# 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. 
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data_16906_83_1_p2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2350681'
loop_
_audit_author_name
_audit_author_address
'Dr. Shibaji Ghosh'
;CSIR Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_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         'C18 H17 Br N4 O2'
_chemical_formula_sum            'C18 H17 Br N4 O2'
_chemical_formula_weight         401.26
_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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.2070(7)
_cell_length_b                   12.3855(8)
_cell_length_c                   13.5520(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713.23(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.823
_cell_measurement_theta_min      2.498
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.531
_exptl_absorpt_coefficient_mu    2.419
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0879 before and 0.0765 after correction. The Ratio of minimum to maximum transmission is 0.8417. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            145680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.441
_diffrn_reflns_theta_min         2.228
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5128
_reflns_number_total             8854
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 1874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         8854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0994
_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:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.63355(2) 0.24416(2) 0.44020(2) 0.05519(9) Uani 1 1 d . . . . .
O1 O 0.28594(19) 0.77513(14) 0.33254(12) 0.0510(4) Uani 1 1 d . . . . .
O0AA O 0.2328(2) 0.53999(15) 0.74013(14) 0.0599(5) Uani 1 1 d . . . . .
N1 N 0.30025(19) 0.95955(15) 0.73359(14) 0.0418(4) Uani 1 1 d . . . . .
N2 N 0.33434(18) 0.67803(14) 0.66152(12) 0.0356(4) Uani 1 1 d . . . . .
N3 N 0.38305(16) 0.61675(13) 0.46587(11) 0.0313(3) Uani 1 1 d . . . . .
N4 N 0.4103(2) 0.88998(15) 0.60552(15) 0.0459(4) Uani 1 1 d . . . . .
C1 C 0.2249(3) 0.9557(2) 0.8182(2) 0.0531(6) Uani 1 1 d . . . . .
H1 H 0.202738 1.018710 0.851682 0.064 Uiso 1 1 calc R . . . .
C2 C 0.3349(2) 0.86770(15) 0.68291(15) 0.0347(4) Uani 1 1 d . . . . .
C3 C 0.29086(19) 0.76562(16) 0.71736(13) 0.0330(4) Uani 1 1 d . . . . .
C4 C 0.3048(2) 0.57177(16) 0.67504(14) 0.0356(4) Uani 1 1 d . . . . .
C5 C 0.3747(2) 0.49459(15) 0.60734(13) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.4176(2) 0.51749(16) 0.51046(13) 0.0315(4) Uani 1 1 d . . . . .
C7 C 0.4569(2) 0.64846(18) 0.37788(15) 0.0407(4) Uani 1 1 d . . . . .
H7A H 0.435253 0.601122 0.323239 0.049 Uiso 1 1 calc R . . . .
H7B H 0.550189 0.642859 0.390527 0.049 Uiso 1 1 calc R . . . .
C8 C 0.4215(3) 0.7637(2) 0.35246(17) 0.0486(5) Uani 1 1 d . . . . .
H8A H 0.445293 0.810439 0.407026 0.058 Uiso 1 1 calc R . . . .
H8B H 0.471289 0.786293 0.295084 0.058 Uiso 1 1 calc R . . . .
C9 C 0.2117(2) 0.7428(2) 0.41671(17) 0.0460(5) Uani 1 1 d . . . . .
H9A H 0.119027 0.750178 0.402388 0.055 Uiso 1 1 calc R . . . .
H9B H 0.232303 0.789877 0.471785 0.055 Uiso 1 1 calc R . . . .
C10 C 0.2408(2) 0.62719(17) 0.44498(16) 0.0379(4) Uani 1 1 d . . . . .
H10A H 0.190586 0.607396 0.502975 0.045 Uiso 1 1 calc R . . . .
H10B H 0.216390 0.579186 0.391512 0.045 Uiso 1 1 calc R . . . .
C11 C 0.4945(2) 0.44094(16) 0.46143(14) 0.0376(4) Uani 1 1 d . . . . .
H11 H 0.525277 0.455034 0.398133 0.045 Uiso 1 1 calc R . . . .
C12 C 0.5247(2) 0.34453(16) 0.50703(16) 0.0385(4) Uani 1 1 d . . . . .
