# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_m
_database_code_depnum_ccdc_archive 'CCDC 2267331'
loop_
_audit_author_name
_audit_author_address
'Lalit Mohan Jha'
;Professor 
India
;
_audit_update_record             
;
2023-06-03 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H17 Cl2 N O2'
_chemical_formula_sum            'C21 H17 Cl2 N O2'
_chemical_formula_weight         386.26
_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                   15.168(8)
_cell_length_b                   5.683(3)
_cell_length_c                   21.306(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.272(9)
_cell_angle_gamma                90
_cell_volume                     1807.1(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    902
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      4.02
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'color less'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7043
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.138
_diffrn_reflns_theta_min         4.017
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2524
_reflns_number_total             4330
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      0.897
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1803
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 1.06865(5) 1.28309(17) 0.40217(4) 0.0405(3) Uani 1 1 d . . . . .
Cl2 Cl 0.08009(6) -0.10344(17) 0.23888(4) 0.0435(3) Uani 1 1 d . . . . .
O1 O 0.70688(13) 0.6202(4) 0.41136(10) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.59184(14) 0.5528(4) 0.46207(10) 0.0330(5) Uani 1 1 d . . . . .
N1 N 0.48183(17) 0.1858(5) 0.41860(13) 0.0285(6) Uani 1 1 d . . . . .
H1 H 0.493(2) 0.294(6) 0.4431(17) 0.033(10) Uiso 1 1 d . . . . .
C1 C 0.9712(2) 1.1425(6) 0.41639(15) 0.0299(7) Uani 1 1 d . . . . .
C2 C 0.9449(2) 0.9346(6) 0.38555(16) 0.0346(8) Uani 1 1 d . . . . .
H2 H 0.9781 0.8690 0.3572 0.042 Uiso 1 1 calc R . . . .
C3 C 0.8678(2) 0.8247(6) 0.39751(15) 0.0327(7) Uani 1 1 d . . . . .
H3 H 0.8495 0.6837 0.3771 0.039 Uiso 1 1 calc R . . . .
C4 C 0.8178(2) 0.9219(5) 0.43935(14) 0.0262(7) Uani 1 1 d . . . . .
C5 C 0.8459(2) 1.1329(6) 0.46929(15) 0.0319(7) Uani 1 1 d . . . . .
H5 H 0.8127 1.1999 0.4974 0.038 Uiso 1 1 calc R . . . .
C6 C 0.9223(2) 1.2445(6) 0.45801(16) 0.0338(8) Uani 1 1 d . . . . .
H6 H 0.9407 1.3861 0.4781 0.041 Uiso 1 1 calc R . . . .
C7 C 0.7346(2) 0.8093(6) 0.45538(16) 0.0304(7) Uani 1 1 d . . . . .
H7A H 0.7468 0.7490 0.4987 0.037 Uiso 1 1 calc R . . . .
H7B H 0.6871 0.9253 0.4525 0.037 Uiso 1 1 calc R . . . .
C8 C 0.63241(19) 0.5035(5) 0.41910(14) 0.0249(6) Uani 1 1 d . . . . .
C9 C 0.60883(19) 0.3153(5) 0.37172(14) 0.0243(6) Uani 1 1 d . . . . .
C10 C 0.6614(2) 0.2832(6) 0.32405(15) 0.0286(7) Uani 1 1 d . . . . .
H10 H 0.7079 0.3877 0.3218 0.034 Uiso 1 1 calc R . . . .
C11 C 0.6459(2) 0.1015(6) 0.28069(16) 0.0334(8) Uani 1 1 d . . . . .
H11 H 0.6804 0.0853 0.2490 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5775(2) -0.0574(6) 0.28524(15) 0.0305(7) Uani 1 1 d . . . . .
H12 H 0.5674 -0.1834 0.2570 0.037 Uiso 1 1 calc R . . . .
C13 C 0.5245(2) -0.0305(5) 0.33111(14) 0.0263(7) Uani 1 1 d . . . . .
