Relevant π‒hole tetrel bonding interactions in ethyl 2-triazolyl-2-oxo-acetate derivatives: Hirshfeld surface analysis and DFT calculations
Ahmed, Muhammad Naeem; Ansar, Khawaja Yasin; Aziz, Shahid; Khan, Saba; Tahir, Muhammad Nawaz; Gil, Diego M.; Frontera, Antonio; CrystEngComm  (2020) –; doi:10.1039/D0CE00335B

data_7240330
_publ_section_title
;
 Relevant \p--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          'C19 H16 F N3 O3'
_chemical_formula_moiety         'C19 H16 F N3 O3'
_chemical_formula_sum            'C19 H16 F N3 O3'
_chemical_formula_weight         353.35
_chemical_name_systematic
;
Ethyl 2-(1-benzyl-4-(4-flourophenyl)-1H-1,2,3-triazol-5-yl)-2-oxoacetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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
;
2020-04-01 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.9640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.5939(14)
_cell_length_b                   7.5267(4)
_cell_length_c                   19.3890(8)
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.000
_cell_measurement_theta_min      1.664
_cell_volume                     3540.2(3)
_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 7.84
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14823
_diffrn_reflns_theta_full        26.952
_diffrn_reflns_theta_max         26.952
_diffrn_reflns_theta_min         1.679
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_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    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0524
_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/[\s^2^(Fo^2^)+(0.0754P)^2^+1.6543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                2426
_reflns_number_total             3806
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d0ce00335b2.cif
_cod_data_source_block           BNAEEM
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7240330
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              49661