C13 C 0.4786(2) 0.31851(17) 0.59988(16) 0.0393(4) Uani 1 1 d . . . . .
H13 H 0.497953 0.252194 0.628575 0.047 Uiso 1 1 calc R . . . .
C14 C 0.4027(2) 0.39419(16) 0.64904(15) 0.0376(4) Uani 1 1 d . . . . .
H14 H 0.369631 0.377648 0.711187 0.045 Uiso 1 1 calc R . . . .
C15 C 0.3566(3) 1.04484(19) 0.6852(2) 0.0557(6) Uani 1 1 d . . . . .
H15 H 0.350861 1.117606 0.701570 0.067 Uiso 1 1 calc R . . . .
C16 C 0.4226(3) 1.0006(2) 0.6085(2) 0.0569(6) Uani 1 1 d . . . . .
H16 H 0.470661 1.040386 0.562983 0.068 Uiso 1 1 calc R . . . .
C17 C 0.1844(3) 0.8591(2) 0.85101(19) 0.0528(6) Uani 1 1 d . . . . .
H17 H 0.134494 0.855784 0.908335 0.063 Uiso 1 1 calc R . . . .
C18 C 0.2154(2) 0.76229(19) 0.80103(14) 0.0414(4) Uani 1 1 d . . . . .
H18 H 0.184686 0.696542 0.824787 0.050 Uiso 1 1 calc R . . . .
H2 H 0.389(3) 0.696(2) 0.6100(19) 0.037(6) Uiso 1 1 d . . . . .


_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 C12 1.8975(19) . ?
O1 C8 1.417(3) . ?
O1 C9 1.427(3) . ?
O0AA C4 1.213(3) . ?
N1 C1 1.382(3) . ?
N1 C2 1.375(3) . ?
N1 C15 1.370(3) . ?
N2 C3 1.395(2) . ?
N2 C4 1.363(3) . ?
N2 H2 0.93(3) . ?
N3 C6 1.415(2) . ?
N3 C7 1.464(2) . ?
N3 C10 1.484(3) . ?
N4 C2 1.330(3) . ?
N4 C16 1.376(3) . ?
C1 H1 0.9300 . ?
C1 C17 1.342(4) . ?
C2 C3 1.421(3) . ?
C3 C18 1.371(3) . ?
C4 C5 1.505(3) . ?
C5 C6 1.413(3) . ?
C5 C14 1.395(3) . ?
C6 C11 1.399(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.512(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.512(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.355(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.413(3) . ?
C18 H18 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
C8 O1 C9 109.77(16) . . ?
C2 N1 C1 122.0(2) . . ?
C15 N1 C1 131.1(2) . . ?
C15 N1 C2 106.92(19) . . ?
C3 N2 H2 114.3(16) . . ?
C4 N2 C3 127.42(17) . . ?
C4 N2 H2 118.3(16) . . ?
C6 N3 C7 116.91(16) . . ?
C6 N3 C10 113.65(16) . . ?
C7 N3 C10 108.95(16) . . ?
C2 N4 C16 103.7(2) . . ?
N1 C1 H1 120.8 . . ?
C17 C1 N1 118.5(2) . . ?
C17 C1 H1 120.8 . . ?
N1 C2 C3 119.40(19) . . ?
N4 C2 N1 111.78(18) . . ?
N4 C2 C3 128.81(18) . . ?
N2 C3 C2 114.41(17) . . ?
C18 C3 N2 127.14(19) . . ?
C18 C3 C2 118.43(18) . . ?
O0AA C4 N2 123.03(19) . . ?
O0AA C4 C5 121.61(19) . . ?
N2 C4 C5 115.24(17) . . ?
C6 C5 C4 125.88(17) . . ?
C14 C5 C4 114.60(17) . . ?
C14 C5 C6 119.45(18) . . ?
C5 C6 N3 119.60(16) . . ?
C11 C6 N3 121.74(16) . . ?
C11 C6 C5 118.65(17) . . ?
N3 C7 H7A 110.0 . . ?
N3 C7 H7B 110.0 . . ?
N3 C7 C8 108.41(17) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
O1 C8 C7 111.8(2) . . ?
O1 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
O1 C9 C10 111.33(19) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N3 C10 C9 108.85(18) . . ?
