0.35457 0.02400 Uiso 1 d R U . .
C C19 0.16091 0.38555 0.48672 0.01857(10) Uani 1 d . . . .
H H4B 0.07889 0.47563 0.03340 0.04800 Uiso 1 d R U . .
H H2A 0.21767 0.32654 0.97918 0.03600 Uiso 1 d R U . .
H H1A 0.07224 0.36564 0.60772 0.03900 Uiso 1 d R U . .
H H2B 0.12511 0.30604 0.94814 0.04200 Uiso 1 d R U . .
H H1B 0.01506 0.33022 0.67597 0.04300 Uiso 1 d R U . .
H H3B 0.16239 0.39479 0.12044 0.04700 Uiso 1 d R U . .
H H3 0.20738 0.38126 0.63905 0.03700 Uiso 1 d R U . .


_geom_special_details            
;                                    
;

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 C4 1.74240(10) . ?
N1 C9 1.33420(10) . ?
N1 H1B 0.89822 . ?
N1 H1A 0.99002 . ?
N2 C10 1.34034(10) . ?
N2 H2B 0.87572 . ?
N2 H2A 0.95447 . ?
O1 C19 1.24874(10) . ?
O3 C16 1.36190(10) . ?
O3 H3B 0.90796 . ?
O2 C19 1.28830(10) . ?
O4 H4B 0.83985 . ?
O4 H4A 0.92882 . ?
N3 C9 1.36153(10) . ?
N3 C8 1.37510(10) . ?
N3 H3 1.05183 . ?
N4 C9 1.33441(10) . ?
N4 C10 1.34193(10) . ?
C1 C7 1.49139(10) . ?
C1 C2 1.39599(10) . ?
C1 C6 1.40400(10) . ?
C2 C3 1.38522(10) . ?
C2 H2 1.08300 . ?
C3 C4 1.38219(10) . ?
C3 H3A 1.08300 . ?
C4 C5 1.38310(10) . ?
C5 C6 1.39520(10) . ?
C5 H5 1.08300 . ?
C6 H6 1.08300 . ?
C7 C10 1.43701(10) . ?
C7 C8 1.36000(10) . ?
C8 C11 1.50322(10) . ?
C11 C12 1.53890(10) . ?
C11 H11A 1.09200 . ?
C11 H11B 1.09200 . ?
C12 H12A 1.09500 . ?
C12 H12C 1.09500 . ?
C12 H12B 1.09500 . ?
C13 C19 1.49267(10) . ?
C13 C14 1.39685(10) . ?
C13 C18 1.39716(10) . ?
C14 C15 1.38690(10) . ?
C14 H14 1.08300 . ?
C15 C16 1.40043(10) . ?
C15 H15 1.08300 . ?
C16 C17 1.39557(10) . ?
C17 C18 1.38456(10) . ?
C17 H17 1.08300 . ?
C18 H18 1.08300 . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 H1B 120.048 . . . ?
C9 N1 H1A 119.431 . . . ?
H1B N1 H1A 120.513 . . . ?
C10 N2 H2B 119.572 . . . ?
C10 N2 H2A 119.195 . . . ?
H2B N2 H2A 117.472 . . . ?
C16 O3 H3B 108.462 . . . ?
H4B O4 H4A 108.628 . . . ?
C9 N3 C8 120.431(1) . . . ?
C9 N3 H3 118.280 . . . ?
C8 N3 H3 121.070 . . . ?
C9 N4 C10 117.085(1) . . . ?
C7 C1 C2 119.502(1) . . . ?
C7 C1 C6 121.679(1) . . . ?
C2 C1 C6 118.813(1) . . . ?
C1 C2 C3 120.855(1) . . . ?
C1 C2 H2 119.577 . . . ?
C3 C2 H2 119.568 . . . ?
C4 C3 C2 119.158(1) . . . ?
C4 C3 H3A 120.686 . . . ?
C2 C3 H3A 120.156 . . . ?
Cl1 C4 C3 118.465(1) . . . ?
Cl1 C4 C5 119.692(1) . . . ?
C3 C4 C5 121.842(1) . . . ?
C4 C5 C6 118.726(1) . . . ?
C4 C5 H5 120.933 . . . ?
C6 C5 H5 120.340 . . . ?
C1 C6 C5 120.597(1) . . . ?
C1 C6 H6 119.644 . . . ?
C5 C6 H6 119.759 . . . ?
C10 C7 C8 116.769(1) . . . ?
C10 C7 C1 119.686(1) . . . ?
C8 C7 C1 123.526(1) . . . ?
N3 C8 C7 119.521(1) . . . ?
N3 C8 C11 115.535(1) . . . ?
C7 C8 C11 124.909(1) . . . ?
N3 C9 N4 122.942(1) . . . ?
N3 C9 N1 117.170(1) . . . ?
N4 C9 N1 119.888(1) . . . ?
N4 C10 N2 117.001(1) . . . ?
N4 C10 C7 123.159(1) . . . ?
N2 C10 C7 119.839(1) . . . ?
C8 C11 C12 113.536(1) . . . ?
C8 C11 H11A 108.735 . . . ?
C8 C11 H11B 108.836 . . . ?
C12 C11 H11A 108.835 . . . ?
C12 C11 H11B 108.699 . . . ?
H11A C11 H11B 108.065 . . . ?
