# 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 2023

####################################################################### 
# 
# 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_6jula_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2192737'
_audit_update_record             
;
2022-07-25 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_audit_creation_date             2022-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1-((1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridine
_chemical_formula_moiety         'C17 H14 Br N5'
_chemical_formula_sum            'C17 H14 Br N5'
_chemical_formula_weight         368.24
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5829(2)
_cell_length_b                   8.3646(4)
_cell_length_c                   16.4765(8)
_cell_angle_alpha                80.4360(10)
_cell_angle_beta                 87.5270(10)
_cell_angle_gamma                85.7270(10)
_cell_volume                     756.26(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8394
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.736
_shelx_estimated_absorpt_T_min   0.702
_exptl_absorpt_coefficient_mu    2.725
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5044
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372.00
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12363
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_min         2.585
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3469
_reflns_number_total             3740
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.041
_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)+(0.0227P)²+0.5790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0655
_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:
 C10(H10A,H10B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C15(H15), C5(H5), C14(H14), C4(H4), C16(H16), C8(H8), C1(H1),
 C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_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
Br Br 1.09037(3) 0.26037(2) 0.03822(2) 0.02269(7) Uani 1 1 d . . . . .
N3 N 0.5063(2) 0.25522(16) 0.50079(8) 0.0129(3) Uani 1 1 d . . . . .
N2 N 0.5108(2) 0.37628(16) 0.43811(8) 0.0132(3) Uani 1 1 d . . . . .
N4 N 0.6233(2) 0.05744(16) 0.66247(8) 0.0130(3) Uani 1 1 d . . . . .
N1 N 0.7405(2) 0.41394(16) 0.42475(8) 0.0122(2) Uani 1 1 d . . . . .
N5 N 0.8106(2) 0.19528(16) 0.75729(8) 0.0135(3) Uani 1 1 d . . . . .
C2 C 1.1633(3) 0.32125(18) 0.19978(10) 0.0129(3) Uani 1 1 d . . . . .
H2 H 1.314287 0.262930 0.194604 0.015 Uiso 1 1 calc R U . . .
C3 C 1.0032(3) 0.34563(19) 0.13606(9) 0.0132(3) Uani 1 1 d . . . . .
C17 C 0.6377(3) 0.10833(18) 0.73741(9) 0.0113(3) Uani 1 1 d . . . . .
C9 C 0.7350(3) 0.21639(19) 0.52713(9) 0.0115(3) Uani 1 1 d . . . . .
C15 C 0.6082(3) 0.1700(2) 0.89175(10) 0.0162(3) Uani 1 1 d . . . . .
H15 H 0.607329 0.193407 0.946250 0.019 Uiso 1 1 calc R U . . .
C5 C 0.7186(3) 0.48975(19) 0.21436(10) 0.0130(3) Uani 1 1 d . . . . .
H5 H 0.566512 0.546697 0.219588 0.016 Uiso 1 1 calc R U . . .
C13 C 0.4400(3) 0.05046(18) 0.78795(10) 0.0127(3) Uani 1 1 d . . . . .
C10 C 0.8000(3) 0.0784(2) 0.59483(10) 0.0154(3) Uani 1 1 d . . . . .
H10A H 0.821074 -0.023460 0.571327 0.018 Uiso 1 1 calc R U . . .
H10B H 0.956082 0.096858 0.616778 0.018 Uiso 1 1 calc R U . . .
C6 C 0.8763(3) 0.46847(18) 0.27894(9) 0.0119(3) Uani 1 1 d . . . . .
C14 C 0.4284(3) 0.0835(2) 0.86840(10) 0.0155(3) Uani 1 1 d . . . . .
H14 H 0.301505 0.047872 0.905769 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7809(3) 0.42861(19) 0.14209(10) 0.0140(3) Uani 1 1 d . . . . .
H4 H 0.673179 0.443528 0.097944 0.017 Uiso 1 1 calc R U . . .
C16 C 0.7918(3) 0.22319(19) 0.83520(10) 0.0149(3) Uani 1 1 d . . . . .
H16 H 0.911139 0.283211 0.853338 0.018 Uiso 1 1 calc R U . . .
C8 C 0.8857(3) 0.31742(19) 0.47867(9) 0.0127(3) Uani 1 1 d . . . . .
H8 H 1.054873 0.319115 0.482261 0.015 Uiso 1 1 calc R U . . .
C1 C 1.0986(3) 0.38374(19) 0.27139(10) 0.0132(3) Uani 1 1 d . . . . .
H1 H 1.206719 0.368572 0.315425 0.016 Uiso 1 1 calc R U . . .
C7 C 0.8075(3) 0.5395(2) 0.35581(10) 0.0163(3) Uani 1 1 d . . . . .
H7A H 0.944506 0.595328 0.371483 0.020 Uiso 1 1 calc R U . . .
H7B H 0.670594 0.621311 0.344294 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4221(3) -0.03019(19) 0.66529(10) 0.0151(3) Uani 1 1 d . . . . .
H11 H 0.372268 -0.079181 0.621342 0.018 Uiso 1 1 calc R U . . .
C12 C 0.3051(3) -0.03654(19) 0.73985(10) 0.0153(3) Uani 1 1 d . . . . .
H12 H 0.161539 -0.088674 0.756734 0.018 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
Br C3 1.8991(15) . ?
N3 N2 1.3215(19) . ?
N3 C9 1.365(2) . ?
N2 N1 1.3435(18) . ?
N4 C17 1.3786(19) . ?
N4 C10 1.453(2) . ?
N4 C11 1.381(2) . ?
N1 C8 1.351(2) . ?
N1 C7 1.469(2) . ?
N5 C17 1.334(2) . ?
N5 C16 1.341(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C2 C1 1.391(2) . ?
C3 C4 1.384(2) . ?
C17 C13 1.419(2) . ?
C9 C10 1.501(2) . ?
C9 C8 1.372(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.383(2) . ?
C15 C16 1.401(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C5 C4 1.393(2) . ?
C13 C14 1.396(2) . ?
C13 C12 1.432(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 C1 1.394(2) . ?
C6 C7 1.509(2) . ?
C14 H14 0.9500 . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C8 H8 0.9500 . ?
C1 H1 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.361(2) . ?
C12 H12 0.9500 . ?

