# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_4cl_nm_dbp_rt
_database_code_depnum_ccdc_archive 'CCDC 1960029'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2019-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Cl2 N O'
_chemical_formula_sum            'C20 H17 Cl2 N O'
_chemical_formula_weight         358.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.4902(4)
_cell_length_b                   14.2399(8)
_cell_length_c                   23.1491(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.323(6)
_cell_angle_gamma                90
_cell_volume                     1753.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7420
_cell_measurement_theta_min      2.8470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11576
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.795
_diffrn_reflns_theta_min         2.861
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   12.00    --   29.89  54.00  47.00  624
  2  ω     -6.00  20.10   0.30   12.00    --   29.89  54.00-180.00   87
  3  ω    -69.00 -18.00   0.30   12.00    --   29.89  54.00-180.00  170
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0007693000
_diffrn_orient_matrix_UB_12      -0.0395275000
_diffrn_orient_matrix_UB_13      -0.0186835000
_diffrn_orient_matrix_UB_21      0.1160722000
_diffrn_orient_matrix_UB_22      -0.0151223000
_diffrn_orient_matrix_UB_23      0.0186985000
_diffrn_orient_matrix_UB_31      -0.0655487000
_diffrn_orient_matrix_UB_32      -0.0262675000
_diffrn_orient_matrix_UB_33      0.0173819000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3158
_reflns_number_total             5387
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0741P)²+0.1853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C6(H6), C15(H15), C9(H9), C19(H19), C12(H12), C8(H8),
 C18(H18), C11(H11)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.87563(13) 0.35220(5) 0.73982(3) 0.0756(2) Uani 1 1 d . . . . .
Cl1 Cl 0.16048(15) 0.37533(6) 0.01335(3) 0.0885(3) Uani 1 1 d . . . . .
O1 O -0.0094(3) 0.42320(13) 0.37526(7) 0.0744(5) Uani 1 1 d . . . . .
N1 N 0.4423(3) 0.21337(12) 0.37414(7) 0.0573(4) Uani 1 1 d . . . . .
C1 C 0.4348(4) 0.27293(14) 0.32234(9) 0.0547(4) Uani 1 1 d . . . . .
H1A H 0.391413 0.235313 0.286319 0.066 Uiso 1 1 calc R . . . .
H1B H 0.599320 0.300306 0.325437 0.066 Uiso 1 1 calc R . . . .
C5 C 0.5364(4) 0.26822(14) 0.42878(9) 0.0569(5) Uani 1 1 d . . . . .
H5A H 0.698500 0.295211 0.428705 0.068 Uiso 1 1 calc R . . . .
H5B H 0.558211 0.227478 0.463270 0.068 Uiso 1 1 calc R . . . .
C3 C 0.1765(4) 0.37623(14) 0.37546(9) 0.0540(5) Uani 1 1 d . . . . .
C4 C 0.3532(4) 0.34546(14) 0.43259(9) 0.0517(4) Uani 1 1 d . . . . .
C2 C 0.2441(4) 0.34962(14) 0.31888(9) 0.0524(4) Uani 1 1 d . . . . .
C13 C 0.3348(4) 0.39020(14) 0.48228(9) 0.0539(5) Uani 1 1 d . . . . .
H13 H 0.208034 0.435113 0.476484 0.065 Uiso 1 1 calc R . . . .
C7 C 0.1535(4) 0.39245(14) 0.20843(9) 0.0530(4) Uani 1 1 d . . . . .
C14 C 0.4804(4) 0.38031(13) 0.54410(9) 0.0516(4) Uani 1 1 d . . . . .
C16 C 0.8366(4) 0.32893(15) 0.62216(9) 0.0587(5) Uani 1 1 d . . . . .
H16 H 0.992477 0.299561 0.633610 0.070 Uiso 1 1 calc R . . . .
C6 C 0.1281(4) 0.39744(14) 0.26989(9) 0.0542(4) Uani 1 1 d . . . . .
