#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:07:04 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286034 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/91/1569194.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1569194
loop_
_publ_author_name
'Lennox, Cameron B.'
'Borchers, Tristan H.'
'Gonnet, Lori'
'Barrett, Christopher J.'
'Koenig, Stefan G.'
'Nagapudi, Karthik'
'Friščić, Tomislav'
_publ_section_title
;
 Direct mechanocatalysis by resonant acoustic mixing (RAM).
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              7475
_journal_page_last               7481
_journal_paper_doi               10.1039/d3sc01591b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33
_chemical_name_systematic
1-(3,5-dimethoxybenzyl)-4-phenyl-1H-1,2,3-triazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-01 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                107.9530(10)
_cell_angle_beta                 101.4800(10)
_cell_angle_gamma                92.5080(10)
_cell_formula_units_Z            2
_cell_length_a                   5.66500(10)
_cell_length_b                   11.8408(2)
_cell_length_c                   12.1314(2)
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.479
_cell_measurement_theta_min      3.930
_cell_volume                     753.81(2)
_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)'
_diffrn_ambient_temperature      298.15
_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_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
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_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
_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_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0504
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2247
_reflns_number_total             2937
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc01591b2.cif
_cod_data_source_block           4e
_cod_depositor_comments          'Adding full bibliography for 1569194.cif.'
_cod_database_code               1569194
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.933
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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_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_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) . . . . ?
