#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240332.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_7240332
loop_
_publ_author_name
'Ahmed, Muhammad Naeem'
'Ansar, Khawaja Yasin'
'Aziz, Shahid'
'Khan, Saba'
'Tahir, Muhammad Nawaz'
'Gil, Diego M.'
'Frontera, Antonio'
_publ_section_title
;
 Relevant π--hole tetrel bonding interactions in ethyl
 2-triazolyl-2-oxo-acetate derivatives: Hirshfeld surface analysis and DFT
 calculations
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00335B
_journal_year                    2020
_chemical_formula_iupac          'C20 H19 N3 O3'
_chemical_formula_moiety         'C20 H19 N3 O3'
_chemical_formula_sum            'C20 H19 N3 O3'
_chemical_formula_weight         349.38
_chemical_name_systematic
;
Ethyl 2-(1-(4-methylbenzyl)-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.877(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2517(3)
_cell_length_b                   17.9945(9)
_cell_length_c                   12.2748(6)
_cell_measurement_reflns_used    2801
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      2.029
_cell_volume                     1795.61(14)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.70
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0250
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16244
_diffrn_reflns_theta_full        27.465
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.029
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0532
_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)+(0.0766P)²+0.4720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                2801
_reflns_number_total             4114
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d0ce00335b2.cif
_cod_data_source_block           DNAEEM
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240332
_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_min   0.925
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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 0.77274(16) 0.37923(7) 0.45265(12) 0.0593(4) Uani 1 1 d . . . . .
O2 O 0.6996(2) 0.49576(8) 0.48494(14) 0.0749(5) Uani 1 1 d . . . . .
O3 O 0.4675(2) 0.46585(8) 0.29288(13) 0.0721(4) Uani 1 1 d . . . . .
N1 N 0.3346(2) 0.23921(9) 0.41336(16) 0.0641(5) Uani 1 1 d . . . . .
N2 N 0.2636(2) 0.25488(10) 0.31187(16) 0.0681(5) Uani 1 1 d . . . . .
N3 N 0.31731(19) 0.32117(9) 0.28530(13) 0.0543(4) Uani 1 1 d . . . . .
C1 C 1.0207(4) 0.32365(18) 0.5357(3) 0.1181(12) Uani 1 1 d . . . . .
H1A H 1.043118 0.311098 0.463698 0.177 Uiso 1 1 calc R U . . .
H1B H 0.960417 0.283971 0.562465 0.177 Uiso 1 1 calc R U . . .
H1C H 1.122507 0.331075 0.585498 0.177 Uiso 1 1 calc R U . . .
C2 C 0.9264(3) 0.38971(14) 0.5288(2) 0.0835(8) Uani 1 1 d . . . . .
H2A H 0.987910 0.430174 0.503206 0.100 Uiso 1 1 calc R U . . .
H2B H 0.903649 0.402604 0.601375 0.100 Uiso 1 1 calc R U . . .
C3 C 0.6721(2) 0.43636(10) 0.44285(16) 0.0514(4) Uani 1 1 d . . . . .
C4 C 0.5138(2) 0.41935(10) 0.36271(15) 0.0498(4) Uani 1 1 d . . . . .
C5 C 0.4287(2) 0.34885(10) 0.37034(14) 0.0457(4) Uani 1 1 d . . . . .
C6 C 0.4375(2) 0.29537(9) 0.45198(15) 0.0483(4) Uani 1 1 d . . . . .
C7 C 0.5323(2) 0.29220(10) 0.56448(15) 0.0473(4) Uani 1 1 d . . . . .
C8 C 0.6190(3) 0.22779(11) 0.60027(18) 0.0602(5) Uani 1 1 d . . . . .
H8 H 0.615638 0.187263 0.552911 0.072 Uiso 1 1 calc R U . . .
C9 C 0.7086(3) 0.22377(14) 0.7043(2) 0.0745(7) Uani 1 1 d . . . . .
H9 H 0.766788 0.180681 0.727361 0.089 Uiso 1 1 calc R U . . .
C10 C 0.7134(3) 0.28289(16) 0.7751(2) 0.0819(7) Uani 1 1 d . . . . .
H10 H 0.774674 0.279963 0.846000 0.098 Uiso 1 1 calc R U . . .
C11 C 0.6274(3) 0.34656(14) 0.74103(18) 0.0759(7) Uani 1 1 d . . . . .
H11 H 0.630192 0.386556 0.789293 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5373(3) 0.35155(11) 0.63617(16) 0.0592(5) Uani 1 1 d . . . . .
H12 H 0.479681 0.394869 0.613578 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2615(3) 0.34937(13) 0.17316(16) 0.0640(5) Uani 1 1 d . . . . .
H13A H 0.243845 0.307568 0.122620 0.077 Uiso 1 1 calc R U . . .
H13B H 0.347911 0.379825 0.151934 0.077 Uiso 1 1 calc R U . . .
C14 C 0.1057(2) 0.39458(11) 0.16037(16) 0.0562(5) Uani 1 1 d . . . . .
C15 C 0.0024(3) 0.39399(12) 0.05994(18) 0.0646(6) Uani 1 1 d . . . . .
H15 H 0.025113 0.363455 0.003313 0.078 Uiso 1 1 calc R U . . .
C16 C -0.1366(3) 0.43928(14) 0.0432(2) 0.0760(7) Uani 1 1 d . . . . .
H16 H -0.205580 0.438790 -0.025199 0.091 Uiso 1 1 calc R U . . .
C17 C -0.1739(3) 0.48458(13) 0.1253(2) 0.0725(6) Uani 1 1 d . . . . .
C18 C -0.0732(3) 0.48266(14) 0.2251(2) 0.0783(7) Uani 1 1 d . . . . .