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
N2 N3 C9 108.66(13) . . ?
N3 N2 N1 107.28(12) . . ?
C17 N4 C10 126.22(13) . . ?
C17 N4 C11 108.11(13) . . ?
C11 N4 C10 125.43(14) . . ?
N2 N1 C8 110.96(13) . . ?
N2 N1 C7 120.62(13) . . ?
C8 N1 C7 128.33(14) . . ?
C17 N5 C16 113.71(14) . . ?
C3 C2 H2 120.6 . . ?
C3 C2 C1 118.82(14) . . ?
C1 C2 H2 120.6 . . ?
C2 C3 Br 118.99(12) . . ?
C4 C3 Br 119.07(12) . . ?
C4 C3 C2 121.94(14) . . ?
N4 C17 C13 107.83(13) . . ?
N5 C17 N4 124.89(14) . . ?
N5 C17 C13 127.28(14) . . ?
N3 C9 C10 123.41(14) . . ?
N3 C9 C8 108.33(14) . . ?
C8 C9 C10 128.17(14) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.15(15) . . ?
C16 C15 H15 119.9 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.84(14) . . ?
C4 C5 H5 119.6 . . ?
C17 C13 C12 106.73(14) . . ?
C14 C13 C17 116.61(14) . . ?
C14 C13 C12 136.60(15) . . ?
N4 C10 C9 114.12(13) . . ?
N4 C10 H10A 108.7 . . ?
N4 C10 H10B 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C5 C6 C1 119.49(14) . . ?
C5 C6 C7 119.91(14) . . ?
C1 C6 C7 120.60(14) . . ?
C15 C14 C13 117.62(15) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C3 C4 C5 118.49(14) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N5 C16 C15 124.58(15) . . ?
N5 C16 H16 117.7 . . ?
C15 C16 H16 117.7 . . ?
N1 C8 C9 104.78(13) . . ?
N1 C8 H8 127.6 . . ?
C9 C8 H8 127.6 . . ?
C2 C1 C6 120.43(14) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
N1 C7 C6 111.80(13) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N4 C11 H11 124.7 . . ?
C12 C11 N4 110.51(14) . . ?
C12 C11 H11 124.7 . . ?
C13 C12 H12 126.6 . . ?
C11 C12 C13 106.82(14) . . ?
C11 C12 H12 126.6 . . ?

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
Br C3 C4 C5 179.65(11) . . . . ?
N3 N2 N1 C8 0.03(16) . . . . ?
N3 N2 N1 C7 176.86(13) . . . . ?
N3 C9 C10 N4 -38.2(2) . . . . ?
N3 C9 C8 N1 0.08(17) . . . . ?
N2 N3 C9 C10 -176.81(13) . . . . ?
N2 N3 C9 C8 -0.07(17) . . . . ?
N2 N1 C8 C9 -0.07(17) . . . . ?
N2 N1 C7 C6 -91.20(17) . . . . ?
N4 C17 C13 C14 177.24(13) . . . . ?
N4 C17 C13 C12 -0.39(17) . . . . ?
N4 C11 C12 C13 -0.61(18) . . . . ?
N5 C17 C13 C14 -2.2(2) . . . . ?
N5 C17 C13 C12 -179.82(15) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C2 C1 C6 0.4(2) . . . . ?
C17 N4 C10 C9 -100.79(18) . . . . ?
C17 N4 C11 C12 0.37(18) . . . . ?
C17 N5 C16 C15 -0.9(2) . . . . ?
C17 C13 C14 C15 0.4(2) . . . . ?
C17 C13 C12 C11 0.61(17) . . . . ?
C9 N3 N2 N1 0.03(16) . . . . ?
C5 C6 C1 C2 0.2(2) . . . . ?
C5 C6 C7 N1 105.19(17) . . . . ?
C10 N4 C17 N5 4.8(2) . . . . ?
C10 N4 C17 C13 -174.61(14) . . . . ?
C10 N4 C11 C12 175.06(14) . . . . ?
C10 C9 C8 N1 176.62(14) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C14 C15 C16 N5 -0.6(3) . . . . ?
C14 C13 C12 C11 -176.30(18) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 178.43(14) . . . . ?
C16 N5 C17 N4 -176.95(14) . . . . ?
C16 N5 C17 C13 2.4(2) . . . . ?
C16 C15 C14 C13 0.9(2) . . . . ?
C8 N1 C7 C6 85.03(19) . . . . ?
C8 C9 C10 N4 145.76(16) . . . . ?
C1 C2 C3 Br -179.93(11) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C6 C7 N1 -75.88(18) . . . . ?
C7 N1 C8 C9 -176.60(14) . . . . ?
C7 C6 C1 C2 -178.71(14) . . . . ?
C11 N4 C17 N5 179.47(14) . . . . ?
C11 N4 C17 C13 0.03(17) . . . . ?
C11 N4 C10 C9 85.47(19) . . . . ?
C12 C13 C14 C15 177.08(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