N3 C10 H10A 109.9 . . ?
N3 C10 H10B 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C6 C11 H11 120.0 . . ?
C12 C11 C6 119.95(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 Br1 118.95(15) . . ?
C11 C12 C13 122.28(19) . . ?
C13 C12 Br1 118.77(16) . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.05(19) . . ?
C14 C13 H13 121.0 . . ?
C5 C14 H14 119.3 . . ?
C13 C14 C5 121.47(19) . . ?
C13 C14 H14 119.3 . . ?
N1 C15 H15 127.4 . . ?
C16 C15 N1 105.3(2) . . ?
C16 C15 H15 127.4 . . ?
N4 C16 H16 123.8 . . ?
C15 C16 N4 112.4(2) . . ?
C15 C16 H16 123.8 . . ?
C1 C17 H17 119.0 . . ?
C1 C17 C18 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C3 C18 C17 119.8(2) . . ?
C3 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 177.95(16) . . . . ?
O1 C9 C10 N3 58.5(2) . . . . ?
O0AA C4 C5 C6 154.2(2) . . . . ?
O0AA C4 C5 C14 -28.9(3) . . . . ?
N1 C1 C17 C18 -0.7(4) . . . . ?
N1 C2 C3 N2 -178.62(18) . . . . ?
N1 C2 C3 C18 -0.4(3) . . . . ?
N1 C15 C16 N4 0.2(4) . . . . ?
N2 C3 C18 C17 177.4(2) . . . . ?
N2 C4 C5 C6 -29.6(3) . . . . ?
N2 C4 C5 C14 147.3(2) . . . . ?
N3 C6 C11 C12 -179.17(19) . . . . ?
N3 C7 C8 O1 -60.2(2) . . . . ?
N4 C2 C3 N2 0.3(3) . . . . ?
N4 C2 C3 C18 178.5(2) . . . . ?
C1 N1 C2 N4 -178.3(2) . . . . ?
C1 N1 C2 C3 0.8(3) . . . . ?
C1 N1 C15 C16 178.1(3) . . . . ?
C1 C17 C18 C3 1.2(4) . . . . ?
C2 N1 C1 C17 -0.3(4) . . . . ?
C2 N1 C15 C16 -0.3(3) . . . . ?
C2 N4 C16 C15 -0.1(3) . . . . ?
C2 C3 C18 C17 -0.6(3) . . . . ?
C3 N2 C4 O0AA 0.6(4) . . . . ?
C3 N2 C4 C5 -175.62(19) . . . . ?
C4 N2 C3 C2 -177.8(2) . . . . ?
C4 N2 C3 C18 4.2(3) . . . . ?
C4 C5 C6 N3 -6.8(3) . . . . ?
C4 C5 C6 C11 172.7(2) . . . . ?
C4 C5 C14 C13 -173.13(19) . . . . ?
C5 C6 C11 C12 1.3(3) . . . . ?
C6 N3 C7 C8 -170.44(18) . . . . ?
C6 N3 C10 C9 168.95(16) . . . . ?
C6 C5 C14 C13 4.0(3) . . . . ?
C6 C11 C12 Br1 -178.12(15) . . . . ?
C6 C11 C12 C13 1.7(3) . . . . ?
C7 N3 C6 C5 164.36(18) . . . . ?
C7 N3 C6 C11 -15.2(3) . . . . ?
C7 N3 C10 C9 -58.8(2) . . . . ?
C8 O1 C9 C10 -58.5(3) . . . . ?
C9 O1 C8 C7 59.3(2) . . . . ?
C10 N3 C6 C5 -67.3(2) . . . . ?
C10 N3 C6 C11 113.1(2) . . . . ?
C10 N3 C7 C8 59.0(2) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
C12 C13 C14 C5 -1.0(3) . . . . ?
C14 C5 C6 N3 176.4(2) . . . . ?
C14 C5 C6 C11 -4.1(3) . . . . ?
C15 N1 C1 C17 -178.4(3) . . . . ?
C15 N1 C2 N4 0.3(3) . . . . ?
C15 N1 C2 C3 179.3(2) . . . . ?
C16 N4 C2 N1 -0.1(3) . . . . ?
C16 N4 C2 C3 -179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
