# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_dbr75vr_a
_database_code_depnum_ccdc_archive 'CCDC 2270282'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Cl N O4'
_chemical_formula_sum            'C20 H20 Cl N O4'
_chemical_formula_weight         373.82
_chemical_absolute_configuration ?
_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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   11.028(5)
_cell_length_b                   24.273(11)
_cell_length_c                   8.467(4)
_cell_angle_alpha                90
_cell_angle_beta                 123.455(13)
_cell_angle_gamma                90
_cell_volume                     1890.9(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      20.625
_cell_measurement_theta_min      2.368
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.168
_diffrn_reflns_av_unetI/netI     0.2241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20330
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      297.26
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2017
_reflns_number_total             4232
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 715 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2097
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.003
_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)+(0.0310P)²+1.3559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1492
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C12(H12), C8(H8), C11(H11), C10(H10), C9(H9)
2.d Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.0748(3) 0.51850(9) -0.0143(4) 0.0724(8) Uani 1 1 d . . . . .
O1 O 0.1282(5) 0.68999(19) 0.4737(7) 0.0396(13) Uani 1 1 d . . . . .
H1 H 0.102127 0.710527 0.383487 0.059 Uiso 1 1 calc R . . . .
O3 O 0.6660(5) 0.7435(2) 0.7050(7) 0.0406(13) Uani 1 1 d . . . . .
O4 O 0.6727(4) 0.6709(2) 0.5431(7) 0.0406(14) Uani 1 1 d . . . . .
O2 O 0.4060(5) 0.7498(2) 0.6779(7) 0.0426(13) Uani 1 1 d . . . . .
N1 N 0.4656(6) 0.6893(2) 0.5158(8) 0.0257(13) Uani 1 1 d . . . . .
C15 C 0.6121(7) 0.7053(3) 0.6007(10) 0.0313(18) Uani 1 1 d . . . . .
C6 C 0.1691(8) 0.5936(3) 0.2651(11) 0.0380(19) Uani 1 1 d . . . . .
H6 H 0.088076 0.584458 0.267084 0.046 Uiso 1 1 calc R . . . .
C5 C 0.2666(7) 0.6327(3) 0.3865(9) 0.0251(16) Uani 1 1 d . . . . .
C13 C 0.2634(7) 0.6665(3) 0.5320(10) 0.0286(17) Uani 1 1 d . . . . .
C4 C 0.3879(7) 0.6456(3) 0.3840(10) 0.0289(17) Uani 1 1 d . . . . .
C14 C 0.3826(7) 0.7085(3) 0.5862(9) 0.0284(17) Uani 1 1 d . . . . .
C1 C 0.1949(8) 0.5686(3) 0.1409(11) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.4133(7) 0.6208(3) 0.2590(10) 0.0337(18) Uani 1 1 d . . . . .
H3 H 0.494380 0.629978 0.257070 0.040 Uiso 1 1 calc R . . . .
C7 C 0.4557(8) 0.6063(3) 0.8102(11) 0.0395(19) Uani 1 1 d . . . . .
C20 C 0.3092(7) 0.6340(3) 0.7141(10) 0.0378(19) Uani 1 1 d . . . . .
H20A H 0.309716 0.659145 0.803501 0.045 Uiso 1 1 calc R . . . .
H20B H 0.236269 0.606120 0.682580 0.045 Uiso 1 1 calc R . . . .
C16 C 0.8288(7) 0.6764(3) 0.6056(11) 0.040(2) Uani 1 1 d . . . . .
C2 C 0.3140(8) 0.5815(3) 0.1351(11) 0.042(2) Uani 1 1 d . . . . .
H2 H 0.328071 0.564108 0.048685 0.050 Uiso 1 1 calc R . . . .
C12 C 0.5813(9) 0.6341(4) 0.9365(11) 0.053(2) Uani 1 1 d . . . . .
H12 H 0.575815 0.670194 0.968827 0.063 Uiso 1 1 calc R . . . .
C8 C 0.4673(10) 0.5531(4) 0.7637(15) 0.072(3) Uani 1 1 d . . . . .
H8 H 0.383786 0.533825 0.675714 0.086 Uiso 1 1 calc R . . . .
C17 C 0.9234(8) 0.6704(3) 0.8185(12) 0.059(2) Uani 1 1 d . . . . .
H17A H 1.023730 0.673788 0.861060 0.089 Uiso 1 1 calc R . . . .
H17B H 0.899151 0.698598 0.876000 0.089 Uiso 1 1 calc R . . . .
H17C H 0.907322 0.634839 0.853724 0.089 Uiso 1 1 calc R . . . .
C11 C 0.7147(10) 0.6095(5) 1.0159(13) 0.072(3) Uani 1 1 d . . . . .