C11 C12 H12A 108.924 . . . ?
C11 C12 H12C 109.419 . . . ?
C11 C12 H12B 109.596 . . . ?
H12A C12 H12C 109.404 . . . ?
H12A C12 H12B 109.686 . . . ?
H12C C12 H12B 109.794 . . . ?
C19 C13 C14 120.745(1) . . . ?
C19 C13 C18 120.615(1) . . . ?
C14 C13 C18 118.622(1) . . . ?
C13 C14 C15 120.973(1) . . . ?
C13 C14 H14 119.527 . . . ?
C15 C14 H14 119.500 . . . ?
C16 C15 C14 119.602(1) . . . ?
C16 C15 H15 120.313 . . . ?
C14 C15 H15 120.085 . . . ?
O3 C16 C17 122.386(1) . . . ?
O3 C16 C15 117.618(1) . . . ?
C17 C16 C15 119.993(1) . . . ?
C16 C17 C18 119.627(1) . . . ?
C16 C17 H17 120.260 . . . ?
C18 C17 H17 120.114 . . . ?
C13 C18 C17 121.167(1) . . . ?
C13 C18 H18 119.481 . . . ?
C17 C18 H18 119.351 . . . ?
O1 C19 O2 123.13(1) . . . ?
O1 C19 C13 119.373(1) . . . ?
O2 C19 C13 117.464(1) . . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C4 C3 C2 . . . . -178.72(1) ?
Cl1 C4 C3 H3A . . . . 0.96 ?
Cl1 C4 C5 C6 . . . . 178.51(1) ?
Cl1 C4 C5 H5 . . . . -1.73 ?
N1 C9 N3 C8 . . . . 176.73(1) ?
N1 C9 N3 H3 . . . . -8.60 ?
N1 C9 N4 C10 . . . . -179.20(1) ?
N2 C10 N4 C9 . . . . -178.15(1) ?
N2 C10 C7 C8 . . . . 178.55(1) ?
N2 C10 C7 C1 . . . . -3.02(1) ?
O1 C19 C13 C14 . . . . 15.50(1) ?
O1 C19 C13 C18 . . . . -162.94(1) ?
O3 C16 C17 C18 . . . . 179.36(1) ?
O3 C16 C17 H17 . . . . -0.52 ?
O3 C16 C15 C14 . . . . -179.76(1) ?
O3 C16 C15 H15 . . . . 0.34 ?
O2 C19 C13 C14 . . . . -166.09(1) ?
O2 C19 C13 C18 . . . . 15.47(1) ?
N3 C9 N4 C10 . . . . 0.66(1) ?
N3 C9 N1 H1B . . . . 178.35 ?
N3 C9 N1 H1A . . . . -2.62 ?
N3 C8 C7 C10 . . . . -1.47(1) ?
N3 C8 C7 C1 . . . . -179.83(1) ?
N3 C8 C11 C12 . . . . -74.88(1) ?
N3 C8 C11 H11A . . . . 163.81 ?
N3 C8 C11 H11B . . . . 46.32 ?
N4 C9 N3 C8 . . . . -3.14(1) ?
N4 C9 N3 H3 . . . . 171.53 ?
N4 C9 N1 H1B . . . . -1.77 ?
N4 C9 N1 H1A . . . . 177.25 ?
N4 C10 N2 H2B . . . . -11.69 ?
N4 C10 N2 H2A . . . . -169.31 ?
N4 C10 C7 C8 . . . . -0.98(1) ?
N4 C10 C7 C1 . . . . 177.44(1) ?
C1 C7 C8 C11 . . . . -2.05(1) ?
C1 C2 C3 C4 . . . . 0.00(1) ?
C1 C2 C3 H3A . . . . -179.71 ?
C1 C6 C5 C4 . . . . 0.45(1) ?
C1 C6 C5 H5 . . . . -179.31 ?
C2 C1 C7 C10 . . . . -61.83(1) ?
C2 C1 C7 C8 . . . . 116.49(1) ?
C2 C1 C6 C5 . . . . 0.37(1) ?
C2 C1 C6 H6 . . . . -179.70 ?
C2 C3 C4 C5 . . . . 0.88(1) ?
H2 C2 C1 C7 . . . . -2.00 ?
H2 C2 C1 C6 . . . . 179.00 ?
H2 C2 C3 C4 . . . . -179.80(1) ?
H2 C2 C3 H3A . . . . 0.51 ?
C3 C4 C5 C6 . . . . -1.09(1) ?
C3 C4 C5 H5 . . . . 178.67 ?
C3 C2 C1 C7 . . . . 178.50(1) ?
C3 C2 C1 C6 . . . . -0.58(1) ?
H3A C3 C4 C5 . . . . -179.00 ?
C4 C5 C6 H6 . . . . -179.49 ?
C5 C6 C1 C7 . . . . -178.70(1) ?
H5 C5 C6 H6 . . . . 0.75 ?
C6 C1 C7 C10 . . . . 117.23(1) ?
C6 C1 C7 C8 . . . . -64.45(1) ?
H6 C6 C1 C7 . . . . 1.00 ?
C7 C10 N4 C9 . . . . 1.40(1) ?
C7 C10 N2 H2B . . . . 168.74 ?
C7 C10 N2 H2A . . . . 11.12 ?
