#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/96/4509677.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509677
loop_
_publ_author_name
'Zhu, Yuan-Yuan'
'Wang, Gui-Tao'
'Wang, Ren-Xiao'
'Li, Zhan-Ting'
_publ_section_title
;
 Intramolecular Six-Membered and Three-Center
 C−H···O Hydrogen Bonding in
 1,4-Diphenyl-1,2,3-Triazoles
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4778
_journal_paper_doi               10.1021/cg9006197
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C32 H36 N6 O4'
_chemical_formula_sum            'C32 H36 N6 O4'
_chemical_formula_weight         568.67
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.121(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.9870(7)
_cell_length_b                   15.866(2)
_cell_length_c                   18.134(2)
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.148
_cell_measurement_theta_min      4.518
_cell_volume                     1426.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8302
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.292
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0789P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                2213
_reflns_number_total             3107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9006197sup1.cif
_cod_data_source_block           cd29152
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4509677
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.156(4) 0.9415(10) 0.1075(8) 0.0334(18) Uani 0.50 1 d PU A 1
C2 C 0.137(4) 0.8587(10) 0.1405(7) 0.0373(19) Uani 0.50 1 d PU A 1
H2 H 0.2372 0.8111 0.1315 0.045 Uiso 0.50 1 calc PR A 1
N1 N -0.0105(18) 0.9925(8) 0.1329(5) 0.0383(13) Uani 0.50 1 d PU A 1
N2 N -0.143(2) 0.9513(8) 0.1787(5) 0.0384(13) Uani 0.50 1 d PU A 1
N3 N -0.059(3) 0.8649(8) 0.1872(9) 0.0329(18) Uani 0.50 1 d PU A 1
C1' C -0.044(5) 0.8726(11) 0.1796(12) 0.0340(18) Uani 0.50 1 d PU A 2
C2' C 0.122(3) 0.8605(10) 0.1271(7) 0.0352(19) Uani 0.50 1 d PU A 2
H2' H 0.1799 0.8093 0.1096 0.042 Uiso 0.50 1 calc PR A 2
N1' N -0.087(2) 0.9516(8) 0.1950(5) 0.0485(18) Uani 0.50 1 d PU A 2
N2' N 0.0514(19) 0.9925(8) 0.1484(5) 0.0466(17) Uani 0.50 1 d PU A 2
N3' N 0.185(3) 0.9338(8) 0.1063(7) 0.0360(19) Uani 0.50 1 d PU A 2
C3 C -0.1706(3) 0.80974(8) 0.23148(7) 0.0373(3) Uani 1 1 d . . .
C4 C -0.3480(3) 0.84007(9) 0.27908(8) 0.0467(4) Uani 1 1 d . A .
H4 H -0.3913 0.8971 0.2783 0.056 Uiso 1 1 calc R . .
C5 C -0.4613(4) 0.78733(10) 0.32754(9) 0.0578(5) Uani 1 1 d . . .
H5 H -0.5804 0.8086 0.3590 0.069 Uiso 1 1 calc R A .
C6 C -0.3970(4) 0.70326(10) 0.32902(9) 0.0586(5) Uani 1 1 d . A .
H6 H -0.4711 0.6677 0.3622 0.070 Uiso 1 1 calc R . .
C7 C -0.2246(4) 0.67108(9) 0.28198(9) 0.0511(4) Uani 1 1 d . . .
H7 H -0.1828 0.6139 0.2835 0.061 Uiso 1 1 calc R A .
C8 C -0.1125(3) 0.72348(8) 0.23222(8) 0.0408(4) Uani 1 1 d . A .
C9 C 0.3403(3) 0.96718(8) 0.05199(7) 0.0368(3) Uani 1 1 d . . .
C10 C 0.4802(3) 0.91327(8) 0.00904(8) 0.0406(4) Uani 1 1 d . A .
C11 C 0.6360(3) 0.94666(8) -0.04207(8) 0.0423(4) Uani 1 1 d . . .
H11 H 0.7280 0.9103 -0.0708 0.051 Uiso 1 1 calc R A .
C12 C 0.1187(3) 0.60759(9) 0.18246(9) 0.0482(4) Uani 1 1 d . A .
H12A H -0.0454 0.5744 0.1761 0.058 Uiso 1 1 calc R . .
H12B H 0.2186 0.5921 0.2293 0.058 Uiso 1 1 calc R . .
C13 C 0.2861(3) 0.59054(9) 0.11988(9) 0.0483(4) Uani 1 1 d . . .
H13 H 0.4498 0.6250 0.1275 0.058 Uiso 1 1 calc R . .
C14 C 0.1376(4) 0.61303(11) 0.04539(9) 0.0678(6) Uani 1 1 d . . .