H11 H 0.798887 0.629104 1.099619 0.086 Uiso 1 1 calc R . . . .
C19 C 0.8456(9) 0.6276(4) 0.5072(15) 0.086(4) Uani 1 1 d . . . . .
H19A H 0.943095 0.626667 0.536805 0.128 Uiso 1 1 calc R . . . .
H19B H 0.825974 0.594166 0.549681 0.128 Uiso 1 1 calc R . . . .
H19C H 0.778418 0.631134 0.372785 0.128 Uiso 1 1 calc R . . . .
C10 C 0.7234(11) 0.5559(6) 0.9712(16) 0.084(4) Uani 1 1 d . . . . .
H10 H 0.813416 0.538760 1.027062 0.101 Uiso 1 1 calc R . . . .
C18 C 0.8475(11) 0.7315(4) 0.5376(16) 0.080(3) Uani 1 1 d . . . . .
H18A H 0.946809 0.735740 0.576393 0.120 Uiso 1 1 calc R . . . .
H18B H 0.785234 0.733133 0.402080 0.120 Uiso 1 1 calc R . . . .
H18C H 0.822264 0.760558 0.591392 0.120 Uiso 1 1 calc R . . . .
C9 C 0.5999(12) 0.5281(4) 0.845(2) 0.106(4) Uani 1 1 d . . . . .
H9 H 0.605711 0.491874 0.813952 0.128 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 1.744(7) . ?
O1 H1 0.8200 . ?
O1 C13 1.407(7) . ?
O3 C15 1.189(8) . ?
O4 C15 1.320(8) . ?
O4 C16 1.502(7) . ?
O2 C14 1.205(8) . ?
N1 C15 1.414(8) . ?
N1 C4 1.431(8) . ?
N1 C14 1.419(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.377(10) . ?
C6 C1 1.374(10) . ?
C5 C13 1.496(9) . ?
C5 C4 1.385(8) . ?
C13 C14 1.521(9) . ?
C13 C20 1.547(10) . ?
C4 C3 1.374(9) . ?
C1 C2 1.376(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.393(9) . ?
C7 C20 1.508(10) . ?
C7 C12 1.372(11) . ?
C7 C8 1.377(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C16 C17 1.512(11) . ?
C16 C19 1.517(10) . ?
C16 C18 1.514(11) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.372(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(13) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.373(14) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C9 1.360(15) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9 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
C13 O1 H1 109.5 . . ?
C15 O4 C16 121.9(6) . . ?
C15 N1 C4 128.7(5) . . ?
C15 N1 C14 121.1(6) . . ?
C14 N1 C4 108.9(5) . . ?
O3 C15 O4 128.3(6) . . ?
O3 C15 N1 123.8(6) . . ?
O4 C15 N1 107.9(6) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C1 C6 C5 118.1(7) . . ?
C6 C5 C13 129.0(6) . . ?
C6 C5 C4 120.5(6) . . ?
C4 C5 C13 110.5(6) . . ?
O1 C13 C5 115.8(6) . . ?
O1 C13 C14 114.0(5) . . ?
O1 C13 C20 104.9(5) . . ?
C5 C13 C14 101.9(5) . . ?
C5 C13 C20 113.5(5) . . ?
C14 C13 C20 106.7(6) . . ?
C5 C4 N1 108.9(6) . . ?
C3 C4 N1 129.5(6) . . ?
C3 C4 C5 121.5(6) . . ?
O2 C14 N1 125.9(6) . . ?
O2 C14 C13 126.5(6) . . ?
N1 C14 C13 107.6(6) . . ?
C6 C1 Cl1 119.5(6) . . ?
C6 C1 C2 122.0(7) . . ?
C2 C1 Cl1 118.4(6) . . ?
C4 C3 H3 121.0 . . ?
C4 C3 C2 118.0(6) . . ?
C2 C3 H3 121.0 . . ?
C12 C7 C20 121.4(7) . . ?
C12 C7 C8 118.1(8) . . ?
C8 C7 C20 120.3(8) . . ?
C13 C20 H20A 108.4 . . ?
C13 C20 H20B 108.4 . . ?
C7 C20 C13 115.5(5) . . ?
C7 C20 H20A 108.4 . . ?
C7 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
O4 C16 C17 108.3(6) . . ?
O4 C16 C19 101.5(6) . . ?
O4 C16 C18 108.3(6) . . ?
C17 C16 C19 111.5(7) . . ?
C17 C16 C18 112.9(8) . . ?
C18 C16 C19 113.4(8) . . ?
C1 C2 C3 120.0(7) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.1(9) . . ?
C11 C12 H12 119.4 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(9) . . ?
C9 C8 H8 119.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.7(10) . . ?
C10 C11 H11 120.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.7(10) . . ?
C9 C10 H10 120.1 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(10) . . ?
C10 C9 H9 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
