# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_f1
_database_code_depnum_ccdc_archive 'CCDC 2195418'
loop_
_audit_author_name
_audit_author_address
'Joyanta Choudhury'
;IISER Bhopal, Department of Chemistry
India
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Br N2 O3, C H Cl'
_chemical_formula_sum            'C25 H20 Br Cl N2 O3'
_chemical_formula_weight         511.79
_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'
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'
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           15
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   13.486(3)
_cell_length_b                   14.311(3)
_cell_length_c                   24.277(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.610(13)
_cell_angle_gamma                90
_cell_volume                     4620(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8705
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.925
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4883
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.6546.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'whiteish colourless'
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             2080
_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  0.1330
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            67246
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.719
_diffrn_reflns_theta_min         2.091
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4087
_reflns_number_total             5977
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         1.263
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.037
_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)+(0.0465P)²+20.9694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1455
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N006(H00A,H00B)
2.b Ternary CH refined with riding coordinates:
 C00C(H00D), C00J(H00J), C0AA(H0AA)
2.c Secondary CH2 refined with riding coordinates:
 C00L(H00F,H00G)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00D(H00E), C00H(H00H), C00K(H00K), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V)
2.e Idealised Me refined as rotating group:
 C00T(H00I,H00L,H00M)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Br01 Br 0.61179(3) 0.26676(3) 0.37702(2) 0.04180(14) Uani 1 1 d . . . . .
O003 O 0.36984(17) 0.21256(16) 0.56216(10) 0.0245(5) Uani 1 1 d . . . . .
O004 O 0.6301(2) 0.53193(18) 0.72067(10) 0.0315(6) Uani 1 1 d . . . . .
O005 O 0.6639(2) 0.56721(18) 0.63579(11) 0.0342(6) Uani 1 1 d . . . . .
N006 N 0.3575(2) 0.1586(2) 0.64725(13) 0.0332(7) Uani 1 1 d . . . . .
H00A H 0.3604 0.1900 0.6789 0.040 Uiso 1 1 d GR . . . .
H00B H 0.2950 0.1604 0.6290 0.040 Uiso 1 1 d GR . . . .
N007 N 0.6071(2) 0.1643(2) 0.72687(14) 0.0363(8) Uani 1 1 d . . . . .
C008 C 0.5181(2) 0.2190(2) 0.63076(14) 0.0237(7) Uani 1 1 d . . . . .
C009 C 0.5273(2) 0.2570(2) 0.53350(14) 0.0220(7) Uani 1 1 d . . . . .
C00A C 0.5808(2) 0.2690(2) 0.48958(14) 0.0244(7) Uani 1 1 d . . . . .
H00C H 0.6492 0.2880 0.4970 0.029 Uiso 1 1 calc R . . . .
C00B C 0.4189(3) 0.1971(2) 0.61501(14) 0.0242(7) Uani 1 1 d . . . . .
C00C C 0.5737(2) 0.2761(2) 0.59328(14) 0.0235(7) Uani 1 1 d . . . . .
H00D H 0.6452 0.2544 0.5990 0.028 Uiso 1 1 calc R . . . .
C00D C 0.4349(3) 0.2270(2) 0.42275(15) 0.0287(7) Uani 1 1 d . . . . .
H00E H 0.4039 0.2180 0.3850 0.034 Uiso 1 1 calc R . . . .
C00E C 0.4282(2) 0.2286(2) 0.52070(14) 0.0227(7) Uani 1 1 d . . . . .
C00F C 0.6470(3) 0.5101(3) 0.66965(15) 0.0271(7) Uani 1 1 d . . . . .
C00G C 0.5664(3) 0.1897(3) 0.68366(16) 0.0279(8) Uani 1 1 d . . . . .
C00H C 0.3808(3) 0.2139(2) 0.46621(15) 0.0259(7) Uani 1 1 d . . . . .
H00H H 0.3123 0.1952 0.4586 0.031 Uiso 1 1 calc R . . . .
