# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Multipolar_MoPro
_database_code_depnum_ccdc_archive 'CCDC 2091231'
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             
;
2022-01-28 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;


_refine_ls_number_constraints    ?
#Added by publCIF




_cell_special_details            ?
#Added by publCIF




_symmetry_space_group_name_H-M   'P 21/c'
#Added by publCIF


_publcif_datablock.id            {8c50a799-5553-43b5-bae9-dca087e1e25d}

_audit_creation_method           'MoPro v20.06             '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H17 Cl N2 O3'
_chemical_formula_sum            'C18 H17 Cl N2 O3'
_chemical_formula_weight         344.777
_chemical_absolute_configuration .

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M_alt 'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   12.4003(3)
_cell_length_b                   7.1632(1)
_cell_length_c                   18.4777(4)
_cell_angle_alpha                90.
_cell_angle_beta                 92.6750(1)
_cell_angle_gamma                90.
_cell_volume                     1639.51(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      45.3
_exptl_crystal_description       neddle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_process_details   Numerical
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.991
_exptl_special_details           ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '1 us'
_reflns_Friedel_coverage         ?
_reflns_Friedel_fraction_full    ?
_reflns_Friedel_fraction_max     ?
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  
'Bruker D8 Venture with PHOTON II Detector (Bruker, 2016)'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14197
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.03691
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         42.47
_reflns_number_total             9233
_reflns_number_gt                9233
_reflns_threshold_expression     >2.0sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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/[1.3895*σ²(Fo²)+0.0005*Yo²]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
# 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         9233
_refine_ls_number_parameters     804
_refine_ls_number_restraints     0
# R_factor is R(F)  &  wR_factor is wR2(I) 
## Refinement was performed using a cutoff  I/sigmaI >   2.00
## R_factor_gt is computed  for  I/sigmaI > 2
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0312
_refine_ls_wR_factor_gt          0.0312
_refine_ls_goodness_of_fit_ref   1.044
# GOF(I) computed assuming  all parameters refined:    1004
_refine_ls_restrained_S_all      0.000
_refine_ls_shift/su_max          -0.012
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        42.47
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.37
_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 0.84398(12) 0.5013(2) 0.45161(10) 0.02524(4) Uani 1 d . . . .
N N1 0.28247(8) 0.67481(14) 0.31785(6) 0.01280(8) Uani 1 d . . . .
O O1 0.35761(7) 0.45109(14) 0.39553(5) 0.01559(8) Uani 1 d . . . .
C C1 0.20748(7) 0.55867(12) 0.27864(6) 0.01244(7) Uani 1 d . . . .
O O2 0.51865(10) 0.29644(16) 0.46203(7) 0.01527(10) Uani 1 d . . . .