H6 H 0.011535 0.441328 0.275968 0.065 Uiso 1 1 calc R . . . .
C15 C 0.7145(4) 0.33649(15) 0.56259(9) 0.0577(5) Uani 1 1 d . . . . .
H15 H 0.789787 0.311828 0.534082 0.069 Uiso 1 1 calc R . . . .
C17 C 0.7248(4) 0.36550(14) 0.66465(9) 0.0564(5) Uani 1 1 d . . . . .
C9 C 0.3543(4) 0.34584(16) 0.13070(10) 0.0611(5) Uani 1 1 d . . . . .
H9 H 0.487837 0.317288 0.119463 0.073 Uiso 1 1 calc R . . . .
C19 C 0.3792(4) 0.41940(15) 0.58890(9) 0.0574(5) Uani 1 1 d . . . . .
H19 H 0.227245 0.451486 0.577883 0.069 Uiso 1 1 calc R . . . .
C12 C -0.0366(4) 0.43355(16) 0.16398(10) 0.0614(5) Uani 1 1 d . . . . .
H12 H -0.167235 0.464781 0.174873 0.074 Uiso 1 1 calc R . . . .
C8 C 0.3506(4) 0.34975(15) 0.19022(10) 0.0590(5) Uani 1 1 d . . . . .
H8 H 0.482589 0.323317 0.218702 0.071 Uiso 1 1 calc R . . . .
C18 C 0.4974(4) 0.41177(16) 0.64831(10) 0.0612(5) Uani 1 1 d . . . . .
H18 H 0.425249 0.437387 0.677105 0.073 Uiso 1 1 calc R . . . .
C10 C 0.1592(4) 0.38442(15) 0.08824(9) 0.0587(5) Uani 1 1 d . . . . .
C11 C -0.0360(4) 0.42909(17) 0.10442(10) 0.0659(6) Uani 1 1 d . . . . .
H11 H -0.165945 0.455958 0.075603 0.079 Uiso 1 1 calc R . . . .
C20 C 0.6036(6) 0.13205(16) 0.37418(11) 0.0756(7) Uani 1 1 d . . . . .
H20A H 0.543313 0.097052 0.338019 0.113 Uiso 1 1 calc GR . . . .
H20B H 0.601432 0.092822 0.407768 0.113 Uiso 1 1 calc GR . . . .
H20C H 0.772436 0.152739 0.376771 0.113 Uiso 1 1 calc GR . . . .


_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
Cl2 C17 1.743(2) . ?
Cl1 C10 1.740(2) . ?
O1 C3 1.220(2) . ?
N1 C1 1.461(2) . ?
N1 C5 1.468(3) . ?
N1 C20 1.458(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.501(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.508(3) . ?
C3 C4 1.499(3) . ?
C3 C2 1.496(3) . ?
C4 C13 1.341(3) . ?
C2 C6 1.341(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.463(3) . ?
C7 C6 1.465(3) . ?
C7 C12 1.400(3) . ?
C7 C8 1.394(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.407(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.380(3) . ?
C16 C17 1.384(3) . ?
C6 H6 0.9300 . ?
C15 H15 0.9300 . ?
C17 C18 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.384(3) . ?
C9 C10 1.376(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.372(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(3) . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 109.33(16) . . ?
C20 N1 C1 110.82(16) . . ?
C20 N1 C5 109.75(17) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.11(15) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
N1 C5 C4 109.95(17) . . ?
H5A C5 H5B 108.2 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
O1 C3 C4 121.47(18) . . ?
O1 C3 C2 121.62(19) . . ?
C2 C3 C4 116.88(17) . . ?
C3 C4 C5 117.20(16) . . ?
C13 C4 C5 126.16(19) . . ?
C13 C4 C3 116.64(18) . . ?
C3 C2 C1 117.27(17) . . ?
C6 C2 C1 126.41(18) . . ?
C6 C2 C3 116.32(18) . . ?
C4 C13 H13 114.6 . . ?