C7 C8 N3 C9 . . . . 3.47(1) ?
C7 C8 N3 H3 . . . . -171.05 ?
C7 C8 C11 C12 . . . . 107.25(1) ?
C7 C8 C11 H11A . . . . -14.05 ?
C7 C8 C11 H11B . . . . -131.55 ?
C8 C11 C12 H12A . . . . -176.44 ?
C8 C11 C12 H12C . . . . -56.88 ?
C8 C11 C12 H12B . . . . 63.56 ?
C9 N3 C8 C11 . . . . -174.52(1) ?
C10 C7 C8 C11 . . . . 176.31(1) ?
C11 C8 N3 H3 . . . . 10.97 ?
H11A C11 C12 H12A . . . . -55.19 ?
H11A C11 C12 H12C . . . . 64.36 ?
H11A C11 C12 H12B . . . . -175.19 ?
H11B C11 C12 H12A . . . . 62.28 ?
H11B C11 C12 H12C . . . . -178.16 ?
H11B C11 C12 H12B . . . . -57.72 ?
C13 C14 C15 C16 . . . . 0.38(1) ?
C13 C14 C15 H15 . . . . -179.72 ?
C13 C18 C17 C16 . . . . 0.50(1) ?
C13 C18 C17 H17 . . . . -179.63 ?
C14 C13 C18 C17 . . . . 0.68(1) ?
C14 C13 C18 H18 . . . . -178.97 ?
C14 C15 C16 C17 . . . . 0.82(1) ?
H14 C14 C13 C19 . . . . 0.53 ?
H14 C14 C13 C18 . . . . 179.00 ?
H14 C14 C15 C16 . . . . -179.74 ?
H14 C14 C15 H15 . . . . 0.16 ?
C15 C16 O3 H3B . . . . 172.07 ?
C15 C16 C17 C18 . . . . -1.25(1) ?
C15 C16 C17 H17 . . . . 178.87 ?
C15 C14 C13 C19 . . . . -179.59(1) ?
C15 C14 C13 C18 . . . . -1.12(1) ?
H15 C15 C16 C17 . . . . -179.08 ?
C16 C17 C18 H18 . . . . -179.86 ?
C17 C16 O3 H3B . . . . -8.52 ?
C17 C18 C13 C19 . . . . 179.15(1) ?
H17 C17 C18 H18 . . . . 0.02 ?
H18 C18 C13 C19 . . . . -0.49 ?

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
C11 H11A C1 1.092 2.584 3.0443(2) 104 1
C11 H11A C6 1.092 2.781 3.3494(2) 112 1
C12 H12B O1 1.095 2.457 3.3722(2) 140 1
N2 H2A C1 0.954 2.462 2.84650(10) 104 1
N2 H2A C2 0.954 2.437 3.0857(2) 125 1
N1 H1A O2 0.990 1.815 2.80410(10) 178 1
N1 H1A C19 0.990 2.640 3.5512(2) 153 1
O3 H3B O4 0.908 1.769 2.67480(10) 175 1
N3 H3 O1 1.052 1.662 2.71000(10) 174 1
N3 H3 C19 1.052 2.515 3.5118(2) 158 1
O4 H4A O2 0.929 1.806 2.69870(10) 160 2
N2 H2B O4 0.876 2.533 3.05460(10) 119 1_556
N1 H1B N4 0.898 2.277 3.1490(2) 164 2_556
C15 H15 C9 1.083 2.765 3.4975(2) 125 7_556
O4 H4B O2 0.840 1.938 2.77680(10) 177 6_565
O4 H4B C19 0.840 2.566 3.3340(2) 153 6_565
C2 H2 O1 1.083 2.491 3.4076(2) 142 6_566
C2 H2 C14 1.083 2.765 3.5006(2) 125 6_566
C15 H15 Cl1 1.083 2.853 3.4757(2) 117 2_656

_vrf_PLAT008_IAM_MoPro           
;
PROBLEM: No _iucr_refine_reflections_details   in the CIF     Please Do !  
RESPONSE: ....
;
####################################################################### 
# 
# 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_IAM_Shelx
_database_code_depnum_ccdc_archive 'CCDC 2386994'
loop_
_audit_author_name
_audit_author_address
'Dr. Maqsood Ahmed'
;Materials Chemistry Laboratory, Institute of Chemistry, The Islamia University of Bahawalpur,
Pakistan
;
_audit_update_record             
;
2025-05-08 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_publcif_datablock.id            {20711e88-f6f5-41a7-94c1-7e6f56cf14e6}
_audit_creation_method           
;FinalCif V126 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2023-12-28
_diffrn_source_power             0.05
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C19 H21 Cl N4 O4'
_chemical_formula_moiety         'C12 H14 Cl N4, C7 H5 O3, H2 O'
_chemical_formula_weight         404.85
_chemical_melting_point          ?
_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'
_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                   16.4563(6)
_cell_length_b                   14.2010(6)
_cell_length_c                   16.4360(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.994(2)
_cell_angle_gamma                90
_cell_volume                     3803.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5867
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.25
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.979
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cobra Cryo device'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'Four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'Glass needle'
_diffrn_reflns_number            24711
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3892
_reflns_number_gt                2929
_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 BIS V6.2.16/2021-10-23 and APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B (2016)'
_computing_data_reduction        'SAINT V8.40B (2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0322P)²+4.4713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3892
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.53803(3) 0.39721(4) 1.12148(3) 0.03089(15) Uani 1 1 d . . . . .