H H2 0.4587(9) 0.369(2) 0.432(12) 0.02490 Uani 1 d D U . .
N N2 0.31822(9) 0.83706(13) 0.28514(6) 0.01331(8) Uani 1 d . . . .
C C2 0.20739(8) 0.55179(14) 0.20320(7) 0.01558(9) Uani 1 d . . . .
H H2A 0.2647(9) 0.6354(17) 0.174(12) 0.02955 Uani 1 d D U . .
C C3 0.13378(9) 0.43705(14) 0.16525(7) 0.01937(9) Uani 1 d . . . .
H H3 0.1329(14) 0.432(2) 0.106(12) 0.03544 Uani 1 d D U . .
O O3 0.62812(12) 0.4149(2) 0.38071(10) 0.02066(15) Uani 1 d . . . .
C C4 0.06083(8) 0.32979(14) 0.20254(7) 0.02104(9) Uani 1 d . . . .
H H4 0.0034(11) 0.2397(19) 0.173(12) 0.04084 Uani 1 d D U . .
C C5 0.06146(8) 0.33766(14) 0.27801(8) 0.01956(9) Uani 1 d . . . .
H H5 0.0040(10) 0.254(2) 0.307(12) 0.03917 Uani 1 d D U . .
C C6 0.13475(8) 0.45198(14) 0.31657(7) 0.01567(8) Uani 1 d . . . .
H H6 0.1347(13) 0.458(2) 0.375(12) 0.03241 Uani 1 d D U . .
C C7 0.36425(7) 0.60736(13) 0.36513(5) 0.01193(8) Uani 1 d . . . .
C C8 0.44737(7) 0.74418(13) 0.36617(5) 0.01298(8) Uani 1 d . . . .
H H8 0.522(12) 0.740(2) 0.3985(8) 0.03081 Uani 1 d D U . .
C C9 0.41516(7) 0.88194(12) 0.31840(5) 0.01245(8) Uani 1 d . . . .
C C10 0.47015(10) 1.05856(16) 0.30038(7) 0.02040(10) Uani 1 d . . . .
H H10A 0.4697(13) 1.075(2) 0.241(12) 0.04004 Uani 1 d D U . .
H H10B 0.554(12) 1.055(2) 0.3222(9) 0.04223 Uani 1 d D U . .
H H10C 0.4278(11) 1.1768(13) 0.324(12) 0.04122 Uani 1 d D U . .
C C11 0.23820(7) 0.97432(12) 0.25996(5) 0.01699(8) Uani 1 d . . . .
H H11A 0.2785(19) 1.093(2) 0.236(12) 0.03624 Uani 1 d D U . .
H H11B 0.1926(19) 1.023(4) 0.306(12) 0.03602 Uani 1 d D U . .
H H11C 0.1828(17) 0.910(3) 0.219(12) 0.03488 Uani 1 d D U . .
C C12 0.70197(8) 0.21650(13) 0.47438(5) 0.01186(8) Uani 1 d . . . .
C C13 0.67934(8) 0.04034(13) 0.50286(5) 0.01426(8) Uani 1 d . . . .
H H13 0.598(12) -0.0147(19) 0.4967(9) 0.02844 Uani 1 d D U . .
C C14 0.75889(9) -0.06564(13) 0.53911(6) 0.01734(9) Uani 1 d . . . .
H H14 0.7400(12) -0.2038(9) 0.560(12) 0.02944 Uani 1 d D U . .
C C15 0.86294(8) 0.00655(16) 0.54879(6) 0.01847(10) Uani 1 d . . . .
H H15 0.9252(9) -0.0744(19) 0.578(12) 0.03253 Uani 1 d D U . .
C C16 0.88745(9) 0.18167(17) 0.52135(6) 0.01758(11) Uani 1 d . . . .
H H16 0.969(12) 0.2385(19) 0.5292(8) 0.03723 Uani 1 d D U . .
C C17 0.80770(8) 0.28454(12) 0.48362(5) 0.01446(8) Uani 1 d . . . .
C C18 0.61354(7) 0.32202(12) 0.43433(5) 0.01277(8) Uani 1 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 C17 1.7289(7) . ?
N1 N2 1.3920(7) . ?
N1 C7 1.3937(8) . ?
N1 C1 1.4208(8) . ?
O1 C7 1.2569(7) . ?
C1 C2 1.3948(9) . ?
C1 C6 1.3956(9) . ?
O2 C18 1.3177(8) . ?
O2 H2 1.04627 . ?
N2 C9 1.3628(8) . ?
N2 C11 1.4576(8) . ?
C2 C3 1.3930(9) . ?
C2 H2A 1.08886 . ?
C3 C4 1.3934(10) . ?
C3 H3 1.08998 . ?
O3 C18 1.2138(8) . ?
C4 C5 1.3953(11) . ?
C4 H4 1.08821 . ?
C5 C6 1.3942(9) . ?
C5 H5 1.08982 . ?
C6 H6 1.08870 . ?
C7 C8 1.4218(8) . ?
C8 C9 1.3709(9) . ?
C8 H8 1.08040 . ?
C9 C10 1.4825(8) . ?
C10 H10B 1.09304 . ?
C10 H10A 1.09712 . ?
C10 H10C 1.09980 . ?
C11 H11A 1.09167 . ?
C11 H11C 1.09265 . ?
C11 H11B 1.09634 . ?
C12 C17 1.4016(8) . ?
C12 C18 1.4986(8) . ?
C12 C13 1.4006(8) . ?
C13 C14 1.3916(9) . ?
C13 H13 1.08837 . ?
C14 C15 1.3938(9) . ?
C14 H14 1.08931 . ?
C15 C16 1.3918(9) . ?
C15 H15 1.08985 . ?
C16 C17 1.3938(9) . ?
C16 H16 1.08872 . ?

