# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_4e
_database_code_depnum_ccdc_archive 'CCDC 2223762'
loop_
_audit_author_name
_audit_author_address
'Cameron B. Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2022-12-01 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-11-23
_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-(3,5-dimethoxybenzyl)-4-phenyl-1H-1,2,3-triazole
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.66500(10)
_cell_length_b                   11.8408(2)
_cell_length_c                   12.1314(2)
_cell_angle_alpha                107.9530(10)
_cell_angle_beta                 101.4800(10)
_cell_angle_gamma                92.5080(10)
_cell_volume                     753.81(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.479
_cell_measurement_theta_min      3.930
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7536
_exptl_transmission_factor_min   0.5401
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21341
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.479
_diffrn_reflns_theta_min         3.930
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2247
_reflns_number_total             2937
_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       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_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         0.151
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      0.963
_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)+(0.0875P)²+0.1858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1604
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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
O1 O 0.7053(3) 0.73019(12) 0.93858(14) 0.0762(5) Uani 1 1 d . . . . .
O2 O 1.1892(3) 0.64437(13) 0.66128(15) 0.0759(5) Uani 1 1 d . . . . .
N1 N 0.2957(3) 0.18498(17) 0.58246(15) 0.0655(5) Uani 1 1 d . . . . .
N2 N 0.4386(3) 0.24117(16) 0.68776(15) 0.0643(5) Uani 1 1 d . . . . .
N3 N 0.6630(2) 0.24798(12) 0.67166(12) 0.0483(4) Uani 1 1 d . . . . .
C1 C 0.1296(5) -0.03519(19) 0.1358(2) 0.0744(7) Uani 1 1 d . . . . .
H1 H 0.064036 -0.078476 0.056370 0.089 Uiso 1 1 calc R U . . .
C2 C 0.0026(4) -0.03503(18) 0.2206(2) 0.0720(6) Uani 1 1 d . . . . .
H2 H -0.150774 -0.077511 0.198151 0.086 Uiso 1 1 calc R U . . .
C3 C 0.0986(3) 0.02719(17) 0.33869(19) 0.0610(5) Uani 1 1 d . . . . .
H3 H 0.010514 0.025896 0.395396 0.073 Uiso 1 1 calc R U . . .
C4 C 0.3560(5) 0.0293(2) 0.16866(19) 0.0742(6) Uani 1 1 d . . . . .
H4 H 0.442634 0.030130 0.111295 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4538(4) 0.09286(18) 0.28732(18) 0.0617(5) Uani 1 1 d . . . . .
H5 H 0.605977 0.136401 0.309107 0.074 Uiso 1 1 calc R U . . .
C6 C 0.3272(3) 0.09205(14) 0.37359(16) 0.0504(4) Uani 1 1 d . . . . .
C7 C 0.4323(3) 0.15660(14) 0.49965(16) 0.0482(4) Uani 1 1 d . . . . .
C8 C 0.6685(3) 0.19732(15) 0.55731(16) 0.0500(4) Uani 1 1 d . . . . .
H8 H 0.803826 0.191093 0.524092 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8653(3) 0.31186(15) 0.77140(16) 0.0525(4) Uani 1 1 d . . . . .
H9A H 1.012939 0.276738 0.758261 0.063 Uiso 1 1 calc R U . . .
H9B H 0.833833 0.303003 0.844211 0.063 Uiso 1 1 calc R U . . .
C10 C 0.9001(3) 0.44294(14) 0.78509(14) 0.0477(4) Uani 1 1 d . . . . .
C11 C 0.7864(3) 0.52377(16) 0.86041(15) 0.0524(4) Uani 1 1 d . . . . .
H11 H 0.695148 0.498469 0.905993 0.063 Uiso 1 1 calc R U . . .
C12 C 1.0390(3) 0.47992(15) 0.71783(16) 0.0515(4) Uani 1 1 d . . . . .
H12 H 1.117262 0.425354 0.668465 0.062 Uiso 1 1 calc R U . . .
C13 C 0.8100(3) 0.64322(16) 0.86720(16) 0.0541(5) Uani 1 1 d . . . . .
C14 C 0.9457(3) 0.68094(16) 0.79951(17) 0.0563(5) Uani 1 1 d . . . . .
H14 H 0.960332 0.760858 0.803993 0.068 Uiso 1 1 calc R U . . .
C15 C 1.0599(3) 0.59930(16) 0.72505(16) 0.0533(4) Uani 1 1 d . . . . .
C16 C 1.3330(4) 0.5682(2) 0.5947(2) 0.0712(6) Uani 1 1 d . . . . .
H16A H 1.443332 0.537323 0.646345 0.107 Uiso 1 1 calc R U . . .
H16B H 1.423035 0.612454 0.559359 0.107 Uiso 1 1 calc R U . . .
H16C H 1.230029 0.503149 0.533402 0.107 Uiso 1 1 calc R U . . .
C17 C 0.5479(4) 0.6957(2) 1.0021(2) 0.0730(6) Uani 1 1 d . . . . .
H17A H 0.418775 0.638375 0.947505 0.110 Uiso 1 1 calc R U . . .
