# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2213403'
loop_
_audit_author_name
_audit_author_address
'PRATAP KUMAR MANDAL'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH, BHOPAL
India
;
_audit_update_record             
;
2022-10-17 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2022-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 Cl2 N O2'
_chemical_formula_sum            'C21 H13 Cl2 N O2'
_chemical_formula_weight         383.22
_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                   10.445(3)
_cell_length_b                   19.168(6)
_cell_length_c                   9.550(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.776(9)
_cell_angle_gamma                90
_cell_volume                     1775.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7856
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             784
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33909
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         2.100
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3363
_reflns_number_total             4385
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.254
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.210
_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)+(0.1048P)²+0.2062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1934
_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:
 C3(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H00C), C17(H00D), C00D(H00E), C4(H00F), C19(H00G), C18(H00J), C14(H00M),
 C10(H00N), C13(H00O), C11(H00P)
2.c :
 C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl00 Cl 0.05808(8) 0.39874(4) -0.39251(7) 0.0706(3) Uani 1 1 d . . . . .
Cl1 Cl 0.94736(7) 0.40540(5) 1.22143(7) 0.0803(3) Uani 1 1 d . . . . .
N1 N 0.50306(16) 0.33868(8) 0.50743(16) 0.0370(4) Uani 1 1 d . . . . .
O1 O 0.41128(19) 0.52418(9) 0.71163(18) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.40206(19) 0.24194(9) 0.25478(18) 0.0621(5) Uani 1 1 d . . . . .
C5 C 0.39519(19) 0.43510(10) 0.5326(2) 0.0369(4) Uani 1 1 d . . . . .
C7 C 0.3957(2) 0.35001(10) 0.3698(2) 0.0384(4) Uani 1 1 d . . . . .
C16 C 0.6150(2) 0.39520(9) 0.7571(2) 0.0366(4) Uani 1 1 d . . . . .
C3 C 0.5948(2) 0.27763(10) 0.5460(2) 0.0445(5) Uani 1 1 d . . . . .
H00A H 0.638259 0.274060 0.654800 0.053 Uiso 1 1 calc R . . . .
H00B H 0.540285 0.235805 0.509431 0.053 Uiso 1 1 calc R . . . .
C9 C 0.2814(2) 0.32980(11) 0.0870(2) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.3283(2) 0.40922(10) 0.3851(2) 0.0393(4) Uani 1 1 d . . . . .
H00C H 0.251639 0.428935 0.310886 0.047 Uiso 1 1 calc R . . . .
C17 C 0.5818(2) 0.39682(10) 0.8854(2) 0.0393(4) Uani 1 1 d . . . . .
H00D H 0.489599 0.395424 0.874750 0.047 Uiso 1 1 calc R . . . .
C00D C 0.6824(2) 0.40044(10) 1.0278(2) 0.0438(5) Uani 1 1 d . . . . .
H00E H 0.658714 0.401559 1.112535 0.053 Uiso 1 1 calc R . . . .
C4 C 0.3541(2) 0.49753(11) 0.5901(2) 0.0443(5) Uani 1 1 d . . . . .
H00F H 0.274624 0.519555 0.526067 0.053 Uiso 1 1 calc R . . . .
C19 C 0.8563(2) 0.40199(12) 0.9182(3) 0.0516(5) Uani 1 1 d . . . . .
H00G H 0.948510 0.404536 0.929648 0.062 Uiso 1 1 calc R . . . .
C12 C 0.1432(2) 0.37118(12) -0.2079(2) 0.0463(5) Uani 1 1 d . . . . .
C20 C 0.8192(2) 0.40237(11) 1.0426(2) 0.0465(5) Uani 1 1 d . . . . .
C2 C 0.7014(2) 0.28142(12) 0.4816(2) 0.0502(5) Uani 1 1 d . . . . .
C18 C 0.7537(2) 0.39776(11) 0.7760(2) 0.0454(5) Uani 1 1 d . . . . .
H00J H 0.777862 0.396600 0.691583 0.054 Uiso 1 1 calc R . . . .
C15 C 0.50630(19) 0.39039(10) 0.6055(2) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.3635(2) 0.30262(11) 0.2408(2) 0.0425(4) Uani 1 1 d . . . . .