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
N2 N1 C7 108.93(4) . . . ?
N2 N1 C1 118.79(4) . . . ?
C7 N1 C1 123.80(4) . . . ?
N1 C1 C2 120.02(5) . . . ?
N1 C1 C6 119.17(5) . . . ?
C2 C1 C6 120.81(5) . . . ?
C18 O2 H2 110.4(5) . . . ?
N1 N2 C9 107.05(4) . . . ?
N1 N2 C11 118.42(4) . . . ?
C9 N2 C11 123.90(5) . . . ?
C1 C2 C3 119.60(6) . . . ?
C1 C2 H2A 120.10(6) . . . ?
C3 C2 H2A 120.3(2) . . . ?
C2 C3 C4 120.11(6) . . . ?
C2 C3 H3 120.0(5) . . . ?
C4 C3 H3 119.9(5) . . . ?
C3 C4 C5 119.90(6) . . . ?
C3 C4 H4 120.3(3) . . . ?
C5 C4 H4 119.83(7) . . . ?
C6 C5 C4 120.51(6) . . . ?
C6 C5 H5 119.6(3) . . . ?
C4 C5 H5 119.89(7) . . . ?
C1 C6 C5 119.08(5) . . . ?
C1 C6 H6 120.7(5) . . . ?
C5 C6 H6 120.2(5) . . . ?
O1 C7 N1 121.88(5) . . . ?
O1 C7 C8 132.10(5) . . . ?
N1 C7 C8 105.98(5) . . . ?
C7 C8 C9 107.35(5) . . . ?
C7 C8 H8 126.4(4) . . . ?
C9 C8 H8 126.3(5) . . . ?
N2 C9 C8 110.18(5) . . . ?
N2 C9 C10 120.35(5) . . . ?
C8 C9 C10 129.47(5) . . . ?
C9 C10 H10B 109.7(5) . . . ?
C9 C10 H10A 109.6(5) . . . ?
C9 C10 H10C 109.5(5) . . . ?
H10B C10 H10A 109.3(8) . . . ?
H10B C10 H10C 109.3(7) . . . ?
H10A C10 H10C 109.5(5) . . . ?
N2 C11 H11A 109.7(7) . . . ?
N2 C11 H11C 109.4(7) . . . ?
N2 C11 H11B 109.6(6) . . . ?
H11A C11 H11C 109.2(7) . . . ?
H11A C11 H11B 109.6(9) . . . ?
H11C C11 H11B 109.3(8) . . . ?
C17 C12 C18 122.92(5) . . . ?
C17 C12 C13 118.05(5) . . . ?
C18 C12 C13 119.02(5) . . . ?
C12 C13 C14 121.49(5) . . . ?
C12 C13 H13 119.3(5) . . . ?
C14 C13 H13 119.2(4) . . . ?
C13 C14 C15 119.37(5) . . . ?
C13 C14 H14 120.3(4) . . . ?
C15 C14 H14 120.3(4) . . . ?
C16 C15 C14 120.28(5) . . . ?
C16 C15 H15 120.0(5) . . . ?
C14 C15 H15 119.8(5) . . . ?
C17 C16 C15 119.79(5) . . . ?
C17 C16 H16 119.9(4) . . . ?
C15 C16 H16 120.3(5) . . . ?
Cl1 C17 C12 121.84(4) . . . ?
Cl1 C17 C16 117.14(4) . . . ?
C12 C17 C16 120.99(5) . . . ?
O2 C18 O3 124.27(5) . . . ?
O2 C18 C12 112.59(5) . . . ?
O3 C18 C12 123.09(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_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 C17 C12 C18 . . . . 2.07(7) ?
Cl1 C17 C12 C13 . . . . -179.20(7) ?
Cl1 C17 C16 C15 . . . . 179.65(7) ?
Cl1 C17 C16 H16 . . . . -0.4(6) ?
N1 N2 C9 C8 . . . . 5.93(6) ?
N1 N2 C9 C10 . . . . -174.40(7) ?
N1 N2 C11 H11A . . . . -179.8(2) ?
N1 N2 C11 H11C . . . . -60.0(3) ?
N1 N2 C11 H11B . . . . 59.8(3) ?
N1 C7 C8 C9 . . . . -2.34(6) ?
N1 C7 C8 H8 . . . . 177.7(5) ?
N1 C1 C2 C3 . . . . 179.80(7) ?
N1 C1 C2 H2A . . . . 0.0(5) ?
N1 C1 C6 C5 . . . . -179.80(7) ?