N1 N 0.06472(11) 0.34752(13) 0.66481(12) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.17440(12) 0.31317(13) 0.93515(11) 0.0240(4) Uani 1 1 d . . . . .
O1 O 0.22188(8) 0.38109(10) 0.54095(8) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.21040(9) 0.38280(10) 0.15324(9) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.08691(8) 0.39311(10) 0.50294(8) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.07456(9) 0.41946(11) 0.04888(9) 0.0251(3) Uani 1 1 d . . . . .
H4A H 0.0199(17) 0.4034(17) 0.0425(15) 0.038 Uiso 1 1 d . U . . .
N3 N 0.20238(9) 0.37556(10) 0.70227(10) 0.0160(3) Uani 1 1 d . . . . .
N4 N 0.11830(9) 0.33071(11) 0.80113(10) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.33386(11) 0.37298(13) 0.90839(12) 0.0163(4) Uani 1 1 d . . . . .
C2 C 0.32940(12) 0.43749(13) 0.97137(12) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.282508 0.476828 0.969683 0.024 Uiso 1 1 calc R U . . .
C3 C 0.39222(12) 0.44524(14) 1.03642(12) 0.0220(4) Uani 1 1 d . . . . .
H3A H 0.388405 0.489274 1.079240 0.026 Uiso 1 1 calc R U . . .
C4 C 0.46056(12) 0.38824(14) 1.03841(12) 0.0205(4) Uani 1 1 d . . . . .
C5 C 0.46769(11) 0.32412(13) 0.97626(12) 0.0189(4) Uani 1 1 d . . . . .
H5 H 0.515324 0.285998 0.977850 0.023 Uiso 1 1 calc R U . . .
C6 C 0.40395(11) 0.31648(13) 0.91153(12) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.408026 0.272342 0.868856 0.022 Uiso 1 1 calc R U . . .
C7 C 0.26403(11) 0.36455(12) 0.84045(11) 0.0154(4) Uani 1 1 d . . . . .
C8 C 0.27012(11) 0.38502(12) 0.76048(12) 0.0165(4) Uani 1 1 d . . . . .
C9 C 0.12864(11) 0.35089(13) 0.72385(12) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.18458(11) 0.33616(13) 0.85850(12) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.34608(11) 0.42077(13) 0.72997(12) 0.0180(4) Uani 1 1 d . . . . .
H11A H 0.385158 0.442425 0.777558 0.022 Uiso 1 1 calc R U . . .
H11B H 0.331372 0.475916 0.694084 0.022 Uiso 1 1 calc R U . . .
C12 C 0.38897(12) 0.34770(14) 0.68205(13) 0.0218(4) Uani 1 1 d . . . . .
H12A H 0.439614 0.374710 0.666998 0.033 Uiso 1 1 calc R U . . .
H12B H 0.352504 0.329817 0.632150 0.033 Uiso 1 1 calc R U . . .
H12C H 0.402202 0.291859 0.716379 0.033 Uiso 1 1 calc R U . . .
C13 C 0.17319(11) 0.38462(12) 0.39851(12) 0.0174(4) Uani 1 1 d . . . . .
C14 C 0.24759(12) 0.35657(13) 0.37507(12) 0.0191(4) Uani 1 1 d . . . . .
H14 H 0.291023 0.337357 0.415909 0.023 Uiso 1 1 calc R U . . .
C15 C 0.25943(12) 0.35617(13) 0.29333(12) 0.0188(4) Uani 1 1 d . . . . .
H15 H 0.310544 0.336584 0.278395 0.023 Uiso 1 1 calc R U . . .
C16 C 0.19610(12) 0.38460(13) 0.23292(12) 0.0185(4) Uani 1 1 d . . . . .
C17 C 0.12188(12) 0.41441(14) 0.25558(12) 0.0205(4) Uani 1 1 d . . . . .
H17 H 0.078836 0.434972 0.214896 0.025 Uiso 1 1 calc R U . . .
C18 C 0.11095(12) 0.41402(13) 0.33750(12) 0.0203(4) Uani 1 1 d . . . . .
H18 H 0.060022 0.434180 0.352484 0.024 Uiso 1 1 calc R U . . .
C19 C 0.16074(11) 0.38562(12) 0.48663(12) 0.0179(4) Uani 1 1 d . . . . .
H4B H 0.0786(16) 0.474(2) 0.0342(17) 0.048(8) Uiso 1 1 d . . . . .
H2A H 0.2137(15) 0.3249(17) 0.9752(16) 0.036(7) Uiso 1 1 d . . . . .
H1A H 0.0713(15) 0.3616(17) 0.6133(17) 0.039(7) Uiso 1 1 d . . . . .
H2B H 0.1260(16) 0.3066(18) 0.9474(16) 0.042(7) Uiso 1 1 d . . . . .
H1B H 0.0165(16) 0.3317(17) 0.6778(16) 0.043(7) Uiso 1 1 d . . . . .
H3B H 0.1640(17) 0.3963(18) 0.1200(17) 0.047(8) Uiso 1 1 d . . . . .
H3 H 0.2061(14) 0.3810(16) 0.6433(16) 0.037(7) Uiso 1 1 d . . . . .