C00I C 0.3108(3) 0.4765(2) 0.54723(15) 0.0261(7) Uani 1 1 d . . . . .
C00J C 0.5734(2) 0.3834(2) 0.60497(14) 0.0248(7) Uani 1 1 d . . . . .
H00J H 0.6024 0.4148 0.5744 0.030 Uiso 1 1 calc R . . . .
C00K C 0.4126(3) 0.4462(2) 0.55214(15) 0.0251(7) Uani 1 1 d . . . . .
H00K H 0.4431 0.4437 0.5196 0.030 Uiso 1 1 calc R . . . .
C00L C 0.6426(3) 0.4064(3) 0.65988(15) 0.0298(8) Uani 1 1 d . . . . .
H00F H 0.6173 0.3752 0.6912 0.036 Uiso 1 1 calc R . . . .
H00G H 0.7110 0.3824 0.6586 0.036 Uiso 1 1 calc R . . . .
C00M C 0.4674(3) 0.4206(2) 0.60233(15) 0.0249(7) Uani 1 1 d . . . . .
C00N C 0.5345(3) 0.2534(2) 0.43559(15) 0.0276(8) Uani 1 1 d . . . . .
C00O C 0.2675(3) 0.4826(2) 0.59634(16) 0.0282(8) Uani 1 1 d . . . . .
C00P C 0.4209(3) 0.4262(3) 0.65107(16) 0.0299(8) Uani 1 1 d . . . . .
H00P H 0.4579 0.4082 0.6863 0.036 Uiso 1 1 calc R . . . .
C00Q C 0.3239(3) 0.4569(3) 0.64787(16) 0.0332(9) Uani 1 1 d . . . . .
H00Q H 0.2947 0.4607 0.6808 0.040 Uiso 1 1 calc R . . . .
C00R C 0.2531(3) 0.4988(3) 0.49461(17) 0.0329(8) Uani 1 1 d . . . . .
H00R H 0.2815 0.4928 0.4615 0.040 Uiso 1 1 calc R . . . .
C00S C 0.1660(3) 0.5154(3) 0.59125(19) 0.0360(9) Uani 1 1 d . . . . .
H00S H 0.1357 0.5215 0.6237 0.043 Uiso 1 1 calc R . . . .
C00T C 0.6313(3) 0.6302(3) 0.73376(17) 0.0380(9) Uani 1 1 d . . . . .
H00I H 0.5823 0.6629 0.7060 0.057 Uiso 1 1 calc GR . . . .
H00L H 0.6986 0.6555 0.7332 0.057 Uiso 1 1 calc GR . . . .
H00M H 0.6137 0.6390 0.7710 0.057 Uiso 1 1 calc GR . . . .
C00U C 0.1131(3) 0.5376(3) 0.5407(2) 0.0390(10) Uani 1 1 d . . . . .
H00U H 0.0459 0.5594 0.5380 0.047 Uiso 1 1 calc R . . . .
C00V C 0.1567(3) 0.5289(3) 0.49178(19) 0.0405(10) Uani 1 1 d . . . . .
H00V H 0.1181 0.5443 0.4565 0.049 Uiso 1 1 calc R . . . .
Cl1 Cl 0.60361(10) 0.88950(9) 0.73906(5) 0.0562(3) Uiso 1 1 d . . . . .
C0AA C 0.5175(9) 0.9490(8) 0.7754(4) 0.153(4) Uiso 1 1 d . . . . .
H0AA H 0.5329 1.0057 0.7994 0.183 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
Br01 C00N 1.907(3) . ?
O003 C00B 1.360(4) . ?
O003 C00E 1.397(4) . ?
O004 C00F 1.334(4) . ?
O004 C00T 1.442(5) . ?
O005 C00F 1.207(4) . ?
N006 C00B 1.349(4) . ?
N007 C00G 1.158(5) . ?
C008 C00B 1.364(5) . ?
C008 C00C 1.512(5) . ?
C008 C00G 1.404(5) . ?
C009 C00A 1.394(4) . ?