H17B H 0.481481 0.764620 1.045102 0.110 Uiso 1 1 calc R U . . .
H17C H 0.636391 0.660739 1.057020 0.110 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
O1 C13 1.368(2) . ?
O1 C17 1.411(3) . ?
O2 C15 1.366(2) . ?
O2 C16 1.416(3) . ?
N1 N2 1.322(2) . ?
N1 C7 1.358(2) . ?
N2 N3 1.327(2) . ?
N3 C8 1.338(2) . ?
N3 C9 1.469(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(4) . ?
C1 C4 1.382(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C6 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.468(2) . ?
C7 C8 1.370(2) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.509(2) . ?
C10 C11 1.384(2) . ?
C10 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C11 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C12 C15 1.387(3) . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C13 O1 C17 118.29(16) . . ?
C15 O2 C16 118.08(16) . . ?
N2 N1 C7 109.11(14) . . ?
N1 N2 N3 106.91(14) . . ?
N2 N3 C8 111.33(14) . . ?
N2 N3 C9 120.50(14) . . ?
C8 N3 C9 128.06(14) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C4 119.6(2) . . ?
C4 C1 H1 120.2 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C6 120.3(2) . . ?
C6 C3 H3 119.9 . . ?
C1 C4 H4 120.0 . . ?
C1 C4 C5 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C3 C6 C7 120.45(17) . . ?
C5 C6 C3 118.67(18) . . ?
C5 C6 C7 120.88(16) . . ?
N1 C7 C6 122.49(15) . . ?
N1 C7 C8 107.39(15) . . ?
C8 C7 C6 130.11(16) . . ?
N3 C8 C7 105.27(15) . . ?
N3 C8 H8 127.4 . . ?
C7 C8 H8 127.4 . . ?
N3 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
N3 C9 C10 111.54(13) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C11 C10 C9 120.04(16) . . ?
C11 C10 C12 120.86(16) . . ?
C12 C10 C9 119.05(15) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C13 119.27(16) . . ?
C13 C11 H11 120.4 . . ?
C10 C12 H12 120.4 . . ?
C10 C12 C15 119.21(16) . . ?
C15 C12 H12 120.4 . . ?
O1 C13 C11 123.96(17) . . ?
O1 C13 C14 115.64(17) . . ?
C14 C13 C11 120.40(17) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.77(17) . . ?
C15 C14 H14 120.1 . . ?
O2 C15 C12 123.76(17) . . ?
O2 C15 C14 115.76(16) . . ?
C14 C15 C12 120.48(16) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 C13 C14 C15 179.61(17) . . . . ?
N1 N2 N3 C8 0.2(2) . . . . ?
N1 N2 N3 C9 176.58(15) . . . . ?
N1 C7 C8 N3 0.06(19) . . . . ?
N2 N1 C7 C6 179.21(16) . . . . ?
N2 N1 C7 C8 0.0(2) . . . . ?
N2 N3 C8 C7 -0.1(2) . . . . ?
N2 N3 C9 C10 -87.79(19) . . . . ?
N3 C9 C10 C11 92.40(19) . . . . ?
N3 C9 C10 C12 -85.08(19) . . . . ?
C1 C2 C3 C6 0.5(3) . . . . ?
C1 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C4 C5 0.6(3) . . . . ?
C2 C3 C6 C5 0.3(3) . . . . ?
C2 C3 C6 C7 -178.80(16) . . . . ?
C3 C6 C7 N1 -18.9(3) . . . . ?
C3 C6 C7 C8 160.11(18) . . . . ?
C4 C1 C2 C3 -1.0(3) . . . . ?
C4 C5 C6 C3 -0.6(3) . . . . ?
C4 C5 C6 C7 178.43(17) . . . . ?
C5 C6 C7 N1 162.09(18) . . . . ?
C5 C6 C7 C8 -18.9(3) . . . . ?
C6 C7 C8 N3 -179.03(16) . . . . ?
C7 N1 N2 N3 -0.1(2) . . . . ?
C8 N3 C9 C10 88.0(2) . . . . ?
C9 N3 C8 C7 -176.22(15) . . . . ?
C9 C10 C11 C13 -176.62(15) . . . . ?
C9 C10 C12 C15 176.30(15) . . . . ?
C10 C11 C13 O1 179.98(17) . . . . ?
C10 C11 C13 C14 0.0(3) . . . . ?
C10 C12 C15 O2 -179.01(17) . . . . ?
C10 C12 C15 C14 0.7(3) . . . . ?
C11 C10 C12 C15 -1.2(3) . . . . ?
C11 C13 C14 C15 -0.4(3) . . . . ?
C12 C10 C11 C13 0.8(3) . . . . ?
C13 C14 C15 O2 179.78(17) . . . . ?
C13 C14 C15 C12 0.0(3) . . . . ?
C16 O2 C15 C12 -7.7(3) . . . . ?
C16 O2 C15 C14 172.57(17) . . . . ?
C17 O1 C13 C11 -5.3(3) . . . . ?
C17 O1 C13 C14 174.70(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