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 C4 1.738(2) . ?
N1 C9 1.329(3) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.88(3) . ?
N2 C10 1.334(3) . ?
N2 H2A 0.87(3) . ?
N2 H2B 0.85(3) . ?
O1 C19 1.250(2) . ?
O3 C16 1.363(2) . ?
O3 H3B 0.90(3) . ?
O2 C19 1.284(2) . ?
O4 H4A 0.92(3) . ?
O4 H4B 0.81(3) . ?
N3 C8 1.371(2) . ?
N3 C9 1.357(2) . ?
N3 H3 0.98(3) . ?
N4 C9 1.336(2) . ?
N4 C10 1.341(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.400(3) . ?
C1 C7 1.492(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.382(3) . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.363(3) . ?
C7 C10 1.438(3) . ?
C8 C11 1.499(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.533(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(3) . ?
C13 C18 1.394(3) . ?
C13 C19 1.491(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(3) . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9500 . ?

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
C9 N1 H1A 119.8(16) . . ?
C9 N1 H1B 118.7(17) . . ?
H1A N1 H1B 121(2) . . ?
C10 N2 H2A 119.3(16) . . ?
C10 N2 H2B 119.6(17) . . ?
H2A N2 H2B 117(2) . . ?
C16 O3 H3B 109.6(17) . . ?
H4A O4 H4B 109(2) . . ?
C8 N3 H3 121.7(14) . . ?
C9 N3 C8 120.86(17) . . ?
C9 N3 H3 117.3(14) . . ?
C9 N4 C10 117.23(16) . . ?
C2 C1 C6 118.56(18) . . ?
C2 C1 C7 119.65(16) . . ?
C6 C1 C7 121.78(17) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.05(18) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 C2 119.30(19) . . ?
C4 C3 H3A 120.4 . . ?
C3 C4 Cl1 118.75(16) . . ?
C3 C4 C5 121.29(18) . . ?
C5 C4 Cl1 119.95(15) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.89(18) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.90(18) . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C1 123.53(17) . . ?
C8 C7 C10 116.71(17) . . ?
C10 C7 C1 119.73(17) . . ?
N3 C8 C11 115.77(16) . . ?
C7 C8 N3 119.35(17) . . ?
C7 C8 C11 124.85(17) . . ?
N1 C9 N3 117.66(18) . . ?
N1 C9 N4 119.61(17) . . ?
N4 C9 N3 122.74(17) . . ?
N2 C10 N4 116.94(18) . . ?
N2 C10 C7 120.03(18) . . ?
N4 C10 C7 123.02(17) . . ?
C8 C11 H11A 108.7 . . ?
C8 C11 H11B 108.7 . . ?
C8 C11 C12 114.06(16) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.23(18) . . ?
C14 C13 C19 121.11(17) . . ?
C18 C13 C19 120.64(17) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.19(18) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.83(18) . . ?
C16 C15 H15 120.1 . . ?
O3 C16 C15 117.82(17) . . ?
O3 C16 C17 122.56(18) . . ?
C17 C16 C15 119.61(18) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.82(18) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.30(18) . . ?
C17 C18 H18 119.3 . . ?
O1 C19 O2 123.08(18) . . ?
O1 C19 C13 119.18(17) . . ?
O2 C19 C13 117.73(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
O4 H4A O2 0.92(3) 1.82(3) 2.701(2) 160(2) 2 yes
C15 H15 Cl1 0.95 2.92 3.480(2) 119.0 2_656 yes
O4 H4B O2 0.81(3) 1.97(3) 2.782(2) 178(3) 6_565 yes
N1 H1A O2 0.89(3) 1.92(3) 2.811(2) 179(3) . yes
N2 H2B O4 0.85(3) 2.54(3) 3.054(2) 120(2) 1_556 yes
N1 H1B N4 0.88(3) 2.29(3) 3.148(2) 164(2) 2_556 yes
O3 H3B O4 0.90(3) 1.78(3) 2.673(2) 176(3) . yes

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 C4 C5 C6 178.32(15) . . . . ?
O3 C16 C17 C18 179.57(17) . . . . ?
N3 C8 C11 C12 -74.9(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C7 C8 N3 -179.69(16) . . . . ?
C1 C7 C8 C11 -1.6(3) . . . . ?
C1 C7 C10 N2 -3.2(3) . . . . ?
C1 C7 C10 N4 177.26(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C7 C8 116.4(2) . . . . ?
C2 C1 C7 C10 -61.7(2) . . . . ?
C2 C3 C4 Cl1 -178.78(15) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 C7 C8 -64.6(3) . . . . ?
C6 C1 C7 C10 117.3(2) . . . . ?
C7 C1 C2 C3 178.27(18) . . . . ?
C7 C1 C6 C5 -178.70(17) . . . . ?
C7 C8 C11 C12 107.0(2) . . . . ?
C8 N3 C9 N1 176.75(17) . . . . ?
C8 N3 C9 N4 -2.9(3) . . . . ?
C8 C7 C10 N2 178.62(17) . . . . ?
C8 C7 C10 N4 -1.0(3) . . . . ?
C9 N3 C8 C7 3.4(3) . . . . ?
C9 N3 C8 C11 -174.79(16) . . . . ?
C9 N4 C10 N2 -178.03(17) . . . . ?
