# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_MANJU01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2039264'
loop_
_audit_author_name
_audit_author_address
'Manju Devi'
;iit delhi
India
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Br N2 0, C H Cl3'
_chemical_formula_sum            'C25 H19 Br Cl3 N2 O'
_chemical_formula_weight         549.67

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'
Br Br -0.2901 2.4595 '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'

_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                   12.0457(6)
_cell_length_b                   13.8112(6)
_cell_length_c                   14.5205(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.314(2)
_cell_angle_gamma                90
_cell_volume                     2413.74(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   0.698
_exptl_transmission_factor_max   0.814
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.056
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69097
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6039
_reflns_number_gt                4488
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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+0.3517P] 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         6039
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0898
_refine_ls_wR_factor_ref         0.2348
_refine_ls_wR_factor_gt          0.2211
_refine_ls_goodness_of_fit_ref   1.460
_refine_ls_restrained_S_all      1.460
_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
Br1 Br 0.66372(4) 0.43028(3) 0.51583(4) 0.0607(2) Uani 1 1 d . . . . .
Cl2 Cl 0.35135(15) 0.98847(13) 0.50570(9) 0.0886(5) Uani 1 1 d . . . . .
Cl1 Cl 0.38070(19) 0.98871(12) 0.70224(9) 0.1022(7) Uani 1 1 d . . . . .
Cl3 Cl 0.3111(2) 0.81521(14) 0.60972(12) 0.1113(7) Uani 1 1 d . . . . .
O1 O 0.6358(3) 0.85153(18) 0.6608(2) 0.0474(7) Uani 1 1 d . . . . .
N2 N 0.6321(3) 0.5208(2) 0.8379(2) 0.0467(8) Uani 1 1 d . . . . .
N1 N 0.8153(3) 0.8216(2) 0.6271(2) 0.0443(7) Uani 1 1 d . . . . .
C8 C 0.7130(3) 0.7957(2) 0.6515(2) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.7112(3) 0.6844(2) 0.6689(2) 0.0328(7) Uani 1 1 d . . . . .
C18 C 0.5807(4) 0.6808(3) 0.8093(2) 0.0403(8) Uani 1 1 d . . . . .
C2 C 0.8264(3) 0.6560(2) 0.6401(2) 0.0366(7) Uani 1 1 d . . . . .
C16 C 0.6965(3) 0.6682(2) 0.7759(2) 0.0381(8) Uani 1 1 d . . . . .
C10 C 0.6215(3) 0.6354(3) 0.5097(2) 0.0385(8) Uani 1 1 d . . . . .
C19 C 0.7131(4) 0.5620(3) 0.7997(3) 0.0466(10) Uani 1 1 d . . . . .
H19 H 0.778132 0.529034 0.787166 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6133(3) 0.6359(3) 0.6132(2) 0.0367(7) Uani 1 1 d . . . . .
H9A H 0.607114 0.569405 0.633914 0.044 Uiso 1 1 calc R U . . .
H9B H 0.545225 0.668840 0.628077 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8847(4) 0.7403(3) 0.6185(2) 0.0414(8) Uani 1 1 d . . . . .
C20 C 0.5464(4) 0.5913(3) 0.8441(3) 0.0447(9) Uani 1 1 d . . . . .
C21 C 0.4453(5) 0.5781(3) 0.8825(3) 0.0577(12) Uani 1 1 d . . . . .
H21 H 0.424832 0.518110 0.905329 0.069 Uiso 1 1 calc R U . . .
C24 C 0.5096(4) 0.7592(3) 0.8160(3) 0.0536(11) Uani 1 1 d . . . . .
H24 H 0.530731 0.819818 0.795110 0.064 Uiso 1 1 calc R U . . .
C3 C 0.8783(4) 0.5675(3) 0.6317(3) 0.0451(9) Uani 1 1 d . . . . .
H3 H 0.841091 0.510359 0.644579 0.054 Uiso 1 1 calc R U . . .
C6 C 0.9926(4) 0.7387(4) 0.5912(3) 0.0568(11) Uani 1 1 d . . . . .
H6 H 1.030152 0.795557 0.577963 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6409(4) 0.5524(3) 0.4583(3) 0.0466(9) Uani 1 1 d . . . . .
C4 C 0.9880(4) 0.5653(3) 0.6035(3) 0.0552(11) Uani 1 1 d . . . . .
H4 H 1.023927 0.506153 0.597806 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0433(4) 0.6489(4) 0.5841(3) 0.0612(12) Uani 1 1 d . . . . .
H5 H 1.116267 0.645550 0.565802 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4067(5) 0.7469(4) 0.8541(3) 0.0661(14) Uani 1 1 d . . . . .
H23 H 0.359000 0.799535 0.858050 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7827(4) 0.7290(3) 0.8337(3) 0.0564(12) Uani 1 1 d . . . . .