C4 C13 C14 130.88(19) . . ?
C14 C13 H13 114.6 . . ?
C12 C7 C6 117.44(19) . . ?
C8 C7 C6 125.59(18) . . ?
C8 C7 C12 117.0(2) . . ?
C15 C14 C13 125.54(17) . . ?
C15 C14 C19 116.86(19) . . ?
C19 C14 C13 117.59(19) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C2 C6 C7 131.11(19) . . ?
C2 C6 H6 114.4 . . ?
C7 C6 H6 114.4 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.58(18) . . ?
C16 C15 H15 119.2 . . ?
C16 C17 Cl2 118.95(18) . . ?
C18 C17 Cl2 120.01(16) . . ?
C18 C17 C16 121.0(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C10 C9 C8 119.6(2) . . ?
C14 C19 H19 118.9 . . ?
C18 C19 C14 122.2(2) . . ?
C18 C19 H19 118.9 . . ?
C7 C12 H12 119.0 . . ?
C11 C12 C7 121.9(2) . . ?
C11 C12 H12 119.0 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 H8 119.3 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 118.95(19) . . ?
C19 C18 H18 120.5 . . ?
C9 C10 Cl1 119.19(17) . . ?
C11 C10 Cl1 120.07(17) . . ?
C11 C10 C9 120.7(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl2 C17 C18 C19 -178.44(16) . . . . ?
Cl1 C10 C11 C12 178.42(17) . . . . ?
O1 C3 C4 C5 164.5(2) . . . . ?
O1 C3 C4 C13 -16.1(3) . . . . ?
O1 C3 C2 C1 -165.0(2) . . . . ?
O1 C3 C2 C6 15.4(3) . . . . ?
N1 C1 C2 C3 23.3(2) . . . . ?
N1 C1 C2 C6 -157.1(2) . . . . ?
N1 C5 C4 C3 -22.3(2) . . . . ?
N1 C5 C4 C13 158.51(19) . . . . ?
C1 N1 C5 C4 65.2(2) . . . . ?
C1 C2 C6 C7 -1.8(4) . . . . ?
C5 N1 C1 C2 -65.8(2) . . . . ?
C5 C4 C13 C14 1.5(4) . . . . ?
C3 C4 C13 C14 -177.78(19) . . . . ?
C3 C2 C6 C7 177.79(19) . . . . ?
C4 C3 C2 C1 17.2(3) . . . . ?
C4 C3 C2 C6 -162.47(18) . . . . ?
C4 C13 C14 C15 16.8(3) . . . . ?
C4 C13 C14 C19 -164.3(2) . . . . ?
C2 C3 C4 C5 -17.6(3) . . . . ?
C2 C3 C4 C13 161.68(18) . . . . ?
C13 C14 C15 C16 -178.84(19) . . . . ?
C13 C14 C19 C18 178.18(19) . . . . ?
C7 C12 C11 C10 -1.2(4) . . . . ?
C14 C19 C18 C17 1.0(3) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C6 C7 C12 C11 -177.1(2) . . . . ?
C6 C7 C8 C9 177.8(2) . . . . ?
C15 C14 C19 C18 -2.8(3) . . . . ?
C15 C16 C17 Cl2 177.91(16) . . . . ?
C15 C16 C17 C18 -2.0(3) . . . . ?
C17 C16 C15 C14 0.1(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C19 C14 C15 C16 2.3(3) . . . . ?
C12 C7 C6 C2 164.0(2) . . . . ?
C12 C7 C8 C9 -1.8(3) . . . . ?
C8 C7 C6 C2 -15.7(4) . . . . ?
C8 C7 C12 C11 2.6(3) . . . . ?
C8 C9 C10 Cl1 -177.71(17) . . . . ?
C8 C9 C10 C11 1.8(3) . . . . ?
C10 C9 C8 C7 -0.3(3) . . . . ?
C20 N1 C1 C2 173.07(19) . . . . ?
C20 N1 C5 C4 -173.07(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.926