C9 N4 C10 C7 1.6(3) . . . . ?
C10 N4 C9 N1 -179.29(17) . . . . ?
C10 N4 C9 N3 0.4(3) . . . . ?
C10 C7 C8 N3 -1.6(3) . . . . ?
C10 C7 C8 C11 176.51(16) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C14 C13 C19 O1 15.5(3) . . . . ?
C14 C13 C19 O2 -165.90(17) . . . . ?
C14 C15 C16 O3 -179.80(17) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
C18 C13 C19 O1 -162.97(17) . . . . ?
C18 C13 C19 O2 15.6(3) . . . . ?
C19 C13 C14 C15 -179.58(17) . . . . ?
C19 C13 C18 C17 179.32(17) . . . . ?


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_vrf_PLAT008_IAM_MoPro           
;
PROBLEM: No _iucr_refine_reflections_details   in the CIF     Please Do !  
RESPONSE: The common reflection file for the three data blocks has been embedded 
with the data block IAM_Shelx of this combined cif.
;
_vrf_PLAT008_ELMAM2              
;
PROBLEM: No _iucr_refine_reflections_details   in the CIF     Please Do !  
RESPONSE: The common reflection file for the three data blocks has been embedded 
with the data block IAM_Shelx of this combined cif.
;
_vrf_PLAT355_ELMAM2              
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O3       - H3B      .       1.02 Ang.  
RESPONSE: During ELMAM2 refinement, H atoms on heteroatoms were freely refined.
The transferred multipolar parameters are more realistic than the van der Waal's distances 
used by the IUCr Checkcif, hence this alert.
;
_vrf_PLAT353_ELMAM2              
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H2A      .       1.08 Ang.  
RESPONSE: During ELMAM2 refinement, H atoms on heteroatoms were freely refined.
The transferred multipolar parameters are more realistic than the van der Waal's distances 
used by the IUCr Checkcif, hence this alert.
;
####################################################################### 
# 
# 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_mo_p3after150tga_aqsa_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2388091'
loop_
_audit_author_name
_audit_author_address
'Dr. Maqsood Ahmed'
;Materials Chemistry Laboratory, Institute of Chemistry, The Islamia University of Bahawalpur, 
Pakistan
;
#Added by publCIF



_audit_update_record             
;
2024-10-01 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_publcif_datablock.id            {6d7673e9-200e-4669-b681-9a129d1f5d22}
# publcif _publ_body_element loop end
_audit_creation_date             2024-09-29
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2020.12.29 svn.rb'efd66209' for OlexSys, GUI svn.r6244)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 Cl N4, C7 H5 O3'
_chemical_formula_sum            'C19 H19 Cl N4 O3'
_chemical_formula_weight         386.83
_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                   23.295(2)
_cell_length_b                   14.4908(15)
_cell_length_c                   11.5884(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.772(3)
_cell_angle_gamma                90
_cell_volume                     3842.9(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3496
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
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    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1895
_diffrn_reflns_av_unetI/netI     0.1518
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14015
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.354
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_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                1502
_reflns_number_total             3496
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2077
_refine_ls_R_factor_gt           0.0763
_refine_ls_restrained_S_all      1.016
_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)+(0.0574P)²+1.1061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1809
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C5(H5), C3(H3A), C2(H2), C18(H18), C17(H17), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.27095(7) 0.88425(10) 0.62193(15) 0.0685(5) Uani 1 1 d . . . . .
O2 O 0.46403(16) 0.2298(2) 0.4501(3) 0.0572(11) Uani 1 1 d . . . . .
O3 O 0.34644(16) -0.1378(2) 0.2243(4) 0.0587(12) Uani 1 1 d . . . . .
H3B H 0.370(2) -0.152(4) 0.170(6) 0.088 Uiso 1 1 d . U . . .
O1 O 0.40222(16) 0.2026(2) 0.5715(3) 0.0550(10) Uani 1 1 d . . . . .
N3 N 0.40645(17) 0.3633(3) 0.6982(4) 0.0446(12) Uani 1 1 d . . . . .
H3 H 0.400220 0.315122 0.654216 0.054 Uiso 1 1 calc R U . . .
N4 N 0.45858(16) 0.4291(3) 0.8710(4) 0.0431(11) Uani 1 1 d . . . . .
N2 N 0.45909(19) 0.5851(3) 0.8914(4) 0.0481(13) Uani 1 1 d . . . . .
H2A H 0.448(2) 0.645(4) 0.876(5) 0.072 Uiso 1 1 d . U . . .
H2B H 0.490(2) 0.574(3) 0.960(5) 0.072 Uiso 1 1 d . U . . .
N1 N 0.4564(2) 0.2720(3) 0.8458(5) 0.0635(16) Uani 1 1 d . . . . .
H1A H 0.488(2) 0.262(4) 0.922(6) 0.095 Uiso 1 1 d . U . . .
H1B H 0.447(3) 0.227(4) 0.804(6) 0.095 Uiso 1 1 d . U . . .
C1 C 0.3649(2) 0.6124(3) 0.6949(5) 0.0408(13) Uani 1 1 d . . . . .
C6 C 0.3115(2) 0.6280(3) 0.7248(5) 0.0463(14) Uani 1 1 d . . . . .
H6 H 0.294120 0.580929 0.760574 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2826(2) 0.7113(4) 0.7035(5) 0.0508(15) Uani 1 1 d . . . . .
