# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_ysr03
_database_code_depnum_ccdc_archive 'CCDC 2035098'
loop_
_audit_author_name
_audit_author_address
Mahesh
;University of hyderabad
India
;
_audit_update_record             
;
2020-10-02 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cl N O2'
_chemical_formula_weight         389.86

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   12.2034(4)
_cell_length_b                   8.3948(3)
_cell_length_c                   19.2731(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.400(3)
_cell_angle_gamma                90.00
_cell_volume                     1973.84(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8017
_cell_measurement_theta_min      2.1080
_cell_measurement_theta_max      25.7620

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18149
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3475
_reflns_number_gt                2399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. 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/[σ²(Fo²)+(0.0596P)²+0.1519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0058(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02534(5) 0.68434(9) 0.10808(4) 0.1006(3) Uani 1 1 d . . .
O1 O 0.47803(10) 0.28103(15) 0.03366(6) 0.0544(4) Uani 1 1 d . . .
N1 N 0.59435(11) 0.53511(17) 0.16801(7) 0.0450(4) Uani 1 1 d . . .
C11 C 0.36246(15) 0.4698(2) 0.08970(9) 0.0464(5) Uani 1 1 d . . .
C15 C 0.58343(16) 0.2243(2) 0.03763(10) 0.0528(5) Uani 1 1 d . . .
C13 C 0.56900(14) 0.4148(2) 0.11781(9) 0.0444(4) Uani 1 1 d . . .
C12 C 0.47044(15) 0.3980(2) 0.08387(9) 0.0470(5) Uani 1 1 d . . .
C8 C 0.15499(16) 0.6001(3) 0.10114(12) 0.0630(6) Uani 1 1 d . . .
C6 C 0.34000(16) 0.5798(2) 0.14113(10) 0.0565(5) Uani 1 1 d . . .
H6 H 0.3954 0.6103 0.1723 0.068 Uiso 1 1 calc R . .
C14 C 0.64327(15) 0.3001(2) 0.08921(9) 0.0482(5) Uani 1 1 d . . .
C19 C 0.75464(16) 0.2536(2) 0.10128(10) 0.0542(5) Uani 1 1 d . . .
C7 C 0.23695(17) 0.6446(2) 0.14677(11) 0.0631(6) Uani 1 1 d . . .
H7 H 0.2231 0.7184 0.1815 0.076 Uiso 1 1 calc R . .
C10 C 0.27760(15) 0.4274(3) 0.04369(10) 0.0608(6) Uani 1 1 d . . .
H10 H 0.2907 0.3542 0.0086 0.073 Uiso 1 1 calc R . .
C24 C 0.60528(15) 0.4941(3) 0.23584(10) 0.0547(5) Uani 1 1 d . . .
C18 C 0.79691(18) 0.1339(3) 0.05681(11) 0.0626(6) Uani 1 1 d . . .
O2 O 0.59084(13) 0.35556(19) 0.25410(7) 0.0752(5) Uani 1 1 d . . .
C9 C 0.17479(17) 0.4921(3) 0.04933(12) 0.0714(6) Uani 1 1 d . . .
H9 H 0.1189 0.4630 0.0182 0.086 Uiso 1 1 calc R . .
C5 C 0.60912(16) 0.6991(2) 0.14275(10) 0.0526(5) Uani 1 1 d . . .
H5A H 0.5635 0.7699 0.1694 0.063 Uiso 1 1 calc R . .
H5B H 0.5838 0.7045 0.0947 0.063 Uiso 1 1 calc R . .
C16 C 0.62441(19) 0.1090(3) -0.00728(11) 0.0661(6) Uani 1 1 d . . .
H16 H 0.5810 0.0636 -0.0423 0.079 Uiso 1 1 calc R . .
C1 C 0.63809(18) 0.6237(3) 0.28663(10) 0.0685(6) Uani 1 1 d . . .
H1A H 0.6354 0.5807 0.3333 0.082 Uiso 1 1 calc R . .
H1B H 0.5846 0.7089 0.2831 0.082 Uiso 1 1 calc R . .
C20 C 0.82343(17) 0.3147(3) 0.15414(12) 0.0703(6) Uani 1 1 d . . .
H20 H 0.7969 0.3923 0.1838 0.084 Uiso 1 1 calc R . .
C4 C 0.72611(19) 0.7582(3) 0.14750(12) 0.0727(7) Uani 1 1 d . . .
H4A H 0.7747 0.6725 0.1343 0.087 Uiso 1 1 calc R . .
H4B H 0.7348 0.8444 0.1146 0.087 Uiso 1 1 calc R . .
C17 C 0.7305(2) 0.0673(3) 0.00296(12) 0.0727(7) Uani 1 1 d . . .
H17 H 0.7609 -0.0078 -0.0264 0.087 Uiso 1 1 calc R . .
C23 C 0.9054(2) 0.0822(3) 0.06849(15) 0.0848(8) Uani 1 1 d . . .
H23 H 0.9336 0.0032 0.0402 0.102 Uiso 1 1 calc R . .
C21 C 0.9291(2) 0.2619(3) 0.16292(16) 0.0915(8) Uani 1 1 d . . .
H21 H 0.9738 0.3052 0.1979 0.110 Uiso 1 1 calc R . .
C2 C 0.75268(19) 0.6945(3) 0.27600(13) 0.0819(8) Uani 1 1 d . . .
H2A H 0.7776 0.7434 0.3192 0.098 Uiso 1 1 calc R . .
H2B H 0.8027 0.6081 0.2661 0.098 Uiso 1 1 calc R . .
C3 C 0.7600(2) 0.8164(3) 0.21896(14) 0.0888(8) Uani 1 1 d . . .
H3A H 0.8350 0.8542 0.2175 0.107 Uiso 1 1 calc R . .
H3B H 0.7142 0.9065 0.2306 0.107 Uiso 1 1 calc R . .
C22 C 0.9700(2) 0.1442(4) 0.11990(18) 0.0990(9) Uani 1 1 d . . .
H22 H 1.0415 0.1080 0.1264 0.119 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 C8 1.741(2) . ?
O1 C15 1.372(2) . ?
O1 C12 1.384(2) . ?
N1 C24 1.355(2) . ?
N1 C13 1.427(2) . ?
N1 C5 1.473(2) . ?
C11 C6 1.387(3) . ?
C11 C10 1.393(2) . ?
C11 C12 1.456(2) . ?
C15 C14 1.375(3) . ?
C15 C16 1.399(3) . ?
C13 C12 1.362(2) . ?
C13 C14 1.441(2) . ?
C8 C7 1.368(3) . ?
C8 C9 1.374(3) . ?
C6 C7 1.377(3) . ?
C14 C19 1.428(3) . ?
C19 C20 1.401(3) . ?
C19 C18 1.425(3) . ?
C10 C9 1.374(3) . ?
C24 O2 1.229(2) . ?
C24 C1 1.511(3) . ?
C18 C23 1.406(3) . ?
C18 C17 1.416(3) . ?
C5 C4 1.512(3) . ?
C16 C17 1.351(3) . ?
C1 C2 1.538(3) . ?
C20 C21 1.370(3) . ?
C4 C3 1.510(3) . ?
C23 C22 1.355(3) . ?
C21 C22 1.391(4) . ?
C2 C3 1.506(3) . ?

