Crystal structure, computational study and Hirshfeld surface analysis of ethyl (2<i>S</i>,3<i>R</i>)-3-(3-amino-1<i>H</i>-1,2,4-triazol-1-yl)-2-hydroxy-3-phenylpropanoate
Ben Ali, Abdelkader; El Bakri, Youness; Lai, Chin-Hung; Sebhaoui, Jihad; El Ghayati, Lhoussaine; Essassi, El Mokhtar; Mague, Joel T.; Acta Crystallographica Section E 75 (2019) 1919–1924; doi:10.1107/S2056989019015743

data_2243211
_publ_section_title
;
 Crystal structure, computational study and Hirshfeld surface analysis of
 ethyl
 (2<i>S</i>,3<i>R</i>)-3-(3-amino-1<i>H</i>-1,2,4-triazol-1-yl)-2-hydroxy-3-phenylpropanoate
;
_journal_coeditor_code           TX2015
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1919
_journal_page_last               1924
_journal_paper_doi               10.1107/S2056989019015743
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C13 H16 N4 O3'
_chemical_formula_moiety         'C13 H16 N4 O3'
_chemical_formula_sum            'C13 H16 N4 O3'
_chemical_formula_weight         276.30
_chemical_name_systematic
'Ethyl (2<i>S</i>,3<i>R</i>)-3-(3-amino-1<i>H</i>-1,2,4-triazol-1-yl)-2-hydroxy-3-phenylpropanoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.3080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4766(2)
_cell_length_b                   9.4841(2)
_cell_length_c                   16.9904(3)
_cell_measurement_reflns_used    8615
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      74.5052
_cell_measurement_theta_min      2.6080
_cell_volume                     1362.05(5)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10203
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         74.497
_diffrn_reflns_theta_min         5.221
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.156
_refine_ls_extinction_coef       0.0057(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0378P)^2^+0.3844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2485
_reflns_number_total             2718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2015sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243211
_cod_database_fobs_code          2243211
_shelx_estimated_absorpt_t_min   0.766
_shelx_estimated_absorpt_t_max   0.934
_shelx_hkl_checksum              35355
_shelx_res_checksum              42629