H5 H 0.246998 0.720875 0.726759 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3075(2) 0.7796(3) 0.6476(5) 0.0446(14) Uani 1 1 d . . . . .
C3 C 0.3611(2) 0.7677(4) 0.6179(5) 0.0619(17) Uani 1 1 d . . . . .
H3A H 0.378293 0.815393 0.582691 0.074 Uiso 1 1 calc R U . . .
C2 C 0.3893(2) 0.6841(4) 0.6407(5) 0.0603(17) Uani 1 1 d . . . . .
H2 H 0.425530 0.675594 0.619369 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3951(2) 0.5226(3) 0.7241(5) 0.0395(13) Uani 1 1 d . . . . .
C8 C 0.3817(2) 0.4447(4) 0.6564(5) 0.0443(14) Uani 1 1 d . . . . .
C9 C 0.4404(2) 0.3549(4) 0.8059(5) 0.0454(14) Uani 1 1 d . . . . .
C10 C 0.4382(2) 0.5119(3) 0.8281(5) 0.0407(13) Uani 1 1 d . . . . .
C11 C 0.3389(2) 0.4391(4) 0.5434(5) 0.0546(16) Uani 1 1 d . . . . .
H11A H 0.358836 0.415509 0.483097 0.065 Uiso 1 1 calc R U . . .
H11B H 0.325295 0.500811 0.520403 0.065 Uiso 1 1 calc R U . . .
C12 C 0.2869(2) 0.3789(4) 0.5483(6) 0.079(2) Uani 1 1 d . . . . .
H12A H 0.261148 0.379524 0.473302 0.118 Uiso 1 1 calc R U . . .
H12B H 0.266672 0.401919 0.607276 0.118 Uiso 1 1 calc R U . . .
H12C H 0.299792 0.316925 0.567503 0.118 Uiso 1 1 calc R U . . .
C13 C 0.4058(2) 0.0954(3) 0.4184(5) 0.0385(13) Uani 1 1 d . . . . .
C18 C 0.4327(2) 0.0661(4) 0.3279(5) 0.0549(16) Uani 1 1 d . . . . .
H18 H 0.464147 0.099793 0.311331 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4147(2) -0.0104(3) 0.2622(5) 0.0521(16) Uani 1 1 d . . . . .
H17 H 0.433028 -0.027566 0.200745 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3685(2) -0.0623(3) 0.2883(5) 0.0439(14) Uani 1 1 d . . . . .
C15 C 0.3427(2) -0.0365(3) 0.3797(5) 0.0459(14) Uani 1 1 d . . . . .
H15 H 0.312278 -0.071594 0.398205 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3614(2) 0.0412(3) 0.4451(5) 0.0458(14) Uani 1 1 d . . . . .
H14 H 0.343715 0.057239 0.507977 0.055 Uiso 1 1 calc R U . . .
C19 C 0.4255(2) 0.1815(3) 0.4839(5) 0.0420(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.738(5) . ?
O2 C19 1.257(5) . ?
O3 H3B 0.93(6) . ?
O3 C16 1.367(6) . ?
O1 C19 1.274(6) . ?
N3 H3 0.8600 . ?
N3 C8 1.362(6) . ?
N3 C9 1.353(6) . ?
N4 C9 1.336(6) . ?
N4 C10 1.350(6) . ?
N2 H2A 0.92(5) . ?
N2 H2B 0.98(5) . ?
N2 C10 1.329(6) . ?
N1 H1A 1.05(6) . ?
N1 H1B 0.82(6) . ?
N1 C9 1.317(6) . ?
C1 C6 1.371(6) . ?
C1 C2 1.390(7) . ?
C1 C7 1.489(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(7) . ?
C4 C3 1.365(7) . ?
C3 H3A 0.9300 . ?
C3 C2 1.381(7) . ?
C2 H2 0.9300 . ?
C7 C8 1.376(7) . ?
C7 C10 1.426(7) . ?
C8 C11 1.493(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.501(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.384(7) . ?
C13 C14 1.380(6) . ?
C13 C19 1.488(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.367(7) . ?
C17 H17 0.9300 . ?
C17 C16 1.391(6) . ?
C16 C15 1.364(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(6) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 H3B 110(4) . . ?
C8 N3 H3 118.6 . . ?
C9 N3 H3 118.6 . . ?
C9 N3 C8 122.7(4) . . ?
C9 N4 C10 117.0(4) . . ?
H2A N2 H2B 117(5) . . ?
C10 N2 H2A 126(4) . . ?
C10 N2 H2B 117(3) . . ?
H1A N1 H1B 117(6) . . ?
C9 N1 H1A 122(3) . . ?
C9 N1 H1B 119(5) . . ?
C6 C1 C2 117.3(5) . . ?
C6 C1 C7 120.0(4) . . ?
C2 C1 C7 122.7(4) . . ?
C1 C6 H6 118.9 . . ?
C1 C6 C5 122.3(5) . . ?
C5 C6 H6 118.9 . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 H5 120.6 . . ?
C5 C4 Cl1 118.3(4) . . ?
C3 C4 Cl1 120.6(4) . . ?
C3 C4 C5 121.1(5) . . ?
C4 C3 H3A 120.4 . . ?
C4 C3 C2 119.2(5) . . ?
