# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_RR_AC_394
_database_code_depnum_ccdc_archive 'CCDC 2381641'
loop_
_audit_author_name
_audit_author_address
'Virender Singh'
;Central University Of Punjab Bathinda
India
;
_audit_update_record             
;
2024-09-03 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H20 Cl N'
_chemical_formula_sum            'C29 H20 Cl N'
_chemical_formula_weight         417.91

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.644(2)
_cell_length_b                   9.9782(13)
_cell_length_c                   15.7628(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.274(5)
_cell_angle_gamma                90
_cell_volume                     2145.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2961
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.12

_exptl_crystal_description       block-shape
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   0.941
_exptl_transmission_factor_max   0.962
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.189
_shelx_estimated_absorpt_T_max   0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III photon detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17848
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.416
_diffrn_reflns_theta_max         23.069
_diffrn_reflns_theta_full        23.069
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2961
_reflns_number_gt                2083
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.4039P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2961
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_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_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 0.61564(7) 0.07134(9) 0.03672(6) 0.0713(4) Uani 1 1 d . . . . .
N1 N 0.40403(18) 0.4958(2) 0.22194(15) 0.0476(7) Uani 1 1 d . . . . .
C15 C 0.4234(2) 0.6325(3) 0.20112(19) 0.0466(8) Uani 1 1 d . . . . .
C4 C 0.4546(2) 0.3943(3) 0.17830(18) 0.0432(8) Uani 1 1 d . . . . .
C13 C 0.2590(2) 0.6468(3) 0.13954(19) 0.0484(8) Uani 1 1 d . . . . .
C5 C 0.4498(2) 0.2612(3) 0.2040(2) 0.0510(8) Uani 1 1 d . . . . .
H5 H 0.413411 0.238622 0.251142 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2312(2) 0.5276(3) 0.17959(19) 0.0489(8) Uani 1 1 d . . . . .
C14 C 0.3530(2) 0.7050(3) 0.16362(19) 0.0493(8) Uani 1 1 d . . . . .
H14 H 0.364348 0.795216 0.152580 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3016(2) 0.4720(3) 0.2463(2) 0.0497(8) Uani 1 1 d . . . . .
H7 H 0.290819 0.375309 0.251572 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5121(2) 0.4252(3) 0.1090(2) 0.0484(8) Uani 1 1 d . . . . .
H3 H 0.517024 0.513665 0.091008 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5190(2) 0.6863(3) 0.2309(2) 0.0510(8) Uani 1 1 d . . . . .
C1 C 0.5539(2) 0.1950(3) 0.0921(2) 0.0511(8) Uani 1 1 d . . . . .
C24 C 0.2939(2) 0.6703(3) 0.4729(2) 0.0522(9) Uani 1 1 d . . . . .
C6 C 0.4983(2) 0.1620(3) 0.1605(2) 0.0556(9) Uani 1 1 d . . . . .
H6 H 0.493278 0.073056 0.177477 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5618(2) 0.3259(3) 0.0670(2) 0.0538(9) Uani 1 1 d . . . . .
H2 H 0.600891 0.347842 0.021438 0.065 Uiso 1 1 calc R U . . .
C22 C 0.2878(2) 0.5357(4) 0.3296(2) 0.0531(9) Uani 1 1 d . . . . .
C23 C 0.2863(3) 0.5951(3) 0.3948(2) 0.0548(9) Uani 1 1 d . . . . .
C12 C 0.1951(3) 0.7032(4) 0.0793(2) 0.0584(9) Uani 1 1 d . . . . .
H12 H 0.212328 0.782127 0.052010 0.070 Uiso 1 1 calc R U . . .
C17 C 0.5628(3) 0.7945(3) 0.1910(2) 0.0601(9) Uani 1 1 d . . . . .
H17 H 0.534360 0.829703 0.141709 0.072 Uiso 1 1 calc R U . . .
C9 C 0.1419(3) 0.4671(4) 0.1592(2) 0.0601(9) Uani 1 1 d . . . . .
H9 H 0.124148 0.387412 0.185375 0.072 Uiso 1 1 calc R U . . .
C10 C 0.0800(3) 0.5261(4) 0.1001(2) 0.0690(11) Uani 1 1 d . . . . .
H10 H 0.019659 0.486952 0.087164 0.083 Uiso 1 1 calc R U . . .
C29 C 0.2327(3) 0.7765(4) 0.4887(2) 0.0687(10) Uani 1 1 d . . . . .
H29 H 0.181187 0.796406 0.451217 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1068(3) 0.6430(4) 0.0597(2) 0.0708(11) Uani 1 1 d . . . . .
H11 H 0.064853 0.681129 0.019166 0.085 Uiso 1 1 calc R U . . .
C21 C 0.5645(3) 0.6334(4) 0.3030(2) 0.0722(11) Uani 1 1 d . . . . .
H21 H 0.536831 0.560575 0.330447 0.087 Uiso 1 1 calc R U . . .
C25 C 0.3667(3) 0.6396(4) 0.5316(2) 0.0739(11) Uani 1 1 d . . . . .
H25 H 0.407449 0.566526 0.522602 0.089 Uiso 1 1 calc R U . . .
C18 C 0.6478(3) 0.8501(4) 0.2238(3) 0.0776(12) Uani 1 1 d . . . . .
H18 H 0.675551 0.923785 0.197365 0.093 Uiso 1 1 calc R U . . .
C19 C 0.6917(3) 0.7971(5) 0.2952(3) 0.0869(13) Uani 1 1 d . . . . .
H19 H 0.749163 0.834823 0.317117 0.104 Uiso 1 1 calc R U . . .
C28 C 0.2484(4) 0.8536(4) 0.5608(3) 0.0856(13) Uani 1 1 d . . . . .
H28 H 0.208434 0.927402 0.570384 0.103 Uiso 1 1 calc R U . . .
C27 C 0.3209(4) 0.8233(5) 0.6176(3) 0.0882(14) Uani 1 1 d . . . . .
H27 H 0.330653 0.875324 0.666060 0.106 Uiso 1 1 calc R U . . .
C20 C 0.6512(3) 0.6891(5) 0.3342(3) 0.0913(14) Uani 1 1 d . . . . .
H20 H 0.681971 0.652577 0.382061 0.110 Uiso 1 1 calc R U . . .
C26 C 0.3793(3) 0.7158(5) 0.6029(3) 0.0903(14) Uani 1 1 d . . . . .
H26 H 0.428660 0.693779 0.642123 0.108 Uiso 1 1 calc R U . . .