N1 C1 C6 H6 . . . . 0.4(6) ?
O1 C7 N1 N2 . . . . -171.86(6) ?
O1 C7 N1 C1 . . . . -24.46(7) ?
O1 C7 C8 C9 . . . . 175.19(7) ?
O1 C7 C8 H8 . . . . -4.7(6) ?
C1 N1 N2 C9 . . . . -156.68(6) ?
C1 N1 N2 C11 . . . . 57.29(7) ?
C1 N1 C7 C8 . . . . 153.38(7) ?
C1 C2 C3 C4 . . . . -0.07(7) ?
C1 C2 C3 H3 . . . . 179.6(6) ?
C1 C6 C5 C4 . . . . 0.05(7) ?
C1 C6 C5 H5 . . . . -179.6(6) ?
O2 C18 C12 C17 . . . . -145.59(7) ?
O2 C18 C12 C13 . . . . 35.69(7) ?
H2 O2 C18 O3 . . . . -0.8(7) ?
H2 O2 C18 C12 . . . . -178.2(6) ?
N2 N1 C7 C8 . . . . 5.98(6) ?
N2 N1 C1 C2 . . . . 29.58(7) ?
N2 N1 C1 C6 . . . . -150.63(7) ?
N2 C9 C8 C7 . . . . -2.24(6) ?
N2 C9 C8 H8 . . . . 177.7(5) ?
N2 C9 C10 H10B . . . . -166.9(5) ?
N2 C9 C10 H10A . . . . -46.9(4) ?
N2 C9 C10 H10C . . . . 73.2(2) ?
C2 C1 N1 C7 . . . . -114.87(7) ?
C2 C1 C6 C5 . . . . 0.00(7) ?
C2 C1 C6 H6 . . . . -179.8(6) ?
C2 C3 C4 C5 . . . . 0.11(8) ?
C2 C3 C4 H4 . . . . -179.8(6) ?
H2A C2 C1 C6 . . . . -179.8(7) ?
H2A C2 C3 C4 . . . . 179.8(7) ?
H2A C2 C3 H3 . . . . -0.5(9) ?
C3 C2 C1 C6 . . . . 0.02(8) ?
C3 C4 C5 C6 . . . . -0.10(8) ?
C3 C4 C5 H5 . . . . 179.6(6) ?
H3 C3 C4 C5 . . . . -179.6(8) ?
H3 C3 C4 H4 . . . . 0.5(10) ?
O3 C18 C12 C17 . . . . 36.95(7) ?
O3 C18 C12 C13 . . . . -141.77(7) ?
C4 C5 C6 H6 . . . . 179.8(6) ?
H4 C4 C5 C6 . . . . 179.8(8) ?
H4 C4 C5 H5 . . . . -0.5(10) ?
H5 C5 C6 H6 . . . . 0.1(10) ?
C6 C1 N1 C7 . . . . 64.92(7) ?
C7 N1 N2 C9 . . . . -7.40(6) ?
C7 N1 N2 C11 . . . . -153.43(7) ?
C7 C8 C9 C10 . . . . 178.13(8) ?
C8 C9 N2 C11 . . . . 149.63(7) ?
C8 C9 C10 H10B . . . . 12.7(6) ?
C8 C9 C10 H10A . . . . 132.7(4) ?
C8 C9 C10 H10C . . . . -107.2(2) ?
H8 C8 C9 C10 . . . . -1.9(7) ?
C9 N2 C11 H11A . . . . 40.2(3) ?
C9 N2 C11 H11C . . . . 160.0(3) ?
C9 N2 C11 H11B . . . . -80.1(4) ?
C10 C9 N2 C11 . . . . -30.70(8) ?
C12 C17 C16 C15 . . . . 1.68(8) ?
C12 C17 C16 H16 . . . . -178.4(6) ?
C12 C13 C14 C15 . . . . 1.44(8) ?
C12 C13 C14 H14 . . . . -178.5(2) ?
C13 C12 C17 C16 . . . . -1.32(8) ?
C13 C14 C15 C16 . . . . -1.09(8) ?
C13 C14 C15 H15 . . . . 178.67(18) ?
H13 C13 C12 C17 . . . . 179.5(8) ?
H13 C13 C12 C18 . . . . -1.7(8) ?
H13 C13 C14 C15 . . . . -178.3(8) ?
H13 C13 C14 H14 . . . . 1.7(8) ?
C14 C13 C12 C17 . . . . -0.24(8) ?
C14 C13 C12 C18 . . . . 178.54(8) ?
C14 C15 C16 C17 . . . . -0.45(8) ?
C14 C15 C16 H16 . . . . 179.6(6) ?
H14 C14 C15 C16 . . . . 178.9(3) ?
H14 C14 C15 H15 . . . . -1.4(3) ?
H15 C15 C16 C17 . . . . 179.8(2) ?
H15 C15 C16 H16 . . . . -0.1(6) ?
C16 C17 C12 C18 . . . . 179.94(8) ?