C2 C3 H3A 120.4 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 H2 119.3 . . ?
C8 C7 C1 122.7(5) . . ?
C8 C7 C10 116.2(5) . . ?
C10 C7 C1 121.0(5) . . ?
N3 C8 C7 118.2(5) . . ?
N3 C8 C11 115.6(5) . . ?
C7 C8 C11 126.1(5) . . ?
N4 C9 N3 121.2(5) . . ?
N1 C9 N3 118.9(5) . . ?
N1 C9 N4 119.8(5) . . ?
N4 C10 C7 123.4(5) . . ?
N2 C10 N4 116.1(5) . . ?
N2 C10 C7 120.5(5) . . ?
C8 C11 H11A 108.7 . . ?
C8 C11 H11B 108.7 . . ?
C8 C11 C12 114.2(5) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C19 120.2(5) . . ?
C14 C13 C18 117.4(5) . . ?
C14 C13 C19 122.3(5) . . ?
C13 C18 H18 118.8 . . ?
C17 C18 C13 122.4(5) . . ?
C17 C18 H18 118.8 . . ?
C18 C17 H17 120.4 . . ?
C18 C17 C16 119.1(5) . . ?
C16 C17 H17 120.4 . . ?
O3 C16 C17 122.9(5) . . ?
C15 C16 O3 117.7(5) . . ?
C15 C16 C17 119.4(5) . . ?
C16 C15 H15 119.6 . . ?
C16 C15 C14 120.7(5) . . ?
C14 C15 H15 119.6 . . ?
C13 C14 C15 120.8(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
O2 C19 O1 123.3(5) . . ?
O2 C19 C13 118.5(5) . . ?
O1 C19 C13 118.1(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 C4 C3 C2 179.2(5) . . . . ?
O3 C16 C15 C14 -177.5(5) . . . . ?
N3 C8 C11 C12 60.7(7) . . . . ?
C1 C6 C5 C4 2.0(8) . . . . ?
C1 C7 C8 N3 -171.8(4) . . . . ?
C1 C7 C8 C11 3.8(8) . . . . ?
C1 C7 C10 N4 166.5(5) . . . . ?
C1 C7 C10 N2 -10.9(7) . . . . ?
C6 C1 C2 C3 0.0(8) . . . . ?
C6 C1 C7 C8 81.2(7) . . . . ?
C6 C1 C7 C10 -95.8(6) . . . . ?
C6 C5 C4 Cl1 -179.7(4) . . . . ?
C6 C5 C4 C3 -3.0(8) . . . . ?
C5 C4 C3 C2 2.6(9) . . . . ?
C4 C3 C2 C1 -1.0(9) . . . . ?
C2 C1 C6 C5 -0.5(8) . . . . ?
C2 C1 C7 C8 -100.8(6) . . . . ?
C2 C1 C7 C10 82.2(7) . . . . ?
C7 C1 C6 C5 177.6(5) . . . . ?
C7 C1 C2 C3 -178.0(6) . . . . ?
C7 C8 C11 C12 -115.0(6) . . . . ?
C8 N3 C9 N4 -9.9(8) . . . . ?
C8 N3 C9 N1 171.3(5) . . . . ?
C8 C7 C10 N4 -10.7(7) . . . . ?
C8 C7 C10 N2 171.9(5) . . . . ?
C9 N3 C8 C7 4.3(7) . . . . ?
C9 N3 C8 C11 -171.7(5) . . . . ?
C9 N4 C10 N2 -176.8(5) . . . . ?
C9 N4 C10 C7 5.7(7) . . . . ?
C10 N4 C9 N3 4.6(7) . . . . ?
C10 N4 C9 N1 -176.6(5) . . . . ?
C10 C7 C8 N3 5.4(7) . . . . ?
C10 C7 C8 C11 -179.0(5) . . . . ?
C13 C18 C17 C16 -1.5(9) . . . . ?
C18 C13 C14 C15 -3.2(8) . . . . ?
C18 C13 C19 O2 4.7(7) . . . . ?
C18 C13 C19 O1 -175.4(5) . . . . ?
C18 C17 C16 O3 177.6(5) . . . . ?
C18 C17 C16 C15 -0.8(8) . . . . ?
C17 C16 C15 C14 1.0(8) . . . . ?
C16 C15 C14 C13 1.1(8) . . . . ?
C14 C13 C18 C17 3.5(8) . . . . ?
C14 C13 C19 O2 -176.2(5) . . . . ?
C14 C13 C19 O1 3.8(7) . . . . ?
C19 C13 C18 C17 -177.3(5) . . . . ?
C19 C13 C14 C15 177.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


_vrf_RINTA01_mo_p3after150tga_aqsa_0m_a 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal quality had gradually deteriorated at high temperature 
resulting in an elevated value of the Rint.
;
_vrf_PLAT020_mo_p3after150tga_aqsa_0m_a 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.190 Report
RESPONSE: The crystal quality had gradually deteriorated at high temperature 
resulting in an elevated value of the Rint.
;
_vrf_PLAT026_mo_p3after150tga_aqsa_0m_a 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        43% Check 
RESPONSE: A low redundancy but complete data set was collected owing to 
deteriorating crystal quality at elevated temperatures using phi scan only, 
in order to verify the atomic positions. Thus the ratio is low.
;
