Crystal structure determination, Hirshfeld surface, crystal void, intermolecular interaction energy analyses, as well as DFT and energy framework calculations of 2-(4-oxo-4,5-dihydro-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-1-yl)acetic acid
Irrou, Ezaddine; Elmachkouri, Younesse Ait; Oubella, Ali; Ouchtak, Hassan; Dalbouha, Samira; Mague, Joel T.; Hökelek, Tuncer; El Ghayati, Lhoussaine; Sebbar, Nada Kheira; Taha, Mohamed Labd; Acta Crystallographica Section E 78 (2022) 953–960; doi:10.1107/S2056989022008489

data_2244154
_publ_section_title
;
 Crystal structure determination, Hirshfeld surface, crystal void,
 intermolecular interaction energy analyses, as well as DFT and energy
 framework calculations of
 2-(4-oxo-4,5-dihydro-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-1-yl)acetic
 acid
;
_journal_coeditor_code           WM5656
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              953
_journal_page_last               960
_journal_paper_doi               10.1107/S2056989022008489
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C7 H6 N4 O3'
_chemical_formula_moiety         'C7 H6 N4 O3'
_chemical_formula_sum            'C7 H6 N4 O3'
_chemical_formula_weight         194.16
_chemical_name_systematic
;
2-(4-Oxo-4,5-dihydro-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-1-yl)acetic acid
;
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 103.1220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3747(4)
_cell_length_b                   4.66990(10)
_cell_length_c                   23.0423(5)
_cell_measurement_reflns_used    5261
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      74.4099
_cell_measurement_theta_min      3.9398
_cell_volume                     1611.20(6)
_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>publCIF</i> (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      296(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  0.0258
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5850
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.402
_diffrn_reflns_theta_min         3.940
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    1.111
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.81
_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    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.329
_refine_ls_extinction_coef       0.0304(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL 2018/3</i> (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0630P)^2^+0.6265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                1503
_reflns_number_total             1598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5656sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2244154
_shelx_estimated_absorpt_t_min   0.780
_shelx_estimated_absorpt_t_max   0.888
_shelx_hkl_checksum              24341
_shelx_res_checksum              51145
_cod_database_fobs_code 2244154