H14A H -0.0311 0.5834 0.0389 0.102 Uiso 1 1 calc R . .
H14B H 0.2451 0.5973 0.0067 0.102 Uiso 1 1 calc R . .
H14C H 0.1046 0.6726 0.0433 0.102 Uiso 1 1 calc R . .
C15 C 0.3686(5) 0.49810(10) 0.12199(11) 0.0724(6) Uani 1 1 d . . .
H15A H 0.2109 0.4634 0.1125 0.109 Uiso 1 1 calc R . .
H15B H 0.4590 0.4848 0.1700 0.109 Uiso 1 1 calc R . .
H15C H 0.4879 0.4877 0.0848 0.109 Uiso 1 1 calc R . .
C16 C 0.6229(4) 0.77398(9) -0.01541(10) 0.0617(5) Uani 1 1 d . A .
H16A H 0.5750 0.7759 -0.0681 0.092 Uiso 1 1 calc R . .
H16B H 0.6023 0.7175 0.0020 0.092 Uiso 1 1 calc R . .
H16C H 0.8071 0.7914 -0.0042 0.092 Uiso 1 1 calc R . .
O1 O 0.0541(2) 0.69530(6) 0.18244(6) 0.0510(3) Uani 1 1 d . . .
O2 O 0.4526(3) 0.82878(6) 0.01996(6) 0.0587(4) Uani 1 1 d . . .
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'
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'
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
N1 C1 C2 110.5(13) . .
N1 C1 C9 122.7(11) . .
C2 C1 C9 126.8(14) . .
N3 C2 C1 105.9(13) . .
N3 C2 H2 127.0 . .
C1 C2 H2 127.0 . .
C1 N1 N2 107.8(11) . .
N1 N2 N3 112.9(10) . .
C3 N3 C2 133.9(13) . .
C3 N3 N2 123.2(12) . .
C2 N3 N2 102.9(11) . .
N1' C1' C2' 114.6(14) . .
N1' C1' C3 113.6(15) . .
C2' C1' C3 131.5(16) . .
N3' C2' C1' 105.7(14) . .
N3' C2' H2' 127.2 . .
C1' C2' H2' 127.2 . .
C1' N1' N2' 103.1(12) . .
N1' N2' N3' 109.3(11) . .
C2' N3' N2' 107.3(12) . .
C2' N3' C9 135.8(12) . .
N2' N3' C9 116.8(10) . .
N3 C3 C4 118.6(6) . .
N3 C3 C8 122.8(6) . .
C4 C3 C8 118.63(13) . .
N3 C3 C1' 0.7(16) . .
C4 C3 C1' 118.9(8) . .
C8 C3 C1' 122.5(8) . .
C5 C4 C3 121.24(14) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C6 C5 C4 119.50(15) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
C5 C6 C7 120.67(14) . .
C5 C6 H6 119.7 . .
C7 C6 H6 119.7 . .
C6 C7 C8 120.26(14) . .
C6 C7 H7 119.9 . .
C8 C7 H7 119.9 . .
O1 C8 C7 123.33(13) . .
O1 C8 C3 117.01(12) . .
C7 C8 C3 119.66(13) . .
C11 C9 C10 118.57(13) 3_675 .
C11 C9 N3' 121.3(6) 3_675 .
C10 C9 N3' 120.1(6) . .
C11 C9 C1 115.2(7) 3_675 .
C10 C9 C1 126.2(7) . .
N3' C9 C1 7.0(11) . .
O2 C10 C11 123.27(13) . .
O2 C10 C9 117.24(12) . .
C11 C10 C9 119.49(12) . .
C10 C11 C9 121.94(13) . 3_675
C10 C11 H11 119.0 . .
C9 C11 H11 119.0 3_675 .
O1 C12 C13 108.58(12) . .
O1 C12 H12A 110.0 . .
C13 C12 H12A 110.0 . .
O1 C12 H12B 110.0 . .
C13 C12 H12B 110.0 . .
H12A C12 H12B 108.4 . .
C12 C13 C14 111.92(14) . .
C12 C13 C15 108.94(13) . .
C14 C13 C15 110.80(13) . .
C12 C13 H13 108.4 . .
C14 C13 H13 108.4 . .
C15 C13 H13 108.4 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O2 C16 H16A 109.5 . .
O2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C8 O1 C12 118.16(11) . .
C10 O2 C16 117.57(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.28(2) .
C1 C2 1.450(19) .
C1 C9 1.491(13) .
C2 N3 1.36(2) .
C2 H2 0.9300 .
N1 N2 1.292(15) .
N2 N3 1.437(19) .
N3 C3 1.349(11) .
C1' N1' 1.31(2) .