C14 C 0.2970(2) 0.39722(11) 0.0432(2) 0.0444(5) Uani 1 1 d . . . . .
H00M H 0.353305 0.428560 0.113609 0.053 Uiso 1 1 calc R . . . .
C10 C 0.1956(2) 0.28341(12) -0.0194(2) 0.0495(5) Uani 1 1 d . . . . .
H00N H 0.185959 0.237910 0.009006 0.059 Uiso 1 1 calc R . . . .
C13 C 0.2293(2) 0.41810(12) -0.1048(2) 0.0463(5) Uani 1 1 d . . . . .
H00O H 0.241251 0.462996 -0.134801 0.056 Uiso 1 1 calc R . . . .
C11 C 0.1250(2) 0.30431(13) -0.1664(2) 0.0534(5) Uani 1 1 d . . . . .
H00P H 0.066070 0.273654 -0.236250 0.064 Uiso 1 1 calc R . . . .
C1 C 0.7871(3) 0.28504(17) 0.4317(4) 0.0771(8) Uani 1 1 d . . . . .
H1 H 0.855712 0.287945 0.391784 0.093 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
Cl00 C12 1.736(2) . ?
Cl1 C20 1.737(2) . ?
N1 C7 1.393(2) . ?
N1 C3 1.470(2) . ?
N1 C15 1.356(2) . ?
O1 C4 1.204(3) . ?
O2 C8 1.222(3) . ?
C5 C6 1.411(3) . ?
C5 C4 1.447(3) . ?
C5 C15 1.402(3) . ?
C7 C6 1.372(3) . ?
C7 C8 1.465(3) . ?
C16 C17 1.393(3) . ?
C16 C18 1.392(3) . ?
C16 C15 1.474(3) . ?
C3 C2 1.460(3) . ?
C9 C8 1.493(3) . ?
C9 C14 1.387(3) . ?
C9 C10 1.397(3) . ?
C17 C00D 1.378(3) . ?
C00D C20 1.384(3) . ?
C19 C20 1.379(3) . ?
C19 C18 1.386(3) . ?
C12 C13 1.389(3) . ?
C12 C11 1.375(3) . ?
C2 C1 1.162(4) . ?
C14 C13 1.384(3) . ?
C10 C11 1.381(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
C7 N1 C3 125.61(15) . . ?
C15 N1 C7 110.07(16) . . ?
C15 N1 C3 124.20(16) . . ?
C6 C5 C4 124.28(18) . . ?
C15 C5 C6 107.05(16) . . ?
C15 C5 C4 128.65(17) . . ?
N1 C7 C8 123.36(17) . . ?
C6 C7 N1 107.09(16) . . ?
C6 C7 C8 129.48(18) . . ?
C17 C16 C15 120.81(17) . . ?
C18 C16 C17 118.20(18) . . ?
C18 C16 C15 120.99(17) . . ?
C2 C3 N1 112.52(17) . . ?
C14 C9 C8 122.21(17) . . ?
C14 C9 C10 119.30(19) . . ?
C10 C9 C8 118.22(19) . . ?
C7 C6 C5 108.29(17) . . ?
C00D C17 C16 121.43(19) . . ?
C17 C00D C20 118.87(19) . . ?
O1 C4 C5 127.3(2) . . ?
C20 C19 C18 118.9(2) . . ?
C13 C12 Cl00 118.41(18) . . ?
C11 C12 Cl00 120.18(16) . . ?
C11 C12 C13 121.4(2) . . ?
C00D C20 Cl1 119.42(17) . . ?
C19 C20 Cl1 119.14(18) . . ?
C19 C20 C00D 121.44(19) . . ?
C1 C2 C3 179.2(3) . . ?
C19 C18 C16 121.19(19) . . ?
N1 C15 C5 107.44(16) . . ?
N1 C15 C16 122.47(16) . . ?
C5 C15 C16 130.05(16) . . ?
O2 C8 C7 122.33(18) . . ?
O2 C8 C9 119.04(17) . . ?
C7 C8 C9 118.63(18) . . ?
C13 C14 C9 120.30(19) . . ?
C11 C10 C9 120.8(2) . . ?
C14 C13 C12 119.2(2) . . ?
C12 C11 C10 118.99(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