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
O2 H2 O1 1.046 1.513 2.5487(6) 169.34 1
O2 H2 C7 1.046 2.382 3.3930(7) 162.05 1
C11 H11C C2 1.093 2.605 3.2202(9) 114.83 1
C10 H10A C8 1.097 2.581 3.5467(10) 146.37 2_655
C13 H13 O2 1.088 2.615 3.5238(8) 140.56 3_656
C14 H14 O1 1.089 2.320 3.3662(8) 160.45 3_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2091232'
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             
;
2022-01-28 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;


_refine_ls_number_constraints    ?
#Added by publCIF




_diffrn_standards_number         ?
#Added by publCIF


_publcif_datablock.id            {6191ef93-2874-4269-b413-02d2823ece98}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Cl N2 O3'
_chemical_formula_sum            'C18 H17 Cl N2 O3'
_chemical_formula_weight         344.78

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

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

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

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

_cell_length_a                   12.4003(3)
_cell_length_b                   7.16320(10)
_cell_length_c                   18.4777(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.6750(10)
_cell_angle_gamma                90
_cell_volume                     1639.51(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      45.3

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   Numerical
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 Venture with PHOTON II Detector (Bruker, 2016)'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            119630
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         45.309
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13656
_reflns_number_gt                9336
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13656
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.84396(2) 0.50207(3) 0.45151(2) 0.02560(6) Uani 1 1 d . . . . .
N1 N 0.28227(5) 0.67434(8) 0.31793(3) 0.01288(10) Uani 1 1 d . . . . .
O1 O 0.35757(5) 0.45123(8) 0.39554(3) 0.01614(10) Uani 1 1 d . . . . .
C1 C 0.20742(5) 0.55855(10) 0.27860(4) 0.01266(10) Uani 1 1 d . . . . .
O2 O 0.51868(4) 0.29650(8) 0.46216(3) 0.01557(10) Uani 1 1 d . . . . .
H2 H 0.4628(14) 0.364(2) 0.4339(9) 0.050(5) Uiso 1 1 d . . . . .
N2 N 0.31849(5) 0.83716(8) 0.28504(4) 0.01339(10) Uani 1 1 d . . . . .
C2 C 0.20734(6) 0.55178(11) 0.20317(4) 0.01598(12) Uani 1 1 d . . . . .
H2A H 0.257249 0.624783 0.177845 0.019 Uiso 1 1 calc R U . . .
C3 C 0.13370(7) 0.43740(12) 0.16524(5) 0.01972(14) Uani 1 1 d . . . . .
H3 H 0.133018 0.432598 0.113841 0.024 Uiso 1 1 calc R U . . .
O3 O 0.62810(5) 0.41511(10) 0.38065(4) 0.02100(12) Uani 1 1 d . . . . .
C4 C 0.06102(7) 0.33001(11) 0.20260(5) 0.02143(16) Uani 1 1 d . . . . .
H4 H 0.011067 0.251354 0.176696 0.026 Uiso 1 1 calc R U . . .
C5 C 0.06153(6) 0.33786(11) 0.27787(5) 0.01986(15) Uani 1 1 d . . . . .
H5 H 0.011576 0.264737 0.303108 0.024 Uiso 1 1 calc R U . . .
C6 C 0.13456(6) 0.45186(11) 0.31646(5) 0.01580(12) Uani 1 1 d . . . . .
H6 H 0.134840 0.457045 0.367840 0.019 Uiso 1 1 calc R U . . .
C7 C 0.36431(6) 0.60720(9) 0.36526(4) 0.01209(10) Uani 1 1 d . . . . .
C8 C 0.44733(6) 0.74422(10) 0.36611(4) 0.01336(11) Uani 1 1 d . . . . .
H8 H 0.513097 0.740830 0.394587 0.016 Uiso 1 1 calc R U . . .
C9 C 0.41529(6) 0.88181(10) 0.31846(4) 0.01281(10) Uani 1 1 d . . . . .
C10 C 0.47020(7) 1.05894(12) 0.30038(5) 0.02020(14) Uani 1 1 d . . . . .
H10A H 0.469594 1.073660 0.247631 0.030 Uiso 1 1 calc R U . . .