C009 C00C 1.506(5) . ?
C009 C00E 1.382(5) . ?
C00A C00N 1.372(5) . ?
C00C C00J 1.562(5) . ?
C00D C00H 1.392(5) . ?
C00D C00N 1.381(5) . ?
C00E C00H 1.386(5) . ?
C00F C00L 1.503(5) . ?
C00I C00K 1.425(5) . ?
C00I C00O 1.415(5) . ?
C00I C00R 1.417(5) . ?
C00J C00L 1.530(5) . ?
C00J C00M 1.517(5) . ?
C00K C00M 1.365(5) . ?
C00M C00P 1.431(5) . ?
C00O C00Q 1.401(6) . ?
C00O C00S 1.432(5) . ?
C00P C00Q 1.370(5) . ?
C00R C00V 1.360(6) . ?
C00S C00U 1.350(6) . ?
C00U C00V 1.416(6) . ?
Cl1 C0AA 1.788(12) . ?
Cl1 C0AA 1.823(12) 2_656 ?
C0AA Cl1 1.823(12) 2_656 ?
C0AA C0AA 1.246(19) 2_656 ?

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
C00B O003 C00E 117.5(3) . . ?
C00F O004 C00T 115.8(3) . . ?
C00B C008 C00C 121.1(3) . . ?
C00B C008 C00G 118.1(3) . . ?
C00G C008 C00C 120.7(3) . . ?
C00A C009 C00C 122.0(3) . . ?
C00E C009 C00A 117.9(3) . . ?
C00E C009 C00C 120.0(3) . . ?
C00N C00A C009 120.0(3) . . ?
O003 C00B C008 121.8(3) . . ?
N006 C00B O003 111.4(3) . . ?
N006 C00B C008 126.8(3) . . ?
C008 C00C C00J 113.9(3) . . ?
C009 C00C C008 108.3(3) . . ?
C009 C00C C00J 109.9(3) . . ?
C00N C00D C00H 118.6(3) . . ?
C009 C00E O003 121.8(3) . . ?
C009 C00E C00H 122.3(3) . . ?
C00H C00E O003 115.9(3) . . ?
O004 C00F C00L 111.7(3) . . ?
O005 C00F O004 123.7(3) . . ?
O005 C00F C00L 124.6(3) . . ?
N007 C00G C008 178.8(4) . . ?
C00E C00H C00D 119.1(3) . . ?
C00O C00I C00K 118.4(3) . . ?
C00O C00I C00R 120.2(3) . . ?
C00R C00I C00K 121.4(3) . . ?
C00L C00J C00C 110.5(3) . . ?
C00M C00J C00C 111.6(3) . . ?
C00M C00J C00L 113.2(3) . . ?
C00M C00K C00I 121.8(3) . . ?
C00F C00L C00J 110.6(3) . . ?
C00K C00M C00J 119.9(3) . . ?
C00K C00M C00P 118.4(3) . . ?
C00P C00M C00J 121.6(3) . . ?
C00A C00N Br01 118.6(3) . . ?
C00A C00N C00D 122.0(3) . . ?
C00D C00N Br01 119.4(3) . . ?
C00I C00O C00S 118.1(4) . . ?
C00Q C00O C00I 119.8(3) . . ?
C00Q C00O C00S 122.1(3) . . ?
C00Q C00P C00M 121.1(3) . . ?
C00P C00Q C00O 120.4(3) . . ?
C00V C00R C00I 119.6(4) . . ?
C00U C00S C00O 120.5(4) . . ?
C00S C00U C00V 120.7(4) . . ?
C00R C00V C00U 120.8(4) . . ?
C0AA Cl1 C0AA 40.3(6) . 2_656 ?
Cl1 C0AA Cl1 108.5(6) . 2_656 ?
C0AA C0AA Cl1 71.3(9) 2_656 . ?
C0AA C0AA Cl1 68.3(9) 2_656 2_656 ?

_olex2_submission_special_instructions 'No special instructions were received'