C1' C2' 1.34(2) .
C1' C3 1.551(14) .
C2' N3' 1.271(19) .
C2' H2' 0.9300 .
N1' N2' 1.316(16) .
N2' N3' 1.415(17) .
N3' C9 1.420(12) .
C3 C4 1.3861(19) .
C3 C8 1.3988(19) .
C4 C5 1.3776(19) .
C4 H4 0.9300 .
C5 C6 1.371(2) .
C5 H5 0.9300 .
C6 C7 1.373(2) .
C6 H6 0.9300 .
C7 C8 1.3879(19) .
C7 H7 0.9300 .
C8 O1 1.3653(16) .
C9 C11 1.3854(18) 3_675
C9 C10 1.3933(19) .
C10 O2 1.3642(15) .
C10 C11 1.3772(19) .
C11 C9 1.3854(18) 3_675
C11 H11 0.9300 .
C12 O1 1.4285(16) .
C12 C13 1.503(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.512(2) .
C13 C15 1.5224(19) .
C13 H13 0.9800 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 O2 1.4161(17) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 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_4
N1 C1 C2 N3 0.6(19) . .
C9 C1 C2 N3 -179.5(15) . .
C2 C1 N1 N2 -1.1(16) . .
C9 C1 N1 N2 179.0(12) . .
C1 N1 N2 N3 1.2(14) . .
C1 C2 N3 C3 178.3(18) . .
C1 C2 N3 N2 0.1(16) . .
N1 N2 N3 C3 -179.2(12) . .
N1 N2 N3 C2 -0.8(15) . .
N1' C1' C2' N3' -2(2) . .
C3 C1' C2' N3' -174(2) . .
C2' C1' N1' N2' 2(2) . .
C3 C1' N1' N2' 176.0(13) . .
C1' N1' N2' N3' -1.9(15) . .
C1' C2' N3' N2' 0.3(18) . .
C1' C2' N3' C9 -177.0(17) . .
N1' N2' N3' C2' 1.0(14) . .
N1' N2' N3' C9 178.9(9) . .
C2 N3 C3 C4 172.7(16) . .
N2 N3 C3 C4 -9.4(18) . .
C2 N3 C3 C8 -6(2) . .
N2 N3 C3 C8 171.5(10) . .
N1' C1' C3 C4 10(2) . .
C2' C1' C3 C4 -177.1(19) . .
N1' C1' C3 C8 -169.5(11) . .
C2' C1' C3 C8 3(3) . .
N3 C3 C4 C5 -177.7(9) . .
C8 C3 C4 C5 1.4(2) . .
C1' C3 C4 C5 -178.4(11) . .
C3 C4 C5 C6 0.2(3) . .
C4 C5 C6 C7 -1.0(3) . .
C5 C6 C7 C8 0.1(3) . .
C6 C7 C8 O1 -178.02(15) . .
C6 C7 C8 C3 1.6(2) . .
N3 C3 C8 O1 -3.6(9) . .
C4 C3 C8 O1 177.31(14) . .
C1' C3 C8 O1 -2.8(11) . .
N3 C3 C8 C7 176.7(9) . .
C4 C3 C8 C7 -2.3(2) . .
C1' C3 C8 C7 177.5(11) . .
C2' N3' C9 C11 178.5(16) . 3_675
N2' N3' C9 C11 1.3(14) . 3_675
C2' N3' C9 C10 -4(2) . .
N2' N3' C9 C10 179.2(7) . .
C2' N3' C9 C1 148(12) . .
N2' N3' C9 C1 -29(10) . .
N1 C1 C9 C11 14.0(18) . 3_675
C2 C1 C9 C11 -165.8(13) . 3_675
N1 C1 C9 C10 -164.1(10) . .
C2 C1 C9 C10 16(2) . .
N1 C1 C9 N3' 166(12) . .
C2 C1 C9 N3' -14(9) . .
C11 C9 C10 O2 -179.88(13) 3_675 .
N3' C9 C10 O2 2.2(7) . .
C1 C9 C10 O2 -1.8(9) . .
C11 C9 C10 C11 -0.4(3) 3_675 .
N3' C9 C10 C11 -178.3(7) . .
C1 C9 C10 C11 177.7(9) . .
O2 C10 C11 C9 179.86(14) . 3_675
C9 C10 C11 C9 0.4(3) . 3_675
O1 C12 C13 C14 -60.11(18) . .
O1 C12 C13 C15 177.01(14) . .
C7 C8 O1 C12 -0.9(2) . .
C3 C8 O1 C12 179.44(13) . .
C13 C12 O1 C8 175.86(13) . .
C11 C10 O2 C16 9.4(2) . .
C9 C10 O2 C16 -171.14(15) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146996