_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 1.740(3) . ?
N1 C4 1.413(4) . ?
N1 C15 1.429(4) . ?
N1 C7 1.476(4) . ?
C15 C14 1.330(4) . ?
C15 C16 1.478(5) . ?
C4 C5 1.391(4) . ?
C4 C3 1.393(4) . ?
C13 C12 1.394(5) . ?
C13 C8 1.403(5) . ?
C13 C14 1.451(4) . ?
C5 C6 1.382(4) . ?
C8 C9 1.391(5) . ?
C8 C7 1.514(5) . ?
C7 C22 1.475(5) . ?
C3 C2 1.379(4) . ?
C16 C21 1.387(5) . ?
C16 C17 1.391(5) . ?
C1 C2 1.369(5) . ?
C1 C6 1.372(5) . ?
C24 C29 1.375(5) . ?
C24 C25 1.376(5) . ?
C24 C23 1.444(5) . ?
C22 C23 1.188(5) . ?
C12 C11 1.375(5) . ?
C17 C18 1.375(5) . ?
C9 C10 1.376(5) . ?
C10 C11 1.381(6) . ?
C29 C28 1.386(6) . ?
C21 C20 1.388(6) . ?
C25 C26 1.365(6) . ?
C18 C19 1.369(6) . ?
C19 C20 1.363(6) . ?
C28 C27 1.354(7) . ?
C27 C26 1.359(6) . ?

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
C4 N1 C15 118.5(2) . . ?
C4 N1 C7 119.1(2) . . ?
C15 N1 C7 113.2(2) . . ?
C14 C15 N1 119.1(3) . . ?
C14 C15 C16 124.6(3) . . ?
N1 C15 C16 116.1(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 N1 121.0(3) . . ?
C3 C4 N1 120.8(3) . . ?
C12 C13 C8 118.5(3) . . ?
C12 C13 C14 123.5(3) . . ?
C8 C13 C14 117.9(3) . . ?
C6 C5 C4 120.8(3) . . ?
C9 C8 C13 120.6(3) . . ?
C9 C8 C7 122.7(3) . . ?
C13 C8 C7 116.7(3) . . ?
C15 C14 C13 121.6(3) . . ?
C22 C7 N1 107.6(3) . . ?
C22 C7 C8 111.6(3) . . ?
N1 C7 C8 110.6(2) . . ?
C2 C3 C4 120.6(3) . . ?
C21 C16 C17 118.5(3) . . ?
C21 C16 C15 119.9(3) . . ?
C17 C16 C15 121.6(3) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 Cl1 119.3(3) . . ?
C6 C1 Cl1 120.4(3) . . ?
C29 C24 C25 118.8(3) . . ?
C29 C24 C23 121.5(3) . . ?
C25 C24 C23 119.7(3) . . ?
C1 C6 C5 119.9(3) . . ?
C1 C2 C3 120.3(3) . . ?
C23 C22 C7 172.4(4) . . ?
C22 C23 C24 174.7(4) . . ?
C11 C12 C13 120.5(3) . . ?
C18 C17 C16 120.7(4) . . ?
C10 C9 C8 119.4(4) . . ?
C9 C10 C11 120.6(4) . . ?
C24 C29 C28 119.6(4) . . ?
C12 C11 C10 120.3(4) . . ?
C16 C21 C20 120.0(4) . . ?
C26 C25 C24 120.4(4) . . ?
C19 C18 C17 120.2(4) . . ?
C20 C19 C18 120.1(4) . . ?
C27 C28 C29 121.0(4) . . ?
C28 C27 C26 119.1(4) . . ?
C19 C20 C21 120.5(4) . . ?
C27 C26 C25 121.1(4) . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.055