H10B H 0.544980 1.055847 0.319989 0.030 Uiso 1 1 calc R U . . .
H10C H 0.432243 1.164164 0.321582 0.030 Uiso 1 1 calc R U . . .
C11 C 0.23813(7) 0.97431(11) 0.25975(5) 0.01732(13) Uani 1 1 d . . . . .
H11A H 0.274495 1.080527 0.238016 0.026 Uiso 1 1 calc R U . . .
H11B H 0.197546 1.017735 0.300779 0.026 Uiso 1 1 calc R U . . .
H11C H 0.188443 0.916703 0.223489 0.026 Uiso 1 1 calc R U . . .
C12 C 0.70199(6) 0.21625(9) 0.47438(4) 0.01217(10) Uani 1 1 d . . . . .
C13 C 0.67944(6) 0.04057(10) 0.50295(4) 0.01452(11) Uani 1 1 d . . . . .
H13 H 0.608132 -0.007573 0.497537 0.017 Uiso 1 1 calc R U . . .
C14 C 0.75905(7) -0.06534(11) 0.53912(5) 0.01758(13) Uani 1 1 d . . . . .
H14 H 0.742648 -0.185850 0.557044 0.021 Uiso 1 1 calc R U . . .
C15 C 0.86283(7) 0.00675(12) 0.54883(5) 0.01863(14) Uani 1 1 d . . . . .
H15 H 0.917228 -0.063723 0.574346 0.022 Uiso 1 1 calc R U . . .
C16 C 0.88734(6) 0.18182(12) 0.52128(4) 0.01762(13) Uani 1 1 d . . . . .
H16 H 0.958198 0.231128 0.528157 0.021 Uiso 1 1 calc R U . . .
C17 C 0.80758(6) 0.28420(10) 0.48365(4) 0.01454(11) Uani 1 1 d . . . . .
C18 C 0.61361(6) 0.32205(10) 0.43418(4) 0.01325(11) 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 C17 1.7369(8) . ?
N1 C7 1.3957(9) . ?
N1 N2 1.3988(8) . ?
N1 C1 1.4194(9) . ?
O1 C7 1.2540(9) . ?
C1 C2 1.3944(11) . ?
C1 C6 1.3960(10) . ?
O2 C18 1.3203(9) . ?
O2 H2 0.976(18) . ?
N2 C9 1.3621(9) . ?
N2 C11 1.4605(10) . ?
C2 C3 1.3917(11) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3923(13) . ?
C3 H3 0.9500 . ?
O3 C18 1.2132(9) . ?
C4 C5 1.3917(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3911(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.4219(10) . ?
C8 C9 1.3682(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.4853(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3980(10) . ?
C12 C17 1.3999(10) . ?
C12 C18 1.5004(9) . ?
C13 C14 1.3912(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.3905(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.3922(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.3912(11) . ?
C16 H16 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
C7 N1 N2 108.67(5) . . ?
C7 N1 C1 124.03(6) . . ?
N2 N1 C1 118.70(6) . . ?
C2 C1 C6 120.77(7) . . ?
C2 C1 N1 120.13(6) . . ?
C6 C1 N1 119.10(7) . . ?
C18 O2 H2 110.2(10) . . ?
C9 N2 N1 107.03(5) . . ?
C9 N2 C11 124.11(6) . . ?
N1 N2 C11 118.15(6) . . ?
C3 C2 C1 119.58(7) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.02(8) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.02(7) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.56(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.05(8) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 N1 121.65(6) . . ?
O1 C7 C8 132.33(7) . . ?
N1 C7 C8 105.98(6) . . ?
C9 C8 C7 107.56(6) . . ?
C9 C8 H8 126.2 . . ?
C7 C8 H8 126.2 . . ?
N2 C9 C8 110.23(6) . . ?
N2 C9 C10 120.14(7) . . ?
C8 C9 C10 129.62(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.98(6) . . ?
C13 C12 C18 119.16(6) . . ?
C17 C12 C18 122.85(6) . . ?
C14 C13 C12 121.49(7) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.42(7) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.26(7) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.69(7) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 121.13(7) . . ?
C16 C17 Cl1 117.05(6) . . ?
C12 C17 Cl1 121.80(6) . . ?
O3 C18 O2 124.34(7) . . ?
O3 C18 C12 123.27(7) . . ?
O2 C18 C12 112.34(6) . . ?

_refine_diff_density_max         0.723
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.077


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
