Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation
Pokhodylo, Nazariy T.; Slyvka, Yuriy I.; Goreshnik, Evgeny A.; Obushak, Mykola D.; Molbank 2022 (2022) M1340–; doi:10.3390/M1340

data_1566574
_publ_section_title
;
 Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate:
 Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT
 Calculation
;
_journal_issue                   1
_journal_name_full               Molbank
_journal_page_first              M1340
_journal_paper_doi               10.3390/M1340
_journal_volume                  2022
_journal_year                    2022
_chemical_formula_moiety         'C11 H10 N4 O3'
_chemical_formula_sum            'C11 H10 N4 O3'
_chemical_formula_weight         246.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.216(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.7940(11)
_cell_length_b                   5.3470(3)
_cell_length_c                   8.9367(5)
_cell_measurement_reflns_used    3473
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.3100
_cell_measurement_theta_min      3.6940
_cell_volume                     1130.30(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -68.00  29.00   1.00    3.88    --  -41.65  57.00 120.00   97
  2  \w    -73.00  32.00   1.00    3.88    --  -41.65  77.00 -90.00  105
  3  \w   -112.00 -15.00   1.00    3.88    --  -41.65 -57.00 -90.00   97
  4  \w     15.00 112.00   1.00    3.88    --   41.65  57.00 150.00   97
  5  \w    -21.00  73.00   1.00    3.88    --   41.65 -77.00-150.00   94
  6  \w    103.00 177.00   1.00   15.49    --  103.35  77.00-180.00   74
  7  \w     79.00 175.00   1.00   15.49    --  103.35  45.00 -90.00   96
  8  \w     76.00 174.00   1.00   15.49    --  103.35  61.00-120.00   98
  9  \w     79.00 175.00   1.00   15.49    --  103.35  45.00 150.00   96
 10  \w     30.00 135.00   1.00   15.49    --  103.35 -77.00   0.00  105
 11  \w     30.00 135.00   1.00   15.49    --  103.35 -77.00 120.00  105
 12  \w    103.00 177.00   1.00   15.49    --  103.35  77.00 -30.00   74
 13  \w     76.00 174.00   1.00   15.49    --  103.35  61.00 150.00   98
 14  \w    103.00 177.00   1.00   15.49    --  103.35  77.00-150.00   74
 15  \w     32.00 127.00   1.00   15.49    --  103.35 -45.00 -90.00   95
 16  \w     79.00 175.00   1.00   15.49    --  103.35  45.00 -30.00   96
 17  \w    103.00 177.00   1.00   15.49    --  103.35  77.00 -60.00   74
 18  \w     76.00 174.00   1.00   15.49    --  103.35  61.00 120.00   98
 19  \w   -112.00 -15.00   1.00    3.88    --  -41.65 -57.00  60.00   97
 20  \w   -112.00 -15.00   1.00    3.88    --  -41.65 -57.00-180.00   97
 21  \w   -112.00 -15.00   1.00    3.88    --  -41.65 -57.00 -30.00   97
 22  \w    -21.00  73.00   1.00    3.88    --   41.65 -77.00 -30.00   94
 23  \w     15.00 112.00   1.00    3.88    --   41.65  57.00  60.00   97
 24  \w     30.00 135.00   1.00   15.49    --  103.35 -77.00-120.00  105
 25  \w     79.00 175.00   1.00   15.49    --  103.35  45.00  60.00   96
 26  \w     79.00 128.00   1.00   15.49    --  103.35  45.00-150.00   49
 27  \w     76.00 174.00   1.00   15.49    --  103.35  61.00   0.00   98
 28  \w    -44.00 -19.00   1.00    3.88    --  -41.77  82.00-161.00   25
 29  \w    110.00 136.00   1.00   15.49    --  103.35 111.00 -90.00   26
 30  \w    -44.00 -19.00   1.00    3.88    --  -41.77  82.00-161.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7978
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.175
_diffrn_reflns_theta_min         3.737
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.663
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 908 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0489P)^2^+0.4843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2015
_reflns_number_total             2090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            s4.cif
_cod_data_source_block           C11H10N4O3
_cod_database_code               1566574
_shelx_shelxl_version_number     2018/3
_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:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              30785
_shelx_hkl_checksum              69688
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;