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
C15 O1 C12 106.63(14) . . ?
C24 N1 C13 119.27(15) . . ?
C24 N1 C5 123.10(16) . . ?
C13 N1 C5 117.62(14) . . ?
C6 C11 C10 117.91(17) . . ?
C6 C11 C12 121.72(16) . . ?
C10 C11 C12 120.37(17) . . ?
O1 C15 C14 111.12(17) . . ?
O1 C15 C16 123.68(18) . . ?
C14 C15 C16 125.2(2) . . ?
C12 C13 N1 124.95(16) . . ?
C12 C13 C14 107.66(16) . . ?
N1 C13 C14 127.17(16) . . ?
C13 C12 O1 109.62(15) . . ?
C13 C12 C11 135.27(17) . . ?
O1 C12 C11 115.08(15) . . ?
C7 C8 C9 120.56(19) . . ?
C7 C8 Cl1 119.43(18) . . ?
C9 C8 Cl1 120.00(17) . . ?
C7 C6 C11 121.09(18) . . ?
C15 C14 C19 118.54(18) . . ?
C15 C14 C13 104.94(17) . . ?
C19 C14 C13 136.52(18) . . ?
C20 C19 C18 118.42(19) . . ?
C20 C19 C14 124.70(19) . . ?
C18 C19 C14 116.87(19) . . ?
C8 C7 C6 119.8(2) . . ?
C9 C10 C11 121.0(2) . . ?
O2 C24 N1 120.33(18) . . ?
O2 C24 C1 122.22(18) . . ?
N1 C24 C1 117.43(18) . . ?
C23 C18 C17 121.0(2) . . ?
C23 C18 C19 118.3(2) . . ?
C17 C18 C19 120.7(2) . . ?
C10 C9 C8 119.70(19) . . ?
N1 C5 C4 114.18(17) . . ?
C17 C16 C15 116.4(2) . . ?
C24 C1 C2 114.80(17) . . ?
C21 C20 C19 121.1(2) . . ?
C3 C4 C5 113.48(19) . . ?
C16 C17 C18 122.3(2) . . ?
C22 C23 C18 121.8(2) . . ?
C20 C21 C22 120.4(3) . . ?
C3 C2 C1 115.47(19) . . ?
C2 C3 C4 115.2(2) . . ?
C23 C22 C21 119.9(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