H13 H 0.4790 -0.1387 0.3330 0.032 Uiso 1 1 calc R . . . .
C14 C 0.53744(18) 0.1564(5) 0.37494(13) 0.0228(6) Uani 1 1 d . . . . .
C15 C 0.42055(19) 0.0043(6) 0.43213(14) 0.0282(7) Uani 1 1 d . . . . .
H15A H 0.4049 0.0360 0.4735 0.034 Uiso 1 1 calc R . . . .
H15B H 0.4515 -0.1458 0.4350 0.034 Uiso 1 1 calc R . . . .
C16 C 0.3352(2) -0.0171(5) 0.38362(14) 0.0258(7) Uani 1 1 d . . . . .
C17 C 0.2813(2) -0.2161(6) 0.38407(16) 0.0312(7) Uani 1 1 d . . . . .
H17 H 0.2985 -0.3331 0.4143 0.037 Uiso 1 1 calc R . . . .
C18 C 0.2025(2) -0.2421(6) 0.34016(16) 0.0322(8) Uani 1 1 d . . . . .
H18 H 0.1671 -0.3753 0.3409 0.039 Uiso 1 1 calc R . . . .
C19 C 0.1772(2) -0.0674(6) 0.29515(15) 0.0301(7) Uani 1 1 d . . . . .
C20 C 0.2286(2) 0.1307(6) 0.29382(16) 0.0313(7) Uani 1 1 d . . . . .
H20 H 0.2111 0.2470 0.2634 0.038 Uiso 1 1 calc R . . . .
C21 C 0.3068(2) 0.1558(5) 0.33815(14) 0.0278(7) Uani 1 1 d . . . . .
H21 H 0.3411 0.2911 0.3375 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.754(3) . ?
Cl2 C19 1.737(3) . ?
O1 C7 1.439(4) . ?
O1 C8 1.345(3) . ?
O2 C8 1.223(3) . ?
N1 C14 1.373(4) . ?
N1 C15 1.451(4) . ?
C1 C2 1.376(4) . ?
C1 C6 1.380(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.508(4) . ?
C5 C6 1.380(4) . ?
C8 C9 1.470(4) . ?
C9 C10 1.411(4) . ?
C9 C14 1.421(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.392(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.404(4) . ?
C15 C16 1.511(4) . ?
C16 C17 1.396(4) . ?
C16 C21 1.393(4) . ?
C17 C18 1.388(5) . ?
C18 C19 1.386(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.386(4) . ?

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
C8 O1 C7 116.2(2) . . ?
C14 N1 C15 122.7(3) . . ?
C2 C1 Cl1 119.3(2) . . ?
C2 C1 C6 121.6(3) . . ?
C6 C1 Cl1 119.0(2) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 121.0(3) . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 123.6(3) . . ?
C5 C4 C7 117.6(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C1 118.8(3) . . ?
O1 C7 C4 109.1(2) . . ?
O1 C8 C9 112.4(2) . . ?
O2 C8 O1 121.6(3) . . ?
O2 C8 C9 125.9(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 C14 119.1(3) . . ?
C14 C9 C8 121.6(3) . . ?
C11 C10 C9 121.9(3) . . ?
C10 C11 C12 118.7(3) . . ?
C13 C12 C11 120.9(3) . . ?
C12 C13 C14 121.6(3) . . ?
N1 C14 C9 121.4(3) . . ?
N1 C14 C13 120.8(3) . . ?
C13 C14 C9 117.8(3) . . ?
N1 C15 C16 115.0(3) . . ?
C17 C16 C15 119.5(3) . . ?
C21 C16 C15 122.7(3) . . ?
C21 C16 C17 117.9(3) . . ?
C18 C17 C16 121.1(3) . . ?
C19 C18 C17 119.3(3) . . ?
C18 C19 Cl2 119.3(2) . . ?
C20 C19 Cl2 119.8(3) . . ?
C20 C19 C18 120.9(3) . . ?
C19 C20 C21 119.4(3) . . ?
C20 C21 C16 121.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