H18 H -0.098829 0.511499 0.282710 0.094 Uiso 1 1 calc R U . . .
C19 C 0.0655(3) 0.43912(14) 0.2430(2) 0.0738(6) Uani 1 1 d . . . . .
H19 H 0.133210 0.439719 0.311882 0.089 Uiso 1 1 calc R U . . .
C20 C -0.3205(4) 0.53609(19) 0.1046(3) 0.1114(11) Uani 1 1 d . . . . .
H20A H -0.357741 0.540927 0.026454 0.167 Uiso 1 1 calc R U . . .
H20B H -0.289504 0.584024 0.135699 0.167 Uiso 1 1 calc R U . . .
H20C H -0.407484 0.516036 0.138591 0.167 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 0.0033 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
_geom_angle_publ_flag
C3 O1 C2 115.19(16) . . ?
N2 N1 C6 108.87(16) . . ?
N1 N2 N3 108.13(16) . . ?
N2 N3 C5 110.43(16) . . ?
N2 N3 C13 118.41(17) . . ?
C5 N3 C13 130.98(17) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 O1 109.9(2) . . ?
C1 C2 H2A 109.7 . . ?
O1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
O1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 O1 126.24(19) . . ?
O2 C3 C4 122.56(18) . . ?
O1 C3 C4 111.09(15) . . ?
O3 C4 C5 123.26(18) . . ?
O3 C4 C3 116.65(17) . . ?
C5 C4 C3 120.05(15) . . ?
N3 C5 C6 104.23(15) . . ?
N3 C5 C4 122.50(16) . . ?
C6 C5 C4 133.23(17) . . ?
N1 C6 C5 108.31(17) . . ?
N1 C6 C7 120.15(16) . . ?
C5 C6 C7 131.52(16) . . ?
C12 C7 C8 119.05(18) . . ?
C12 C7 C6 121.54(16) . . ?
C8 C7 C6 119.42(17) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.90(19) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
N3 C13 C14 114.22(17) . . ?
N3 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 118.3(2) . . ?
C15 C14 C13 118.46(19) . . ?
C19 C14 C13 123.13(18) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 117.9(2) . . ?
C18 C17 C20 121.0(3) . . ?
C16 C17 C20 121.0(3) . . ?
C17 C18 C19 121.5(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C3 1.314(2) . ?
O1 C2 1.452(3) . ?
O2 C3 1.192(2) . ?
O3 C4 1.212(2) . ?
N1 N2 1.313(3) . ?
N1 C6 1.352(2) . ?
N2 N3 1.332(2) . ?
N3 C5 1.361(2) . ?
N3 C13 1.465(3) . ?
C1 C2 1.415(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(3) . ?
C4 C5 1.461(3) . ?
C5 C6 1.382(2) . ?
C6 C7 1.467(3) . ?
C7 C12 1.380(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.364(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.506(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.373(3) . ?
C14 C19 1.377(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(4) . ?
C17 C20 1.511(4) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13B O3 0.97 2.40 2.930(3) 113.6 . yes
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
C6 N1 N2 N3 -1.1(2) . . . . ?
N1 N2 N3 C5 1.3(2) . . . . ?
N1 N2 N3 C13 176.97(17) . . . . ?
C3 O1 C2 C1 177.5(2) . . . . ?
C2 O1 C3 O2 4.6(3) . . . . ?
C2 O1 C3 C4 -179.11(18) . . . . ?
O2 C3 C4 O3 44.1(3) . . . . ?
O1 C3 C4 O3 -132.29(18) . . . . ?
O2 C3 C4 C5 -137.7(2) . . . . ?
O1 C3 C4 C5 45.9(2) . . . . ?
N2 N3 C5 C6 -1.0(2) . . . . ?
C13 N3 C5 C6 -175.92(19) . . . . ?
N2 N3 C5 C4 177.24(16) . . . . ?
C13 N3 C5 C4 2.3(3) . . . . ?
O3 C4 C5 N3 17.2(3) . . . . ?
C3 C4 C5 N3 -160.86(17) . . . . ?
O3 C4 C5 C6 -165.2(2) . . . . ?
C3 C4 C5 C6 16.8(3) . . . . ?
N2 N1 C6 C5 0.5(2) . . . . ?
N2 N1 C6 C7 179.58(17) . . . . ?
N3 C5 C6 N1 0.3(2) . . . . ?
C4 C5 C6 N1 -177.64(19) . . . . ?
N3 C5 C6 C7 -178.65(18) . . . . ?
C4 C5 C6 C7 3.4(3) . . . . ?
N1 C6 C7 C12 -131.4(2) . . . . ?
C5 C6 C7 C12 47.5(3) . . . . ?
N1 C6 C7 C8 48.3(3) . . . . ?
C5 C6 C7 C8 -132.8(2) . . . . ?
C12 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 179.64(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C6 C7 C12 C11 180.0(2) . . . . ?
N2 N3 C13 C14 90.0(2) . . . . ?
C5 N3 C13 C14 -95.4(2) . . . . ?
N3 C13 C14 C15 -149.65(19) . . . . ?
N3 C13 C14 C19 33.4(3) . . . . ?
C19 C14 C15 C16 1.7(3) . . . . ?
C13 C14 C15 C16 -175.5(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C15 C16 C17 C20 177.1(2) . . . . ?
C16 C17 C18 C19 2.5(4) . . . . ?
C20 C17 C18 C19 -176.3(3) . . . . ?
C17 C18 C19 C14 -1.3(4) . . . . ?
C15 C14 C19 C18 -0.9(4) . . . . ?
C13 C14 C19 C18 176.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102502251