H17A H 0.772565 0.796439 0.819749 0.085 Uiso 1 1 calc R U . . .
H17B H 0.856461 0.709693 0.819028 0.085 Uiso 1 1 calc R U . . .
H17C H 0.772257 0.718421 0.898156 0.085 Uiso 1 1 calc R U . . .
C22 C 0.3742(5) 0.6576(4) 0.8861(3) 0.0684(14) Uani 1 1 d . . . . .
H22 H 0.304318 0.650429 0.910232 0.082 Uiso 1 1 calc R U . . .
C11 C 0.6001(4) 0.7219(3) 0.4589(3) 0.0540(10) Uani 1 1 d . . . . .
H11 H 0.587431 0.779200 0.490376 0.065 Uiso 1 1 calc R U . . .
C25 C 0.3892(5) 0.9193(3) 0.6039(3) 0.0582(12) Uani 1 1 d . . . . .
H25 H 0.467008 0.900027 0.598746 0.070 Uiso 1 1 calc R U . . .
C12 C 0.5979(5) 0.7224(4) 0.3642(3) 0.0703(15) Uani 1 1 d . . . . .
H12 H 0.584590 0.779780 0.332099 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6154(5) 0.6375(5) 0.3170(3) 0.0797(17) Uani 1 1 d . . . . .
H13 H 0.612468 0.638028 0.252943 0.096 Uiso 1 1 calc R U . . .
C14 C 0.6368(5) 0.5528(4) 0.3625(3) 0.0693(14) Uani 1 1 d . . . . .
H14 H 0.648568 0.496060 0.329865 0.083 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
Br1 C15 1.897(4) . ?
Cl2 C25 1.761(5) . ?
Cl1 C25 1.726(5) . ?
Cl3 C25 1.722(5) . ?
O1 C8 1.220(5) . ?
N2 C19 1.276(6) . ?
N2 C20 1.424(5) . ?
N1 C8 1.344(5) . ?
N1 C7 1.408(5) . ?
C8 C1 1.558(4) . ?
C1 C2 1.516(5) . ?
C1 C9 1.554(5) . ?
C1 C16 1.587(5) . ?
C18 C24 1.386(6) . ?
C18 C20 1.405(5) . ?
C18 C16 1.506(6) . ?
C2 C3 1.382(5) . ?
C2 C7 1.401(5) . ?
C16 C19 1.519(5) . ?
C16 C17 1.555(5) . ?
C10 C15 1.393(5) . ?
C10 C11 1.422(6) . ?
C10 C9 1.510(5) . ?
C19 H19 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C6 1.374(6) . ?
C20 C21 1.372(7) . ?
C21 C22 1.395(7) . ?
C21 H21 0.9300 . ?
C24 C23 1.387(7) . ?
C24 H24 0.9300 . ?
C3 C4 1.400(7) . ?
C3 H3 0.9300 . ?
C6 C5 1.388(7) . ?
C6 H6 0.9300 . ?
C15 C14 1.390(6) . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C23 C22 1.380(8) . ?
C23 H23 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C22 H22 0.9300 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9300 . ?
C25 H25 0.9800 . ?
C12 C13 1.378(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(9) . ?
C13 H13 0.9300 . ?
C14 H14 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
C19 N2 C20 106.9(3) . . ?
C8 N1 C7 111.4(3) . . ?
O1 C8 N1 124.9(3) . . ?
O1 C8 C1 126.2(3) . . ?
N1 C8 C1 108.9(3) . . ?
C2 C1 C9 115.4(3) . . ?
C2 C1 C8 101.0(3) . . ?
C9 C1 C8 110.9(3) . . ?
C2 C1 C16 111.9(3) . . ?
C9 C1 C16 109.6(3) . . ?
C8 C1 C16 107.5(3) . . ?
C24 C18 C20 118.1(4) . . ?
C24 C18 C16 134.2(4) . . ?
C20 C18 C16 107.7(3) . . ?
C3 C2 C7 118.9(4) . . ?
C3 C2 C1 132.5(3) . . ?
C7 C2 C1 108.6(3) . . ?
C18 C16 C19 98.8(3) . . ?
C18 C16 C17 111.7(3) . . ?
C19 C16 C17 108.7(3) . . ?
C18 C16 C1 116.1(3) . . ?
C19 C16 C1 109.9(3) . . ?
C17 C16 C1 110.8(3) . . ?
C15 C10 C11 116.4(3) . . ?
C15 C10 C9 123.8(3) . . ?
C11 C10 C9 119.7(3) . . ?
N2 C19 C16 115.7(4) . . ?
N2 C19 H19 122.1 . . ?
C16 C19 H19 122.1 . . ?
C10 C9 C1 116.1(3) . . ?
C10 C9 H9A 108.3 . . ?
C1 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C1 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C6 C7 C2 122.7(4) . . ?
C6 C7 N1 127.6(4) . . ?
C2 C7 N1 109.7(3) . . ?
C21 C20 C18 122.8(4) . . ?
C21 C20 N2 126.3(4) . . ?
C18 C20 N2 110.8(4) . . ?
C20 C21 C22 117.9(4) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 H21 121.1 . . ?
C18 C24 C23 119.8(4) . . ?
C18 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C7 C6 C5 117.4(4) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C14 C15 C10 122.2(4) . . ?
C14 C15 Br1 116.3(4) . . ?
C10 C15 Br1 121.4(3) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C22 C23 C24 120.9(5) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C22 C21 120.5(5) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
Cl3 C25 Cl1 111.8(3) . . ?
Cl3 C25 Cl2 111.6(3) . . ?
Cl1 C25 Cl2 110.3(3) . . ?
Cl3 C25 H25 107.6 . . ?
Cl1 C25 H25 107.6 . . ?
Cl2 C25 H25 107.6 . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.2(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?

_refine_diff_density_max         1.436
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.210

